has part BFO:0000051 chebi_ontology false has_part has_part electron -1 0.000548579903 CHEBI:10545 Elementary particle not affected by the strong force having a spin 1/2, a negative elementary charge and a rest mass of 0.000548579903(13) u, or 0.51099906(15) MeV. KEGG:C05359 PMID:21614077 [*-] beta beta(-) beta-particle chebi_ontology e e(-) e- electron negatron 2-hydroxyglutarate(2-) -2 146.022 146.09814 2-hydroxyglutarate 2-hydroxypentanedioate A dicarboxylic acid dianion resulting from the removal of a proton from both of the carboxylic acid groups of 2-hydroxyglutaric acid. Beilstein:5736650 C5H6O5 CHEBI:11596 HWXBTNAVRSUOJR-UHFFFAOYSA-L InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/p-2 MetaCyc:2-HYDROXYGLUTARIC_ACID OC(CCC([O-])=O)C([O-])=O Reaxys:5736650 chebi_ontology 4-amino-3-hydroxybutanoate -1 118.050 118.11126 4-Amino-3-hydroxybutanoate C4H8NO3 CAS:352-21-6 CHEBI:11955 InChI=1S/C4H9NO3/c5-2-3(6)1-4(7)8/h3,6H,1-2,5H2,(H,7,8)/p-1 KEGG:C03678 NCC(O)CC([O-])=O The conjugate base of gamma-amino-beta-hydroxybutyric acid arising from deprotonation of the carboxy group. YQGDEPYYFWUPGO-UHFFFAOYSA-M chebi_ontology 5-aminolevulinate -1 130.050 130.12196 5-amino-4-oxopentanoate Beilstein:3937762 C5H8NO3 CHEBI:12109 InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)/p-1 NCC(=O)CCC([O-])=O ZGXJTSGNIOSYLO-UHFFFAOYSA-M chebi_ontology vitamin A A group of fat-soluble retinoids produced via metabolism of provitamin A carotenoids. Vitamin A is involved in immune function, vision, reproduction, and cellular communication. CHEBI:12777 Wikipedia:Vitamin_A chebi_ontology steroid aldehyde Any steroid substituted by a formyl group. CHEBI:131565 chebi_ontology steroid aldehydes Mycoplasma genitalium metabolite Any bacterial metabolite produced during a metabolic reaction in Mycoplasma genitalium. CHEBI:131604 Mycoplasma genitalium metabolites chebi_ontology C27-steroid A steroid compound with a structure based on a 27-carbon (cholestane) skeleton. C27-steroids CHEBI:131619 chebi_ontology C19-steroid A steroid compound with a structure based on a 19-carbon (androstane) skeleton. C19-steroids CHEBI:131621 chebi_ontology dicarboxylic acids and O-substituted derivatives A class of carbonyl compound encompassing dicarboxylic acids and any derivatives obtained by substitution of either one or both of the carboxy hydrogens. CHEBI:131927 chebi_ontology dicarboxylic acids and derivatives 1,4-naphthoquinones A naphthoquinone in which the oxo groups of the quinone moiety are at positions 1 and 4 of the parent naphthalene ring. CHEBI:132142 chebi_ontology hyaluronate (C14H20NO11)n.H2O -1 0.0 0.0 A carbohydrate acid derivative anion obtained by deprotonation of the carboxy groups of hyaluronic acid; major species at pH 7.3. CHEBI:132153 chebi_ontology hyaluronan hyaluronate polyanion citrate(4-) -4 187.996 188.092 2-oxido-1,2,3-propanetricarboxylate 2-oxidopropane-1,2,3-tricarboxylate A citrate anion obtained by deprotonation of the three carboxy groups as well as the hydroxy group of citric acid. C(=O)([O-])C(CC(=O)[O-])(CC(=O)[O-])[O-] C6H4O7 CHEBI:132362 Chemspider:34552020 InChI=1S/C6H7O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h1-2H2,(H,7,8)(H,9,10)(H,11,12)/q-1/p-3 KSXLKRAZYZIYCZ-UHFFFAOYSA-K chebi_ontology citric acid tetraanion bleaching agent A reagent that lightens or whitens a substrate through chemical reaction. Bleaching reactions usually involve oxidative or reductive processes that degrade colour systems. Bleaching can occur by destroying one or more of the double bonds in the conjugated chain, by cleaving the conjugated chain, or by oxidation of one of the other moieties in the conjugated chain. Their reactivity results in many bleaches having strong bactericidal, disinfecting, and sterilising properties. CHEBI:132717 Wikipedia:Bleach chebi_ontology ethylmalonate A dicarboxylic acid anion obtained by deprotonation of at least one of the carboxy groups of ethylmalonic acid. CHEBI:132938 chebi_ontology ethylmalonate anion ethylmalonic acid anion ethylmalonate(2-) -2 130.027 130.099 A dicarboxylic acid dianion resulting from the removal of a proton from both of the carboxylic acid groups of ethylmalonic acid. C5H6O4 CHEBI:132939 InChI=1S/C5H8O4/c1-2-3(4(6)7)5(8)9/h3H,2H2,1H3,(H,6,7)(H,8,9)/p-2 Reaxys:3904851 UKFXDFUAPNAMPJ-UHFFFAOYSA-L [O-]C(C(C(=O)[O-])CC)=O chebi_ontology ethylpropanedioate 2-hydroxyglutarate 2-hydroxyglutarate anion 2-hydroxyglutaric acid anion A dicarboxylic acid anion obtained by deprotonation of at least one of the carboxy groups of 2-hydroxyglutaric acid. CHEBI:132941 chebi_ontology oxalate A dicarboxylic acid anion obtained by deprotonation of at least one of the carboxy groups of oxalic acid. CHEBI:132952 chebi_ontology ethanedioic acid anion ethanedioic acid anions oxalate anion oxalate anions oxalates oxalic acid anion oxalic acid anions methylsuccinate 2-methylbutanedioic acid anion 2-methylbutanedioic acid anions A dicarboxylic acid anion obtained by deprotonation of at least one of the carboxy groups of 3-methylsuccinic acid. CHEBI:132961 chebi_ontology methylsuccinate anion methylsuccinates methylsuccinic acid anion methylsuccinic acid anions hippurate An N-acylglycinate obtained by deprotonation of the carboxy group of hippuric acid (N-benzoylglycine) and its derivatives. CHEBI:132966 N-benzoylglycinate N-benzoylglycinates N-benzoylglycine anion N-benzoylglycine anions chebi_ontology hippurates 5-ammoniolevulinic acid +1 132.066 132.138 4-carboxy-2-oxobutan-1-aminium 5-aminolevulinic acid cation 5-aminolevulinic acid(1+) A primary ammonium ion obtained by protonation of the amino group of 5-aminolevulinic acid. C(C(=O)C[NH3+])CC(=O)O C5H10NO3 CHEBI:132970 InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)/p+1 ZGXJTSGNIOSYLO-UHFFFAOYSA-O chebi_ontology bradykinin(2+) +2 1-[(2S)-2-azaniumyl-5-carbamimidamidopentanoyl]-L-prolyl-L-prolylglycyl-L-phenylalanyl-L-seryl-L-prolyl-N-[(1S)-4-carbamimidamido-1-carboxylatobutyl]-L-phenylalaninamide 1-[(2S)-2-azaniumyl-5-{[azaniumyl(imino)methyl]amino}pentanoyl]-L-prolyl-L-prolylglycyl-L-phenylalanyl-L-seryl-L-prolyl-N-[(1S)-4-{[azaniumyl(imino)methyl]amino}-1-carboxylatobutyl]-L-phenylalaninamide 1061.577 1062.226 A peptide cation obtained by deprotonation of the carboxy group and protonation of the amino and guanidino groups of bradykinin; major species at pH 7.3. C(=[NH2+])(NCCC[C@@H](C(=O)N1[C@H](C(N2[C@H](C(=O)NCC(N[C@H](C(N[C@H](C(=O)N3[C@H](C(=O)N[C@H](C(N[C@H](C([O-])=O)CCCNC(=[NH2+])N)=O)CC=4C=CC=CC4)CCC3)CO)=O)CC=5C=CC=CC5)=O)CCC2)=O)CCC1)[NH3+])N C50H75N15O11 CHEBI:132988 InChI=1S/C50H73N15O11/c51-32(16-7-21-56-49(52)53)45(72)65-25-11-20-39(65)47(74)64-24-9-18-37(64)43(70)58-28-40(67)59-34(26-30-12-3-1-4-13-30)41(68)62-36(29-66)46(73)63-23-10-19-38(63)44(71)61-35(27-31-14-5-2-6-15-31)42(69)60-33(48(75)76)17-8-22-57-50(54)55/h1-6,12-15,32-39,66H,7-11,16-29,51H2,(H,58,70)(H,59,67)(H,60,69)(H,61,71)(H,62,68)(H,75,76)(H4,52,53,56)(H4,54,55,57)/p+2/t32-,33-,34-,35-,36-,37-,38-,39-/m0/s1 QXZGBUJJYSLZLT-FDISYFBBSA-P chebi_ontology radiosensitizing agent A drug that makes increases the sensitivity of tumour cells to radiation therapy. CHEBI:132992 PMID:12520460 Wikipedia:Radiosensitizer chebi_ontology radiosensitiser radiosensitisers radiosensitising agent radiosensitising agents radiosensitizer radiosensitizers radiosensitizing agents 3-hydroxydicarboxylate(2-) -2 132.006 132.072 3-hydroxydicarboxylic acid dianion(2-) A dicarboxylic acid dianion that results from the removal of a proton from both of the carboxylic acid groups of any 3-hydroxydicarboxylic acid. C(*C(CC(=O)[O-])O)([O-])=O C4H4O5R CHEBI:133251 a 3-hydroxy dicarboxylic acid chebi_ontology saturated dicarboxylic acid dianion(2-) -2 87.980 88.019 A carboxylic acid dianion obtained by deprotonation of both carboxy groups of any dicarboxylic acid that contains no carbon-carbon double bonds. C2O4R CHEBI:133291 [O-]C(*C([O-])=O)=O a saturated dicarboxylic acid chebi_ontology saturated dicarboxylate(2-) oxo dicarboxylic acid dianion A dicarboxylic acid dianion obtained by deprotonation of both carboxy groups of any oxo dicarboxylic acid. CHEBI:133294 chebi_ontology oxo dicarboxylic acid homovanillate (4-hydroxy-3-methoxyphenyl)acetate -1 181.050 181.166 3-methoxy-4-hydroxyphenylacetate A hydroxy monocarboxylic acid anion which is obtained by deprotonation of the carboxy group of homovanillic acid. C1=C(C(=CC(=C1)CC([O-])=O)OC)O C9H9O4 CHEBI:133744 InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)/p-1 QRMZSPFSDQBLIX-UHFFFAOYSA-M chebi_ontology citrate anion A tricarboxylic acid anion obtained by deprotonation of at least one of the carboxy groups of citric acid. CHEBI:133748 chebi_ontology citrate citrate anions volatile organic compound Any organic compound having an initial boiling point less than or equal to 250 degreeC (482 degreeF) measured at a standard atmospheric pressure of 101.3 kPa. CHEBI:134179 VOC VOCs Wikipedia:Volatile_organic_compound chebi_ontology volatile organic compounds alkanesulfonate oxoanion -1 93.972 94.091 An alkanesulfonate in which the carbon at position 1 is attached to R, which can represent hydrogens, a carbon chain, or other groups. C(S([O-])(=O)=O)* CH2O3SR CHEBI:134249 CHEBI:22318 MetaCyc:Alkanesulfonates alkanesulfonate oxoanions alkanesulfonates an alkanesulfonate chebi_ontology guaiacols 0 1-hydroxy-2-methoxybenzenes 120.021 120.106 2-methoxyphenol 2-methoxyphenol derivative 2-methoxyphenol derivatives 2-methoxyphenols Any phenol carrying an additional methoxy substituent at the ortho-position. C1(=C(C(=C(C(=C1*)*)*)OC)O)* C7H4O2R4 CHEBI:134251 CHEBI:13645 MetaCyc:Guaiacols a guaiacol catechol monomethyl ether catechol monomethyl ethers chebi_ontology o-methoxyphenol o-methoxyphenols ortho-methoxyphenol ortho-methoxyphenols allylic alcohol 0 53.003 53.040 An alcohol where the hydroxy group is attached to a saturated carbon atom adjacent to a double bond (R groups may be H, organyl, etc.). C(C(=C(*)*)*)(O)(*)* C3HOR5 CHEBI:134361 allylic alcohols chebi_ontology primary allylic alcohol 0 55.018 55.055 An allylic alcohol in which the carbon atom that links the double bond to the hydroxy group is also attached to two hydrogens. C(C(=C(*)*)*)(O)([H])[H] C3H3OR3 CHEBI:134394 chebi_ontology primary allylic alcohols 3-oxo-5alpha-steroid 0 273.222 273.434 3-oxo 5alpha- steroid 3-oxo 5alpha- steroids 3-oxo 5alpha-steroids A 3-oxo steroid that has alpha configuration at position 5. C12C(C3C(C(CC3)*)(C)CC1)CC[C@@]4(C2(CCC(C4)=O)C)[H] C19H29OR CHEBI:13601 CHEBI:1622 CHEBI:20150 KEGG:C02940 MetaCyc:3-Oxo-5-Alpha-Steroids a 3-oxo-5alpha-steroid chebi_ontology glycol A diol in which the two hydroxy groups are on different carbon atoms, usually but not necessarily adjacent. CHEBI:13643 Glykol a glycol chebi_ontology glycols 3-oxo-Delta(4)-steroid group 0 94.042 94.111 An organic group derived from any 3-oxo-Delta(4)-steroid. C1=C(C*)*C(CC1=O)* C6H6O CHEBI:136849 a 3-oxo-Delta4-steroid group chebi_ontology pro-agent A compound that, on administration, undergoes conversion by biochemical (enzymatic), chemical (possibly following an enzymatic step), or physical (e.g. photochemical) activation processes before becoming the active agent for which it is a pro-agent. CHEBI:136859 PMID:26449612 chebi_ontology pro-agents proagent proagents 5beta steroid 5beta steroids 5beta-steroid 5beta-steroids Any steroid that has beta-configuration at position 5. CHEBI:136889 chebi_ontology quinine(1+) (9R)-9-hydroxy-6'-methoxy-8alpha-cinchonan-1-ium +1 325.192 325.42470 C20H25N2O2 CHEBI:137041 InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/p+1/t13-,14-,19-,20+/m0/s1 LOUPRKONTZGTKE-WZBLMQSHSA-O The monoprotonated form of quinine, the predominant species at pH7.3. [H][C@]1(C[C@@H]2CC[N@H+]1C[C@@H]2C=C)[C@H](O)c1ccnc2ccc(OC)cc12 chebi_ontology quinine tertiary ammonium ion +1 15.011 15.015 An organic cation obtained by protonation of any tertiary amine. CHEBI:137982 HNR3 [NH+](*)(*)* a tertiary amine chebi_ontology tertiary amine(1+) tertiary ammonium ions 3-(1-methylpyrrolidin-2-yl)pyridine 0 162.116 162.232 3-(1-methylpyrrolidin-2-yl)pyridine An N-alkylpyrrolidine that consists of N-methylpyrrolidine bearing a pyridin-3-yl substituent at position 2. C10H14N2 C=1C=C(C2N(CCC2)C)C=NC1 CHEBI:138000 InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3 SNICXCGAKADSCV-UHFFFAOYSA-N chebi_ontology endocrine disruptor Any compound that can disrupt the functions of the endocrine (hormone) system CHEBI:138015 PMID:27929035 PMID:28356401 PMID:28526231 Wikipedia:Endocrine_disruptor chebi_ontology endocrine disrupting chemical endocrine disrupting chemicals endocrine disrupting compound endocrine disrupting compounds endocrine disruptors endocrine-disrupting chemical endocrine-disrupting chemicals hormonally active agent hormonally active agents inorganic acid A Bronsted acid derived from one or more inorganic compounds. Inorganic acids (also known as mineral acids) form hydrons and conjugate base ions when dissolved in water. CHEBI:138103 Wikipedia:Mineral_acid chebi_ontology inorganic acids mineral acid mineral acids Delta(5),Delta(7)-sterol 0 271.206 271.418 Any sterol containing two double bonds between positions 5-6 and 7-8. C12C(C3C(C(CC3)*)(C)CC1)=CC=C4C2(CCC(C4)O)C C19H27OR CHEBI:138131 MetaCyc:Delta5-Delta7-Steroids a Delta(5),Delta(7)-sterol chebi_ontology 17alpha-hydroxy-C21-steroid 0 304.277 304.511 Any C21-steroid carrying a hydroxy substituent at the 17alpha-position. Note that individual examples may have ring substituents at other positions and/or contain double bonds, aromatic A-rings, expanded/contracted rings etc., so the formula and mass may vary from that given for the generic structure. C1CCCC2C1(C3C(CC2)C4C(CC3)([C@](CC4)(CC)O)C)C C21H36O CHEBI:138141 InChI=1S/C21H36O/c1-4-21(22)14-11-18-16-9-8-15-7-5-6-12-19(15,2)17(16)10-13-20(18,21)3/h15-18,22H,4-14H2,1-3H3/t15?,16?,17?,18?,19?,20?,21-/m1/s1 JSIVWCLRCGAVHN-ILZKQPLKSA-N MetaCyc:17a-hydroxy-C21-steroids a 17alpha-hydroxy-C21-steroid chebi_ontology bile acids Any member of a group of hydroxy steroids occuring in bile, where they are present as the sodium salts of their amides with glycine or taurine. In mammals bile acids almost invariably have 5beta-configuration, while in lower vertebrates, some bile acids, known as allo-bile acids, have 5alpha-configuration. CHEBI:138366 chebi_ontology apoprotein An apoprotein is a protein devoid of its characteristic prosthetic group or metal. CHEBI:13850 KEGG:C16240 apoprotein apoproteins chebi_ontology gas molecular entity Any main group molecular entity that is gaseous at standard temperature and pressure (STP; 0degreeC and 100 kPa). CHEBI:138675 Wikipedia:https://en.wikipedia.org/wiki/Gas chebi_ontology gas molecular entities gaseous molecular entities gaseous molecular entity carotenoid beta-end group 0 255.211 255.418 Any carotenoid derivative with an beta-end group C1(=C(CCCC1(C)C)C)/C=C/C(=C/C=C/C(=C/*)/C)/C C19H27R CHEBI:139120 MetaCyc:Carotenoid-beta-end-group a carotenoid beta-end derivative chebi_ontology carbamate -1 60.009 60.03212 Beilstein:3903503 CAS:302-11-4 CH2NO2 CHEBI:13941 Carbamat Gmelin:239604 InChI=1S/CH3NO2/c2-1(3)4/h2H2,(H,3,4)/p-1 KXDHJXZQYSOELW-UHFFFAOYSA-M Karbamat NC([O-])=O carbamate carbamate ion carbamic acid, ion(1-) chebi_ontology alpha-hydroxy ketone An alpha-oxyketone that has a hydroxy group as the alpha-oxy moiety. CHEBI:139588 PMID:15326516 PMID:19908854 PMID:20382022 PMID:23295224 alpha-hydroxy ketones alpha-hydroxy-ketone alpha-hydroxy-ketones alpha-hydroxyketone alpha-hydroxyketones chebi_ontology retinoid anion A carboxylic acid anion obtained by deprotonation of any retinoid carboxy group. CHEBI:139589 chebi_ontology retinoate retinoates retinoid anions retinoid carboxylate anion retinoid carboxylate anions retinoid carboxylic acid anion retinoid carboxylic acid anions primary alpha-hydroxy ketone *C(C(O)([H])[H])=O 0 59.013 59.044 An alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a -CH2 (methylene) group. C2H3O2R CHEBI:139590 chebi_ontology primary alpha-hydroxy ketones primary alpha-hydroxy-ketone primary alpha-hydroxy-ketones primary alpha-hydroxyketone primary alpha-hydroxyketones tertiary alpha-hydroxy ketone 0 56.998 57.028 An alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing two organyl groups. C(C(=O)*)(O)(*)* C2HO2R3 CHEBI:139592 chebi_ontology tertiary alpha-hydroxy ketones tertiary alpha-hydroxy-ketone tertiary alpha-hydroxy-ketones tertiary alpha-hydroxyketone tertiary alpha-hydroxyketones secondary carboxamide 0 43.006 43.025 A carboxamide resulting from the formal condensation of a carboxylic acid with a primary amine; formula RC(=O)NHR(1). CHEBI:140325 CHNOR2 N(C(*)=O)(*)[H] chebi_ontology secondary carboxamides fatty acid 4:0 *C(O)=O 0 44.998 45.017 Any saturated fatty acid containing 4 carbons. CHEBI:140601 CHO2R chebi_ontology alkylcob(III)alamin 0 1328.564 1329.350 C62H88CoN13O14PR CHEBI:140785 MetaCyc:CPD-20938 [Co-3]1234(N5C6=C(C7=[N+]4C(=CC8=[N+]3C(=C(C9=[N+]2[C@@]([C@]5([C@@H]([C@@]6(C)CCC(=O)NC[C@H](OP(O[C@@H]%10[C@H](O[C@H](N%11C=[N+]1C%12=CC(=C(C=C%12%11)C)C)[C@@H]%10O)CO)(=O)[O-])C)CC(=O)N)[H])([C@]([C@@H]9CCC(N)=O)(CC(=O)N)C)C)C)[C@](C)([C@@H]8CCC(=O)N)CC(N)=O)C([C@@H]7CCC(=O)N)(C)C)C)* an alkylcob(III)alamin chebi_ontology 24G7 epitope 0 134.048 134.136 An antigenic epitope recognized by an anti-bilirubin monoclonal antibody designated 24G7. A substructure of bilirubin IXalpha, it is the region containing the oxo group at C-1, the methyl group at C-2, C-(4, 5, 6, 9), and N-21 and -22. C(=CC(NC(=*)*)=*)(NC(C(C)=*)=O)* C7H6N2O CHEBI:142163 chebi_ontology purines D-ribonucleoside 0 251.078 251.219 A purine ribonucleoside that is a purine derivative attached to a beta-D-ribofuranosyl residue at position 9 via a glycosidic (N-glycosyl) linkage. C1(=*)NC(=NC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)* C10H11N4O4R2 CHEBI:142355 a purine D-ribonucleoside chebi_ontology glutamate(1-) -1 146.045 146.12136 2-ammoniopentanedioate An alpha-amino-acid anion that is the conjugate base of glutamic acid, having anionic carboxy groups and a cationic amino group C5H8NO4 CHEBI:14321 Gmelin:327908 InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/p-1 WHUUTDBJXJRKMK-UHFFFAOYSA-M [NH3+]C(CCC([O-])=O)C([O-])=O chebi_ontology glutamate glutamate(1-) glutamic acid monoanion hydrogen glutamate electron donor A molecular entity that can transfer an electron to another molecular entity. CHEBI:15022 Elektronendonator chebi_ontology donneur d'electron electron donor retinal 0 284.214 284.43572 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal An enal that consists of 3,7-dimethyl-9-nona-2,4,6,8-tetraenal (double bond geometry unspecified) carrying a 2,6,6-trimethylcyclohex-1-en-1-yl group at the 9-position. C20H28O CHEBI:15035 InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3 MetaCyc:Retinals NCYCYZXNIZJOKI-UHFFFAOYSA-N Reaxys:2055098 [H]C(=O)C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C chebi_ontology retinal retinoate -1 299.201 299.42718 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate C20H27O2 CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC([O-])=O CHEBI:15036 InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/p-1 SHGAZHPCJJPHSC-UHFFFAOYSA-M chebi_ontology retinoate sulfide(2-) -2 31.972 32.06600 A divalent inorganic anion obtained by removal of both protons from hydrogen sulfide. CAS:18496-25-8 CHEBI:15138 InChI=1S/S/q-2 S S(2-) Sulfide UCKMPCXJQFINFW-UHFFFAOYSA-N UM-BBD_compID:c0569 [S--] chebi_ontology sulfanediide sulfide sulfide(2-) sulphide xanthine A purine nucleobase found in humans and other organisms. C5H4N4O2 CHEBI:15318 ECMDB:ECMDB00292 KNApSAcK:C00019660 PMID:24629268 YMDB:YMDB00263 chebi_ontology acceptor A A molecular entity that can accept an electron, a pair of electrons, an atom or a group from another molecular entity. Acceptor Akzeptor CHEBI:13699 CHEBI:15339 CHEBI:2377 Hydrogen-acceptor KEGG:C00028 KEGG:C16722 Oxidized donor accepteur acceptor chebi_ontology acetone 0 2-Propanone 58.042 58.07914 A methyl ketone that consists of propane bearing an oxo group at C2. ACETONE Aceton Acetone Azeton Beilstein:635680 C3H6O CAS:67-64-1 CC(C)=O CHEBI:13708 CHEBI:15347 CHEBI:22182 CHEBI:2398 CHEBI:40571 CSCPPACGZOOCGX-UHFFFAOYSA-N Dimethyl ketone Dimethylketon Gmelin:1466 HMDB:HMDB0001659 InChI=1S/C3H6O/c1-3(2)4/h1-2H3 KEGG:C00207 KEGG:D02311 LIPID_MAPS_instance:LMFA12000057 MetaCyc:ACETONE PDBeChem:ACN PMID:17190852 PMID:17347819 Propanon Pyroacetic ether Reaxys:635680 UM-BBD_compID:c0556 Wikipedia:Acetone acetone beta-Ketopropane chebi_ontology dimethylcetone dimethylketone methyl ketone propan-2-one propanone choline +1 104.108 104.17080 2-hydroxy-N,N,N-trimethylethanaminium A choline that is the parent compound of the cholines class, consisting of ethanolamine having three methyl substituents attached to the amino function. Beilstein:1736748 Bilineurine C5H14NO CAS:62-49-7 CHEBI:13985 CHEBI:15354 CHEBI:23212 CHEBI:3665 CHEBI:41524 CHOLINE ION C[N+](C)(C)CCO Choline DrugBank:DB00122 Drug_Central:3097 ECMDB:ECMDB00097 Gmelin:324597 HMDB:HMDB0000097 InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1 KEGG:C00114 KEGG:D07690 KNApSAcK:C00007298 MetaCyc:CHOLINE N,N,N-trimethylethanol-ammonium N-trimethylethanolamine OEYIOHPDSNJKLS-UHFFFAOYSA-N PDBeChem:CHT PMID:10930630 PMID:12826235 PMID:12946691 PMID:14972364 PMID:16210714 PMID:17087106 PMID:17283071 PMID:17344490 PMID:18204095 PMID:18230680 PMID:18786517 PMID:18786520 PMID:19246089 PMID:20038853 PMID:20446114 PMID:22770225 PMID:22961562 PMID:23095202 PMID:23616508 PMID:23637565 PMID:23733158 PMID:6420466 PMID:7590654 PMID:9517478 Reaxys:1736748 Wikipedia:Choline YMDB:YMDB00227 chebi_ontology choline trimethylethanolamine acetylcholine +1 146.118 146.20748 2-acetyloxy-N,N,N-trimethylethanaminium ACETYLCHOLINE ACh Acetylcholine Actylcholine is an ester of acetic acid and choline, which acts as a neurotransmitter. Azetylcholin Beilstein:1764436 C7H16NO2 CAS:51-84-3 CC(=O)OCC[N+](C)(C)C CHEBI:12686 CHEBI:13715 CHEBI:15355 CHEBI:22197 CHEBI:2416 CHEBI:40559 DrugBank:DB03128 Drug_Central:65 Gmelin:326108 InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1 KEGG:C01996 LINCS:LSM-5888 O-Acetylcholine OIPILFWXSMYKGL-UHFFFAOYSA-N PDBeChem:ACH PMID:14764638 PMID:15014918 PMID:15231705 PMID:15361288 PMID:18050502 PMID:18407448 PMID:19255787 PMID:20963497 PMID:21130809 PMID:21246223 PMID:21545631 PMID:21601579 Wikipedia:Acetylcholine acetylcholine chebi_ontology choline acetate cysteine 0 121.020 121.15922 2-Amino-3-mercaptopropionic acid 2-amino-3-mercaptopropanoic acid 2-amino-3-sulfanylpropanoic acid A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3. Beilstein:1721406 C C3H7NO2S CAS:3374-22-9 CHEBI:14061 CHEBI:15356 CHEBI:23508 CHEBI:4050 Cys Cystein Cysteine Gmelin:2933 Hcys InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6) KEGG:C00736 KNApSAcK:C00001351 KNApSAcK:C00007323 NC(CS)C(O)=O PMID:17439666 PMID:25181601 Reaxys:1721406 Wikipedia:Cysteine XUJNEKJLAYXESH-UHFFFAOYSA-N Zystein chebi_ontology cisteina cysteine pyruvate -1 2-oxopropanoate 2-oxopropanoate 2-oxopropanoic acid, ion(1-) 87.008 87.05412 A 2-oxo monocarboxylic acid anion that is the conjugate base of pyruvic acid, arising from deprotonation of the carboxy group. Beilstein:3587721 C3H3O3 CAS:57-60-3 CC(=O)C([O-])=O CHEBI:14987 CHEBI:15361 CHEBI:26462 Gmelin:2502 InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)/p-1 KEGG:C00022 LCTONWCANYUPML-UHFFFAOYSA-M PMID:17190852 PMID:21603897 PMID:21823181 PMID:21854850 PMID:22006570 PMID:22016370 PMID:22215378 PMID:22311625 PMID:22451307 PMID:22458763 Reaxys:3587721 UM-BBD_compID:c0159 chebi_ontology pyruvate acetic acid 0 60.021 60.05200 A simple monocarboxylic acid containing two carbons. ACETIC ACID AcOH Acetic acid Beilstein:506007 C2H4O2 CAS:64-19-7 CC(O)=O CH3-COOH CH3CO2H CHEBI:15366 CHEBI:22169 CHEBI:2387 CHEBI:40486 Drug_Central:4211 E 260 E-260 E260 Essigsaeure Ethanoic acid Ethylic acid Gmelin:1380 HMDB:HMDB0000042 HOAc INS No. 260 InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4) KEGG:C00033 KEGG:D00010 KNApSAcK:C00001176 LIPID_MAPS_instance:LMFA01010002 MeCO2H MeCOOH MetaCyc:ACET Methanecarboxylic acid PDBeChem:ACT PDBeChem:ACY PMID:12005138 PMID:15107950 PMID:16630552 PMID:16774200 PMID:17190852 PMID:19416101 PMID:19469536 PMID:22153255 PMID:22173419 PPDB:1333 QTBSBXVTEAMEQO-UHFFFAOYSA-N Reaxys:506007 Wikipedia:Acetic_acid acetic acid acide acetique chebi_ontology ethoic acid all-trans-retinoic acid (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid 0 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ECL) 300.209 300.43512 A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry. AGN 100335 Acide retinoique (French) (DSL) Beilstein:2057223 C20H28O2 CAS:302-79-4 CC(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(C)=C/C(O)=O CHEBI:15367 CHEBI:45376 CHEBI:8815 DrugBank:DB00755 Drug_Central:2722 HMDB:HMDB0001852 InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+ KEGG:C00777 KEGG:D00094 LIPID_MAPS_instance:LMPR01090019 PDBeChem:REA PMID:11073974 PMID:11214352 PMID:11332619 PMID:11343416 PMID:11437362 PMID:11556813 PMID:11722649 PMID:11896294 PMID:11904404 PMID:14581379 PMID:14605492 PMID:14627725 PMID:14704332 PMID:14705145 PMID:14978018 PMID:15194426 PMID:15318809 PMID:15327395 PMID:15359008 PMID:15376324 PMID:15476854 PMID:15537748 PMID:15539337 PMID:15675886 PMID:15839997 PMID:16569247 PMID:16685080 PMID:16688769 PMID:16720557 PMID:16819260 PMID:16847436 PMID:16920920 PMID:17073551 PMID:17166212 PMID:17204142 PMID:18052213 PMID:18085670 PMID:18162363 PMID:18183617 PMID:18318655 PMID:18322276 PMID:18400206 PMID:18404486 PMID:18440196 PMID:18678272 PMID:18819820 PMID:18977311 PMID:19112091 PMID:19144697 PMID:19427305 PMID:19587328 PMID:19597529 PMID:19814868 PMID:19841174 PMID:21898109 PMID:21924320 PMID:21993673 PMID:22134377 PMID:22177959 PMID:22180426 PMID:22244299 PMID:22261335 PMID:22428994 PMID:22514600 PMID:22532966 PMID:22534100 PMID:22538278 PMID:22741806 RETINOIC ACID Reaxys:2057223 Renova Retin-A Retinoic acid Retisol-A Ro 1-5488 SHGAZHPCJJPHSC-YCNIQYBTSA-N Stieva-A Tretin M Tretinoine (French) (EINECS) Vesanoid Vitamin A acid Wikipedia:Tretinoin all-(E)-Retinoic acid all-trans-Retinoic acid all-trans-Tretinoin all-trans-Vitamin A acid all-trans-Vitamin A1 acid all-trans-beta-Retinoic acid beta-Retinoic acid chebi_ontology trans-Retinoic acid tretinoin biopterin 0 2-Amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone 2-amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone 2-amino-6-(1,2-dihydroxypropyl)pteridin-4(3H)-one 237.086 237.21554 A pterin derivative that consists of pterin bearing amino, oxo and 1,2-dihydroxypropyl substituents at positions 2, 4 and 6 respectively. The parent of the class of biopterins; the L-erythro isomer occurs widely in nature. Biopterin C9H11N5O3 CAS:22150-76-1 CC(O)C(O)c1cnc2nc(N)[nH]c(=O)c2n1 CHEBI:13904 CHEBI:15373 CHEBI:22880 CHEBI:3107 DrugBank:DB03886 InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17) KEGG:C06313 LHQIJBMDNUYRAM-UHFFFAOYSA-N PMID:22770225 Reaxys:234314 Wikipedia:Biopterin chebi_ontology water 0 18.011 18.01530 An oxygen hydride consisting of an oxygen atom that is covalently bonded to two hydrogen atoms. BOUND WATER Beilstein:3587155 CAS:7732-18-5 CHEBI:10743 CHEBI:13352 CHEBI:15377 CHEBI:27313 CHEBI:42043 CHEBI:42857 CHEBI:43228 CHEBI:44292 CHEBI:44701 CHEBI:44819 CHEBI:5585 Gmelin:117 H2O H2O HMDB:HMDB0002111 HOH InChI=1S/H2O/h1H2 KEGG:C00001 KEGG:D00001 MetaCyc:WATER MolBase:1 PDBeChem:HOH PDBeChem:MTO Reaxys:3587155 WATER Wasser Water Wikipedia:Water XLYOFNOQVPJJNP-UHFFFAOYSA-N [H]O[H] [OH2] acqua agua aqua chebi_ontology dihydridooxygen dihydrogen oxide eau hydrogen hydroxide oxidane water dioxygen 0 31.990 31.99880 CAS:7782-44-7 CHEBI:10745 CHEBI:13416 CHEBI:15379 CHEBI:23833 CHEBI:25366 CHEBI:30491 CHEBI:44742 CHEBI:7860 Disauerstoff E 948 E-948 E948 Gmelin:485 HMDB:HMDB0001377 InChI=1S/O2/c1-2 KEGG:C00007 KEGG:D00003 MYMOFIZGZYHOMD-UHFFFAOYSA-N MetaCyc:OXYGEN-MOLECULE MolBase:750 O2 O2 O=O OXYGEN MOLECULE Oxygen PDBeChem:OXY PMID:10906528 PMID:16977326 PMID:18210929 PMID:18638417 PMID:19840863 PMID:7710549 PMID:9463773 Wikipedia:Oxygen [OO] chebi_ontology dioxygen dioxygene molecular oxygen ATP 0 506.996 507.18100 ADENOSINE-5'-TRIPHOSPHATE ATP Adenosine 5'-triphosphate Adenosine triphosphate An adenosine 5'-phosphate in which the 5'-phosphate is a triphosphate group. It is involved in the transportation of chemical energy during metabolic pathways. Beilstein:73010 C10H16N5O13P3 CAS:56-65-5 CHEBI:10789 CHEBI:10841 CHEBI:13236 CHEBI:15422 CHEBI:22249 CHEBI:2359 CHEBI:40938 DrugBank:DB00171 Drug_Central:91 Gmelin:34857 H4atp HMDB:HMDB0000538 InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1 KEGG:C00002 KEGG:D08646 KNApSAcK:C00001491 Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O PDBeChem:ATP Patent:US3079379 Reaxys:73010 Wikipedia:Adenosine_triphosphate ZKHQWZAMYRWXGA-KQYNXXCUSA-N adenosine 5'-(tetrahydrogen triphosphate) chebi_ontology glycine 0 75.032 75.06664 Aminoacetic acid Aminoessigsaeure Beilstein:635782 C2H5NO2 CAS:56-40-6 CHEBI:10792 CHEBI:14344 CHEBI:15428 CHEBI:24368 CHEBI:42964 CHEBI:5460 DHMQDGOQFOQNFH-UHFFFAOYSA-N DrugBank:DB00145 Drug_Central:1319 ECMDB:ECMDB00123 G GLYCINE Gly Glycin Glycine Glycocoll Glykokoll Glyzin Gmelin:1808 H2N-CH2-COOH HMDB:HMDB0000123 Hgly InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5) KEGG:C00037 KEGG:D00011 KNApSAcK:C00001361 Leimzucker MetaCyc:GLY NCC(O)=O PDBeChem:GLY PMID:10930630 PMID:11019925 PMID:11174716 PMID:11542461 PMID:11806864 PMID:12631515 PMID:12754315 PMID:12770151 PMID:12921899 PMID:15331688 PMID:15388434 PMID:15710237 PMID:16105183 PMID:16151895 PMID:16214212 PMID:16417482 PMID:16444815 PMID:16664855 PMID:16901953 PMID:16918424 PMID:16986325 PMID:16998855 PMID:17154252 PMID:17383967 PMID:17582620 PMID:17970719 PMID:18079355 PMID:18396796 PMID:18440992 PMID:18593588 PMID:18816054 PMID:18840508 PMID:19028609 PMID:19120667 PMID:19449910 PMID:19526731 PMID:19544666 PMID:19738917 PMID:19916621 PMID:19924257 PMID:21751272 PMID:22044190 PMID:22079563 PMID:22234938 PMID:22264337 PMID:22293292 PMID:22401276 PMID:22434786 Reaxys:635782 The simplest (and the only achiral) proteinogenic amino acid, with a hydrogen atom as its side chain. Wikipedia:Glycine YMDB:YMDB00016 aminoacetic acid aminoethanoic acid chebi_ontology glycine squalene (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene (all-E)-2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene 0 410.391 410.71800 A triterpene consisting of 2,6,10,15,19,23-hexamethyltetracosane having six double bonds at the 2-, 6-, 10-, 14-, 18- and 22-positions with (all-E)-configuration. Beilstein:1728920 C30H50 CAS:111-02-4 CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C CHEBI:10795 CHEBI:10843 CHEBI:15104 CHEBI:15440 CHEBI:26746 CHEBI:9245 InChI=1S/C30H50/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h15-18,23-24H,9-14,19-22H2,1-8H3/b27-17+,28-18+,29-23+,30-24+ KEGG:C00751 KNApSAcK:C00003755 LIPID_MAPS_instance:LMPR0106010002 PMID:16341241 PMID:24362891 Spinacene Squalene Supraene YYGNTYWPHWGJRM-AAJYLUCBSA-N chebi_ontology squalene prostaglandin E2 (15S)-prostaglandin E2 (5Z,11alpha,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoate (5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid (E,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acid (Z)-7-((1R,2R,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic acid 0 352.225 352.46510 Beilstein:2224724 C20H32O5 CAS:363-24-6 CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O CHEBI:10910 CHEBI:10911 CHEBI:114125 CHEBI:15551 CHEBI:26323 CHEBI:4625 CHEBI:8512 Dinoproston Dinoprostone DrugBank:DB00917 Drug_Central:913 HMDB:HMDB0001220 InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1 KEGG:C00584 KEGG:D00079 LIPID_MAPS_instance:LMFA03010003 MetaCyc:5Z13E-15S-1115-DIHYDROXY-9-OXOPROS PGE2 PMID:24501112 PMID:7224729 PMID:7836930 Patent:DE2011969 Patent:GB851827 Patent:NL6505799 Patent:US3598858 Prepidil Propess Prostaglandin E2 Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins. Prostin E2 Reaxys:2224724 Wikipedia:Prostaglandin_E2 XEYBRNLFEZDVAW-ARSRFYASSA-N chebi_ontology dinoprostona dinoprostone dinoprostonum sarcosine (methylamino)acetic acid (methylamino)ethanoic acid 0 89.048 89.09322 A N-alkylglycine that is the N-methyl derivative of glycine. It is an intermediate in the metabolic pathway of glycine. Beilstein:1699442 C3H7NO2 CAS:107-97-1 CHEBI:10876 CHEBI:12609 CHEBI:15065 CHEBI:15611 CHEBI:21765 CHEBI:45381 CHEBI:45442 CHEBI:45531 CHEBI:45614 CHEBI:9029 CNCC(O)=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N Gmelin:2018 HMDB:HMDB0000271 InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6) KEGG:C00213 L-sarcosine MeGly MetaCyc:SARCOSINE N-Methylglycine N-methylaminoacetic acid PDBeChem:SAR PMID:11272730 PMID:11850512 PMID:15023571 PMID:15331688 PMID:16154544 PMID:17095900 PMID:17190852 PMID:17901997 PMID:19433577 PMID:19577367 PMID:19619564 PMID:19944746 Reaxys:1699442 SARCOSINE Sar Sarcosine UM-BBD_compID:c0135 Wikipedia:Sarcosine chebi_ontology methylaminoacetic acid sarcosine sarcosinic acid 5-methyltetrahydrofolic acid 0 459.187 459.45580 5-Methyltetrahydrofolate C20H25N7O6 CAS:134-35-0 CHEBI:12146 CHEBI:15641 CHEBI:2097 CN1[C@@H](CNc2ccc(cc2)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CNc2nc(N)[nH]c(=O)c12 DrugBank:DB04789 InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12-,13-/m0/s1 KEGG:C00440 KNApSAcK:C00007252 N-(5-methyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid N-[4-({[(6S)-2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-L-glutamic acid ZNOVTXRBGFNYRX-STQMWFEESA-N [(6S)-5-methyl-5,6,7,8-tetrahydropteroyl]glutamate chebi_ontology allantoin (2,5-Dioxo-4-imidazolidinyl)urea 0 158.044 158.11560 2,5-Dioxo-4-imidazolidinyl-urea 4-ureido-2,5-imidazolidinedione 5-Ureido-2,4-imidazolidindione 5-Ureidohydantoin Allantoin An imidazolidine-2,4-dione that is 5-aminohydantoin in which a carbamoyl group is attached to the exocyclic nitrogen. C4H6N4O3 CAS:97-59-6 CHEBI:13761 CHEBI:15676 CHEBI:22354 CHEBI:2594 Drug_Central:4268 Glyoxyldiureide HMDB:HMDB0000462 InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11) KEGG:C01551 KEGG:D00121 KNApSAcK:C00007468 LINCS:LSM-5190 MetaCyc:ALLANTOIN N-(2,5-Dioxo-4-imidazolidinyl)urea N-(2,5-dioxoimidazolidin-4-yl)urea NC(=O)NC1NC(=O)NC1=O PMID:11157020 PMID:14619112 PMID:17190852 POJWUDADGALRAB-UHFFFAOYSA-N Patent:US2158098 Reaxys:83514 Wikipedia:Allantoin allantoin chebi_ontology aldose 0 90.07790 Aldehydic parent sugars (polyhydroxy aldehydes H[CH(OH)]nC(=O)H, n >= 2) and their intramolecular hemiacetals. Aldose C2H4O2(CH2O)n CHEBI:13755 CHEBI:15693 CHEBI:22305 CHEBI:2561 KEGG:C01370 Wikipedia:Aldose aldoses an aldose chebi_ontology L-alpha-amino acid 0 74.024 74.05870 Any alpha-amino acid having L-configuration at the alpha-carbon. C2H4NO2R CHEBI:13072 CHEBI:13243 CHEBI:13797 CHEBI:15705 CHEBI:21224 CHEBI:6175 KEGG:C00151 L-2-Amino acid L-Amino acid L-alpha-amino acid L-alpha-amino acids L-alpha-amino acids N[C@@H]([*])C(O)=O chebi_ontology carnosine 0 226.107 226.23262 A dipeptide that is the N-(beta-alanyl) derivative of L-histidine. C9H14N4O3 CAS:305-84-0 CHEBI:13948 CHEBI:15727 CHEBI:23040 CHEBI:3428 CQOVPNPJLQNMDC-ZETCQYMHSA-N Carnosine HMDB:HMDB0000033 InChI=1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1 KEGG:C00386 MetaCyc:CARNOSINE N(alpha)-(beta-alanyl)-L-histidine NCCC(=O)N[C@@H](Cc1c[nH]cn1)C(O)=O Nalpha-(beta-alanyl)-L-histidine PMID:16804013 PMID:18019400 PMID:18076890 PMID:18773880 PMID:24398899 Reaxys:87671 Wikipedia:Carnosine chebi_ontology primary alcohol *C(O)([H])[H] 0 1-Alcohol 31.018 31.034 A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it. CH3OR CHEBI:13676 CHEBI:14887 CHEBI:15734 CHEBI:26262 CHEBI:57489 CHEBI:8406 KEGG:C00226 Primary alcohol a primary alcohol chebi_ontology primary alcohols formate -1 44.998 45.01744 A monocarboxylic acid anion that is the conjugate base of formic acid. Induces severe metabolic acidosis and ocular injury in human subjects. BDAGIHXWWSANSR-UHFFFAOYSA-M Beilstein:1901205 CAS:71-47-6 CHEBI:14276 CHEBI:15740 CHEBI:24081 CHO2 Gmelin:1006 HCO2 anion HMDB:HMDB0000142 InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)/p-1 KEGG:C00058 MetaCyc:FORMATE PMID:17190852 PMID:3946945 Reaxys:1901205 UM-BBD_compID:c0106 Wikipedia:Formate [H]C([O-])=O aminate chebi_ontology formate formiate formic acid, ion(1-) formylate hydrogen carboxylate methanoate hexadecanoic acid 0 1-Pentadecanecarboxylic acid 1-hexyldecanoic acid 16:00 256.240 256.42410 A straight-chain, sixteen-carbon, saturated long-chain fatty acid. Beilstein:607489 C16 C16 fatty acid C16:0 C16H32O2 CAS:57-10-3 CCCCCCCCCCCCCCCC(O)=O CH3-[CH2]14-COOH CHEBI:14730 CHEBI:15756 CHEBI:233028 CHEBI:24540 CHEBI:24541 CHEBI:24542 CHEBI:24550 CHEBI:29889 CHEBI:35978 CHEBI:44952 DrugBank:DB03796 FA 16:0 Gmelin:190200 HMDB:HMDB0000220 Hexadecanoate Hexadecylic acid Hexaectylic acid IPCSVZSSVZVIGE-UHFFFAOYSA-N InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18) KEGG:C00249 KEGG:D05341 KNApSAcK:C00001233 KNApSAcK:C00030479 LIPID_MAPS_instance:LMFA01010001 MetaCyc:PALMITATE PALMITIC ACID PDBeChem:PLM PMID:12492626 PMID:15357969 PMID:1589452 PMID:16509590 PMID:16884313 PMID:17439666 PMID:17502136 PMID:20001317 PMID:22735334 PMID:25584012 PMID:28600633 PPDB:1336 Palmitate Palmitic acid Palmitinic acid Palmitinsaeure Pentadecanecarboxylic acid Reaxys:607489 Wikipedia:Palmitic_acid cetylic acid chebi_ontology hexadecanoic acid hexadecoic acid n-hexadecanoic acid n-hexadecoic acid palmitic acid N-acyl-D-amino acid 0 101.011 101.06080 Any N-acyl-amino acid in which the amino acid moiety has D configuration. C3H3NO3R2 CHEBI:12474 CHEBI:15778 CHEBI:21631 CHEBI:7224 OC(=O)[C@@H]([*])NC([*])=O chebi_ontology malonate(2-) (-)OOC-CH2-COO(-) -2 101.995 102.04558 A dicarboxylic acid dianion obtained by the deprotonation of the carboxy groups of malonic acid. Beilstein:3904386 C3H2O4 CAS:156-80-9 CHEBI:14563 CHEBI:15792 CHEBI:25130 CHEBI:44151 DrugBank:DB02201 Gmelin:141932 InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)/p-2 KEGG:C00383 MALONATE ION OFOBLEOULBTSOW-UHFFFAOYSA-L PDBeChem:MLI Reaxys:3904386 [O-]C(=O)CC([O-])=O chebi_ontology malo malonate malonic acid, ion(2-) propanedioate propanedioic acid, ion(2-) (R)-2-hydroxyglutarate(2-) (2R)-2-hydroxypentanedioate (R)-2-hydroxyglutarate -2 146.022 146.09814 A 2-hydroxyglutarate(2-) that has (2R)-configuration. C5H6O5 CHEBI:10974 CHEBI:15801 CHEBI:18650 HWXBTNAVRSUOJR-GSVOUGTGSA-L InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/p-2/t3-/m1/s1 KEGG:C01087 MetaCyc:R-2-HYDROXYGLUTARATE O[C@H](CCC([O-])=O)C([O-])=O chebi_ontology isoamylol 0 1-HYDROXY-3-METHYLBUTANE 2-methyl-4-butanol 3-Methylbutanol 3-methyl-1-butanol 3-methylbutan-1-ol 3-methylbutanol 88.089 88.14818 An primary alcohol that is butan-1-ol in which a hydrogen at position 3 has been replaced by a methyl group. Beilstein:1718835 C5H12O CAS:123-51-3 CC(C)CCO CHEBI:11855 CHEBI:15837 CHEBI:1597 CHEBI:20125 CHEBI:43359 DrugBank:DB02296 Gmelin:49460 HMDB:HMDB0006007 InChI=1S/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3 Iso-amylalkohol Isoamyl alcohol Isopentyl alcohol Isopentylalkohol KEGG:C07328 PDBeChem:IP3 PHTQWCKDNZKARW-UHFFFAOYSA-N PMID:23043843 PMID:23698045 PMID:24487533 PMID:24767042 PMID:24804072 PMID:24862930 Reaxys:1718835 YMDB:YMDB00570 alcool isoamylique chebi_ontology i-amyl alcohol isoamylol isobutylcarbinol isopentan-1-ol isopentanol primary isoamyl alcohol polypeptide A peptide containing ten or more amino acid residues. C4H6N2O3R2(C2H2NOR)n CHEBI:14860 CHEBI:15841 CHEBI:8314 KEGG:C00403 Polypeptid Polypeptide chebi_ontology polipeptido polypeptides quinine (-)-Quinine (-)-quinine (8S,9R)-quinine (9R)-6'-methoxy-8alpha-cinchonan-9-ol (R)-(-)-quinine (R)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methanol 0 324.184 324.41680 6'-methoxycinchonidine A cinchona alkaloid that is cinchonidine in which the hydrogen at the 6-position of the quinoline ring is substituted by methoxy. Beilstein:91867 C20H24N2O2 CAS:130-95-0 CHEBI:127176 CHEBI:15001 CHEBI:15854 CHEBI:26499 CHEBI:355947 CHEBI:569215 CHEBI:602929 CHEBI:8723 Chinin DrugBank:DB00468 Drug_Central:4523 InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1 KEGG:C06526 KEGG:D08460 KNApSAcK:C00002193 LOUPRKONTZGTKE-WZBLMQSHSA-N PMID:10821711 PMID:10891117 PMID:10937718 PMID:11212126 PMID:11549443 PMID:11728183 PMID:11844668 PMID:11855978 PMID:12127529 PMID:12213073 PMID:12217353 PMID:12477351 PMID:12502361 PMID:12798326 PMID:12873511 PMID:14761192 PMID:15026051 PMID:15027870 PMID:15225721 PMID:15857133 PMID:16524728 PMID:16933872 PMID:17482816 PMID:17506538 PMID:17570664 PMID:17850126 PMID:18348514 PMID:18788725 PMID:2579237 PMID:2657065 PMID:7009867 PMID:8182707 Quinine Wikipedia:Quinine [H][C@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@H](O)c1ccnc2ccc(OC)cc12 chebi_ontology chinine chininum quinina quinine bromide -1 78.918 79.90400 BROMIDE ION Beilstein:3587179 Br Br(-) Br- Bromide CAS:24959-67-9 CHEBI:13918 CHEBI:15858 CHEBI:3178 CHEBI:49515 CPELXLSAUQHCOX-UHFFFAOYSA-M Gmelin:14908 InChI=1S/BrH/h1H/p-1 KEGG:C00720 KEGG:C01324 PDBeChem:BR [Br-] bromide bromide(1-) bromine anion chebi_ontology sterol 0 275.237 275.450 3-hydroxysteroids Any 3-hydroxy steroid whose skeleton is closely related to cholestan-3-ol (additional carbon atoms may be present in the side chain). C12C(C3C(C(CC3)*)(C)CC1)CCC4C2(CCC(C4)O)C C19H31OR CHEBI:13688 CHEBI:15114 CHEBI:15889 CHEBI:26771 CHEBI:9266 KEGG:C00370 LIPID_MAPS_class:LMST01 MetaCyc:Sterols Sterol Wikipedia:Sterol a sterol chebi_ontology sterols taurine 0 125.015 125.148 2-Aminoethanesulfonic acid 2-aminoethanesulfonic acid 2-aminoethyl sulfonate Aminoethylsulfonic acid An amino sulfonic acid that is the 2-amino derivative of ethanesulfonic acid. It is a naturally occurring amino acid derived from methionine and cysteine metabolism. An abundant component of fish- and meat-based foods, it has been used as an oral supplement in the treatment of disorders such as cystic fibrosis and hypertension. Beilstein:1751215 C(CS(O)(=O)=O)N C2H7NO3S CAS:107-35-7 CHEBI:15195 CHEBI:15891 CHEBI:26852 CHEBI:45877 CHEBI:9406 DrugBank:DB01956 Drug_Central:4486 Gmelin:82121 HMDB:HMDB0000251 InChI=1S/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6) KEGG:C00245 KEGG:D00047 KNApSAcK:C00048188 MetaCyc:TAURINE PDBeChem:TAU PMID:10098958 PMID:10325611 PMID:10349454 PMID:10827156 PMID:11162030 PMID:11842876 PMID:11918831 PMID:11931837 PMID:12297216 PMID:12499349 PMID:12834252 PMID:14992292 PMID:15503229 PMID:15780050 PMID:15911239 PMID:16169526 PMID:16444816 PMID:16923232 PMID:17053427 PMID:17081118 PMID:17875433 PMID:17997039 PMID:18060526 PMID:18171928 PMID:19074966 PMID:19212411 PMID:19309105 PMID:19940987 PMID:2122710 PMID:21761941 PMID:22770225 PMID:2370482 PMID:24027187 PMID:2494044 PMID:27291853 PMID:27334436 PMID:27345710 PMID:27380030 PMID:27412799 PMID:27471162 PMID:27535560 PMID:3106924 PMID:3393260 PMID:6198473 PMID:7588651 PMID:8692051 PMID:8818047 PMID:9635063 Reaxys:1751215 Taurine Wikipedia:Taurine XOAAWQZATWQOTB-UHFFFAOYSA-N beta-aminoethylsulfonic acid chebi_ontology long-chain fatty acid 0 44.998 A fatty acid with a chain length ranging from C13 to C22. CHEBI:13655 CHEBI:14529 CHEBI:15904 CHEBI:25075 CHEBI:6528 CHO2R Higher fatty acid KEGG:C00638 LCFA LCFAs Long-chain fatty acid OC([*])=O chebi_ontology long-chain fatty acids ribitol (2R,3s,4S)-pentane-1,2,3,4,5-pentol (2R,3s,4S)-pentane-1,2,3,4,5-pentol 0 152.068 152.14578 A pentitol (five-carbon sugar alcohol) having meso-configuration, being derived from ribose by reduction of the carbonyl group. It occurs naturally in the plant Adonis vernalis. Adonitol Beilstein:1720524 C5H12O5 CAS:488-81-3 CHEBI:15043 CHEBI:15963 CHEBI:21074 CHEBI:26552 CHEBI:27854 CHEBI:4230 CHEBI:48505 CHEBI:57591 CHEBI:8841 D-Adonitol D-Ribitol D-ribitol Gmelin:82894 HEBKCHPVOIAQTA-ZXFHETKHSA-N HMDB:HMDB0000508 InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5- KEGG:C00474 KNApSAcK:C00001171 L-ribitol MetaCyc:RIBITOL OC[C@H](O)[C@H](O)[C@H](O)CO PMID:15234337 PMID:16664320 PMID:16901854 PMID:17336832 PMID:17979222 PMID:23564164 PMID:24643482 PMID:25108762 Reaxys:1720524 Ribitol Wikipedia:Ribitol chebi_ontology meso-ribitol D-glutamic acid (2R)-2-aminopentanedioic acid (R)-2-aminopentanedioic acid 0 147.053 147.12930 An optically active form of glutamic acid having D-configuration. Beilstein:1723800 C5H9NO4 CAS:6893-26-1 CHEBI:15966 CHEBI:21023 CHEBI:4183 D-2-Aminoglutaric acid D-Glutamic acid D-Glutaminic acid D-Glutaminsaeure D-glutamic acid DGL DrugBank:DB02517 Gmelin:201189 HMDB:HMDB0003339 InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m1/s1 KEGG:C00217 KNApSAcK:C00019577 MetaCyc:D-GLT N[C@H](CCC(O)=O)C(O)=O PDBeChem:DGL Reaxys:1723800 WHUUTDBJXJRKMK-GSVOUGTGSA-N chebi_ontology glutamic acid D-form polynucleotide (C5H8O6PR)n.C10H17O10PR2 0 A nucleobase-containing molecular entity with a polymeric structure comprised of a linear sequence of 13 or more nucleotide residues. CHEBI:13672 CHEBI:14859 CHEBI:15986 CHEBI:8312 KEGG:C00419 Polynucleotide chebi_ontology polynucleotides (4-hydroxyphenyl)pyruvic acid (p-hydroxyphenyl)pyruvic acid 0 180.042 180.15742 3-(4-HYDROXY-PHENYL)PYRUVIC ACID 3-(4-hydroxyphenyl)-2-oxopropanoic acid 3-(4-hydroxyphenyl)pyruvic acid 3-(p-hydroxyphenyl)-2-oxopropanoic acid 4-hydroxy alpha-oxobenzenepropanoic acid 4-hydroxyphenylpyruvic acid An oxo carboxylic acid that is pyruvic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. Beilstein:2691632 C9H8O4 CAS:156-39-8 CHEBI:1431 CHEBI:15999 CHEBI:20426 CHEBI:42422 DrugBank:DB07718 HMDB:HMDB0000707 InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13) KEGG:C01179 KKADPXVIOXHVKN-UHFFFAOYSA-N KNApSAcK:C00007512 MetaCyc:P-HYDROXY-PHENYLPYRUVATE OC(=O)C(=O)Cc1ccc(O)cc1 PDBeChem:ENO PMID:11073718 PMID:9106023 Reaxys:2691632 chebi_ontology p-Hydroxyphenylpyruvic acid (R)-lactate (2R)-2-hydroxypropanoate (R)-lactate -1 89.024 89.07000 An optically active form of lactate having (R)-configuration. Beilstein:4655978 C3H5O3 CHEBI:11001 CHEBI:16004 CHEBI:18684 C[C@@H](O)C([O-])=O D-2-hydroxypropanoate D-2-hydroxypropionate D-lactate Gmelin:362716 InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/p-1/t2-/m1/s1 JVTAAEKCZFNVCJ-UWTATZPHSA-M KEGG:C00256 MetaCyc:D-LACTATE Reaxys:4655978 chebi_ontology 5-oxoproline 0 129.043 129.11400 2-pyrrolidone-5-carboxylic acid 5-OXOPROLINE 5-Oxoproline 5-Pyrrolidone-2-carboxylic acid 5-oxo-DL-proline 5-oxoproline 5-oxopyrrolidine-2-carboxylic acid An oxoproline having the oxo group placed at the 5-position. It is an intermediate metabolite in the glutathione cycle. Beilstein:82131 C5H7NO3 CAS:149-87-1 CHEBI:12157 CHEBI:16010 CHEBI:20624 CHEBI:2116 CHEBI:44943 Glp InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9) OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N PMID:17439666 PMID:22770225 PMID:23217740 Pyroglutamate Pyroglutamic acid Reaxys:82131 Wikipedia:Pyroglutamic_acid chebi_ontology L-glutamic acid (2S)-2-aminopentanedioic acid (S)-2-aminopentanedioic acid (S)-glutamic acid 0 147.053 147.12930 An optically active form of glutamic acid having L-configuration. BPDB:2297 Beilstein:1723801 C5H9NO4 CAS:56-86-0 CHEBI:16015 CHEBI:21304 CHEBI:42825 CHEBI:6224 DrugBank:DB00142 Drug_Central:1310 E GLUTAMIC ACID Glu Glutamate Gmelin:3502 HMDB:HMDB0000148 InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1 KEGG:C00025 KEGG:D00007 KNApSAcK:C00001358 L-Glu L-Glutamic acid L-Glutaminic acid L-Glutaminsaeure L-glutamic acid LINCS:LSM-36375 MetaCyc:GLT N[C@@H](CCC(O)=O)C(O)=O PDBeChem:GLU_LFOH PMID:15739367 PMID:15930465 PMID:16719819 PMID:16892196 PMID:19581495 PMID:22219301 PMID:22735334 Reaxys:1723801 WHUUTDBJXJRKMK-VKHMYHEASA-N Wikipedia:L-Glutamic_Acid acide glutamique acido glutamico acidum glutamicum chebi_ontology glutamic acid D-mannose 0 180.15588 A mannose with D-configuration. C6H12O6 CHEBI:12999 CHEBI:16024 CHEBI:21057 D-manno-hexose D-mannose chebi_ontology halide anion -1 0.0 0.0 A monoatomic monoanion resulting from the addition of an electron to any halogen atom. CHEBI:14384 CHEBI:16042 CHEBI:5605 HX Halide KEGG:C00462 X [*-] a halide anion chebi_ontology halide anions halide ions halide(1-) halides halogen anion 1,5-anhydro-D-glucitol (2R,3S,4R,5S)-2-(hydroxymethyl)oxane-3,4,5-triol 0 1,5-ANHYDROSORBITOL 1,5-Anhydro-D-glucitol 1,5-Anhydro-D-sorbitol 1,5-Anhydroglucitol 1,5-anhydro-D-glucitol 1,5-anhydro-D-sorbitol 1,5-anhydroglucitol 164.068 164.15648 An anhydro sugar of D-glucitol. C6H12O5 CAS:154-58-5 CHEBI:11176 CHEBI:16070 CHEBI:18943 CHEBI:40816 CHEBI:550 HMDB:HMDB0002712 InChI=1S/C6H12O5/c7-1-4-6(10)5(9)3(8)2-11-4/h3-10H,1-2H2/t3-,4+,5+,6+/m0/s1 KEGG:C07326 MPCAJMNYNOGXPB-SLPGGIOYSA-N OC[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O PDBeChem:ASO PMID:15277408 PMID:18492944 PMID:19796288 Reaxys:80736 Wikipedia:1,5-Anhydroglucitol chebi_ontology gamma-amino-beta-hydroxybutyric acid 0 119.058 119.11920 3-hydroxy-GABA 4-Amino-3-hydroxybutanoic acid 4-amino-3-hydroxybutanoic acid 4-amino-3-hydroxybutyric acid A gamma-amino acid comprising 4-aminobutyric acid having a 2-hydroxy substituent. Beilstein:1721708 Beilstein:1752568 C4H9NO3 CAS:352-21-6 CHEBI:16080 CHEBI:1780 CHEBI:20311 Drug_Central:1263 GABOB InChI=1S/C4H9NO3/c5-2-3(6)1-4(7)8/h3,6H,1-2,5H2,(H,7,8) KEGG:C03678 KEGG:D00174 NCC(O)CC(O)=O YQGDEPYYFWUPGO-UHFFFAOYSA-N chebi_ontology gamma-Amino-beta-hydroxybutyric acid gamma-amino-beta-hydroxybutyric acid thiosulfate(2-) -2 111.929 112.13020 A divalent inorganic anion obtained by removal of both protons from thiosulfuric acid. CAS:14383-50-7 CHEBI:15242 CHEBI:16094 CHEBI:45922 CHEBI:9569 DHCDFWKWKRSZHF-UHFFFAOYSA-L Gmelin:2031 Hyposulfite InChI=1S/H2O3S2/c1-5(2,3)4/h(H2,1,2,3,4)/p-2 O3S2 PDBeChem:THJ S2O3 S2O3(2-) TETRATHIONATE Thiosulfate [O-]S([S-])(=O)=O [SO3S](2-) chebi_ontology sulfurothioate thiosulfate thiosulfate ion(2-) thiosulphate trioxido-1kappa(3)O-disulfate(S--S)(2-) trioxidosulfidosulfate(2-) cholesterol (3beta,14beta,17alpha)-cholest-5-en-3-ol 0 386.355 386.655 A cholestanoid consisting of cholestane having a double bond at the 5,6-position as well as a 3beta-hydroxy group. Beilstein:2060565 C1[C@@]2([C@]3(CC[C@]4([C@]([C@@]3(CC=C2C[C@H](C1)O)[H])(CC[C@@]4([C@H](C)CCCC(C)C)[H])[H])C)[H])C C27H46O CAS:57-88-5 CHEBI:13982 CHEBI:16113 CHEBI:23204 CHEBI:3659 CHEBI:41564 CHOLESTEROL Cholest-5-en-3beta-ol Cholesterin Cholesterol DrugBank:DB04540 Gmelin:550297 HMDB:HMDB0000067 HVYWMOMLDIMFJA-DPAQBDIFSA-N InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1 KEGG:C00187 KEGG:D00040 KNApSAcK:C00003648 LIPID_MAPS_instance:LMST01010001 MetaCyc:CHOLESTEROL PDBeChem:CLR PMID:10901445 PMID:11412894 PMID:16341241 PMID:24287311 PMID:25308664 PMID:25451949 PMID:25522988 PMID:25658343 PMID:25977713 PMID:4696527 PMID:8838010 Reaxys:2060565 Wikipedia:Cholesterol chebi_ontology cholest-5-en-3beta-ol cholesterol cyclopentanol 0 86.073 86.13230 C5H10O CAS:96-41-3 CHEBI:14057 CHEBI:16133 CHEBI:23494 CHEBI:4022 Cyclopentanol Cyclopentyl alcohol Hydroxycyclopentane InChI=1S/C5H10O/c6-5-3-1-2-4-5/h5-6H,1-4H2 KEGG:C02020 MetaCyc:CYCLOPENTANOL OC1CCCC1 PMID:22145629 PMID:24273356 Reaxys:1900556 The simplest member of the class of cyclopentanols bearing a single hydroxy substituent. The parent of the class of cyclopentanols. Wikipedia:Cyclopentanol XCIXKGXIYUWCLL-UHFFFAOYSA-N chebi_ontology cyclopentanol ammonia 0 17.027 17.03056 AMMONIA Ammonia Ammoniak An azane that consists of a single nitrogen atom covelently bonded to three hydrogen atoms. Beilstein:3587154 CAS:7664-41-7 CHEBI:13405 CHEBI:13406 CHEBI:13407 CHEBI:13771 CHEBI:16134 CHEBI:22533 CHEBI:44269 CHEBI:44284 CHEBI:44404 CHEBI:7434 Drug_Central:4625 Gmelin:79 H3N HMDB:HMDB0000051 InChI=1S/H3N/h1H3 KEGG:C00014 KEGG:D02916 KNApSAcK:C00007267 MetaCyc:AMMONIA MolBase:930 NH3 PDBeChem:NH3 PMID:110589 PMID:11139349 PMID:11540049 PMID:11746427 PMID:11783653 PMID:13753780 PMID:14663195 PMID:15092448 PMID:15094021 PMID:15554424 PMID:15969015 PMID:16008360 PMID:16050680 PMID:16348008 PMID:16349403 PMID:16614889 PMID:16664306 PMID:16842901 PMID:17025297 PMID:17439666 PMID:17569513 PMID:17737668 PMID:18670398 PMID:22002069 PMID:22081570 PMID:22088435 PMID:22100291 PMID:22130175 PMID:22150211 PMID:22240068 PMID:22290316 PMID:22342082 PMID:22385337 PMID:22443779 PMID:22560242 QGZKDVFQNNGYKY-UHFFFAOYSA-N R-717 Reaxys:3587154 Wikipedia:Ammonia [H]N([H])[H] [NH3] ammonia ammoniac amoniaco azane chebi_ontology spirit of hartshorn isobutyric acid 0 2,2-dimethylacetic acid 2-METHYL-PROPIONIC ACID 2-Methylpropanoate 2-Methylpropanoic acid 2-Methylpropionsaeure 2-methylpropanoic acid 88.052 88.10512 A branched fatty acid comprising propanoic acid carrying a methyl branch at C-2. BPDB:3128 Beilstein:635770 C4H8O2 CAS:79-31-2 CC(C)C(O)=O CHEBI:1212 CHEBI:16135 CHEBI:19710 CHEBI:25337 CHEBI:40653 CHEBI:43397 Dimethylacetic acid DrugBank:DB02531 Gmelin:49630 HMDB:HMDB0001873 ISOBUTYRIC ACID InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6) Isobutanoate Isobuttersaeure Isobutyrate Isobutyric acid KEGG:C02632 KNApSAcK:C00029462 KQNPFQTWMSNSAP-UHFFFAOYSA-N LIPID_MAPS_instance:LMFA01020071 MetaCyc:ISOBUTYRATE PDBeChem:ALQ PDBeChem:ISB PMID:10757489 PMID:17580301 PMID:17877388 PPDB:3128 Reaxys:635770 UM-BBD_compID:c0383 Wikipedia:Isobutyric_acid alpha-isobutyric acid alpha-methylpropanoic acid alpha-methylpropionic acid chebi_ontology iso-C3H7COOH iso-butyric acid isobutanoic acid isopropylformic acid hydrogen sulfide 0 33.988 34.08188 A sulfur hydride consisting of a single sulfur atom bonded to two hydrogen atoms. A highly poisonous, flammable gas with a characteristic odour of rotten eggs, it is often produced by bacterial decomposition of organic matter in the absence of oxygen. Beilstein:3535004 CAS:7783-06-4 CHEBI:13356 CHEBI:14414 CHEBI:16136 CHEBI:24639 CHEBI:43058 CHEBI:45489 CHEBI:5787 Drug_Central:4260 Gmelin:303 H2S H2S HYDROSULFURIC ACID Hydrogen sulfide Hydrogen-sulfide InChI=1S/H2S/h1H2 KEGG:C00283 KNApSAcK:C00007266 MolBase:1709 PDBeChem:H2S PMID:11788560 PMID:14654297 PMID:15003943 PMID:15607739 PMID:16446402 PMID:18098324 PMID:18524810 PMID:18948540 PMID:19695225 PMID:22004989 PMID:22378060 PMID:22448627 PMID:22473176 PMID:22486842 PMID:22520971 PMID:22787557 RWSOTUBLDIXVET-UHFFFAOYSA-N Schwefelwasserstoff Sulfide UM-BBD_compID:c0239 Wikipedia:Hydrogen_sulfide [H]S[H] [SH2] acide sulfhydrique chebi_ontology dihydridosulfur dihydrogen monosulfide dihydrogen sulfide dihydrogen(sulfide) hydrogen monosulfide hydrogen sulfide hydrogen sulphide hydrogene sulfure sulfane sulfure d'hydrogene chondroitin D-glucuronate (C14H21NO11)nH2O 0.0 A mucopolysaccharide composed of repeating beta-D-glucopyranuronosyl-(1->3)-beta-D-N-acetylgalactosaminyl units. CHEBI:13989 CHEBI:13992 CHEBI:16137 CHEBI:23221 CHEBI:3673 Chondroitin Chondroitin-D-glucuronate KEGG:C00401 KEGG:G11334 chebi_ontology chondroitin D-glucuronic acid retinyl ester 0 313.217 313.45380 A carboxylic ester obtained by formal condensation of the hydroxy group of retinol with the carboxy group of any carboxylic acid. C21H29O2R CC(=CCOC([*])=O)C=CC=C(C)C=CC1=C(C)CCCC1(C)C CHEBI:15039 CHEBI:16179 CHEBI:26540 CHEBI:8818 Retinyl ester chebi_ontology retinyl ester retinyl esters N-acylglycine 0 102.019 102.06880 An N-acyl-amino acid in which amino acid specified is glycine. C3H4NO3R CHEBI:12484 CHEBI:16180 CHEBI:21660 CHEBI:7238 KEGG:C02055 MetaCyc:CPD-426 N-Acylglycine OC(=O)CNC([*])=O chebi_ontology methane 0 16.031 16.04246 A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC). Beilstein:1718732 CAS:74-82-8 CH4 CH4 CHEBI:14585 CHEBI:16183 CHEBI:25220 CHEBI:6811 Gmelin:59 HMDB:HMDB0002714 InChI=1S/CH4/h1H4 KEGG:C01438 MetaCyc:CH4 Methan Methane PDBeChem:CH3 PMID:17791569 PMID:23104415 PMID:23353606 PMID:23376302 PMID:23397538 PMID:23718889 PMID:23739479 PMID:23742231 PMID:23756351 PMID:24132456 PMID:24161402 PMID:24259373 Patent:FR994032 Patent:US2583090 Reaxys:1718732 UM-BBD_compID:c0095 VNWKTOKETHGBQD-UHFFFAOYSA-N Wikipedia:Methane [H]C([H])([H])[H] chebi_ontology marsh gas metano methane methyl hydride tetrahydridocarbon sulfate -2 95.952 96.06360 A sulfur oxoanion obtained by deprotonation of both OH groups of sulfuric acid. Beilstein:3648446 CAS:14808-79-8 CHEBI:15135 CHEBI:16189 CHEBI:45687 CHEBI:9335 Gmelin:2120 HMDB:HMDB0001448 InChI=1S/H2O4S/c1-5(2,3)4/h(H2,1,2,3,4)/p-2 KEGG:C00059 KEGG:D05963 MetaCyc:SULFATE O4S PDBeChem:SO4 PMID:11200094 PMID:11452993 PMID:11581495 PMID:11798107 PMID:12166931 PMID:12668033 PMID:14597181 PMID:15093386 PMID:15984785 PMID:16186560 PMID:16345535 PMID:16347366 PMID:16348007 PMID:16483812 PMID:16534979 PMID:16656509 PMID:16742508 PMID:16742518 PMID:17120760 PMID:17420092 PMID:17439666 PMID:17709180 PMID:18398178 PMID:18815700 PMID:18846414 PMID:19047345 PMID:19244483 PMID:19544990 PMID:19628332 PMID:19812358 QAOWNCQODCNURD-UHFFFAOYSA-L Reaxys:3648446 SO4(2-) SULFATE ION Sulfate Sulfate anion(2-) Sulfate dianion Sulfate(2-) Sulfuric acid ion(2-) Wikipedia:Sulfate [O-]S([O-])(=O)=O [SO4](2-) chebi_ontology sulfate sulphate sulphate ion tetraoxidosulfate(2-) tetraoxosulfate(2-) tetraoxosulfate(VI) urea 0 1728 60.032 60.05534 A carbonyl group with two C-bound amine groups. Beilstein:635724 CAS:57-13-6 CH4N2O CHEBI:15292 CHEBI:16199 CHEBI:27218 CHEBI:46379 CHEBI:9888 Carbamide DrugBank:DB03904 Drug_Central:4264 E927b ECMDB:ECMDB04172 Gmelin:1378 H2NC(O)NH2 HMDB:HMDB0000294 Harnstoff InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4) KEGG:C00086 KEGG:D00023 KNApSAcK:C00007314 Karbamid MetaCyc:UREA NC(N)=O PDBeChem:URE PMID:18037357 PMID:22770225 PPDB:1728 Reaxys:635724 UM-BBD_compID:c0165 UREA Urea Wikipedia:Urea XSQUKJJJFZCRTK-UHFFFAOYSA-N YMDB:YMDB00003 carbamide carbonyldiamide chebi_ontology ur urea uree hydroxide -1 17.003 17.00734 CAS:14280-30-9 CHEBI:13365 CHEBI:13419 CHEBI:16234 CHEBI:44641 CHEBI:5594 Gmelin:24714 HO HO- HYDROXIDE ION Hydroxide ion InChI=1S/H2O/h1H2/p-1 KEGG:C01328 OH(-) OH- PDBeChem:OH XLYOFNOQVPJJNP-UHFFFAOYSA-M [O-][H] chebi_ontology hydridooxygenate(1-) hydroxide oxidanide ethanol 0 1-hydroxyethane 46.042 46.06844 A primary alcohol that is ethane in which one of the hydrogens is substituted by a hydroxy group. Aethanol Aethylalkohol Alkohol Beilstein:1718733 C2H5OH C2H6O CAS:64-17-5 CCO CHEBI:14222 CHEBI:16236 CHEBI:23978 CHEBI:30878 CHEBI:30880 CHEBI:42377 CHEBI:44594 CHEBI:4879 Dehydrated ethanol DrugBank:DB00898 Drug_Central:1076 ETHANOL EtOH Ethanol Ethyl alcohol Gmelin:787 HMDB:HMDB0000108 InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3 KEGG:C00469 KEGG:D00068 KEGG:D06542 KNApSAcK:C00019560 LFQSCWFLJHTTHZ-UHFFFAOYSA-N MetaCyc:ETOH Methylcarbinol MolBase:858 MolBase:859 PDBeChem:EOH PDBeChem:OHE PMID:11046114 PMID:11090978 PMID:11198720 PMID:11200745 PMID:11262320 PMID:11303910 PMID:11333032 PMID:11505026 PMID:11590970 PMID:11728426 PMID:11750186 PMID:11754521 PMID:11810019 PMID:11826039 PMID:11981228 PMID:12824058 PMID:12829422 PMID:12888778 PMID:12946583 PMID:14674846 PMID:15019421 PMID:15239123 PMID:15285839 PMID:15464411 PMID:15465973 PMID:15749123 PMID:15900217 PMID:15902919 PMID:16084479 PMID:16133132 PMID:16352430 PMID:16390872 PMID:16737463 PMID:16891664 PMID:16934862 PMID:17043811 PMID:17190852 PMID:17663926 PMID:17687877 PMID:18095657 PMID:18249266 PMID:18320157 PMID:18347649 PMID:18408978 PMID:18411066 PMID:18456322 PMID:18513832 PMID:18922656 PMID:18925476 PMID:19280886 PMID:19359288 PMID:19384566 PMID:19458312 PMID:19851413 PMID:19901811 PMID:21600756 PMID:21762181 PMID:21881875 PMID:21967628 PMID:22019193 PMID:22222864 PMID:22261437 PMID:22286266 PMID:22306018 PMID:22331491 PMID:22336593 PPDB:1373 Reaxys:1718733 UM-BBD_compID:c0038 Wikipedia:Ethanol [CH2Me(OH)] [OEtH] alcohol alcohol etilico alcool ethylique chebi_ontology etanol ethanol hydroxyethane spiritus vini hydrogen peroxide 0 34.005 34.01468 An inorganic peroxide consisting of two hydroxy groups joined by a covalent oxygen-oxygen single bond. Beilstein:3587191 CAS:7722-84-1 CHEBI:13354 CHEBI:13355 CHEBI:16240 CHEBI:24637 CHEBI:44812 CHEBI:5586 Drug_Central:3281 Gmelin:509 H2O2 H2O2 HMDB:HMDB0003125 HOOH HYDROGEN PEROXIDE Hydrogen peroxide InChI=1S/H2O2/c1-2/h1-2H KEGG:C00027 KEGG:D00008 MHAJPDPJQMAIIY-UHFFFAOYSA-N MetaCyc:HYDROGEN-PEROXIDE MolBase:932 Oxydol PDBeChem:PEO PMID:10455187 PMID:10557015 PMID:10849784 PMID:11033421 PMID:11105916 PMID:11318558 PMID:11387393 PMID:11809417 PMID:11864786 PMID:11893576 PMID:12867293 PMID:12934880 PMID:14679422 PMID:15028418 PMID:15133946 PMID:15298493 PMID:16337875 PMID:16463018 PMID:16864869 PMID:17020896 PMID:17179007 PMID:17610934 PMID:17948137 PMID:18179203 PMID:18182702 PMID:18306736 PMID:18443210 PMID:18592736 PMID:19107210 PMID:19229032 PMID:19297450 PMID:19509065 PMID:26352695 PMID:26365231 PMID:7548021 PMID:7581816 PMID:8048546 PMID:8375042 PMID:8451754 PMID:9051670 PMID:9100841 PMID:9168257 PMID:9202721 PMID:9558114 PPDB:387 Reaxys:3587191 Wikipedia:Hydrogen_peroxide [H]OO[H] [OH(OH)] bis(hydridooxygen)(O--O) chebi_ontology dihydrogen dioxide dihydrogen peroxide dihydrogen(peroxide) dioxidane hydrogen peroxide perhydrol phospholipid A lipid containing phosphoric acid as a mono- or di-ester. The term encompasses phosphatidic acids and phosphoglycerides. C5H6O8PR3 CHEBI:14816 CHEBI:16247 CHEBI:26063 CHEBI:8150 KEGG:C00865 Phospholipid a phospholipid derivative chebi_ontology phospholipids phytanic acid 0 3,7,11,15-Tetramethyl-hexadecansaeure 3,7,11,15-tetramethyl hexadecanoic acid 3,7,11,15-tetramethyl-hexadecanoic acid 3,7,11,15-tetramethylhexadecanoic acid 312.303 312.53040 A branched-chain saturated fatty acid consisting of hexadecanoic acid carrying methyl substituents at positions 3, 7, 11 and 15. Beilstein:1789963 C20H40O2 CAS:14721-66-5 CC(C)CCCC(C)CCCC(C)CCCC(C)CC(O)=O CHEBI:16285 CHEBI:26111 CHEBI:8189 InChI=1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22) KEGG:C01607 LIPID_MAPS_instance:LMFA01020251 PMID:12187408 PMID:17956237 PMID:9819701 Phytanic acid RLCKHJSFHOZMDR-UHFFFAOYSA-N Reaxys:1789963 chebi_ontology nitrite -1 45.993 46.00554 CAS:14797-65-0 CHEBI:14658 CHEBI:16301 CHEBI:44396 CHEBI:7585 Gmelin:977 IOVCWXUNBOPUCH-UHFFFAOYSA-M InChI=1S/HNO2/c2-1-3/h(H,2,3)/p-1 KEGG:C00088 NITRITE ION NO2 NO2 NO2(-) Nitrit Nitrite PDBeChem:NO2 The nitrogen oxoanion formed by loss of a proton from nitrous acid. Wikipedia:Nitrite [NO2](-) [O-]N=O chebi_ontology dioxidonitrate(1-) dioxonitrate(1-) dioxonitrate(III) nitrite nitrite anion nitrite(1-) nitrous acid, ion(1-) D-proline (2R)-pyrrolidine-2-carboxylic acid (R)-2-Carboxypyrrolidine (R)-pyrrolidine-2-carboxylic acid 0 115.063 115.13050 Beilstein:80811 C5H9NO2 CAS:344-25-2 CHEBI:13008 CHEBI:16313 CHEBI:21070 CHEBI:42012 CHEBI:42129 CHEBI:42213 CHEBI:4226 CHEBI:45156 D-PROLINE D-Prolin D-Proline D-proline DPR DrugBank:DB02853 Gmelin:833984 HMDB:HMDB0003411 InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m1/s1 KEGG:C00763 MetaCyc:D-PROLINE OC(=O)[C@H]1CCCN1 ONIBWKKTOPOVIA-SCSAIBSYSA-N PDBeChem:DPR PMID:19023642 PMID:20023020 PMID:20959625 PMID:21374575 PMID:21563681 PMID:22475019 PMID:22479580 Reaxys:80811 The D-enantiomer of proline. Wikipedia:D-proline chebi_ontology 17beta-hydroxy-5alpha-androstan-3-one 0 17beta-Hydroxy-5alpha-androstan-3-one 17beta-Hydroxyandrostan-3-one 17beta-hydroxy-5alpha-androstan-3-one 17beta-hydroxyandrostan-3-one 290.225 290.44030 4,5alpha-dihydrotestosterone 5alpha-DHT 5alpha-Dihydrotestosterone 5alpha-dihydrotestosterone A 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5. Androstanolone C19H30O2 CAS:521-18-6 CHEBI:11341 CHEBI:11342 CHEBI:16330 CHEBI:19175 CHEBI:41876 CHEBI:793 DHT DIHYDROTESTOSTERONE Dihydrotestosteron DrugBank:DB02901 Drug_Central:3927 HMDB:HMDB0002961 InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1 KEGG:C03917 KEGG:D07456 LIPID_MAPS_instance:LMST02020042 MetaCyc:17-BETA-HYDROXY-5ALPHA-ANDROSTAN-3-O NVKAWKQGWWIWPM-ABEVXSGRSA-N PDBeChem:DHT PMID:15251265 PMID:15811352 PMID:18076420 Stanolone Wikipedia:Dihydrotestosterone [H][C@@]12CC[C@@]3([H])[C@]4([H])CC[C@H](O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CCC(=O)C2 androstanolona androstanolone androstanolonum chebi_ontology dihydrotestosterone adenosine (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol 0 267.097 267.24152 6-Amino-9-beta-D-ribofuranosyl-9H-purine 9-beta-D-Ribofuranosidoadenine 9-beta-D-Ribofuranosyl-9H-purin-6-amine 9-beta-D-ribofuranosyl-9H-purin-6-amine A ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a beta-N(9)-glycosidic bond. ADENOSINE Ade-Rib Adenine Deoxyribonucleoside Adenocard Adenocor Adenoscan Adenosin Adenosine Adenyldeoxyriboside Ado Beilstein:93029 C10H13N5O4 CAS:58-61-7 CHEBI:13734 CHEBI:16335 CHEBI:22237 CHEBI:2472 CHEBI:40558 CHEBI:40825 CHEBI:40906 Deoxyadenosine Desoxyadenosine DrugBank:DB00640 Drug_Central:90 ECMDB:ECMDB00050 Gmelin:53385 HMDB:HMDB0000050 InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1 KEGG:C00212 KEGG:D00045 KNApSAcK:C00007444 LINCS:LSM-28568 MetaCyc:ADENOSINE Nc1ncnc2n(cnc12)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N PDBeChem:ADN PMID:11213237 PMID:11820865 PMID:11978011 PMID:16183671 PMID:16917093 PMID:17190852 PMID:18000974 PMID:323854 Reaxys:93029 Wikipedia:Adenosine YMDB:YMDB00058 adenosine beta-D-Adenosine chebi_ontology hyaluronic acid (C14H21NO12)n 0 395.31608 A mucopolysaccharide composed of N-acetylglucosamine and glucuronic acid subunits. It is found in the connective tissues of vertebrates. Beilstein:8538277 CAS:9004-61-9 CHEBI:14412 CHEBI:16336 CHEBI:24622 CHEBI:24623 CHEBI:5772 HMDB:HMDB0010366 Hyaluronic acid Hyaluronsaeure KEGG:C00518 KEGG:D08043 KEGG:G10505 PMID:11122186 PMID:18056362 PMID:18290544 Reaxys:8187837 Wikipedia:Hyaluronan [beta-D-glucopyranuronosyl-(1->3)-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->4)]n [beta-N-Acetyl-D-glucosaminyl(1,4)beta-D-glucuronosyl(1,3)]n acide hyaluronique acido hialuronico chebi_ontology hyaluronan menaquinone (C5H8)nC11H8O2 0 Any member of the class of menaquinones that is 2-methyl-1,4-naphthoquinone with an unsaturated isoprenoid chain at the 3-position. CAS:11032-49-8 CHEBI:14582 CHEBI:16374 CHEBI:25184 CHEBI:6749 KEGG:C00828 Menaquinone Menatetrenone Wikipedia:Vitamin_K2 a menaquinone chebi_ontology vitamin K2 D-cysteine (2S)-2-amino-3-mercaptopropanoic acid (2S)-2-amino-3-sulfanylpropanoic acid (S)-2-amino-3-mercaptopropanoic acid 0 121.020 121.15922 An optically active form of cysteine having D-configuration. Beilstein:1721407 C3H7NO2S CAS:921-01-7 CHEBI:12919 CHEBI:16375 CHEBI:20921 CHEBI:4111 CHEBI:41887 D-Amino-3-mercaptopropionic acid D-CYSTEINE D-Cystein D-Cysteine D-Zystein D-cysteine DCY DrugBank:DB03201 ECMDB:ECMDB03417 Gmelin:363236 HMDB:HMDB0003417 InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m1/s1 KEGG:C00793 KNApSAcK:C00007323 N[C@H](CS)C(O)=O PDBeChem:DCY PMID:13761469 PMID:23340406 PMID:24800864 Reaxys:1721407 XUJNEKJLAYXESH-UWTATZPHSA-N YMDB:YMDB00913 chebi_ontology iodide -1 126.904 126.90447 Beilstein:3587184 CAS:20461-54-5 CHEBI:14460 CHEBI:16382 CHEBI:49698 CHEBI:5946 Gmelin:14912 I I(-) I- IODIDE ION InChI=1S/HI/h1H/p-1 Iodide KEGG:C00708 PDBeChem:IOD XMBWDFGMSWQBCA-UHFFFAOYSA-M [I-] chebi_ontology iodide iodide(1-) iodine anion organic sulfide 31.972 CHEBI:13694 CHEBI:16385 CHEBI:26960 CHEBI:9340 Compounds having the structure RSR (R =/= H). Such compounds were once called thioethers. KEGG:C00297 RSR SR2 Sulfide Thioether chebi_ontology organic sulfides sulfides thioether thioethers sphingosine (2S,3R)-(E)-2-amino-1,3-dihydroxy-4-octadecene (2S,3R,4E)-2-amino-3-hydroxyoctadec-4-ene-1-ol (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol (2S,3R,E)-2-aminooctadec-4-ene-1,3-diol (4E)-sphing-4-enine (4E)-sphingenine (E)-2-amino-4-octadecan-1,3-diol (E)-D-erythro-4-octadecene-1,3-diol 0 2-amino-4-octadecene-1,3-diol 299.282 299.49190 A sphing-4-enine in which the double bond is trans. Beilstein:1727294 Beilstein:4676153 C18 sphingosine C18H37NO2 CAS:123-78-4 CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO CHEBI:15102 CHEBI:16393 CHEBI:207585 CHEBI:26741 CHEBI:9224 D-(+)-erythro-1,3-dihydroxy-2-amino-4-trans-octadecene D-erythro-sphingosine DrugBank:DB03203 HMDB:HMDB0000252 InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1 KEGG:C00319 LIPID_MAPS_instance:LMSP01010001 PDBeChem:SQS PMID:10453988 PMID:16341241 PMID:24731183 PMID:8482346 Reaxys:1727294 Sph Sphing-4-enine Sphingenine Sphingoid Sphingosine Sphingosine d18:1 WWUZIQQURGPMPG-KRWOKUGFSA-N chebi_ontology sphingosin trans-4-sphingenine trans-D-erythro-2-amino-4-octadecene-1,3-diol alanine 0 2-Aminopropanoic acid 2-Aminopropionic acid 2-aminopropanoic acid 89.048 89.09322 A ALA Alanin Alanine An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2. Beilstein:635807 C3H7NO2 CAS:302-72-7 CC(N)C(O)=O CHEBI:13748 CHEBI:16449 CHEBI:22277 CHEBI:2539 Drug_Central:4306 Gmelin:2449 InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6) KEGG:C01401 PMID:17439666 PMID:22264337 QNAYBMKLOCPYGJ-UHFFFAOYSA-N Reaxys:635807 Wikipedia:Alanine alanina alanine chebi_ontology pentan-2-one 0 2-Pentanone 2-pentanone 86.073 86.13230 A pentanone carrying an oxo substituent at position 2. AGR:IND500714276 C5H10O CAS:107-87-9 CCCC(C)=O CHEBI:14748 CHEBI:16472 CHEBI:25886 CHEBI:7978 HMDB:HMDB0034235 InChI=1S/C5H10O/c1-3-4-5(2)6/h3-4H2,1-2H3 KEGG:C01949 LIPID_MAPS_instance:LMFA12000003 MetaCyc:PENTAN-2-ONE Methyl propyl ketone PDBeChem:PNH PMID:22364569 Pentan-2-one Reaxys:506058 Wikipedia:Pentan-2-one XNLICIUVMPYHGG-UHFFFAOYSA-N chebi_ontology pentan-2-one N-acylneuraminic acid 0 294.083 294.23530 5-alkanamido-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid Any neuraminic acid carrying an N-acyl substituent. C10H16NO9R CHEBI:12485 CHEBI:16498 CHEBI:21664 CHEBI:7240 KEGG:C00591 N-Acylneuraminate N-acylneuraminic acids [H][C@]1(OC(O)(C[C@H](O)[C@H]1NC([*])=O)C(O)=O)[C@H](O)[C@H](O)CO chebi_ontology carbon dioxide 0 43.990 44.010 A one-carbon compound with formula CO2 in which the carbon is attached to each oxygen atom by a double bond. A colourless, odourless gas under normal conditions, it is produced during respiration by all animals, fungi and microorganisms that depend directly or indirectly on living or decaying plants for food. Beilstein:1900390 CARBON DIOXIDE CAS:124-38-9 CHEBI:13282 CHEBI:13283 CHEBI:13284 CHEBI:13285 CHEBI:16526 CHEBI:23011 CHEBI:3283 CHEBI:48829 CO2 CO2 CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Drug_Central:4256 E 290 E-290 E290 Gmelin:989 HMDB:HMDB0001967 InChI=1S/CO2/c2-1-3 KEGG:C00011 KEGG:D00004 MetaCyc:CARBON-DIOXIDE MolBase:752 O=C=O PDBeChem:CO2 PMID:10826146 PMID:11094503 PMID:11584085 PMID:11802652 PMID:14639145 PMID:15050588 PMID:16591971 PMID:16656478 PMID:16659660 PMID:17190796 PMID:17448243 PMID:17878298 PMID:17884085 PMID:19043767 PMID:19259576 PMID:19854893 PMID:23384758 PMID:23828359 PMID:24258718 PMID:8482095 PMID:8818713 PMID:8869828 PMID:9611769 PMID:9730350 PPDB:119 R-744 Reaxys:1900390 UM-BBD_compID:c0131 Wikipedia:Carbon_dioxide [CO2] carbon dioxide carbonic anhydride chebi_ontology dioxidocarbon methanedione protein polypeptide chain A naturally occurring polypeptide synthesized at the ribosome. CHEBI:16541 CHEBI:8526 KEGG:C00017 Protein chebi_ontology polypeptide chain protein polypeptide chains ethanethioic S-acid 0 75.998 76.11856 A thioacetic acid that is acetic acid in which the oxygen atom of the hydroxy group has been replaced by a sulfur atom. Beilstein:773684 C2H4OS CAS:507-09-5 CC(S)=O CH3COSH CHEBI:16555 CHEBI:9547 DUYAAUVXQSMXQP-UHFFFAOYSA-N Gmelin:49262 InChI=1S/C2H4OS/c1-2(3)4/h1H3,(H,3,4) KEGG:C01857 PMID:23298036 Reaxys:773684 Thioacetic acid acetyl mercaptan chebi_ontology ethanethioic S-acid thioacetic S-acid butane-2,3-dione 0 2,3-Butadione 2,3-Butanedione 2,3-Diketobutane 2,3-Dioxobutane 2,3-butandione 86.037 86.08924 An alpha-diketone that is butane substituted by oxo groups at positions 2 and 3. It is a metabolite produced during the malolactic fermentation. Beilstein:605398 Biacetyl C4H6O2 CAS:431-03-8 CC(=O)C(C)=O CHEBI:14134 CHEBI:16583 CHEBI:4479 Diacetyl Dimethyl glyoxal Dimethylglyoxal HMDB:HMDB0003407 InChI=1S/C4H6O2/c1-3(5)4(2)6/h1-2H3 KEGG:C00741 PMID:15654607 PMID:24614328 QSJXEFYPDANLFS-UHFFFAOYSA-N Reaxys:605398 butane-2,3-dione chebi_ontology diacetyl 5alpha-cholest-8-en-3beta-ol (5alpha)-cholest-8-en-3beta-ol 0 386.355 386.65354 5alpha-Cholest-8-en-3beta-ol 5alpha-cholest-8-en-3beta-ol A cholestanoid that is 5alpha-cholestane substituted by a beta-hydroxy group at position 3. C27H46O CAS:566-97-2 CHEBI:12170 CHEBI:16608 CHEBI:20645 CHEBI:2139 Cholestenol HMDB:HMDB0006841 InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-21,23-24,28H,6-17H2,1-5H3/t19-,20+,21+,23-,24+,26+,27-/m1/s1 KEGG:C03845 LIPID_MAPS_instance:LMST01010096 MetaCyc:CPD-8621 PMID:5642322 QETLKNDKQOXZRP-XTGBIJOFSA-N Reaxys:2337227 Zymostenol [H][C@@]12CCC3=C(CC[C@]4(C)[C@]([H])(CC[C@@]34[H])[C@H](C)CCCC(C)C)[C@@]1(C)CC[C@H](O)C2 chebi_ontology carbohydrate Any member of the class of organooxygen compounds that is a polyhydroxy-aldehyde or -ketone or a lactol resulting from their intramolecular condensation (monosaccharides); substances derived from these by reduction of the carbonyl group (alditols), by oxidation of one or more hydroxy groups to afford the corresponding aldehydes, ketones, or carboxylic acids, or by replacement of one or more hydroxy group(s) by a hydrogen atom; and polymeric products arising by intermolecular acetal formation between two or more such molecules (disaccharides, polysaccharides and oligosaccharides). Carbohydrates contain only carbon, hydrogen and oxygen atoms; prior to any oxidation or reduction, most have the empirical formula Cm(H2O)n. Compounds obtained from carbohydrates by substitution, etc., are known as carbohydrate derivatives and may contain other elements. Cyclitols are generally not regarded as carbohydrates. CHEBI:15131 CHEBI:16646 CHEBI:23008 CHEBI:9318 Kohlenhydrat Kohlenhydrate Wikipedia:Carbohydrate carbohidrato carbohidratos carbohydrate carbohydrates chebi_ontology glucide glucides glucido glucidos hydrates de carbone saccharide saccharides saccharidum (S)-lactate (+)-lactate (2S)-2-hydroxypropanoate (S)-lactate -1 89.024 89.07000 An optically active form of lactate having (S)-configuration. Beilstein:4655977 C3H5O3 CHEBI:11065 CHEBI:12411 CHEBI:16651 CHEBI:18783 C[C@H](O)C([O-])=O Gmelin:324523 InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/p-1/t2-/m0/s1 JVTAAEKCZFNVCJ-REOHCLBHSA-M KEGG:C00186 L(+)-lactate L-(+)-lactate L-lactate MetaCyc:L-LACTATE Reaxys:4655977 UM-BBD_compID:c0152 chebi_ontology peptide (C2H2NOR)nC2H3NOR 0 Amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another with formal loss of water. The term is usually applied to structures formed from alpha-amino acids, but it includes those derived from any amino carboxylic acid. X = OH, OR, NH2, NHR, etc. CHEBI:14753 CHEBI:16670 CHEBI:25906 CHEBI:7990 KEGG:C00012 Peptid Peptide chebi_ontology peptides peptido peptidos nucleoside 5'-phosphate 0 196.014 196.09510 A ribosyl or deoxyribosyl derivative of a pyrimidine or purine base in which C-5 of the ribose ring is mono-, di-, tri- or tetra-phosphorylated. C5H9O6PR2 CHEBI:14674 CHEBI:16701 CHEBI:25603 CHEBI:7650 KEGG:C01117 Nucleoside 5'-phosphate O[C@H]1[C@@H]([*])[C@H]([*])O[C@@H]1COP(O)(O)=O chebi_ontology nucleoside 5'-phosphates adenine 0 135.054 135.12690 6-Aminopurine 9H-purin-6-amine A ADENINE Ade Adenin Adenine Beilstein:608603 C5H5N5 CAS:73-24-5 CHEBI:13733 CHEBI:16708 CHEBI:22236 CHEBI:2470 CHEBI:40579 DrugBank:DB00173 Drug_Central:89 GFFGJBXGBJISGV-UHFFFAOYSA-N Gmelin:3903 HMDB:HMDB0000034 InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10) KEGG:C00147 KEGG:D00034 KNApSAcK:C00001490 MetaCyc:ADENINE Nc1ncnc2[nH]cnc12 PDBeChem:ADE PMID:11985597 PMID:12829005 PMID:12951489 PMID:15063338 PMID:15715490 PMID:17439666 PMID:8070089 Reaxys:608603 The parent compound of the 6-aminopurines, composed of a purine having an amino group at C-6. Wikipedia:Adenine adenine chebi_ontology benzene 0 78.047 78.11184 A six-carbon aromatic annulene in which each carbon atom donates one of its two 2p electrons into a delocalised pi system. A toxic, flammable liquid byproduct of coal distillation, it is used as an industrial solvent. Benzene is a carcinogen that also damages bone marrow and the central nervous system. BENZENE Beilstein:969212 Benzen Benzene Benzine Benzol Bicarburet of hydrogen C6H6 CAS:71-43-2 CHEBI:13876 CHEBI:16716 CHEBI:22703 CHEBI:3025 CHEBI:41187 Coal naphtha Gmelin:1671 HMDB:HMDB0001505 InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H KEGG:C01407 Mineral naphtha PDBeChem:BNZ PMID:11684179 PMID:11993966 PMID:12857942 PMID:14677922 PMID:15468289 PMID:15935818 PMID:16161967 PMID:17373369 PMID:18072742 PMID:18407866 PMID:18409691 PMID:18836923 PMID:19228219 PMID:21325737 PMID:23088855 PMID:23222815 PMID:23534829 PMID:6353911 PMID:8124204 Phene Pyrobenzol Pyrobenzole Reaxys:969212 UHOVQNZJYSORNB-UHFFFAOYSA-N UM-BBD_compID:c0142 Wikipedia:Benzene [6]annulene benzene benzole c1ccccc1 chebi_ontology cyclohexatriene phenyl hydride D-alpha-amino acid 0 74.024 74.05870 C2H4NO2R CHEBI:12909 CHEBI:13625 CHEBI:16733 CHEBI:20906 CHEBI:4097 D-Amino acid D-alpha-amino acid D-alpha-amino acids D-alpha-amino acids KEGG:C00405 N[C@H]([*])C(O)=O chebi_ontology creatinine 0 1-Methylglycocyamidine 1-Methylhydantoin-2-imide 1-methylglycocyamidine 113.059 113.11800 2-Amino-1-methylimidazolin-4-one 2-amino-1,5-dihydro-1-methyl-4H-Imidazol-4-one 2-imino-1-methylimidazolidin-4-one A lactam obtained by formal cyclocondensation of creatine. It is a metabolite of creatine. C4H7N3O CAS:60-27-5 CHEBI:14029 CHEBI:16737 CHEBI:23406 CHEBI:3910 CN1CC(=O)NC1=N Creatine anhydride Creatinine DDRJAANPRJIHGJ-UHFFFAOYSA-N HMDB:HMDB0000562 InChI=1S/C4H7N3O/c1-7-2-3(8)6-4(7)5/h2H2,1H3,(H2,5,6,8) KEGG:C00791 KEGG:D03600 Kreatinin MetaCyc:CREATININE PMID:11256540 PMID:11981083 PMID:17190852 PMID:17422601 PMID:18182718 PMID:19236048 PMID:19715855 PMID:19968328 PMID:21775764 PMID:22047975 PMID:22121923 PMID:22166252 PMID:22207347 PMID:22212624 PMID:22223530 PMID:22331238 PMID:22338083 PMID:22349552 PMID:22390548 PMID:22432114 PMID:22441184 PMID:22459582 PMID:22498455 Reaxys:112064 Wikipedia:Creatinine chebi_ontology creatinina creatinine orotic acid 0 156.017 156.09630 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6. Beilstein:383901 C5H4N2O4 CAS:65-86-1 CHEBI:16742 CHEBI:25720 CHEBI:44781 CHEBI:7787 DrugBank:DB02262 Drug_Central:3402 Gmelin:101990 HMDB:HMDB0000226 InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11) KEGG:C00295 KEGG:D00055 KNApSAcK:C00019689 MetaCyc:OROTATE OC(=O)c1cc(=O)[nH]c(=O)[nH]1 OROTIC ACID Orotic acid Orotsaeure PDBeChem:ORO PMID:11059538 PMID:22019295 PMID:22285839 PMID:22307261 PMID:22371390 PMID:22634191 PMID:22707164 PMID:22770225 PMID:22863860 PMID:7264771 PXQPEWDEAKTCGB-UHFFFAOYSA-N Reaxys:383901 Uracil-6-carboxylic acid Wikipedia:Orotic_acid chebi_ontology ADP 0 427.029 427.20110 5'-adenylphosphoric acid A purine ribonucleoside 5'-diphosphate having adenine as the nucleobase. ADENOSINE-5'-DIPHOSPHATE ADP Adenosine 5'-diphosphate Beilstein:67722 C10H15N5O10P2 CAS:20398-34-9 CAS:58-64-0 CHEBI:13222 CHEBI:16761 CHEBI:22244 CHEBI:2342 CHEBI:40553 COMe:MOL000173 DrugBank:DB03431 Gmelin:88452 H3adp InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1 KEGG:C00008 KEGG:G11113 KNApSAcK:C00019353 Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O PDBeChem:ADP PMID:16295522 Reaxys:67722 XTWYTFMLZFPYCI-KQYNXXCUSA-N adenosine 5'-(trihydrogen diphosphate) chebi_ontology tryptamine 0 160.100 160.21570 1H-indole-3-ethanamine 2-(1H-INDOL-3-YL)ETHANAMINE 2-(1H-indol-3-yl)ethanamine 2-(3-indolyl)ethylamine 3-(2-Aminoethyl)indole APJYDQYYACXCRM-UHFFFAOYSA-N An aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position. Beilstein:125513 C10H12N2 CAS:61-54-1 CHEBI:15274 CHEBI:16765 CHEBI:27161 CHEBI:46157 CHEBI:9767 DrugBank:DB08653 Gmelin:603448 HMDB:HMDB0000303 InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2 KEGG:C00398 KNApSAcK:C00001434 MetaCyc:TRYPTAMINE NCCc1c[nH]c2ccccc12 PDBeChem:TSS PMID:16126914 PMID:22770225 PMID:24345948 PMID:24558969 Reaxys:125513 Tryptamine Wikipedia:Tryptamine chebi_ontology (S)-2-hydroxyglutarate(2-) (2S)-2-hydroxypentanedioate (S)-2-hydroxyglutarate -2 146.022 146.09814 A 2-hydroxyglutarate(2-) that has (2S)-configuration. Beilstein:5257108 C5H6O5 CHEBI:11036 CHEBI:16782 CHEBI:18738 HWXBTNAVRSUOJR-VKHMYHEASA-L InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/p-2/t3-/m0/s1 KEGG:C03196 MetaCyc:CPD-381 O[C@@H](CCC([O-])=O)C([O-])=O Reaxys:5257108 chebi_ontology 2-oxoglutarate(2-) -2 144.006 144.08226 2-ketoglutarate 2-oxoglutarate 2-oxopentanedioate 2-oxopentanedioic acid, ion(2-) An oxo dicarboxylate obtained by deprotonation of both carboxy groups of 2-oxoglutaric acid. Beilstein:3664503 C5H4O5 CAS:64-15-3 CHEBI:11638 CHEBI:16810 CHEBI:19748 Gmelin:602479 InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)/p-2 KEGG:C00026 KPGXRSRHYNQIFN-UHFFFAOYSA-L MetaCyc:2-KETOGLUTARATE PMID:11913971 PMID:15612731 PMID:17190852 PMID:19376872 PMID:21184277 PMID:21196226 PMID:21791173 Reaxys:3664503 [O-]C(=O)CCC(=O)C([O-])=O alpha-ketoglutarate chebi_ontology methionine 0 149.051 149.21238 2-Amino-4-(methylthio)butyric acid 2-amino-4-(methylsulfanyl)butanoic acid 2-amino-4-(methylthio)butanoic acid A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4. Beilstein:636185 C5H11NO2S CAS:59-51-8 CHEBI:14590 CHEBI:16811 CHEBI:25229 CHEBI:6829 CSCCC(N)C(O)=O DL-Methionine FFEARJCKVFRZRR-UHFFFAOYSA-N Gmelin:3117 Hmet InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8) KEGG:C01733 KEGG:D04983 M Met Methionin Methionine PMID:16702333 PMID:22264337 PMID:2543976 Racemethionine Reaxys:636185 UM-BBD_compID:c0094 Wikipedia:Methionine alpha-amino-gamma-methylmercaptobutyric acid chebi_ontology methionine metionina galactitol (2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol 0 182.079 182.17180 An optically inactive hexitol having meso-configuration. Beilstein:1721903 C6H14O6 CAS:608-66-2 CHEBI:14286 CHEBI:16813 CHEBI:24139 CHEBI:5251 CHEBI:53575 D-Dulcitol D-galactitol Dulcitol Dulcose Euonymit FBPFZTCFMRRESA-GUCUJZIJSA-N Galactitol Gmelin:83163 HMDB:HMDB0000107 InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6- KEGG:C01697 KNApSAcK:C00001160 L-galactitol Melampyrin Melampyrit OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO PMID:16664750 PMID:16901854 PMID:17336832 PMID:17979222 PMID:21501963 PMID:22155165 PMID:22628202 PMID:22654107 PMID:23830453 PMID:24643482 Reaxys:1721903 Wikipedia:Galactitol chebi_ontology galactitol meso-galactitol corticosterone (11beta)-11,21-dihydroxypregn-4-ene-3,20-dione 0 11beta,21-Dihydroxy-4-pregnene-3,20-dione 11beta,21-dihydroxypregn-4-ene-3,20-dione 11beta,21-dihydroxyprogesterone 17-deoxycortisol 346.214 346.46050 A 21-hydroxy steroid that consists of pregn-4-ene substituted by hydroxy groups at positions 11 and 21 and oxo groups at positions 3 and 20. Corticosterone is a 21-carbon steroid hormone of the corticosteroid type produced in the cortex of the adrenal glands. Beilstein:2339601 C21H30O4 CAS:50-22-6 CHEBI:14022 CHEBI:16827 CHEBI:19131 CHEBI:3891 CHEBI:41361 CHEBI:57911 CORTICOSTERONE Corticosterone HMDB:HMDB0001547 InChI=1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19+,20-,21-/m0/s1 KEGG:C02140 Kendall's compound B LINCS:LSM-5814 LIPID_MAPS_instance:LMST02030186 MetaCyc:CORTICOSTERONE OMFXVFTZEKFJBZ-HJTSIMOOSA-N PDBeChem:C0R PMID:10438974 PMID:11448093 PMID:16817814 PMID:24446162 Reichstein's substance H Wikipedia:Corticosterone [H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])[C@@H](O)C[C@]12C)C(=O)CO chebi_ontology corticosterone 3-hydroxy-3-methylglutaric acid (S)-3-Hydroxy-3-methylglutaric acid (S)-Meglutol 0 162.053 162.14060 3-HYDROXY-3-METHYL-GLUTARIC ACID 3-Hydroxy-3-methylpentanedioic acid 3-hydroxy-3-methylpentanedioic acid A dicarboxylic acid that is glutaric acid in which one of the two hydrogens at position 3 is substituted by a hydroxy group, while the other is substituted by a methyl group. It has been found to accumulate in urine of patients suffering from HMG-CoA lyase (3-hydroxy-3-methylglutaryl-CoA lyase, EC 4.1.3.4) deficiency. It occurs as a plant metabolite in Crotalaria dura. Beilstein:1769194 C6H10O5 CAS:503-49-1 CC(O)(CC(O)=O)CC(O)=O CHEBI:11044 CHEBI:1524 CHEBI:16831 CHEBI:18746 CHEBI:20043 CHEBI:391 CHEBI:43804 Dicrotalic acid DrugBank:DB04377 Drug_Central:1670 HMDB:HMDB0000355 InChI=1S/C6H10O5/c1-6(11,2-4(7)8)3-5(9)10/h11H,2-3H2,1H3,(H,7,8)(H,9,10) KEGG:C03761 KEGG:D04897 KNApSAcK:C00001187 MetaCyc:CPD-547 NPOAOTPXWNWTSH-UHFFFAOYSA-N PDBeChem:MAH PMID:10916782 PMID:17941049 PMID:3063529 PMID:4717513 PMID:6083597 PMID:9658458 Reaxys:1769194 beta-Hydroxy-beta-methylglutaric acid beta-hydroxy-beta-methylglutaric acid chebi_ontology meglutol meglutolum glutathione 0 307.084 307.325 5-L-Glutamyl-L-cysteinylglycine A tripeptide compound consisting of glutamic acid attached via its side chain to the N-terminus of cysteinylglycine. C10H17N3O6S CAS:70-18-8 CHEBI:12402 CHEBI:14327 CHEBI:16856 CHEBI:24334 CHEBI:42873 CHEBI:43049 CHEBI:5437 DrugBank:DB00143 Drug_Central:1312 GSH Glutathione Glutathione-SH HMDB:HMDB0000125 InChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1 KEGG:C00051 KEGG:D00014 KNApSAcK:C00001518 L-gamma-glutamyl-L-cysteinylglycine MetaCyc:GLUTATHIONE N-(N-gamma-L-Glutamyl-L-cysteinyl)glycine N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(=O)O)C(=O)O PDBeChem:GSH PMID:17439666 PMID:4200890 PMID:4745654 RWSXRVCMGQZWBV-WDSKDSINSA-N Reaxys:1729812 Reduced glutathione Wikipedia:Glutathione chebi_ontology gamma-L-Glutamyl-L-cysteinyl-glycine nucleoside diphosphate 0 292.983 293.08240 C5H11O10P2R CHEBI:13401 CHEBI:13662 CHEBI:14675 CHEBI:16862 CHEBI:25606 CHEBI:7428 CHEBI:7652 KEGG:C00454 NDP Nucleoside diphosphate O[C@H]1[C@H]([*])O[C@H](COP(O)(=O)OP(O)(O)=O)[C@H]1O chebi_ontology nucleoside diphosphates gamma-aminobutyric acid 0 103.063 103.11980 4-Aminobutanoic acid 4-Aminobutyric acid 4-aminobutanoic acid 4-aminobutanoic acid 4-aminobutyric acid 4Abu A gamma-amino acid that is butanoic acid with the amino substituent located at C-4. BPDB:2298 BTCSSZJGUNDROE-UHFFFAOYSA-N Beilstein:906818 C4H9NO2 CAS:56-12-2 CHEBI:16865 CHEBI:1786 CHEBI:193777 CHEBI:20318 CHEBI:40483 DrugBank:DB02530 Drug_Central:1262 GABA GAMMA-AMINO-BUTANOIC ACID Gmelin:49775 HMDB:HMDB0000112 InChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7) KEGG:C00334 KEGG:D00058 KNApSAcK:C00001337 LIPID_MAPS_instance:LMFA01100039 MetaCyc:4-AMINO-BUTYRATE NCCCC(O)=O PDBeChem:ABU PMID:10630630 PMID:10930630 PMID:16276116 PMID:21614609 PMID:22770225 Reaxys:906818 Wikipedia:Gamma-Aminobutyric_acid chebi_ontology gamma-Aminobuttersaeure gamma-Aminobutyric acid gamma-amino-n-butyric acid gamma-aminobutanoic acid gamma-aminobutyric acid omega-aminobutyric acid piperidic acid piperidinic acid creatine ((amino(imino)methyl)(methyl)amino)acetic acid (N-methylcarbamimidamido)acetic acid (alpha-methylguanido)acetic acid 0 131.069 131.13328 A glycine derivative having methyl and amidino groups attached to the nitrogen. Beilstein:907175 C4H9N3O2 CAS:57-00-1 CHEBI:14028 CHEBI:16919 CHEBI:23404 CHEBI:3909 CHEBI:41678 CN(CC(O)=O)C(N)=N CVSVTCORWBXHQV-UHFFFAOYSA-N Creatin Creatine DrugBank:DB00148 Drug_Central:4661 Gmelin:240513 HMDB:HMDB0000064 InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9) KEGG:C00300 Kreatin MetaCyc:CREATINE Methylglycocyamine N-(aminoiminomethyl)-N-methylglycine N-Methyl-N-guanylglycine N-[(E)-AMINO(IMINO)METHYL]-N-METHYLGLYCINE N-[amino(imino)methyl]-N-methylglycine N-amidinosarcosine N-carbamimidoyl-N-methylglycine N-methyl-N-guanylglycine PDBeChem:CRN PMID:11356982 PMID:11483809 PMID:11867929 PMID:12085493 PMID:12184144 PMID:12878267 PMID:16445883 PMID:17190852 PMID:17253521 PMID:18555535 PMID:19082141 PMID:19651674 PMID:19741514 PMID:19968328 PMID:21556832 PMID:21660517 PMID:21698493 PMID:22038587 PMID:22101931 PMID:22196490 PMID:22252611 PMID:22347384 PMID:22386973 PMID:22422801 PMID:22429992 PMID:22465051 PMID:22521466 PMID:7752905 Reaxys:907175 Wikipedia:Creatine alpha-Methylguanidino acetic acid chebi_ontology 5-oxo-D-proline (2R)-5-oxopyrrolidine-2-carboxylic acid 0 129.043 129.11400 5-Oxo-D-proline 5-oxo-D-proline Beilstein:82133 C5H7NO3 CAS:4042-36-8 CHEBI:12152 CHEBI:16924 CHEBI:20618 CHEBI:2112 D-5-Pyrrolidone-2-carboxylic acid D-Pyroglutamic acid DrugBank:DB03088 Gmelin:1473408 HMDB:HMDB0000267 InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m1/s1 KEGG:C02237 MetaCyc:CPD-656 OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N PMID:22770225 Reaxys:82133 The D-enantiomer of 5-oxoproline. chebi_ontology citrate(3-) -3 189.004 189.09970 2-hydroxy-1,2,3-propanetricarboxylate 2-hydroxy-1,2,3-propanetricarboxylate(3-) 2-hydroxy-1,2,3-propanetricarboxylic acid, ion(3-) 2-hydroxypropane-1,2,3-tricarboxylate 2-hydroxytricarballylate A tricarboxylic acid trianion, obtained by deprotonation of the three carboxy groups of citric acid. Beilstein:1884707 C6H5O7 CAS:126-44-3 CHEBI:13999 CHEBI:16947 CHEBI:23321 CHEBI:42563 CITRATE ANION Gmelin:4239 InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/p-3 KEGG:C00158 KRKNYBCHXYNGOX-UHFFFAOYSA-K OC(CC([O-])=O)(CC([O-])=O)C([O-])=O PDBeChem:FLC Reaxys:1884707 chebi_ontology cit cit(3-) citrate beta-alanine 0 3-Aminopropionic acid 3-aminopropanoic acid 3-aminopropanoic acid 89.048 89.09322 A naturally-occurring beta-amino acid comprising propionic acid with the amino group in the 3-position. BETA-ALANINE Beilstein:906793 C3H7NO2 CAS:107-95-9 CHEBI:10343 CHEBI:12389 CHEBI:16958 CHEBI:22821 CHEBI:41050 DrugBank:DB03107 Gmelin:49614 H-beta-Ala-OH HMDB:HMDB0000056 InChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6) KEGG:C00099 KEGG:D07561 KNApSAcK:C00001333 MetaCyc:B-ALANINE NCCC(O)=O PDBeChem:BAL PMID:11139233 PMID:11850512 PMID:12107759 PMID:12887142 PMID:14363188 PMID:16934791 PMID:18528519 PMID:18613640 PMID:19239140 PMID:19955842 PMID:20199122 PMID:20386120 PMID:20479615 PMID:20994958 PMID:22735334 Reaxys:906793 UCMIRNVEIXFBKS-UHFFFAOYSA-N Wikipedia:Beta-Alanine bAla beta-Alanine beta-alanine beta-aminopropionic acid chebi_ontology omega-aminopropionic acid 11-deoxycorticosterone 0 11-Deoxycorticosterone 21-Hydroxy-4-pregnene-3,20-dione 21-hydroxypregn-4-ene-3,20-dione 21-hydroxyprogesterone 330.219 330.46110 4-pregnen-21-ol-3,20-dione A mineralocorticoid that is progesterone substituted at position 21 by a hydroxy group. Beilstein:2062123 C21H30O3 CAS:64-85-7 CHEBI:11314 CHEBI:16973 CHEBI:19123 CHEBI:39642 CHEBI:713 CHEBI:86536 Cortexone DESOXYCORTICOSTERONE DOC Deoxycorticosterone Desoxycortone Drug_Central:820 InChI=1S/C21H30O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1 KEGG:C03205 KEGG:D07792 Kendall's desoxy compound B LIPID_MAPS_instance:LMST02030087 MetaCyc:11-DEOXYCORTICOSTERONE PDBeChem:1CA PMID:22770225 Reaxys:2062123 Reichstein's substance Q Wikipedia:Desoxycorticosterone ZESRJSPZRDMNHY-YFWFAHHUSA-N [H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(=O)CO chebi_ontology desoxycortone D-ribose 0 150.12990 A ribose in which the chiral carbon atom furthest away from the aldehyde group (C4') has the same configuration as in D-glyceraldehyde. C5H10O5 CHEBI:13011 CHEBI:16988 CHEBI:21078 D-Rib D-ribo-pentose D-ribose DrugBank:DB01936 PMID:24404872 PMID:24752650 chebi_ontology bilirubin IXalpha 0 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionic acid 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid 2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acid 3,18-diethenyl-2,7,13,17-tetramethyl-1,19-dioxo-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acid 584.263 584.66230 8,12-bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbiladiene-ac-1,19(21H,24H)-dione A member of the class of biladienes that is a linear tetrapyrrole with the dipyrrole units being of both exovinyl and endovinyl type. A product of heme degradation, it is produced in the reticuloendothelial system by the reduction of biliverdin and transported to the liver as a complex with serum albumin. BPYKTIZUTYGOLE-IFADSCNNSA-N Beilstein:74376 Bilirubin C33H36N4O6 CAS:635-65-4 CC1=C(C=C)\C(NC1=O)=C\c1[nH]c(Cc2[nH]c(\C=C3NC(=O)C(C=C)=C/3C)c(C)c2CCC(O)=O)c(CCC(O)=O)c1C CHEBI:13898 CHEBI:16990 CHEBI:22870 CHEBI:3099 Gmelin:411033 HMDB:HMDB0000054 InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14- KEGG:C00486 KNApSAcK:C00029828 MetaCyc:BILIRUBIN PMID:12799017 PMID:18442622 PMID:23763371 PMID:8605219 PMID:9587403 Reaxys:74376 Wikipedia:Bilirubin bilirubin bilirubin(Z,Z) bilirubin-IXalpha chebi_ontology oxalic acid 0 89.995 90.03490 An alpha,omega-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2. Beilstein:385686 C2H2O4 CAS:144-62-7 CHEBI:16995 CHEBI:25730 CHEBI:44583 CHEBI:7811 DrugBank:DB03902 Ethandisaeure Ethanedioic acid Gmelin:2208 H2ox HMDB:HMDB0002329 HOOCCOOH InChI=1S/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6) KEGG:C00209 KNApSAcK:C00001198 LIPID_MAPS_instance:LMFA01170031 MUBZPKHOEPUJKR-UHFFFAOYSA-N MetaCyc:OXALATE OC(=O)C(O)=O OXALIC ACID Oxalic acid Oxalsaeure PDBeChem:OXD PMID:15587083 PMID:22735334 Reaxys:385686 Wikipedia:Oxalic_acid chebi_ontology ethane-1,2-dioic acid oxalic acid propane-1,2-diol 0 1,2-Propanediol 1,2-Propylenglykol 1,2-dihydroxypropane 2-hydroxypropanol 76.052 76.09442 C3H8O2 CAS:57-55-6 CC(O)CO CH3CH(OH)CH2OH CHEBI:14899 CHEBI:16997 CHEBI:8469 DNIAPMSPPWPWGF-UHFFFAOYSA-N DrugBank:DB01839 Drug_Central:4024 HMDB:HMDB0001881 HOCH2CH(OH)CH3 HOCH2CH(OH)Me InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3 KEGG:C00583 KEGG:D00078 KNApSAcK:C00007410 LINCS:LSM-36856 MeCH(OH)CH2OH PMID:15665701 PMID:16078503 PMID:18346395 PMID:18845115 PMID:21616561 PPD PPDB:1304 Propane-1,2-diol Propylene glycol Reaxys:1340498 The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze. VSDB:1304 Wikipedia:Propylene_glycol alpha-propyleneglycol chebi_ontology isopropylene glycol methyl glycol methylethyl glycol methylethylene glycol monopropylene glycol propane-1,2-diol cholesteryl ester 0 413.342 413.65570 A sterol ester obtained by formal condensation of the carboxy group of any carboxylic acid with the 3-hydroxy group of cholesterol. C28H45O2R CHEBI:13983 CHEBI:17002 CHEBI:23205 CHEBI:3660 Cholesterol ester KEGG:C02530 [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC([*])=O)[C@H](C)CCCC(C)C a cholesterol ester chebi_ontology cholesterol esters cholesteryl esters N-acetylneuraminic acid 0 309.106 309.26990 5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid Aceneuramic acid An N-acylneuraminic acid where the N-acyl group is specified as acetyl. Beilstein:2951361 C11H19NO9 CAS:131-48-6 CHEBI:17012 CHEBI:21620 CHEBI:7214 InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11?/m0/s1 KEGG:C00270 KNApSAcK:C00019584 N-Acetylneuraminic acid Neu5Ac NeuAc O-sialic acid PMID:14960498 PMID:16209099 PMID:16624269 PMID:18487279 PMID:19329108 PMID:7508418 Reaxys:1398688 SQVRNKJHWKZAKO-LUWBGTNYSA-N Wikipedia:N-acetylneuraminic_acid [H][C@]1(OC(O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO aceneuramic acid acide aceneuramique acidium aceneuramicum acido aceneuramico chebi_ontology progesterone (S)-4-Pregnene-3,20-dione (S)-Pregn-4-en-3,20-dione (S)-Progesterone 0 17alpha-progesterone 314.225 314.46170 4-Pregnene-3,20-dione A C21-steroid hormone in which a pregnane skeleton carries oxo substituents at positions 3 and 20 and is unsaturated at C(4)-C(5). As a hormone, it is involved in the female menstrual cycle, pregnancy and embryogenesis of humans and other species. Agolutin Akrolutin Beilstein:1915950 C21H30O2 CAS:57-83-0 CHEBI:14896 CHEBI:17026 CHEBI:18798 CHEBI:26269 CHEBI:439 CHEBI:45786 CHEBI:8453 Crinone Delta(4)-pregnene-3,20-dione DrugBank:DB00396 Drug_Central:2279 Gelbkoerperhormon Gmelin:708590 HMDB:HMDB0001830 InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1 KEGG:C00410 KEGG:D00066 MetaCyc:PROGESTERONE PDBeChem:STR PMID:10438974 PMID:9506942 PROGESTERONE Progesteron Progesterone RJKFOVLPORLFTN-LEKSSAKUSA-N Reaxys:1915950 Wikipedia:Progesterone [H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@H](CC[C@@]21[H])C(C)=O chebi_ontology corpus luteum hormone luteohormone pregn-4-ene-3,20-dione progesterone chitin (1->4)-2-acetamido-2-deoxy-beta-D-glucan 0 An aminoglycan consisting of beta-(1->4)-linked N-acetyl-D-glucosamine residues. CAS:1398-61-4 CHEBI:13962 CHEBI:17029 CHEBI:23099 CHEBI:3596 Chitin H2O(C8H13NO5)n KEGG:C00461 KEGG:G10483 [1,4-(N-Acetyl-beta-D-glucosaminyl)]n [4)-beta-D-GlcpNAc(1->]n beta-1,4-Poly-N-acetyl-D-glucosamine chebi_ontology chitin primary aliphatic amine 0 30.034 30.04920 CH4NR CHEBI:13431 CHEBI:17062 CHEBI:8749 KEGG:C00375 NC[*] RCH2NH2 chebi_ontology primary aliphatic amines 2-hydroxyglutaric acid 0 148.037 148.11402 2-hydroxyglutaric acid 2-hydroxypentanedioic acid A 2-hydroxydicarboxylic acid that is glutaric acid in which one hydrogen alpha- to a carboxylic acid group is substituted by a hydroxy group. Beilstein:1723805 C5H8O5 CAS:2889-31-8 CHEBI:1160 CHEBI:17084 HWXBTNAVRSUOJR-UHFFFAOYSA-N InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10) KEGG:C02630 MetaCyc:2-HYDROXYGLUTARIC_ACID OC(CCC(O)=O)C(O)=O PMID:17439666 Reaxys:1723805 Wikipedia:Alpha-Hydroxyglutaric_acid alpha-hydroxyglutaric acid chebi_ontology ketone 0 27.995 A compound in which a carbonyl group is bonded to two carbon atoms: R2C=O (neither R may be H). CHEBI:13427 CHEBI:13646 CHEBI:17087 CHEBI:24974 CHEBI:6127 CHEBI:8742 COR2 KEGG:C01450 Keton Ketone R-CO-R' Wikipedia:Ketone [*]C([*])=O a ketone cetone chebi_ontology ketones ketones glycoprotein A compound in which a carbohydrate component is covalently bound to a protein component. CHEBI:14349 CHEBI:17089 CHEBI:5481 CHEBI:5493 Glycoprotein Glykoprotein Glykoproteine KEGG:C00326 chebi_ontology glicoproteina glicoproteinas glycoproteine glycoproteines glycoproteins erythritol (2R,3S)-butane-1,2,3,4-tetrol 0 122.058 122.11980 Beilstein:1719753 C4H10O4 CAS:149-32-6 CHEBI:14215 CHEBI:17113 CHEBI:23946 CHEBI:372804 CHEBI:44263 CHEBI:4840 DrugBank:DB04481 Erythrit Erythrite Erythritol Erythrol Gmelin:82499 HMDB:HMDB0002994 InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4+ KEGG:C00503 KNApSAcK:C00001161 L-erythritol MESO-ERYTHRITOL MetaCyc:ERYTHRITOL OC[C@H](O)[C@H](O)CO PDBeChem:MRY PMID:12639570 PMID:163226 PMID:16901854 PMID:17336832 PMID:17979222 PMID:18369603 PMID:19632091 PMID:22770225 PMID:23421980 PMID:23574577 PMID:23890177 PMID:24643482 PMID:25108762 PMID:9862657 Phycite Phycitol Reaxys:1735878 The meso-diastereomer of butane-1,2,3,4-tetrol. UNXHWFMMPAWVPI-ZXZARUISSA-N Wikipedia:Erythritol chebi_ontology erythritol erythro-tetritol meso-erythritol mesoerythritol hexanoate -1 1-hexanoate 1-pentacarboxylate 1-pentanecarboxylate 115.076 115.15034 A short-chain fatty acid anion that is the conjugate base of hexanoic acid (also known as caproic acid). Beilstein:3601453 C6H11O2 CAS:151-33-7 CCCCCC([O-])=O CH3-[CH2]4-COO(-) CHEBI:14398 CHEBI:17120 CHEBI:24569 ECMDB:ECMDB21229 FUZZWVXGSFPDMH-UHFFFAOYSA-M Gmelin:326340 InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)/p-1 KEGG:C01585 MetaCyc:HEXANOATE butylacetate caproate capronate chebi_ontology hexanoate hexoate hexylate n-caproate n-hexanoate n-hexoate n-hexylate nPnCO2 anion pentanecarboxylate pentylformate carnitine 0 161.105 161.19894 3-hydroxy-4-(trimethylammonio)butanoate An amino-acid betaine that is butanoate substituted with a hydroxy group at position C-3 and a trimethylammonium group at C-4. Beilstein:1866665 C7H15NO3 CAS:461-06-3 CHEBI:11817 CHEBI:13947 CHEBI:17126 CHEBI:20047 CHEBI:23038 C[N+](C)(C)CC(O)CC([O-])=O D,L-carnitine DrugBank:DB02648 InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3 KEGG:C00487 MetaCyc:DL-CARNITINE PHIQHXFUZVPYII-UHFFFAOYSA-N PMID:22770225 PMID:23868375 Patent:US4255449 Patent:US4315944 Reaxys:1866665 Wikipedia:Carnitine carnitine chebi_ontology octopamine 0 1-(4-Hydroxyphenyl)-2-aminoethanol 1-(p-hydroxyphenyl)-2-aminoethanol 153.079 153.17848 4-(2-amino-1-hydroxyethyl)phenol Beilstein:1211019 C8H11NO2 CAS:104-14-3 CHEBI:11191 CHEBI:17134 CHEBI:25655 CHEBI:571 Drug_Central:3396 InChI=1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2 KEGG:C04227 LINCS:LSM-4975 NCC(O)c1ccc(O)cc1 Octopamin Octopamine Octopamine is a biogenic phenylethanolamine, which has been found to act as a neurotransmitter, neurohormone or neuromodulator in invertebrates. QHGUCRYDKWKLMG-UHFFFAOYSA-N alpha-(aminomethyl)-4-hydroxybenzenemethanol alpha-(aminomethyl)-p-hydroxybenzyl alcohol beta-hydroxytyramine chebi_ontology norsynephrine octopaminum p-Hydroxyphenylethanolamine hydrogensulfite -1 80.965 81.07214 Bisulfite CAS:15181-46-1 CHEBI:13367 CHEBI:17137 CHEBI:5598 Gmelin:1455 HO3S HSO3(-) HSO3- Hydrogen sulfite InChI=1S/H2O3S/c1-4(2)3/h(H2,1,2,3)/p-1 KEGG:C11481 LSNNMFCWUKXFEE-UHFFFAOYSA-M OS([O-])=O PDBeChem:SO3 [SO2(OH)](-) bisulfite bisulphite chebi_ontology hydrogen sulfite(1-) hydrogen(trioxidosulfate)(1-) hydrogensulfite(1-) hydrogentrioxosulfate(1-) hydrogentrioxosulfate(IV) hydrosulfite anion hydroxidodioxidosulfate(1-) monohydrogentrioxosulfate xylitol (2R,3R,4S)-Pentane-1,2,3,4,5-pentaol (2R,3r,4S)-pentane-1,2,3,4,5-pentol 0 152.068 152.14580 A pentitol (five-carbon sugar alcohol) having meso-configuration, being derived from xylose by reduction of the carbonyl group. Beilstein:1720523 C5H12O5 CAS:87-99-0 CHEBI:10078 CHEBI:15328 CHEBI:17151 CHEBI:253147 CHEBI:27339 CHEBI:46522 CHEBI:60939 D-XYLITOL DrugBank:DB01904 Drug_Central:4604 Gmelin:82893 HEBKCHPVOIAQTA-SCDXWVJYSA-N HMDB:HMDB0002917 InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+ KEGG:C00379 KEGG:D00061 L-xylitol MetaCyc:XYLITOL OC[C@H](O)[C@@H](O)[C@H](O)CO PDBeChem:XYL PMID:11154411 PMID:11163479 PMID:12061879 PMID:15377394 PMID:16708791 PMID:16901854 PMID:17216457 PMID:17216458 PMID:17336832 PMID:17979222 PMID:18316079 PMID:20030329 PMID:22735334 PMID:22791282 PMID:23247825 PMID:23287496 PMID:23338824 PMID:23589387 PMID:23597921 PMID:23615861 PMID:23796483 PMID:23916161 PMID:23957303 PMID:24012734 PMID:24643482 PMID:25108762 Reaxys:1720523 Wikipedia:Xylitol Xylit Xylitol chebi_ontology meso-xylitol xylite xylitol nucleoside 5'-monophosphate 0 213.016 C5H10O7PR CHEBI:14676 CHEBI:17188 CHEBI:25607 CHEBI:7439 CHEBI:7653 CHEBI:7654 KEGG:C01329 KEGG:C02520 NMP Nucleoside monophosphate Nucleoside phosphate O[C@H]1[C@H]([*])O[C@H](COP(O)(O)=O)[C@H]1O chebi_ontology nucleoside monophosphate nucleoside monophosphates L-proline (-)-(S)-proline (-)-2-pyrrolidinecarboxylic acid (-)-proline (2S)-pyrrolidine-2-carboxylic acid (S)-2-carboxypyrrolidine (S)-2-pyrrolidinecarboxylic acid (S)-pyrrolidine-2-carboxylic acid 0 115.063 115.13050 2-Pyrrolidinecarboxylic acid Beilstein:80810 C5H9NO2 CAS:147-85-3 CHEBI:13154 CHEBI:17203 CHEBI:184637 CHEBI:21373 CHEBI:42067 CHEBI:45040 CHEBI:45100 CHEBI:45159 CHEBI:6286 DrugBank:DB00172 Drug_Central:4125 Gmelin:50152 HMDB:HMDB0000162 InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1 KEGG:C00148 KEGG:D00035 KNApSAcK:C00001388 L-(-)-proline L-Prolin L-Proline L-alpha-pyrrolidinecarboxylic acid L-proline L-pyrrolidine-2-carboxylic acid MetaCyc:PRO OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N P PDBeChem:PRO PMID:11076505 PMID:12770004 PMID:14975886 PMID:15576824 PMID:15838615 PMID:15894682 PMID:15973048 PMID:16033917 PMID:16190672 PMID:16501220 PMID:16656443 PMID:16657874 PMID:16668324 PMID:17127472 PMID:17608428 PMID:18551589 PMID:18802692 PMID:18973300 PMID:19215998 PMID:19580280 PMID:19656302 PMID:19688381 PMID:19811425 PMID:22139509 PMID:22201772 PMID:22451406 PMID:22475019 PMID:22482728 PMID:22491679 PMID:22770225 PROLINE Pyrrolidine in which the pro-S hydrogen at position 2 is substituted by a carboxylic acid group. L-Proline is the only one of the twenty DNA-encoded amino acids which has a secondary amino group alpha to the carboxyl group. It is an essential component of collagen and is important for proper functioning of joints and tendons. It also helps maintain and strengthen heart muscles. Reaxys:80810 Wikipedia:L-proline chebi_ontology prolina proline prolinum 3beta-hydroxy-Delta(5)-steroid 0 273.222 273.434 3beta-hydroxy Delta(5)-steroids 3beta-hydroxy-Delta(5)-steroids Any 3beta-hydroxy-steroid that contains a double bond between positions 5 and 6. C12C(C3C(C(CC3)*)(C)CC1)CC=C4C2(CC[C@@H](C4)O)C C19H29OR CHEBI:13608 CHEBI:136845 CHEBI:1722 CHEBI:20245 KEGG:C03836 MetaCyc:3b-hydroxy-D5-steroids a 3beta-hydroxy-Delta(5)-steroid chebi_ontology homocysteine 0 135.035 135.18580 2-Amino-4-mercaptobutyric acid 2-amino-4-sulfanylbutanoic acid A sulfur-containing amino acid consisting of a glycine core with a 2-mercaptoethyl side-chain. C4H9NO2S CHEBI:14408 CHEBI:17230 CHEBI:5751 FFFHZYDWPBMWHY-UHFFFAOYSA-N HMDB:HMDB0000742 Hcy Homocysteine InChI=1S/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7) KEGG:C05330 NC(CCS)C(O)=O PMID:11133260 PMID:16596805 PMID:18370634 Wikipedia:Homocysteine chebi_ontology homocysteine glucose 0 180.15588 An aldohexose used as a source of energy and metabolic intermediate. C6H12O6 CAS:50-99-7 CHEBI:14313 CHEBI:17234 CHEBI:24277 CHEBI:33929 CHEBI:5418 DL-glucose Glc Glucose Glukose KEGG:C00293 Wikipedia:Glucose chebi_ontology gluco-hexose glucose 7H-purine 0 120.044 120.11222 7H-purine Beilstein:3200 C5H4N4 CHEBI:14968 CHEBI:17258 CHEBI:8639 Gmelin:601779 HMDB:HMDB0001366 InChI=1S/C5H4N4/c1-4-5(8-2-6-1)9-3-7-4/h1-3H,(H,6,7,8,9) KDCGOANMDULRCW-UHFFFAOYSA-N KEGG:C15587 Purine Purine base Reaxys:3200 The 7H-tautomer of purine. c1ncc2[nH]cnc2n1 chebi_ontology propionate -1 73.029 73.07060 Beilstein:3587503 C3H5O2 CAS:72-03-7 CCC([O-])=O CH3-CH2-COO(-) CHEBI:14903 CHEBI:17272 CHEBI:26290 EtCO2 anion Gmelin:1820 InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)/p-1 KEGG:C00163 PMID:17951291 PMID:18375549 PMID:2647392 The conjugate base of propionic acid; a key precursor in lipid biosynthesis. UM-BBD_compID:c0277 XBDQKXXYIPTUBI-UHFFFAOYSA-M carboxylatoethane chebi_ontology ethanecarboxylate ethylformate metacetonate methylacetate propanate propanoate propanoate propanoic acid, ion(1-) propionate pseudoacetate 3-hydroxy-3-methylglutarate(2-) -2 160.037 160.12470 3-hydroxy-3-methylglutarate 3-hydroxy-3-methylpentanedioate A dicarboxylic acid dianion that results from the removal of a proton from both of the carboxylic acid groups of 3-hydroxy-3-methylglutaric acid. C6H8O5 CC(O)(CC([O-])=O)CC([O-])=O CHEBI:11813 CHEBI:17325 CHEBI:20042 InChI=1S/C6H10O5/c1-6(11,2-4(7)8)3-5(9)10/h11H,2-3H2,1H3,(H,7,8)(H,9,10)/p-2 KEGG:C03761 MetaCyc:CPD-547 NPOAOTPXWNWTSH-UHFFFAOYSA-L chebi_ontology nucleoside triphosphate 0 372.949 388.09680 C5H12O13P3R CHEBI:13411 CHEBI:14677 CHEBI:17326 CHEBI:25610 CHEBI:7442 CHEBI:7655 C[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O KEGG:C00201 NTP Nucleoside triphosphate chebi_ontology nucleoside triphosphates all-trans-retinol (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol 0 286.230 286.45160 A retinol in which all four exocyclic double bonds have E- (trans-) geometry. Alphalin Beilstein:403040 C20H30O CAS:11103-57-4 CAS:68-26-8 CC(\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C)=C/CO CHEBI:12783 CHEBI:17336 CHEBI:22349 CHEBI:8816 Chocola A DrugBank:DB00162 Drug_Central:2831 FPIPGXGPPPQFEQ-OVSJKPMPSA-N Gmelin:247497 InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+ KEGG:C00473 KEGG:C17276 KEGG:D00069 KEGG:D06543 LIPID_MAPS_instance:LMPR01090000 LIPID_MAPS_instance:LMPR01090001 PDBeChem:RTL Retinol Vitamin A Vitamin A1 Wikipedia:Vitamin_A all-trans-Retinol all-trans-retinol all-trans-retinyl alcohol all-trans-vitamin A alcohol chebi_ontology testosterone 0 17beta-Hydroxy-4-androsten-3-one 17beta-hydroxy-4-androsten-3-one 17beta-hydroxyandrost-4-en-3-one 288.209 288.42440 4-androsten-17beta-ol-3-one An androstanoid having 17beta-hydroxy and 3-oxo groups, together with unsaturation at C-4-C-5.. Androderm Beilstein:1915399 Beilstein:3653705 C19H28O2 CAS:58-22-0 CHEBI:15214 CHEBI:17347 CHEBI:26883 CHEBI:45798 CHEBI:9461 DrugBank:DB00624 Drug_Central:2607 Gmelin:538843 HMDB:HMDB0000234 InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1 KEGG:C00535 KEGG:D00075 KNApSAcK:C00003675 LIPID_MAPS_instance:LMST02020002 MUMGGOZAMZWBJJ-DYKIIFRCSA-N PDBeChem:TES PMID:10438974 PMID:11786693 PMID:18900503 PMID:24498482 Reaxys:1915399 TESTOSTERONE Testosteron Testosterone Wikipedia:Testosterone [H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@H](O)CC[C@@]21[H] chebi_ontology testosterona testosterone testosterone testosteronum sulfite -2 79.957 80.06420 CAS:14265-45-3 CHEBI:15139 CHEBI:17359 CHEBI:45548 Gmelin:1449 InChI=1S/H2O3S/c1-4(2)3/h(H2,1,2,3)/p-2 LSNNMFCWUKXFEE-UHFFFAOYSA-L O3S PDBeChem:SO3 SO3 SO3(2-) SULFITE ION Sulfite is an inorganic anion, which is the conjugate base of hydrogen sulfite. [O-]S([O-])=O [SO3](2-) chebi_ontology sulfite sulphite trioxidosulfate(2-) trioxosulfate(2-) trioxosulfate(IV) hypoxanthine 0 1,7-dihydro-6H-purin-6-one 136.039 136.11162 6(1H)-purinone 6-oxopurine 9H-purin-6(1H)-one A purine nucleobase that consists of purine bearing an oxo substituent at position 6. Beilstein:5811 C5H4N4O CAS:68-94-0 CHEBI:14431 CHEBI:17368 CHEBI:24762 CHEBI:43237 CHEBI:5841 DrugBank:DB04076 ECMDB:ECMDB00157 FDGQSTZJBFJUBT-UHFFFAOYSA-N Gmelin:464558 HMDB:HMDB0000157 HYPOXANTHINE Hyp Hypoxanthine InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10) KEGG:C00262 KNApSAcK:C00001502 MetaCyc:HYPOXANTHINE O=c1[nH]cnc2nc[nH]c12 PDBeChem:HPA PMID:14253484 PMID:22735334 PMID:23400363 PMID:23670363 Purine-6-ol Reaxys:5811 Wikipedia:Hypoxanthine YMDB:YMDB00555 chebi_ontology hypoxanthine purin-6(1H)-one (2S)-2-hydroxy monocarboxylic acid (2S)-2-hydroxy monocarboxylic acids (S)-2-Hydroxy acid (S)-2-Hydroxyalkanoic acid (S)-2-Hydroxycarboxylic acid (S)-2-Hydroxymonocarboxylic acid (S)-2-hydroxy acid 0 75.008 75.044 A 2-hydroxy monocarboxylic acid in which the carbon at position 2 has (S)-configuration. C([C@@H](O)*)(=O)O C2H3O3R CHEBI:11031 CHEBI:17375 CHEBI:18737 CHEBI:378 CHEBI:381 chebi_ontology cystine 0 240.024 240.30256 3,3'-disulfanediylbis(2-aminopropanoic acid) 3,3'-dithiobis(2-aminopropanoic acid) A sulfur-containing amino acid obtained by the oxidation of two cysteine molecules which are then linked via a disulfide bond. Beilstein:1728091 C6H12N2O4S2 CAS:923-32-0 CHEBI:14062 CHEBI:17376 CHEBI:23513 CHEBI:4052 Cystin Cystine Dicysteine Gmelin:83347 InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12) KEGG:C01420 LEVWYRKDKASIDU-UHFFFAOYSA-N NC(CSSCC(N)C(O)=O)C(O)=O PMID:18608550 PMID:24327171 PMID:24525029 PMID:24525030 Reaxys:1728091 Wikipedia:Cystine Zystin alpha-Diamino-beta-dithiolactic acid chebi_ontology cistina cystine porphobilinogen 0 226.095 226.22924 3-[5-(aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid A dicarboxylic acid that is pyrole bearing aminomethyl, carboxymethyl and 2-carboxyethyl substituents at positions 2, 3 and 4 respectively. Beilstein:220051 C10H14N2O4 CAS:487-90-1 CHEBI:14867 CHEBI:17381 CHEBI:26212 CHEBI:44832 CHEBI:8335 DrugBank:DB02272 HMDB:HMDB0000245 InChI=1S/C10H14N2O4/c11-4-8-7(3-10(15)16)6(5-12-8)1-2-9(13)14/h5,12H,1-4,11H2,(H,13,14)(H,15,16) KEGG:C00931 KNApSAcK:C00007339 MetaCyc:PORPHOBILINOGEN NCc1[nH]cc(CCC(O)=O)c1CC(O)=O PDBeChem:PBG PMID:21383008 PMID:21627493 PMID:22279024 PMID:22740490 PMID:22770225 PMID:22974111 Porphobilinogen QSHWIQZFGQKFMA-UHFFFAOYSA-N Reaxys:220051 Wikipedia:Porphobilinogen chebi_ontology valeric acid 0 1-butanecarboxylic acid 102.068 102.13170 A straight-chain saturated fatty acid containing five carbon atoms. Beilstein:969454 C5H10O2 CAS:109-52-4 CCCCC(O)=O CH3-[CH2]3-COOH CHEBI:113448 CHEBI:17418 CHEBI:27263 CHEBI:27264 CHEBI:43606 CHEBI:44803 CHEBI:7980 DrugBank:DB02406 Gmelin:26714 HMDB:HMDB0000892 InChI=1S/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7) KEGG:C00803 KNApSAcK:C00001208 LIPID_MAPS_instance:LMFA01010005 NQPDZGIKBAWPEJ-UHFFFAOYSA-N PDBeChem:PEI PENTANOIC ACID PMID:20507156 PPDB:3130 Pentanoate Pentanoic acid Reaxys:969454 Valerate Valerianic acid Valeriansaeure Valeric acid chebi_ontology n-BuCOOH n-Pentanoate n-Valeric acid n-pentanoic acid n-valeric acid pentanoic acid pentoic acid propylacetic acid valeric acid, normal methylmalonate(2-) -2 116.011 116.07216 A C4-dicarboxylate resulting from the removal of a proton from both carboxylic acid groups of methylmalonic acid. Beilstein:3904597 C4H4O4 CC(C([O-])=O)C([O-])=O CHEBI:14603 CHEBI:17453 CHEBI:25317 Gmelin:142212 InChI=1S/C4H6O4/c1-2(3(5)6)4(7)8/h2H,1H3,(H,5,6)(H,7,8)/p-2 KEGG:C02170 MetaCyc:CPD-546 Reaxys:3904597 ZIYVHBGGAOATLY-UHFFFAOYSA-L chebi_ontology methylmalonate methylmalonate dianion methylpropanedioate aldehyde 0 29.003 29.01800 A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group. Aldehyd Aldehyde CHEBI:13432 CHEBI:13753 CHEBI:13805 CHEBI:13806 CHEBI:17478 CHEBI:22291 CHEBI:2554 CHEBI:8750 CHOR KEGG:C00071 RC(=O)H RCHO [H]C([*])=O aldehido aldehidos aldehyde aldehydes aldehydes aldehydum an aldehyde chebi_ontology homocystine 0 268.055 268.356 4,4'-Dithiobis(2-aminobutyric acid) 4,4'-disulfanediylbis(2-aminobutanoic acid) 4,4'-dithiobis(2-aminobutyric acid) An organic disulfide obtained by oxidative dimerisation of homocysteine. C(C(CCSSCCC(C(=O)O)N)N)(O)=O C8H16N2O4S2 CAS:462-10-2 CHEBI:14409 CHEBI:17485 CHEBI:24611 CHEBI:5752 HMDB:HMDB0000575 Homocystine InChI=1S/C8H16N2O4S2/c9-5(7(11)12)1-3-15-16-4-2-6(10)8(13)14/h5-6H,1-4,9-10H2,(H,11,12)(H,13,14) KEGG:C01817 PMID:11592966 PMID:11896744 Reaxys:1728581 ZTVZLYBCZNMWCF-UHFFFAOYSA-N chebi_ontology 3',5'-cyclic AMP 0 3',5'-Cyclic AMP 329.053 329.20614 A 3',5'-cyclic purine nucleotide having having adenine as the nucleobase. ADENOSINE-3',5'-CYCLIC-MONOPHOSPHATE Adenosine 3',5'-cyclic phosphate Adenosine 3',5'-phosphate Beilstein:52645 C10H12N5O6P CAS:60-92-4 CHEBI:11673 CHEBI:1325 CHEBI:17489 CHEBI:19827 CHEBI:41588 Cyclic AMP Cyclic adenylic acid DrugBank:DB02527 HMDB:HMDB0000058 IVOMOUWHDPKRLL-KQYNXXCUSA-N InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1 KEGG:C00575 KNApSAcK:C00001497 MetaCyc:CAMP Nc1ncnc2n(cnc12)[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1O PDBeChem:CMP PMID:16295522 PMID:18372334 PMID:22770225 Reaxys:52645 Wikipedia:Cyclic_AMP adenosine 3',5'-(hydrogen phosphate) adenosine 3',5'-cyclic monophosphate cAMP chebi_ontology alditol (CH2O)nC2H6O2 0 A carbohydrate that is an acyclic polyol having the general formula HOCH2[CH(OH)]nCH2OH (formally derivable from an aldose by reduction of the carbonyl group). Alditol CHEBI:13754 CHEBI:17522 CHEBI:22298 CHEBI:2556 Glycitol KEGG:C00717 Sugar alcohol Wikipedia:Glycerin alditol alditols chebi_ontology hydrogencarbonate -1 60.993 61.01684 Acid carbonate BICARBONATE ION BVKZGUZCCUSVTD-UHFFFAOYSA-M Beilstein:3903504 Bicarbonate CAS:71-52-3 CHEBI:13363 CHEBI:17544 CHEBI:22863 CHEBI:40961 CHEBI:5589 CHO3 Gmelin:49249 HCO3(-) HCO3- HMDB:HMDB0000595 Hydrogencarbonate InChI=1S/CH2O3/c2-1(3)4/h(H2,2,3,4)/p-1 KEGG:C00288 MetaCyc:HCO3 OC([O-])=O PDBeChem:BCT PMID:17215880 PMID:17505962 PMID:28732801 PMID:29150416 PMID:29460248 PMID:29466234 PMID:4208463 The carbon oxoanion resulting from the removal of a proton from carbonic acid. Wikipedia:Bicarbonate [CO2(OH)](-) chebi_ontology hydrogen carbonate hydrogen(trioxidocarbonate)(1-) hydrogencarbonate hydrogencarbonate(1-) hydrogentrioxocarbonate(1-) hydrogentrioxocarbonate(IV) hydroxidodioxidocarbonate(1-) 5-aminolevulinic acid 0 131.058 131.12990 5-ALA 5-Amino-4-oxopentanoate 5-Amino-4-oxovaleric acid 5-Aminolevulinate 5-amino-4-oxopentanoic acid Beilstein:1759139 C5H9NO3 CAS:106-60-5 CHEBI:17549 CHEBI:2034 CHEBI:20547 DrugBank:DB00855 Drug_Central:166 HMDB:HMDB0001149 InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9) KEGG:C00430 KEGG:D07567 KNApSAcK:C00007378 LINCS:LSM-5677 NCC(=O)CCC(O)=O PMID:11303952 PMID:15756058 PMID:15996585 PMID:18982627 PMID:19378778 PMID:22378066 PMID:22700502 PMID:23242333 PMID:23291627 PMID:23299429 PMID:23307195 PMID:23339045 PMID:23360321 PMID:7890117 Reaxys:1759139 The simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp. Wikipedia:Aminolevulinic_acid ZGXJTSGNIOSYLO-UHFFFAOYSA-N aminolevulinic acid chebi_ontology dALA delta-ALA delta-aminolevulinic acid O-phosphoethanolamine 0 141.019 141.06302 2-amino-ethanol dihydrogen phosphate 2-amino-ethanol phosphate 2-aminoethyl dihydrogen phosphate Beilstein:1758916 C2H8NO4P CAS:1071-23-4 CHEBI:12694 CHEBI:14224 CHEBI:14814 CHEBI:17553 CHEBI:23980 CHEBI:44681 CHEBI:4881 DrugBank:DB01738 EAP Ethanolamine phosphate Gmelin:663022 InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6) KEGG:C00346 MetaCyc:PHOSPHORYL-ETHANOLAMINE NCCOP(O)(O)=O O-Phosphoethanolamine O-Phosphorylethanolamine O-phosphocolamine OPE PDBeChem:OPE PE PEA PETN PMID:1112054 PMID:7791524 Phosphoethanolamine Reaxys:1758916 SUHOOTKUPISOBE-UHFFFAOYSA-N The ethanolamine mono-ester of phosphoric acid, and a metabolite of phospholipid metabolism. This phosphomonoester shows strong structural similarity to the inhibitory neurotransmitter GABA, and is decreased in post-mortem Alzheimer's disease brain. chebi_ontology colamine phosphate colamine phosphoric acid colaminphosphoric acid ethanolamine O-phosphate ethanolamine acid phosphate mono(2-aminoethyl) phosphate monoaminoethyl phosphate pEtN phosphonoethanolamine phosphoric acid 2-aminoethyl phenyl ester phosphoryl-ethanolamine L-cysteine (2R)-2-amino-3-mercaptopropanoic acid (2R)-2-amino-3-sulfanylpropanoic acid (R)-2-amino-3-mercaptopropanoic acid 0 121.020 121.15800 An optically active form of cysteine having L-configuration. Beilstein:1721408 C C3H7NO2S CAS:52-90-4 CHEBI:13095 CHEBI:17561 CHEBI:21261 CHEBI:41227 CHEBI:41700 CHEBI:41768 CHEBI:41781 CHEBI:41811 CHEBI:6207 CYSTEINE Cys DrugBank:DB00151 Drug_Central:769 E 920 E-920 E920 ECMDB:ECMDB00574 FREE CYSTEINE Gmelin:49991 HMDB:HMDB0000574 InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1 KEGG:C00097 KEGG:D00026 KNApSAcK:C00001351 L-2-Amino-3-mercaptopropionic acid L-Cystein L-Cysteine L-Zystein L-cysteine MetaCyc:CYS N[C@@H](CS)C(O)=O PDBeChem:CYS PMID:11732994 PMID:13761469 PMID:22735334 Reaxys:1721408 Wikipedia:Cysteine XUJNEKJLAYXESH-REOHCLBHSA-N YMDB:YMDB00046 chebi_ontology uracil 0 112.027 112.08684 2,4(1H,3H)-pyrimidinedione 2,4-Dioxopyrimidine 2,4-Pyrimidinedione A common and naturally occurring pyrimidine nucleobase in which the pyrimidine ring is substituted with two oxo groups at positions 2 and 4. Found in RNA, it base pairs with adenine and replaces thymine during DNA transcription. Beilstein:606623 C4H4N2O2 CAS:66-22-8 CHEBI:15288 CHEBI:17568 CHEBI:27210 CHEBI:46375 CHEBI:9882 DrugBank:DB03419 Gmelin:2896 HMDB:HMDB0000300 ISAKRJDGNUQOIC-UHFFFAOYSA-N InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8) KEGG:C00106 KEGG:D00027 KNApSAcK:C00001513 MetaCyc:URACIL O=c1cc[nH]c(=O)[nH]1 PDBeChem:URA PMID:11279060 PMID:12855717 PMID:15274295 PMID:16834123 PMID:17439666 PMID:18533995 PMID:18815805 PMID:19175333 PMID:22020693 PMID:22074393 PMID:22120518 PMID:22171528 PMID:22237209 PMID:22299724 PMID:22356544 PMID:22447672 PMID:22483865 PMID:22567906 PMID:22685418 PMID:3654008 Reaxys:606623 U URACIL Ura Uracil Urazil Wikipedia:Uracil chebi_ontology pyrimidine-2,4(1H,3H)-dione uracil toluene 0 92.063 92.13842 Beilstein:635760 C7H8 CAS:108-88-3 CHEBI:15248 CHEBI:17578 CHEBI:27022 CHEBI:44023 CHEBI:9624 Cc1ccccc1 DrugBank:DB01900 Gmelin:2456 InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3 KEGG:C01455 PDBeChem:MBN PMID:11182169 PMID:11314682 PMID:11846266 PMID:11991009 PMID:12062755 PMID:12213539 PMID:12237258 PMID:12784113 PMID:12876426 PMID:14512097 PMID:14559343 PMID:14605898 PMID:15015825 PMID:15019953 PMID:15119846 PMID:15193425 PMID:15542760 PMID:15567510 PMID:15695158 PMID:15796064 PMID:16316648 PMID:16348226 PMID:16601996 PMID:17145141 PMID:17175136 PMID:17497535 PMID:17725881 PMID:18397809 PMID:18832024 PMID:19261054 PMID:19384711 PMID:19429395 PMID:19635754 PMID:19765629 PMID:19825861 PMID:19928203 PMID:19969016 PMID:20347282 PMID:20837561 PMID:21430649 PMID:21655021 PMID:21731073 PMID:21802510 PMID:21840036 Reaxys:635760 TOLUENE The simplest member of the class toluenes consisting of a benzene core which bears a single methyl substituent. Toluen Toluene Toluol UM-BBD_compID:c0114 Wikipedia:Toluene YXFVVABEGXRONW-UHFFFAOYSA-N chebi_ontology methylbenzene phenylmethane toluene beta-carotene 0 1,1'-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl]bis(2,6,6-trimethylcyclohexene) 536.438 536.87264 A cyclic carotene obtained by dimerisation of all-trans-retinol. A strongly-coloured red-orange pigment abundant in plants and fruit and the most active and important provitamin A carotenoid. BETA-CAROTENE Beilstein:1917416 C40H56 CAS:7235-40-7 CC(\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C CHEBI:10355 CHEBI:12392 CHEBI:17579 CHEBI:22834 CHEBI:40987 COMe:MOL000093 Drug_Central:345 HMDB:HMDB0000561 InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+ KEGG:C02094 KEGG:D03101 KNApSAcK:C00000919 LIPID_MAPS_instance:LMPR01070000 LIPID_MAPS_instance:LMPR01070001 MetaCyc:CPD1F-129 OENHQHLEOONYIE-JLTXGRSLSA-N PDBeChem:BCR PMID:11171227 PMID:11182771 PMID:11332447 PMID:11359610 PMID:11382814 PMID:11567548 PMID:11677037 PMID:11714348 PMID:11962062 PMID:12081834 PMID:12891827 PMID:14658721 PMID:14764912 PMID:14976384 PMID:14997360 PMID:15113067 PMID:15333155 PMID:15695449 PMID:15789045 PMID:15909543 PMID:15949680 PMID:15949683 PMID:16036331 PMID:16087476 PMID:16338959 PMID:16563447 PMID:17004738 PMID:17625873 PMID:17708644 PMID:17851775 PMID:18429004 PMID:18766464 PMID:18767554 PMID:18794175 PMID:19480350 PMID:19574250 PMID:19669835 PMID:19703237 PMID:19852884 PMID:19888275 PMID:19896667 PMID:19937581 PMID:20074992 PMID:20515074 PMID:22079732 PMID:22309480 PMID:22428124 PMID:22489215 PMID:22534340 PMID:22575730 Reaxys:1917416 Wikipedia:Beta_Carotene all-trans-beta-carotene beta,beta-carotene beta-Carotene beta-Karotin chebi_ontology octane 0 114.141 114.22852 A straight chain alkane composed of 8 carbon atoms. Beilstein:1696875 C8H18 CAS:111-65-9 CCCCCCCC CH3-[CH2]6-CH3 CHEBI:14680 CHEBI:17590 CHEBI:25465 CHEBI:25645 CHEBI:44621 CHEBI:7723 DrugBank:DB02440 Gmelin:82412 HMDB:HMDB0001485 InChI=1S/C8H18/c1-3-5-7-8-6-4-2/h3-8H2,1-2H3 KEGG:C01387 LIPID_MAPS_instance:LMFA11000002 MetaCyc:CPD-148 N-OCTANE Octane Oktan PDBeChem:OCT PMID:11255151 PMID:24354334 Reaxys:1696875 TVMXDCGIABBOFY-UHFFFAOYSA-N UM-BBD_compID:c0044 Wikipedia:Octane chebi_ontology n-Octane n-Oktan octane D-aldohexose Any D-aldose having a chain of six carbon atoms in the molecule. C6H12O6 CHEBI:12990 CHEBI:17608 CHEBI:21038 D-aldohexose D-aldohexoses chebi_ontology (3,4-dihydroxyphenyl)acetate (3,4-dihydroxyphenyl)acetate -1 167.034 167.13878 3,4-dihydroxyphenylacetate A dihydroxy monocarboxylic acid anion that is the conjugate base of (3,4-dihydroxyphenyl)acetic acid, arising from deprotonation of the carboxy group. C8H7O4 CFFZDZCDUFSOFZ-UHFFFAOYSA-M CHEBI:11696 CHEBI:11697 CHEBI:17612 CHEBI:19889 InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)/p-1 KEGG:C01161 Oc1ccc(CC([O-])=O)cc1O UM-BBD_compID:c0272 chebi_ontology homoprotocatechuate sphingomyelin d18:1 0 491.325 491.622 Any sphingomyelin having sphingosine as the sphingoid component. C24H48N2O6PR CHEBI:15101 CHEBI:17636 CHEBI:26740 CHEBI:9223 KEGG:C00550 LIPID_MAPS_instance:LMSP03010000 N-acyl-4-sphingenyl-1-O-phosphorylcholines O=P(OCC[N+](C)(C)C)(OC[C@H](NC(*)=O)[C@@H](/C=C/CCCCCCCCCCCCC)O)[O-] PMID:3196084 Sphingomyelin ceramide phosphocholine chebi_ontology sphingomyelin sphingomyelins cortisol (11beta)-11,17,21-trihydroxypregn-4-ene-3,20-dione 0 11beta,17,21-trihydroxypregn-4-ene-3,20-dione 11beta,17alpha,21-Trihydroxy-4-pregnene-3,20-dione 11beta,17alpha,21-trihydroxy-4-pregnene-3,20-dione 11beta-hydrocortisone 17-hydroxycorticosterone 362.209 362.45990 4-pregnen-11beta,17alpha,21-triol-3,20-dione A 17alpha-hydroxy-C21-steroid that is pregn-4-ene substituted by oxo groups at positions 3 and 20 and hydroxy groups at positions 11, 17 and 21. Cortisol is a corticosteroid hormone or glucocorticoid produced by zona fasciculata of the adrenal cortex, which is a part of the adrenal gland. It is usually referred to as the "stress hormone" as it is involved in response to stress and anxiety, controlled by corticotropin-releasing hormone (CRH). It increases blood pressure and blood sugar, and reduces immune responses Beilstein:1354819 C21H30O5 CAS:50-23-7 CHEBI:14023 CHEBI:17650 CHEBI:24633 CHEBI:3893 CHEBI:58221 Cortisol DrugBank:DB00741 Drug_Central:1388 Hydrocortisone InChI=1S/C21H30O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-16,18,22,24,26H,3-8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1 JYGXADMDTFJGBT-VWUMJDOOSA-N KEGG:C00735 KEGG:D00088 Kendall's compound F LINCS:LSM-5980 LIPID_MAPS_instance:LMST02030001 PDBeChem:HCY PMID:10438974 PMID:2268561 Patent:US2602769 Reichstein's substance M Wikipedia:Hydrocortisone [H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])[C@@H](O)C[C@@]1(C)[C@@]2([H])CC[C@]1(O)C(=O)CO chebi_ontology cortisol hidrocortisona hydrocortisone hydrocortisonum ribonucleoside diphosphate 0 292.983 293.083 C5H11O10P2R CHEBI:15046 CHEBI:17668 CHEBI:26557 CHEBI:8845 KEGG:C03723 Ribonucleoside diphosphate chebi_ontology ribonucleoside diphosphate ribonucleoside diphosphates (S)-nicotine (-)-3-(1-Methyl-2-pyrrolidyl)pyridine (-)-3-(N-Methylpyrrolidino)pyridine (-)-nicotine (R)-3-(1-Methyl-2-pyrrolidinyl)pyridine (S)-(-)-nicotine (S)-3-(1-methylpyrrolidin-2-yl)pyridine (S)-3-(N-methylpyrrolidin-2-yl)pyridine (S)-Nicotine (S)-nicotine 0 1-Methyl-2-(3-pyridyl)pyrrolidine 162.116 162.232 3-(1-Methyl-2-pyrollidinyl)pyridine 3-(1-Methylpyrrolidin-2-yl)pyridine 3-(2-(N-methylpyrrolidinyl))pyridine 3-(N-methylpyrollidino)pyridine 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum. BPDB:485 Beilstein:3604351 Beilstein:82109 C10H14N2 C=1C=C([C@]2(N(CCC2)C)[H])C=NC1 CAS:54-11-5 CHEBI:14653 CHEBI:17688 CHEBI:25536 CHEBI:44268 CHEBI:7562 DrugBank:DB00184 Drug_Central:1920 HMDB:HMDB0001934 InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-/m0/s1 KEGG:C00745 KEGG:D03365 KNApSAcK:C00002057 L(-)-nicotine L-3-(1-Methyl-2-pyrrolidyl)pyridine L-Nicotine LINCS:LSM-2093 MetaCyc:NICOTINE Nicotine PDBeChem:NCT PMID:11209966 PMID:11322615 PMID:11406005 PMID:11719700 PMID:11768184 PMID:11821649 PMID:11851194 PMID:12575980 PMID:12692774 PMID:12769614 PMID:12850578 PMID:12971663 PMID:13590907 PMID:14674846 PMID:14761239 PMID:14975706 PMID:15019421 PMID:15027713 PMID:15251917 PMID:15276225 PMID:15380834 PMID:15502843 PMID:15527885 PMID:15707677 PMID:15734728 PMID:15826609 PMID:15894687 PMID:15902919 PMID:15960296 PMID:15963341 PMID:16059663 PMID:16212709 PMID:16333621 PMID:16370520 PMID:16496293 PMID:17023324 PMID:17206646 PMID:17292347 PMID:17350101 PMID:17498763 PMID:17504235 PMID:17525204 PMID:17560039 PMID:17683794 PMID:18380035 PMID:18383130 PMID:18490768 PMID:18683238 PMID:18685152 PMID:18805442 PMID:18922921 PMID:19100291 PMID:19100331 PMID:19287496 PMID:19389046 PMID:19448649 PMID:19465085 PMID:19850423 PMID:19954906 PMID:21521420 PMID:21636612 PMID:21822688 PMID:21945235 PMID:21947355 PMID:22030716 PMID:22129149 PMID:22218403 PMID:22265518 PMID:22331007 PMID:22377934 PMID:22459798 PMID:22529223 PMID:22530136 PMID:27951416 PMID:28187919 PMID:28391535 PMID:28574230 PMID:28641297 PMID:28678400 PMID:28683421 PMID:28686840 PMID:28698187 PMID:28700952 PMID:28704277 PMID:28710519 PMID:28711472 PMID:28714396 PMID:28718768 PMID:28718828 PMID:28726253 PMID:28735272 Reaxys:82109 SNICXCGAKADSCV-JTQLQIEISA-N Wikipedia:Nicotine chebi_ontology sphingosine-1-phosphocholine (2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl 2-(trimethylammonio)ethyl phosphate 0 464.338 464.61930 A phosphosphingolipid consisting of sphingosine having a phosphocholine moiety attached to its primary hydroxyl group. Beilstein:7342520 C23H49N2O5P CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP([O-])(=O)OCC[N+](C)(C)C CHEBI:15103 CHEBI:17689 CHEBI:26744 CHEBI:9226 InChI=1S/C23H49N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3/b18-17+/t22-,23+/m0/s1 JLVSPVFPBBFMBE-HXSWCURESA-N LIPID_MAPS_instance:LMSP01060001 PMID:14741383 chebi_ontology sphing-4-enine-1-phosphocholine sphingosylphosphocholine betaine sphingosylphosphorylcholine glycerol 0 1,2,3-Propanetriol 1,2,3-Trihydroxypropane 92.047 92.09382 A triol with a structure of propane substituted at positions 1, 2 and 3 by hydroxy groups. Beilstein:635685 C3H8O3 CAS:56-81-5 CHEBI:131422 CHEBI:14334 CHEBI:17754 CHEBI:24351 CHEBI:42998 CHEBI:5448 DrugBank:DB04077 Drug_Central:1316 ECMDB:ECMDB00131 GLYCEROL Glycerin Glyceritol Glycerol Glyzerin Gmelin:26279 Gro HMDB:HMDB0000131 InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2 KEGG:C00116 KEGG:D00028 KNApSAcK:C00001163 LINCS:LSM-37180 MetaCyc:GLYCEROL OCC(O)CO Oelsuess PDB:2AJS PDB:2D03 PDBeChem:GOL PEDCQBHIVMGVHV-UHFFFAOYSA-N PMID:11958517 PMID:12672239 PMID:12689633 PMID:14559393 PMID:14563847 PMID:15342117 PMID:15786693 PMID:16244855 PMID:16258193 PMID:16319039 PMID:16349488 PMID:16651733 PMID:16664750 PMID:16901854 PMID:17336832 PMID:17439666 PMID:17979222 PMID:19184438 PMID:19231894 PMID:19460032 PMID:19548674 PMID:19795216 PMID:19956799 PMID:22705534 PMID:23562176 PMID:23747440 PMID:24643482 PMID:25108762 PMID:7031247 PMID:7392035 PPDB:1317 Propanetriol Reaxys:635685 Trihydroxypropane UM-BBD_compID:c0066 Wikipedia:Glycerol YMDB:YMDB00283 chebi_ontology glycerine glycerol glycerol glycerolum glycyl alcohol propane-1,2,3-triol cystathionine 0 2-amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid 222.067 222.26314 A modified amino acid generated by enzymic means from homocysteine and serine. C7H14N2O4S CAS:535-34-2 CHEBI:14059 CHEBI:17755 CHEBI:4048 Cystathionine DL-Cystathionine ILRYLPWNYFXEMH-UHFFFAOYSA-N InChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13) KEGG:C00542 NC(CCSCC(N)C(O)=O)C(O)=O PMID:12907234 PMID:15033753 PMID:22212096 PMID:22264337 Reaxys:2416815 S-(2-amino-2-carboxyethyl)homocysteine chebi_ontology cystathione cystathionine cholesta-5,7-dien-3beta-ol (3beta)-cholesta-5,7-dien-3-ol 0 384.339 384.63766 5,7-cholestadien-3-beta-ol 5,7-cholestadien-3beta-ol 7-Dehydrocholesterol Beilstein:2224615 C27H44O CAS:434-16-2 CHEBI:13981 CHEBI:17759 CHEBI:23181 CHEBI:3658 Cholesta-5,7-dien-3beta-ol Gmelin:893079 InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1 KEGG:C01164 KNApSAcK:C00023747 LIPID_MAPS_instance:LMST01010069 Provitamin D3 UCTLRSWJYQTBFZ-DDPQNLDTSA-N [H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C chebi_ontology cholesta-5,7-dien-3beta-ol ceramide 0 100.040 100.09590 C4H6NO2R3 CHEBI:12487 CHEBI:13954 CHEBI:17761 CHEBI:23074 CHEBI:7242 Cer Ceramide Ceramides (N-acyl-sphingoid bases) are a major subclass of sphingoid base derivatives with an amide-linked fatty acid. The fatty acids are typically saturated or monounsaturated with chain lengths from 14 to 26 carbon atoms; the presence of a hydroxyl group on carbon 2 is fairly common. Ceramides are generally precursors of more complex sphingolipids. In the illustrated generalised structure, R(1) = OH, OX (where X = acyl, glycosyl, phosphate, phosphonate, etc.), or H. KEGG:C00195 LIPID_MAPS_class:LMSP02 N-acylated sphingoid O[C@H]([*])[C@H](C[*])NC([*])=O PMID:7542630 Wikipedia:Ceramide a ceramide ceramides chebi_ontology methanol 0 32.026 32.04186 Beilstein:1098229 CAS:67-56-1 CH3OH CH4O CHEBI:14588 CHEBI:17790 CHEBI:25227 CHEBI:44080 CHEBI:44553 CHEBI:6816 CO Gmelin:449 HMDB:HMDB0001875 InChI=1S/CH4O/c1-2/h2H,1H3 KEGG:C00132 KEGG:D02309 METHANOL MeOH MetaCyc:METOH Methanol Methyl alcohol Methylalkohol OKKJLVBELUTLKV-UHFFFAOYSA-N PDBeChem:MOH PMID:11141607 PMID:11430978 PMID:11489599 PMID:11680737 PMID:11684179 PMID:14012711 PMID:14678513 PMID:14760634 PMID:15172721 PMID:15906011 PMID:16705261 PMID:17451998 PMID:17733096 PMID:19064074 PMID:19850112 PMID:20314698 Reaxys:1098229 The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group. UM-BBD_compID:c0132 Wikipedia:Methanol carbinol chebi_ontology methanol spirit of wood wood alcohol wood naphtha wood spirit serine 0 105.043 105.09262 2-Amino-3-hydroxypropionic acid 2-amino-3-hydroxypropanoic acid 3-Hydroxyalanine An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group. Beilstein:1721402 C3H7NO3 CAS:302-84-1 CHEBI:15081 CHEBI:17822 CHEBI:26648 CHEBI:9116 Gmelin:26429 InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7) KEGG:C00716 KNApSAcK:C00001393 MTCFGRXMJLQNBG-UHFFFAOYSA-N NC(CO)C(O)=O Reaxys:1721402 Serin Serine Wikipedia:Serine chebi_ontology serine calcitriol (1S,3R,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol (1S,3R,5Z,7E)-9,10-secocholesta-5,7,10-triene-1,3,25-triol (1alpha,3beta,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol (5Z,7E)-(1S,3R)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol 0 1,25-DHCC 1-alpha-25-Dihydroxyvitamin D3 1alpha,25(OH)2D3 1alpha,25-dihydroxycholecalciferol 1alpha,25-dihydroxyvitamin D3 416.329 416.63646 5-{2-[1-(5-HYDROXY-1,5-DIMETHYL-HEXYL)-7A-METHYL-OCTAHYDRO-INDEN-4-YLIDENE]-ETHYLIDENE}-4-METHYLENE-CYCLOHEXANE-1,3-DIOL A hydroxycalciol that is calcidiol in which the pro-S hydrogen of calcidiol is replaced by a hydroxy group. It is the active form of vitamin D3, produced fom calciol via hydoxylation in the liver to form calcidiol, which is subsequently oxidised in the kidney to give calcitriol. Beilstein:2227647 C27H44O3 CAS:32222-06-3 CHEBI:13932 CHEBI:17823 CHEBI:19209 CHEBI:3307 CHEBI:46435 Calcijex Calcitriol Decostriol DrugBank:DB00136 Drug_Central:466 GMRQFYUYWCNGIN-NKMMMXOESA-N InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1 KEGG:C01673 KEGG:D00129 LIPID_MAPS_instance:LMST03020258 MetaCyc:CALCITRIOL PDBeChem:VDX PMID:10217585 PMID:15928596 PMID:19429426 PMID:20599255 PMID:22905919 PMID:23103122 PMID:23144765 PMID:6687801 Reaxys:2227647 Rocaltrol Wikipedia:Calcitriol [H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C)[C@H](C)CCCC(C)(C)O calcitriol calcitriol calcitriolum chebi_ontology triglyceride 0 173.009 173.10030 C6H5O6R3 CHEBI:15255 CHEBI:17855 CHEBI:27085 CHEBI:9664 KEGG:C00422 LIPID_MAPS_class:LMGL0301 Triacylglycerol Triglycerid Triglyceride Triglyzerid [*]C(=O)OCC(COC([*])=O)OC([*])=O a triacylglycerol chebi_ontology triacylglycerols triglycerides triglycerides glutaric acid 0 1,3-Propanedicarboxylic acid 1,5-pentanedioic acid 132.042 132.11462 An alpha,omega-dicarboxylic acid that is a linear five-carbon dicarboxylic acid. Beilstein:1209725 C5H8O4 CAS:110-94-1 CHEBI:17859 CHEBI:24330 CHEBI:43097 CHEBI:5434 DrugBank:DB03553 GLUTARIC ACID Glutaric acid Glutarsaeure Gmelin:26809 HMDB:HMDB0000661 InChI=1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9) JFCQEDHGNNZCLN-UHFFFAOYSA-N KEGG:C00489 KNApSAcK:C00001184 LIPID_MAPS_instance:LMFA01170046 OC(=O)CCCC(O)=O PDBeChem:GUA PMID:24297153 PMID:24587932 PMID:24900967 Pentanedioic acid Reaxys:1209725 Wikipedia:Glutaric_acid chebi_ontology pentanedioic acid hydrogen chloride 0 35.977 36.46064 A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms. CAS:7647-01-0 CHEBI:13364 CHEBI:17883 CHEBI:24635 CHEBI:5590 Chlorwasserstoff ClH Cl[H] Drug_Central:4568 Gmelin:322 HCl HCl HMDB:HMDB0002306 Hydrochloride Hydrogen chloride Hydrogenchlorid InChI=1S/ClH/h1H KEGG:C01327 KEGG:D02057 MetaCyc:HCL PMID:15823700 PMID:17492841 PMID:22804993 Reaxys:1098214 VEXZGXHMUGYJMC-UHFFFAOYSA-N Wasserstoffchlorid Wikipedia:HCl Wikipedia:Hydrochloric_acid [HCl] chebi_ontology chlorane chloridohydrogen chlorure d'hydrogene cloruro de hidrogeno hydrochloric acid hydrogen chloride donor A molecular entity that can transfer ("donate") an electron, a pair of electrons, an atom or a group to another molecular entity. CHEBI:14202 CHEBI:17891 CHEBI:4697 Donator Donor KEGG:C01351 chebi_ontology donneur donor (2R)-2-hydroxy monocarboxylic acid (2R)-2-hydroxy monocarboxylic acids (2R)-Hydroxy-carboxylate (R)-2-Hydroxyacid (R)-2-Hydroxycarboxylic acid (R)-2-hydroxyacid 0 75.008 75.04340 A 2-hydroxy monocarboxylic acid having (2R)-configuration. C2H3O3R CHEBI:10973 CHEBI:17893 CHEBI:18649 CHEBI:309 KEGG:C02489 KEGG:C15487 O[C@H]([*])C(O)=O chebi_ontology all-trans-retinal (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal 0 284.214 284.43572 A retinal in which all four exocyclic double bonds have E- (trans-) geometry. C20H28O CAS:116-31-4 CHEBI:12776 CHEBI:17898 CHEBI:22348 CHEBI:8814 HMDB:HMDB0001358 InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+ KEGG:C00376 LIPID_MAPS_instance:LMPR01090002 MetaCyc:RETINAL NCYCYZXNIZJOKI-OVSJKPMPSA-N PDBeChem:RET PMID:12168520 PMID:15500295 PMID:15686550 PMID:15724104 PMID:16054134 PMID:16128572 PMID:17326003 PMID:21447403 PMID:21995425 PMID:22162152 PMID:22198730 PMID:22220722 PMID:22417174 PMID:22428905 PMID:22431612 PMID:22515697 PMID:22529810 PMID:22559266 PMID:22621924 PMID:22841964 PMID:22879987 Retinal Retinene Vitamin A aldehyde Wikipedia:Retinal [H]C(=O)\C=C(C)\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C all-trans-Retinal all-trans-Retinene all-trans-Vitamin A aldehyde all-trans-retinal all-trans-retinaldehyde chebi_ontology retinaldehyde D-glucitol (-)-sorbitol (2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol 0 182.079 182.17176 Beilstein:1721899 Beilstein:4656395 C6H14O6 CAS:50-70-4 CHEBI:12954 CHEBI:13020 CHEBI:17924 CHEBI:21091 CHEBI:4246 CHEBI:45559 D-(-)-sorbitol D-Glucitol D-SORBITOL D-Sorbit D-Sorbitol D-glucitol D-sorbitol DrugBank:DB01638 Drug_Central:2462 E 420 E-420 E420 FBPFZTCFMRRESA-JGWLITMVSA-N G-ol Glc-ol Gmelin:83162 HMDB:HMDB0000247 InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1 KEGG:C00794 KEGG:D00096 KNApSAcK:C00001173 L-Gulitol OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO PDBeChem:SOR PMID:16901854 PMID:17336832 PMID:17979222 PMID:19443021 PMID:19695255 PMID:22735334 PMID:22878210 PMID:23683321 PMID:24643482 PMID:25108762 PMID:25568069 PPDB:1320 Reaxys:1721899 The D-enantiomer of glucitol (also known as D-sorbitol). Wikipedia:Sorbitol chebi_ontology calcidiol (3S,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol (3S,5Z,7E)-9,10-secocholesta-5,7,10-triene-3,25-diol (3beta,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol (5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol 0 25(OH)D3 25-Hydroxyvitamin D3 25-hydroxycholecalciferol 25-hydroxyvitamin D3 3-{2-[1-(5-HYDROXY-1,5-DIMETHYL-HEXYL)-7A-METHYL-OCTAHYDRO-INDEN-4-YLIDENE]-ETHYLIDENE}-4-METHYLENE-CYCLOHEXANOL 400.334 400.63706 A hydroxycalciol that is calciol in which the hydrogen at position 25 has been replaced by a hydroxy group. A prehormone resulting from the oxidation of calciol in the liver, it is further hydroxylated in the kidney to give calcitriol, the active form of vitamin D3. Beilstein:4270041 C27H44O2 CAS:19356-17-3 CHEBI:13931 CHEBI:17933 CHEBI:19815 CHEBI:3304 CHEBI:46387 Calcidiol Calcifediol Calcifediol anhydrous DrugBank:DB00146 Drug_Central:464 InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23+,24-,25+,27-/m1/s1 JWUBBDSIWDLEOM-DTOXIADCSA-N KEGG:C01561 LIPID_MAPS_instance:LMST03020246 PDBeChem:VDY PMID:16549446 PMID:18689406 PMID:22487892 PMID:22536761 PMID:23090338 PMID:23566108 PMID:9080330 Rayaldee Reaxys:4270041 Wikipedia:Calcifediol [H][C@@]1(CC[C@]2([H])[C@]1(C)CCC\C2=C/C=C1/C[C@@H](O)CCC1=C)[C@H](C)CCCC(C)(C)O calcidiol calcifediol calcifediolum chebi_ontology butyrate -1 1-butanoate 1-butyrate 1-propanecarboxylate 87.045 87.09718 A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group. Beilstein:3601060 C4H7O2 CAS:461-55-2 CCCC([O-])=O CH3-[CH2]2-COO(-) CHEBI:13924 CHEBI:17968 CHEBI:22946 FERIUCNNQQJTOY-UHFFFAOYSA-M Gmelin:324289 InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)/p-1 KEGG:C00246 MetaCyc:BUTYRIC_ACID PMID:17190852 PMID:7496326 Reaxys:3601060 UM-BBD_compID:c0035 butanate butanoate butanoate butanoic acid, ion(1-) butyrate chebi_ontology n-butanoate n-butyrate propanecarboxylate propylformate ribonucleoside triphosphate 0 372.949 373.063 C5H12O13P3R CHEBI:15047 CHEBI:17972 CHEBI:26559 CHEBI:8846 KEGG:C03802 Ribonucleoside triphosphate chebi_ontology ribonucleoside triphosphates chloride -1 34.969 35.45270 A halide anion formed when chlorine picks up an electron to form an an anion. Beilstein:3587171 CAS:16887-00-6 CHEBI:13291 CHEBI:13970 CHEBI:17996 CHEBI:3616 CHEBI:3731 CHEBI:48804 CHLORIDE ION Chloride Chloride ion Chloride(1-) Chlorine anion Cl Cl(-) Cl- Gmelin:14910 InChI=1S/ClH/h1H/p-1 KEGG:C00115 KEGG:C00698 PDBeChem:CL UM-BBD_compID:c0884 VEXZGXHMUGYJMC-UHFFFAOYSA-M [Cl-] chebi_ontology chloride chloride(1-) dialkyl ketone 0 27.995 28.01010 CHEBI:14136 CHEBI:18044 CHEBI:23663 CHEBI:4485 COR2 Dialkyl ketone KEGG:C02146 [*]C([*])=O chebi_ontology dialkyl ketone dialkyl ketones lipid 'Lipids' is a loosely defined term for substances of biological origin that are soluble in nonpolar solvents. They consist of saponifiable lipids, such as glycerides (fats and oils) and phospholipids, as well as nonsaponifiable lipids, principally steroids. CHEBI:14517 CHEBI:18059 CHEBI:25054 CHEBI:6486 KEGG:C01356 Lipid chebi_ontology lipids phylloquinone 0 2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione 2-Methyl-3-[(2E)-3,7,11,15-tetramethyl-2-hexadecenyl]naphthoquinone 2-Methyl-3-phytyl-1,4-naphthochinon 2-Methyl-3-phytyl-1,4-naphthoquinone 2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dione 3-Phytylmenadione 450.350 450.69570 A member of the class of phylloquinones that consists of 1,4-naphthoquinone having methyl and phytyl groups at positions 2 and 3 respectively. The parent of the class of phylloquinones. C31H46O2 CAS:84-80-0 CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(C)C(=O)c2ccccc2C1=O CHEBI:11611 CHEBI:14833 CHEBI:18067 CHEBI:26105 CHEBI:45148 CHEBI:8181 DrugBank:DB01022 Drug_Central:2843 HMDB:HMDB0003555 InChI=1S/C31H46O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1 KEGG:C02059 KEGG:D00148 KNApSAcK:C00002868 MBWXNTAXLNYFJB-NKFFZRIASA-N PDBeChem:PQN PHYLLOQUINONE PMID:11003724 PMID:15686525 PMID:19588895 PMID:19996170 PMID:21169510 PMID:21645693 PMID:21844348 PMID:21914559 Phyllochinon Phyllochinonum Phylloquinone Phytomenadione Phytonadione Phytonadionum Phytylmenadione Reaxys:2568816 Vitamin K1 Wikipedia:Phytonadione alpha-phylloquinone chebi_ontology fitomenadiona phylloquinone phytomenadionum trans-Phylloquinone glycosaminoglycan Any polysaccharide containing a substantial proportion of aminomonosaccharide residues. CHEBI:14361 CHEBI:18085 CHEBI:24398 CHEBI:5495 Glycosaminoglycan Glykosaminoglykan KEGG:C02545 Wikipedia:Glycosaminoglycan chebi_ontology glicosaminoglicano glycosaminoglycan glycosaminoglycane glycosaminoglycans N-benzoylglycine 0 179.058 179.17270 An N-acylglycine in which the acyl group is specified as benzoyl. Benzamidoacetic acid Benzamidoessigsaeure Benzoylaminoacetic acid Benzoylaminoessigsaeure C9H9NO3 CAS:495-69-2 CHEBI:12492 CHEBI:14400 CHEBI:18089 CHEBI:24595 CHEBI:5725 HMDB:HMDB0000714 Hippurate Hippuric acid Hippursaeure InChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12) KEGG:C01586 KNApSAcK:C00030483 MetaCyc:CPD-425 N-Benzoylglycine N-benzoylglycine OC(=O)CNC(=O)c1ccccc1 PMID:14646363 PMID:15879000 PMID:16760132 PMID:17190852 PMID:19283696 PMID:19891605 PMID:20405919 PMID:22770225 PMID:7153346 PMID:8734460 PMID:9120876 PMID:9609721 Phenylcarbonylaminoacetic acid QIAFMBKCNZACKA-UHFFFAOYSA-N Reaxys:1073987 Wikipedia:Hippuric_acid chebi_ontology trans-4-hydroxy-L-proline (2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acid (2S,4R)-trans-4-hydroxyproline (4R)-4-hydroxy-L-proline 0 131.058 131.12990 An optically active form of 4-hydroxyproline having L-trans-configuration. C5H9NO3 CAS:51-35-4 CHEBI:10714 CHEBI:12864 CHEBI:18095 CHEBI:27060 CHEBI:43172 CHEBI:43210 CHEBI:43227 CHEBI:43318 CHEBI:49360 Drug_Central:4272 HMDB:HMDB0000725 Hydroxy-L-proline Hydroxyproline Hyp Hypro InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1 KEGG:C01157 KNApSAcK:C00001370 L-4-Hydroxyproline L-threo-4-hydroxyproline MetaCyc:4-HYDROXY-L-PROLINE O[C@H]1CN[C@@H](C1)C(O)=O PDBeChem:HYP PMID:1117843 PMID:1166829 PMID:12148113 PMID:14104082 PMID:14995121 PMID:15558350 PMID:16096557 PMID:16656634 PMID:16662024 PMID:16665943 PMID:17021603 PMID:19286848 PMID:590925 PMID:616023 PMID:6616407 PMID:6625779 PMID:6783274 PMID:7248905 PMID:7283558 PMID:7446210 PMID:899882 PMID:946341 PMMYEEVYMWASQN-DMTCNVIQSA-N Reaxys:81441 chebi_ontology delta-hydroxyproline trans-4-Hydroxy-L-proline trans-4-hydroxy-L-proline trans-Hydroxyproline trans-L-Hydroxyproline cyclohexanol 0 1-Cyclohexanol 100.089 100.15888 An alcohol that consists of cyclohexane bearing a single hydroxy substituent. The parent of the class of cyclohexanols. C6H12O CAS:108-93-0 CHEBI:14051 CHEBI:18099 CHEBI:23471 CHEBI:4013 CHEBI:41739 Cyclohexan-1-ol Cyclohexanol Cyclohexyl alcohol DrugBank:DB03703 HPXRVTGHNJAIIH-UHFFFAOYSA-N Hexahydrophenol Hexalin Hydrophenol Hydroxycyclohexane InChI=1S/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2 KEGG:C00854 MetaCyc:CYCLOHEXANOL OC1CCCCC1 PDBeChem:CXL PMID:11682644 PMID:23825601 Reaxys:906744 UM-BBD_compID:c0175 Wikipedia:Cyclohexanol chebi_ontology cyclohexanol 4-hydroxyphenylacetic acid (4-hydroxyphenyl)acetic acid (p-hydroxyphenyl)acetic acid 0 152.047 152.14732 4-Hydroxyphenylacetate 4-Hydroxyphenylacetic acid 4-carboxymethylphenol 4-hydroxybenzeneacetic acid 4-hydroxyphenylacetic acid A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. C8H8O3 CAS:156-38-7 CHEBI:12014 CHEBI:18101 CHEBI:1874 CHEBI:20419 CHEBI:40091 HMDB:HMDB0000020 InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11) KEGG:C00642 MetaCyc:4-HYDROXYPHENYLACETATE OC(=O)Cc1ccc(O)cc1 PDBeChem:4HP PMID:11339992 PMID:21476434 PMID:22296160 PMID:24636068 PMID:24831010 PMID:7126379 PMID:977696 Reaxys:1448766 UM-BBD_compID:c0271 Wikipedia:4-hydroxyphenylacetic_acid XQXPVVBIMDBYFF-UHFFFAOYSA-N chebi_ontology p-hydroxyphenylacetic acid hexose Any six-carbon monosaccharide which in its linear form contains either an aldehyde group at position 1 (aldohexose) or a ketone group at position 2 (ketohexose). CHEBI:14399 CHEBI:18133 CHEBI:24590 CHEBI:5709 Hexose KEGG:C00738 chebi_ontology hexose hexoses trimethylamine (CH3)3N 0 59.073 59.11030 A tertiary amine that is ammonia in which each hydrogen atom is substituted by an methyl group. Beilstein:956566 C3H9N CAS:75-50-3 CHEBI:15261 CHEBI:18139 CHEBI:27125 CHEBI:27127 CHEBI:9732 CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N Gmelin:1309 HMDB:HMDB0000906 InChI=1S/C3H9N/c1-4(2)3/h1-3H3 KEGG:C00565 KNApSAcK:C00001433 MetaCyc:TRIMETHYLAMINE N(CH3)3 N,N,N-trimethylamine N,N-Dimethylmethanamine N,N-dimethylmethanamine NMe3 PDBeChem:KEN PMID:14047118 PMID:15304308 PMID:15752091 PMID:17190852 PMID:1801314 PMID:24591617 PMID:2501587 PMID:5161463 Reaxys:956566 TMA Trimethylamin Trimethylamine Wikipedia:Trimethylamine chebi_ontology tridimethylaminomethane hydrogen halide 0 CHEBI:13368 CHEBI:18140 CHEBI:37140 CHEBI:5599 HX HX [F,Cl,Br,I] chebi_ontology hydrogen halide hydrogen halides hydrogen halides polysaccharide A biomacromolecule consisting of large numbers of monosaccharide residues linked glycosidically. This term is commonly used only for those containing more than ten monosaccharide residues. CHEBI:14864 CHEBI:18154 CHEBI:26205 CHEBI:8322 Glycan Glycane Glykan Glykane KEGG:C00420 Polysaccharide chebi_ontology glycans polisacarido polisacaridos polysaccharides 5-oxo-L-proline (-)-2-pyrrolidone-5-carboxylic acid (2S)-5-oxopyrrolidine-2-carboxylic acid (S)-(-)-2-pyrrolidone-5-carboxylic acid (S)-pyroglutamic acid 0 129.043 129.11400 5-Oxo-L-proline 5-Pyrrolidone-2-carboxylic acid 5-oxo-L-proline An optically active form of 5-oxoproline having L-configuration. Beilstein:5251861 Beilstein:82132 C5H7NO3 CAS:98-79-3 CHEBI:12153 CHEBI:18183 CHEBI:20619 CHEBI:2113 CHEBI:44704 DrugBank:DB03088 Gmelin:1125330 HMDB:HMDB0000267 InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1 KEGG:C01879 KNApSAcK:C00007403 L-5-Pyrrolidone-2-carboxylic acid L-Pyroglutamic acid MetaCyc:5-OXOPROLINE OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N PDBeChem:PCA PMID:17439666 PMID:22560249 PMID:22619187 PYROGLUTAMIC ACID Pyroglutamate Pyroglutamic acid Reaxys:82132 Wikipedia:Pyroglutamic_acid YMDB:YMDB00107 chebi_ontology pidolic acid tyrosine 0 181.074 181.18858 2-Amino-3-(p-hydroxyphenyl)propionic acid 2-amino-3-(4-hydroxyphenyl)propanoic acid 3-(p-Hydroxyphenyl)alanine An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring. Beilstein:515881 C9H11NO3 CAS:55520-40-6 CAS:556-03-6 CHEBI:15277 CHEBI:18186 CHEBI:27176 CHEBI:9800 Gmelin:27744 InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13) KEGG:C01536 KNApSAcK:C00001397 NC(Cc1ccc(O)cc1)C(O)=O OUYCCCASQSFEME-UHFFFAOYSA-N PMID:17190852 Reaxys:515881 Tyr Tyrosin Tyrosine Y chebi_ontology tirosina tyrosine citrulline 0 175.096 175.18584 2-Amino-5-uredovaleric acid 2-amino-5-(carbamoylamino)pentanoic acid Beilstein:1725417 Beilstein:2328251 C6H13N3O3 CAS:627-77-0 CHEBI:14002 CHEBI:18211 CHEBI:3730 Cit Citrullin Citrulline DL-2-amino-5-ureidovaleric acid InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12) N(5)-(aminocarbonyl)-DL-ornithine N(5)-(aminocarbonyl)ornithine N(5)-carbamoyl-DL-ornithine N(5)-carbamoylornithine NC(CCCNC(N)=O)C(O)=O PMID:11094453 PMID:11113071 PMID:11696417 PMID:1378088 PMID:16082501 PMID:16708633 PMID:17005970 PMID:17513438 PMID:17558653 PMID:17693747 PMID:18437289 PMID:18440672 PMID:18989563 PMID:19144577 PMID:21129371 PMID:21482070 RHGKLRLOHDJJDR-UHFFFAOYSA-N Reaxys:1725417 The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position. Wikipedia:Citrulline chebi_ontology citrulina citrulline dl-citrulline glutamic acid 0 147.053 147.12930 2-Aminoglutaric acid 2-aminopentanedioic acid An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2. Beilstein:1723799 C5H9NO4 CAS:617-65-2 CHEBI:18237 CHEBI:24314 CHEBI:5431 DL-Glutamic acid DL-Glutaminic acid E Glu Glutamate Glutamic acid Glutaminic acid Glutaminsaeure Gmelin:101971 InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10) KEGG:C00302 KEGG:D04341 KNApSAcK:C00001358 KNApSAcK:C00019577 NC(CCC(O)=O)C(O)=O PMID:15739367 PMID:17190852 PMID:24616376 PMID:24984001 Reaxys:1723799 WHUUTDBJXJRKMK-UHFFFAOYSA-N Wikipedia:Glutamic_acid chebi_ontology glutamic acid 4-hydroxy-L-proline (2S)-4-hydroxypyrrolidine-2-carboxylic acid 0 131.058 131.12990 4-Hydroxy-L-proline 4-hydroxy-L-proline C5H9NO3 CAS:51-35-4 CHEBI:11999 CHEBI:18240 CHEBI:1852 HMDB:HMDB0006055 InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3?,4-/m0/s1 KEGG:C01015 KNApSAcK:C00001370 L-Hydroxyproline OC1CN[C@@H](C1)C(O)=O PMMYEEVYMWASQN-BKLSDQPFSA-N Reaxys:81441 The L-stereoisomer of 4-hydroxyproline. Wikipedia:4-hydroxy-L-proline chebi_ontology cis-4-Hydroxy-L-Proline hydroxy-L-proline dopamine 0 153.079 153.17840 2-(3,4-Dihydroxyphenyl)ethylamine 2-(3,4-dihydroxyphenyl)ethylamine 3,4-Dihydroxyphenethylamine 3-Hydroxytyramine 4-(2-Aminoethyl)-1,2-benzenediol 4-(2-Aminoethyl)benzene-1,2-diol 4-(2-aminoethyl)-1,2-benzenediol 4-(2-aminoethyl)benzene-1,2-diol 4-(2-aminoethyl)catechol 4-(2-aminoethyl)pyrocatechol C8H11NO2 CAS:51-61-6 CHEBI:11695 CHEBI:11930 CHEBI:14203 CHEBI:1764 CHEBI:18243 CHEBI:23886 CHEBI:43686 Catechol in which the hydrogen at position 4 is substituted by a 2-aminoethyl group. Deoxyepinephrine Dopamine DrugBank:DB00988 Drug_Central:947 HMDB:HMDB0000073 Hydroxytyramin InChI=1S/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2 KEGG:C03758 KEGG:D07870 KNApSAcK:C00001408 LINCS:LSM-4630 MetaCyc:DOPAMINE NCCc1ccc(O)c(O)c1 PMID:10629745 PMID:11149432 PMID:9422813 Reaxys:1072822 VYFYYTLLBUKUHU-UHFFFAOYSA-N Wikipedia:Dopamine chebi_ontology dopamina dopamine dopaminum iron atom 0 26Fe 55.84500 55.935 An iron group element atom that has atomic number 26. CAS:7439-89-6 CHEBI:13322 CHEBI:18248 CHEBI:24872 CHEBI:5974 DrugBank:DB01592 Eisen Fe Fe HMDB:HMDB0015531 InChI=1S/Fe Iron KEGG:C00023 Reaxys:4122945 WebElements:Fe XEEYBQQBJWHFJM-UHFFFAOYSA-N [Fe] chebi_ontology fer ferrum hierro iron iron ribonucleoside 0 133.050 Any nucleoside where the sugar component is D-ribose. C5H9O4R CHEBI:13014 CHEBI:13015 CHEBI:13685 CHEBI:18254 CHEBI:21085 CHEBI:26560 CHEBI:4240 CHEBI:8844 KEGG:C00911 OC[C@H]1O[C@@H]([*])[C@H](O)[C@@H]1O Ribonucleoside a ribonucleoside chebi_ontology ribonucleosides ornithine 0 132.090 132.16106 2,5-Diaminopentanoic acid 2,5-Diaminovaleric acid 2,5-diaminopentanoic acid AHLPHDHHMVZTML-UHFFFAOYSA-N An alpha-amino acid that is pentanoic acid bearing two amino substituents at positions 2 and 5. Beilstein:1722296 C5H12N2O2 CAS:616-07-9 CHEBI:18257 CHEBI:7784 DL-Ornithine Gmelin:847696 InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9) KEGG:C01602 KNApSAcK:C00001384 NCCCC(N)C(O)=O Orn Ornithine PMID:15449570 PMID:17190852 PMID:22264337 Reaxys:1722296 chebi_ontology ornithine 3,3',5-triiodo-L-thyronine 0 3,3',5-triiodo-L-thyronine 3,5,3'-Triiodo-L-thyronine 3,5,3'-Triiodothyronine 3,5,3'TRIIODOTHYRONINE 4-(4-hydroxy-3-iodophenoxy)-3,5-diiodo-L-phenylalanine 650.790 650.97350 AUYYCJSJGJYCDS-LBPRGKRZSA-N An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxine in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism. Beilstein:2710227 C15H12I3NO4 CAS:6893-02-3 CHEBI:11701 CHEBI:11702 CHEBI:13059 CHEBI:18258 CHEBI:19894 CHEBI:45840 CHEBI:9722 DrugBank:DB00279 Drug_Central:1585 HMDB:HMDB0000265 InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1 KEGG:C02465 KEGG:D08128 L-3,5,3'-Triiodothyronine L-T3 LINCS:LSM-3991 Liothyronine MetaCyc:CPD-10813 N[C@@H](Cc1cc(I)c(Oc2ccc(O)c(I)c2)c(I)c1)C(O)=O O-(4-hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine PDBeChem:T3 PMID:11738632 PMID:15206581 PMID:19339791 Reaxys:2710227 T3 Tertroxin Tresitope Triiodothyronine Wikipedia:Triiodothyronine chebi_ontology liothyronine liothyroninum liotironina dihydrogen 0 2.01588 2.016 An elemental molecule consisting of two hydrogens joined by a single bond. CAS:1333-74-0 CHEBI:13350 CHEBI:18276 CHEBI:25363 CHEBI:5785 E 949 E-949 E949 Gmelin:3 H2 H2 HMDB:HMDB0001362 Hydrogen InChI=1S/H2/h1H KEGG:C00282 MetaCyc:HYDROGEN-MOLECULE MolBase:748 PMID:15303745 PMID:16517646 PMID:18706888 PMID:19905000 PMID:19908827 PMID:20568549 PMID:24171421 Reaxys:3587189 UFHFLCQGNIYNRP-UHFFFAOYSA-N Wikipedia:Hydrogen [H][H] chebi_ontology dihydrogen molecular hydrogen nucleobase Base CHEBI:13873 CHEBI:18282 CHEBI:25598 CHEBI:2995 KEGG:C00701 That part of DNA or RNA that may be involved in pairing. Wikipedia:Nucleobase a nucleobase chebi_ontology nucleobases L-fucose (-)-L-fucose (-)-fucose 0 164.15648 6-deoxy-L-galactose Any form of fucose having L configuration. C6H12O5 CAS:2438-80-4 CHEBI:13102 CHEBI:18287 CHEBI:21293 L-(-)-fucose L-Fuc L-fucose L-galactomethylose PMID:20877283 chebi_ontology histamine 0 111.080 111.14518 1H-Imidazole-4-ethanamine 2-(1H-imidazol-4-yl)ethanamine 2-(4-Imidazolyl)ethylamine A member of the class of imidazoles that is 1H-imidazole substituted at position C-4 by a 2-aminoethyl group. Beilstein:2012 C5H9N3 CAS:51-45-6 CHEBI:14401 CHEBI:18295 CHEBI:24596 CHEBI:43187 CHEBI:817 Drug_Central:1375 Gmelin:2968 HISTAMINE HMDB:HMDB0000870 Histamine InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8) KEGG:C00388 KEGG:D08040 KNApSAcK:C00001414 MetaCyc:HISTAMINE NCCc1c[nH]cn1 NTYJJOPFIAHURM-UHFFFAOYSA-N PDBeChem:HSM PMID:16399866 PMID:19547708 PMID:19843401 PMID:22770225 PMID:24101735 Reaxys:2012 Wikipedia:Histamine chebi_ontology alkane 0 15.023 Alkan Alkane An acyclic branched or unbranched hydrocarbon having the general formula CnH2n+2, and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. CH3R CHEBI:13435 CHEBI:18310 CHEBI:22317 CHEBI:2576 C[*] KEGG:C01371 RH alcane alcanes alcano alcanos alkane alkanes an alkane chebi_ontology diphosphate(4-) -4 173.912 173.94332 CAS:14000-31-8 CHEBI:13420 CHEBI:18361 CHEBI:42009 DIPHOSPHATE Diphosphat Diphosphate Gmelin:26938 InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4 KEGG:C00013 O7P2 P2O7(4-) PDBeChem:DPO PPi Pyrophosphat Pyrophosphate XPPKVPWEQAFLFU-UHFFFAOYSA-J [O-]P([O-])(=O)OP([O-])([O-])=O [O3POPO3](4-) chebi_ontology diphosphate mu-oxido-bis(trioxidophosphate)(4-) mu-oxo-hexaoxodiphosphate pyrophosphate ion phosphate(3-) -3 94.953 94.97136 A phosphate ion that is the conjugate base of hydrogenphosphate. Beilstein:3903772 CAS:14265-44-2 CHEBI:14791 CHEBI:18367 CHEBI:45024 CHEBI:7793 Gmelin:1997 InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3 KEGG:C00009 NBIIXXVUZAFLBC-UHFFFAOYSA-K O4P Orthophosphate PDBeChem:PO4 PHOSPHATE ION PO4(3-) Phosphate Reaxys:3903772 [O-]P([O-])([O-])=O [PO4](3-) chebi_ontology phosphate tetraoxidophosphate(3-) tetraoxophosphate(3-) tetraoxophosphate(V) nucleoside 3',5'-cyclic phosphate 0 178.003 178.07980 A ribosyl or deoxyribosyl derivative of a pyrimidine or purine base in which C-3 and C-5 of the ribose ring are engaged in formation of a cyclic mono-, di-, tri- or tetra-phosphate. C5H7O5PR2 CHEBI:1331 CHEBI:14672 CHEBI:18375 CHEBI:19833 OP1(=O)OC[C@H]2O[C@@H]([*])[C@H]([*])[C@@H]2O1 chebi_ontology nucleoside 3',5'-cyclic phosphates dermatan sulfate Any of a group of glycosaminoglycans with repeating units consisting of variously sulfated beta1->4-linked L-iduronyl-(alpha1->3)-N-acetyl-D-galactosamine units. Beilstein:8390617 CAS:24967-94-0 CHEBI:14127 CHEBI:18376 CHEBI:23644 CHEBI:4440 Chondroitin sulfate B Dermatan L-iduronate H2O.(C14H20NO13S)n KEGG:C00426 beta-Heparin chebi_ontology phenylacetate -1 135.045 135.13998 2-phenylacetate 2-phenylethanoate A monocarboxylic acid anion that is the conjugate base of phenylacetic acid. Beilstein:3539899 C8H7O2 CHEBI:14779 CHEBI:18401 CHEBI:25975 Gmelin:327522 InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)/p-1 MetaCyc:PHENYLACETATE Reaxys:3539899 UM-BBD_compID:c0211 WLJVXDMOQOGPHL-UHFFFAOYSA-M [O-]C(=O)Cc1ccccc1 chebi_ontology phenylacetate phenylacetate anion phenylacetate(1-) phenylacetic acid anion cobamamide (5,6-Dimethylbenzimidazolyl)cobamide coenzyme (5,6-dimethylbenzimidazolyl)cobamide coenzyme 0 1578.658 1579.58180 5'-Deoxy-5'-adenosyl vitamin B12 5'-Deoxy-5'-adenosyl-5,6-dimethylbenzimidazolylcobamide 5'-Deoxy-5'-adenosylcobalamin 5'-deoxyadenosyl vitamin B12 5'-deoxyadenosyl-5,6-dimethylbenzimidazolylcobamide 5'-deoxyadenosylcobalamin 5,6-Dimethylbenzimidazolyl-5-deoxyadenosyl-cobamide 5,6-Dimethylbenzimidazolyl-Co-5'-deoxy-5'-adenosylcobamide A member of the class of cobalamins that is vitamin B12 in which the cyano group is replaced by a 5'-deoxyadenos-5'-yl moiety. It is one of the two metabolically active form of vitamin B12. Adenosylcob(III)alamin Adenosylcobalamin AdoCbl Beilstein:4122932 C72H100CoN18O17P CAS:13870-90-1 CHEBI:13739 CHEBI:18408 CHEBI:23340 CHEBI:3797 Calomide Coalpha-[alpha-(5,6-dimethylbenzimidazolyl)]-Cobeta-(5'-deoxy-5'-adenosyl)cobamide Coalpha-[alpha-(5,6-dimethylbenzimidazolyl)]-Cobeta-adenosylcobamide Cobalamin coenzyme Cobamamide Coenzyme B12 DBC coenzyme DMBC coenzyme Deoxyadenosylcobalamin Dibencozide Funacomide Gmelin:439994 HMDB:HMDB0002086 InChI=1S/C62H90N13O14P.C10H12N5O3.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;4-,6-,7-,10-;/m11./s1 KEGG:C00194 MetaCyc:ADENOSYLCOBALAMIN PDBeChem:B1Z PMID:11792214 PMID:12093296 PMID:17011224 Reaxys:4122932 Vitamin B12 coenzyme Wikipedia:Cobamamide ZIHHMGTYZOSFRC-OUCXYWSSSA-L [H][C@]12[C@H](CC(N)=O)[C@@]3(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@@H]4[C@@H](CO)O[C@@H]([C@@H]4O)n4c[n+](c5cc(C)c(C)cc45)[Co-3]456(C[C@H]7O[C@H]([C@H](O)[C@@H]7O)n7cnc8c(N)ncnc78)N1C3=C(C)C1=[N+]4C(=CC3=[N+]5C(=C(C)C4=[N+]6[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]3CCC(N)=O)C(C)(C)[C@@H]1CCC(N)=O adenosylcob(III)alamin adenosylcobalamin alpha-(5,6-Dimethylbenzimidazolyl)cobamide coenzyme chebi_ontology cobamamid cobamamida cobamamide cobamamidum cobamide coenzyme coenzyme B-12 5-methyltetrahydrofolate(2-) (2S)-2-{[4-({[(6S)-2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]amino}pentanedioate (6S)-5-methyl-5,6,7,8-tetrahydrofolate (6S)-5-methyltetrahydrofolate -2 457.171 457.43990 Beilstein:10132446 C20H23N7O6 CHEBI:18608 CN1[C@@H](CNc2ccc(cc2)C(=O)N[C@@H](CCC([O-])=O)C([O-])=O)CNc2nc(N)[nH]c(=O)c12 InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/p-2/t12-,13-/m0/s1 ZNOVTXRBGFNYRX-STQMWFEESA-L chebi_ontology nicotine (+-)-3-(1-Methyl-2-pyrrolidinyl)pyridine (+-)-nicotine (R,S)-nicotine (RS)-nicotine A racemate composed of equimolar amounts of (R)- and (S)-nicotine. Beilstein:82108 Beilstein:82111 CAS:22083-74-5 CHEBI:18723 DrugBank:DB00184 HMDB:HMDB0014330 KEGG:C16150 KNApSAcK:C00002057 PMID:10751565 PMID:11192937 PMID:11471991 PMID:11559179 PMID:11682702 PMID:11714820 PMID:11719700 PMID:11801622 PMID:11818389 PMID:11860617 PMID:12197757 PMID:12700710 PMID:12965231 PMID:14715938 PMID:15183514 PMID:15251917 PMID:15313135 PMID:15458549 PMID:15707677 PMID:15894687 PMID:15960296 PMID:15961264 PMID:16496293 PMID:16950410 PMID:17167832 PMID:17206646 PMID:17438652 PMID:17498149 PMID:17942810 PMID:18077004 PMID:18311975 PMID:18380035 PMID:18383130 PMID:18651995 PMID:18922921 PMID:19100331 PMID:19287496 PMID:19389046 PMID:19465085 PMID:20338106 PMID:20528766 PMID:21636612 PMID:21822688 PMID:21945235 PMID:22129149 PMID:22218403 PMID:22331007 PMID:22377934 PMID:22448647 PMID:22459798 PMID:22529223 PMID:22573728 PMID:22585541 PMID:22589423 PMID:22770225 PMID:22792725 PMID:22855884 PMID:22930863 PMID:22935730 PMID:23108361 PMID:23117126 PMID:7097594 PMID:7564279 PMID:7566693 PMID:7807214 PMID:7896575 PMID:8156919 PMID:8545712 PMID:8764340 PMID:9203638 PMID:9450943 PMID:9621392 Reaxys:82108 UM-BBD_compID:c0468 Wikipedia:Nicotine chebi_ontology nicotin nikotin rac-3-(1-methylpyrrolidin-2-yl)pyridine 17-oxo steroid 17-keto steroids 17-ketosteroids 17-oxo steroids Any oxo steroid carrying the oxo group at position 17. CHEBI:19168 chebi_ontology 3',5'-cyclic purine nucleotide 3',5'-cyclic purine nucleotides CHEBI:19834 chebi_ontology 3-hydroxybutyric acid (1)-3-Hydroxybutyric acid 0 104.047 104.10452 3 HBA 3-Hydroxybuttersaeure 3-OH-butyric acid 3-hydroxybutanoic acid A straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an energy source by the brain during fasting in humans. Also used to synthesise biodegradable plastics. BHBA Beilstein:773861 C4H8O3 CAS:300-85-6 CC(O)CC(O)=O CHEBI:20067 DL-beta-Hydroxybutyric acid HMDB:HMDB0000357 InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7) LIPID_MAPS_instance:LMFA01050005 PMID:10855969 PMID:17190852 PMID:17579249 PMID:6061736 Reaxys:773861 WHBMMWSBFZVSSR-UHFFFAOYSA-N Wikipedia:3-hydroxybutyrate beta-Hydroxy-n-butyric acid beta-Hydroxybuttersaeure beta-hydroxy-n-butyric acid beta-hydroxybutanoic acid beta-hydroxybutyric acid chebi_ontology vanillylmandelic acid 0 198.053 198.17270 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid 3-methoxy-4-hydroxymandelic acid An aromatic ether that is the 3-O-methyl ether of 3,4-dihydroxymandelic acid. Beilstein:2213227 C9H10O5 CAS:55-10-7 CGQCWMIAEPEHNQ-UHFFFAOYSA-N CHEBI:20106 COc1cc(ccc1O)C(O)C(O)=O HMDB:HMDB0000291 InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13) KEGG:C05584 MetaCyc:VANILLYL_MANDELATE PMID:13756637 PMID:23112240 PMID:23399766 PMID:23830883 PMID:24327171 Reaxys:2213227 Vanillylmandelic acid Vanilmandelic acid Wikipedia:Vanillylmandelic_acid chebi_ontology hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid 4-hydroxyproline 0 131.058 131.12990 4-hydroxyproline 4Hyp A monohydroxyproline where the hydroxy group is located at the 4-position. It is found in fibrillar collagen. C5H9NO3 CHEBI:20392 InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9) OC1CNC(C1)C(O)=O PMID:21988268 PMID:24563386 PMID:24695516 PMID:436278 PMMYEEVYMWASQN-UHFFFAOYSA-N Wikipedia:Hydroxyproline chebi_ontology 5-methyltetrahydrofolate 5-methyltetrahydrofolates A group of heterocyclic compounds based on the 5-methyl-5,6,7,8-tetrahydropteroic acid skeleton conjugated with one or more L-glutamic acid or L-glutamate units. CHEBI:20612 chebi_ontology 5beta-cholane 0 330.329 330.59028 5beta-cholane Beilstein:2048472 C24H42 CHEBI:20664 InChI=1S/C24H42/c1-5-8-17(2)20-12-13-21-19-11-10-18-9-6-7-15-23(18,3)22(19)14-16-24(20,21)4/h17-22H,5-16H2,1-4H3/t17-,18+,19+,20-,21+,22+,23+,24-/m1/s1 QSHQKIURKJITMZ-OBUPQJQESA-N [H][C@@]12CCCC[C@]1(C)[C@@]1([H])CC[C@]3(C)[C@]([H])(CC[C@@]3([H])[C@]1([H])CC2)[C@H](C)CCC chebi_ontology 6-aminopurines 6-aminopurines Any compound having 6-aminopurine (adenine) as part of its structure. CHEBI:20706 PMID:1646334 PMID:18524423 PMID:7342604 chebi_ontology vitamin C CHEBI:21241 PMID:21885436 Vitamin C chebi_ontology vitamina C vitamine C vitaminum C Mo-molybdopterin cofactor A molybdopterin cofactor in which the coordinated metal is a mononuclear molybdenum or molybdate species. CAS:73508-07-3 CHEBI:21437 CHEBI:60198 DrugBank:DB02137 KEGG:C18237 Mo-molybdopterin cofactors Moco Molybdenum cofactor chebi_ontology molybdenum cofactor N-acetylneuraminates CHEBI:21619 N-acetylneuraminate chebi_ontology N-acetylneuraminic acids CHEBI:21622 chebi_ontology N-acylglucosamine CHEBI:21638 N-acylglucosamine N-acylglucosamines chebi_ontology N-acyl-L-amino acid Any N-acylamino acid having L-configuration. CHEBI:21644 chebi_ontology N-acyl-hexosamine CHEBI:21656 N-acyl-hexosamine N-acyl-hexosamines chebi_ontology N-acylneuraminates CHEBI:21663 N-acylneuraminate chebi_ontology N-glycosyl compound A glycosyl compound arising formally from the elimination of water from a glycosidic hydroxy group and an H atom bound to a nitrogen atom, thus creating a C-N bond. CHEBI:21731 N-glycoside N-glycosides N-glycosyl compounds chebi_ontology glycosylamine glycosylamines N-methyl-amino acid An amino acid derivative in which at least one of the hydrogens of the amino group has been replaced by a methyl group. CHEBI:21760 N-methyl-amino acids chebi_ontology N-methylglycines An N-alkylglycine that is sarcosine and derivatives of sarcosine arising by replacement of the hydrogen attached to the nitrogen by a hydrocarbyl group. CHEBI:21766 chebi_ontology L-fucopyranose 0 164.068 164.15650 6-Deoxy-L-galactose 6-deoxy-L-galactopyranose Beilstein:1905878 C6H12O5 CAS:2438-80-4 CHEBI:2181 C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O Gmelin:863814 InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6?/m0/s1 KEGG:C01019 L-Fucose L-fucopyranose L-fucose PMID:19913595 PMID:25728407 PMID:27145048 PMID:27782805 PMID:7688662 Reaxys:1905878 SHZGCJCMOBCMKK-DHVFOXMCSA-N The pyranose form of L-fucose. chebi_ontology acaricide A substance used to destroy pests of the subclass Acari (mites and ticks). Akarizid Akarizide CHEBI:22153 Wikipedia:Acaricide acaricides chebi_ontology miticide acetamides CHEBI:22160 Compounds with the general formula RNHC(=O)CH3. chebi_ontology acyl group An organic group formed by removing one or more hydroxy groups from an oxoacid that has the general structure RkE(=O)l(OH)m (l =/= 0). Although the term is almost always applied to organic compounds, with carboxylic acid as the oxoacid, acyl groups can in principle be derived from other types of acids such as sulfonic acids or phosphonic acids. CHEBI:22221 acyl group acyl groups alkanoyl alkanoyl group chebi_ontology groupe acyle adenosine phosphate CHEBI:22256 adenosine phosphates chebi_ontology adenosines CHEBI:22260 chebi_ontology aldonate CHEBI:22299 aldonate aldonates chebi_ontology aldonic acid Any carbohydrate acid formed by oxidising the aldehyde functional group of an aldose to a carboxylic acid functional group. Aldonic acids have the general formula HOCH2[CH(OH)]nC(=O)OH. CHEBI:22301 aldonic acid aldonic acids chebi_ontology aldoxime 0 44.014 44.03270 CH2NOR CHEBI:22307 KEGG:C02658 Oximes of aldehydes RCH=NOH. [H]C([*])=NO aldoxime aldoximes aldoximes chebi_ontology alkaline earth metal atom CHEBI:22313 Erdalkalimetall Erdalkalimetalle alkaline earth metal alkaline earth metals alkaline-earth metal alkaline-earth metals chebi_ontology metal alcalino-terreux metal alcalinoterreo metales alcalinoterreos metaux alcalino-terreux alkali metal atom Alkalimetall Alkalimetalle CHEBI:22314 alkali metal alkali metals chebi_ontology metal alcalin metal alcalino metales alcalinos metaux alcalins alkaloid Alkaloid Alkaloide Any of the naturally occurring, basic nitrogen compounds (mostly heterocyclic) occurring mostly in the plant kingdom, but also found in bacteria, fungi, and animals. By extension, certain neutral compounds biogenetically related to basic alkaloids are also classed as alkaloids. Amino acids, peptides, proteins, nucleotides, nucleic acids, amino sugars and antibiotics are not normally regarded as alkaloids. Compounds in which the nitrogen is exocyclic (dopamine, mescaline, serotonin, etc.) are usually classed as amines rather than alkaloids. CHEBI:22315 Wikipedia:Alkaloid alcaloide alcaloides alkaloids chebi_ontology alkyl group A univalent group -CnH2n+1 derived from an alkane by removal of a hydrogen atom from any carbon atom. CHEBI:22323 alkyl group alkyl groups chebi_ontology groupe alkyle grupo alquilo grupos alquilo aliphatic sulfide CHEBI:22327 aliphatic thioether aliphatic thioethers chebi_ontology alkylamines Any amine formally derived from ammonia by replacing one, two or three hydrogen atoms by alkyl groups. CHEBI:22331 chebi_ontology alkylating agent CHEBI:22333 Highly reactive chemical that introduces alkyl radicals into biologically active molecules and thereby prevents their proper functioning. It could be used as an antineoplastic agent, but it might be very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. It could also be used as a component of poison gases. chebi_ontology amino alcohol An alcohol containing an amino functional group in addition to the alcohol-defining hydroxy group. CHEBI:22478 amino alcohols aminoalcohol aminoalcohols chebi_ontology aminobenzoate CHEBI:22494 aminobenzoates chebi_ontology aminodiol An amino alcohol having two hydroxy functional groups. CHEBI:22501 amino diol amino diols aminodiols chebi_ontology aminoglycan CHEBI:22506 aminoglycans chebi_ontology aminopurine Any purine having at least one amino substituent. CHEBI:22527 aminopurines chebi_ontology anhydro sugar CHEBI:22558 Intramolecular ethers formally arising by elimination of water from two hydroxy groups of a single molecule of a monosaccharide (aldose or ketose) or monosaccharide derivative. anhydro sugar anhydro sugars anhydrosugars chebi_ontology sugar anhydride sugar anhydrides anion A monoatomic or polyatomic species having one or more elementary charges of the electron. Anion Anionen CHEBI:22563 anion aniones anions chebi_ontology antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. CHEBI:22586 antioxidants antioxydant antoxidant chebi_ontology antiviral agent A substance that destroys or inhibits replication of viruses. CHEBI:22587 anti-viral agent anti-viral agents antiviral antiviral agents antivirals chebi_ontology ascorbate A ketoaldonate that is the conjugate base of ascorbic acid. CHEBI:22651 chebi_ontology ascorbic acid CHEBI:22652 chebi_ontology asparagine 0 132.053 132.11800 2,4-diamino-4-oxobutanoic acid 2-amino-3-carbamoylpropanoic acid ASN An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group. Asn Asparagin Beilstein:1723525 C4H8N2O3 CAS:3130-87-8 CHEBI:22653 DCXYFEDJOCDNAF-UHFFFAOYSA-N DL-Asparagine Gmelin:279043 Hasp InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9) KEGG:C16438 N NC(CC(N)=O)C(O)=O PMID:22264337 PMID:22770225 Reaxys:1723525 Wikipedia:Asparagine asparagina asparagine chebi_ontology auxin Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow"). CHEBI:22676 Wikipedia:Auxin auxins chebi_ontology base A molecular entity having an available pair of electrons capable of forming a covalent bond with a hydron (Bronsted base) or with the vacant orbital of some other molecular entity (Lewis base). Base Base1 Base2 Basen CHEBI:22695 KEGG:C00701 Nucleobase base bases chebi_ontology benzaldehydes Any arenecarbaldehyde that consists of a formyl substituted benzene ring and its substituted derivatives thereof. CHEBI:22698 chebi_ontology benzenes Any benzenoid aromatic compound consisting of the benzene skeleton and its substituted derivatives. CHEBI:22712 chebi_ontology benzoates A monocarboxylic acid anion obtained by deprotonation of the carboxy group of any benzoic acid. CHEBI:22718 benzoate anion chebi_ontology benzopyran CHEBI:22727 Wikipedia:Benzopyran benzopyrans chebi_ontology benzopyrrole CHEBI:22728 benzopyrroles chebi_ontology benzyl group 0 91.055 91.13048 Bn C6H5-CH2- C7H7 CHEBI:22744 benzyl chebi_ontology phenylalanine side-chain phenylmethyl amino-acid betaine Any amino acid-derived zwitterion - such as glycine betaine (N,N,N-trimethylammonioacetate) - in which the ammonium nitrogen carries three methyl substituents. CHEBI:22860 amino acid betaines amino-acid betaines betaines chebi_ontology bile salt A sodium salt of the conjugate of any bile acid with either glycine or taurine. Bile acid CHEBI:22868 KEGG:C01558 bile salts chebi_ontology biopterins CHEBI:22881 MetaCyc:All-Biopterines chebi_ontology bisphenol By usage, the methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). The term also includes analogues in the the methylene (or substituted methylene) group has been replaced by a heteroatom. CHEBI:22901 Wikipedia:Bisphenol bisphenols chebi_ontology phytogenic insecticide An insecticide compound naturally occurring in plants. CHEBI:22917 botanical insecticide botanical insecticides chebi_ontology phytogenic insecticides branched-chain amino acid Any amino acid in which the parent hydrocarbon chain has one or more alkyl substituents CHEBI:22918 branched chain amino acids chebi_ontology bromine atom 0 35Br 78.918 79.90400 Br Br Brom CHEBI:22927 InChI=1S/Br WKBOTKDWSSQWDR-UHFFFAOYSA-N WebElements:Br [Br] brome bromine bromine bromo bromum chebi_ontology bromine molecular entity CHEBI:22928 bromine compounds bromine molecular entities bromine molecular entity chebi_ontology butanone Any ketone that is butane substituted by an oxo group at unspecified position. CHEBI:22951 butanones chebi_ontology cadmium atom 0 112.41100 113.903 48Cd BDOSMKKIYDKNTQ-UHFFFAOYSA-N CAS:7440-43-9 CHEBI:22977 Cd Cd InChI=1S/Cd KEGG:C01413 Kadmium WebElements:Cd [Cd] cadmio cadmium cadmium chebi_ontology calcium atom 0 20Ca 39.963 40.07800 CAS:7440-70-2 CHEBI:22984 Ca Ca Calcium DrugBank:DB01373 InChI=1S/Ca KEGG:C00076 Kalzium OYPRJOBELJOOCE-UHFFFAOYSA-N WebElements:Ca [Ca] calcio calcium calcium chebi_ontology calcium molecular entity CHEBI:22985 calcium compounds calcium molecular entities calcium molecular entity chebi_ontology carbamate ester Any ester of carbamic acid or its N-substituted derivatives. CHEBI:23003 Wikipedia:Carbamate carbamate esters carbamates chebi_ontology carbamoyl group -C(O)NH2 -CONH2 0 44.014 44.03272 CH2NO CHEBI:23004 PMID:24168430 The univalent carboacyl group formed by loss of -OH from the carboxy group of carbamic acid. aminocarbonyl carbamoyl carbamyl carbamyl group carboxamide chebi_ontology carbon oxide CHEBI:23014 carbon oxides chebi_ontology oxides of carbon carbonates CHEBI:23016 Organooxygen compounds that are salts or esters of carbonic acid, H2CO3. chebi_ontology carbonyl group 0 27.995 28.01010 >C=O CHEBI:23019 CO carbonyl carbonyl group chebi_ontology carotene CHEBI:23042 Hydrocarbon carotenoids. carotene carotenes carotenes chebi_ontology carotenoid CAS:36-88-4 CHEBI:23044 One of a class of tetraterpenoids (C40), formally derived from the acyclic parent, psi,psi-carotene by hydrogenation, dehydrogenation, cyclization, oxidation, or combination of these processes. This class includes carotenes, xanthophylls and certain compounds that arise from rearrangement of the skeleton of psi,psi-carotene or by loss of part of this structure. Retinoids are excluded. a carotenoid carotenes and carotenoids carotenoid carotenoids chebi_ontology carotenol CHEBI:23045 carotenols chebi_ontology hydroxycarotenoids cerebroside Any member of a group of glycosphingolipids, also known as monoglycosylceramides, which are important components in animal muscle and nerve cell membranes. CHEBI:23079 cerebrosides chebi_ontology monoglycosylceramide monoglycosylceramides chloride salt CHEBI:23114 chebi_ontology chloride salts chlorides chlorine atom 0 17Cl 34.969 35.45270 CHEBI:23116 Chlor Cl Cl InChI=1S/Cl WebElements:Cl ZAMOUSCENKQFHK-UHFFFAOYSA-N [Cl] chebi_ontology chlore chlorine chlorine chlorum cloro chlorine molecular entity A halogen molecular entity containing one or more atoms of chlorine. CHEBI:23117 chebi_ontology choline ester CHEBI:23213 CHEBI:3666 chebi_ontology choline esters cholines A quaternary ammonium ion based on the choline ion and its substituted derivatives thereof. CHEBI:23217 chebi_ontology chromanol Any member of the class of chromanes that is chromane substituted by one or more hydroxy groups. CHEBI:23229 chebi_ontology chromanes CHEBI:23230 chebi_ontology chromophore CHEBI:23240 The part (atom or group of atoms) of a molecular entity in which the electronic transition responsible for a given spectral band is approximately localized. Wikipedia:Chromophore chebi_ontology chromophore chromophores citrullines CHEBI:23324 chebi_ontology cob(III)alamins CHEBI:23333 chebi_ontology cobalamins CHEBI:23334 chebi_ontology cobamides CHEBI:23341 chebi_ontology coenzyme A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons. CHEBI:23354 chebi_ontology coenzyme coenzymes cofactor An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group). CHEBI:23357 Wikipedia:Cofactor_(biochemistry) chebi_ontology cofactor cofactors colchicine 0 399.168 399.43704 An alkaloid that is a carbotricyclic compound comprising 5,6,7,9-tetrahydrobenzo[a]heptalene having four methoxy substituents at the 1-, 2-, 3- and 10-positions as well as an oxo group at the 9-position and an acetamido group at the 7-position. It has been isolated from the plants belonging to genus Colchicum. Beilstein:2228812 C22H25NO6 CAS:54192-66-4 CHEBI:23359 COc1cc2CCC(NC(C)=O)c3cc(=O)c(OC)ccc3-c2c(OC)c1OC DrugBank:DB01394 HMDB:HMDB0015466 IAKHMKGGTNLKSZ-UHFFFAOYSA-N InChI=1S/C22H25NO6/c1-12(24)23-16-8-6-13-10-19(27-3)21(28-4)22(29-5)20(13)14-7-9-18(26-2)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24) LINCS:LSM-6449 N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)acetamide PMID:10680067 PMID:24074178 PMID:7200520 PMID:9819133 Reaxys:2228812 chebi_ontology compatible osmolytes CHEBI:23366 chebi_ontology molecular entity Any constitutionally or isotopically distinct atom, molecule, ion, ion pair, radical, radical ion, complex, conformer etc., identifiable as a separately distinguishable entity. CHEBI:23367 chebi_ontology entidad molecular entidades moleculares entite moleculaire molecular entities molecular entity molekulare Entitaet copper molecular entity CHEBI:23377 chebi_ontology copper compounds copper molecular entities copper molecular entity cobalt-corrinoid hexaamide CHEBI:23390 chebi_ontology pseudohalogen oxoacid CHEBI:23423 chebi_ontology cyclic amide CHEBI:23443 CHEBI:3990 chebi_ontology cyclic amide cyclic amides cyclic nucleotide CHEBI:23447 chebi_ontology cyclic nucleotides cyclic peptide CHEBI:23449 Cyclopeptid Zyklopeptid chebi_ontology cyclic peptides peptide cyclique peptido ciclico cyclohexanols An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton. CHEBI:23480 chebi_ontology cyclopentanes CHEBI:23493 Cyclopentane and its derivatives formed by substitution. chebi_ontology cyclopentanols An alcohol in which one or more hydroxy groups are attached to a cyclopentane skeleton. CHEBI:23495 chebi_ontology cystathionines CHEBI:23505 chebi_ontology cysteine derivative An amino acid derivative resulting from reaction of cysteine at the amino group, carboxy group, or thiol group, or from the replacement of any hydrogen of cysteine by a heteroatom. The definition normally excludes peptides containing cysteine residues. CHEBI:23509 chebi_ontology cysteine derivative deoxygalactose CHEBI:23622 chebi_ontology deoxygalactose deoxygalactoses deoxyhexose Any C6 deoxy sugar having at least one hydroxy group replaced by hydrogen. CHEBI:23628 chebi_ontology deoxyhexose deoxyhexoses deoxy sugar Any sugar having a hydroxy group replaced with a hydrogen atom. CHEBI:23639 chebi_ontology deoxy sugars deoxysugar deoxysugars diazole An azole that is either one of a pair of heterocyclic organic compounds comprising three carbon atoms and two nitrogen atoms arranged in a ring. CHEBI:23677 chebi_ontology diazoles dicarboxylic acid amide CHEBI:23690 chebi_ontology dicarboxylic acid amides ({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(9H-purin-9-yl)oxolan-2-yl]methyl phosphonato}oxy)(phosphonatooxy)phosphinate CHEBI:237958 chebi_ontology diol A compound that contains two hydroxy groups, generally assumed to be, but not necessarily, alcoholic. Aliphatic diols are also called glycols. CHEBI:23824 Wikipedia:Diol chebi_ontology diols diterpenoid Any terpenoid derived from a diterpene. The term includes compounds in which the C20 skeleton of the parent diterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups). C20 isoprenoids CHEBI:23849 LIPID_MAPS_class:LMPR0104 chebi_ontology diterpenoides diterpenoids drug Any substance which when absorbed into a living organism may modify one or more of its functions. The term is generally accepted for a substance taken for a therapeutic purpose, but is also commonly used for abused substances. CHEBI:23888 chebi_ontology drugs medicine icosanoid Any member of the group of signalling molecules arising from oxidation of the three C20 essential fatty acids (EFAs) icosapentaenoic acid (EPA), arachidonic acid (AA) and dihomo-gamma-linolenic acid (DGLA). CHEBI:23899 LIPID_MAPS_class:LMFA03 PMID:12697726 PMID:16107763 PMID:19160658 PMID:2657063 Wikipedia:Eicosanoid chebi_ontology eicosanoid eicosanoids icosanoid icosanoids monoatomic anion CHEBI:23905 chebi_ontology monoatomic anions monoatomic cation CHEBI:23906 chebi_ontology monoatomic cations enzyme inhibitor A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. CHEBI:23924 chebi_ontology enzyme inhibitor enzyme inhibitors inhibidor enzimatico inhibidores enzimaticos inhibiteur enzymatique inhibiteurs enzymatiques estradiol 0 272.178 272.38196 A 3-hydroxy steroid that is estra-1,3,5(10)-triene substituted by hydroxy groups at positions 3 and 17. C18H24O2 CHEBI:23965 CHEBI:42364 InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17?,18+/m1/s1 PMID:10696569 PMID:24084694 VOXZDWNPVJITMN-WKUFJEKOSA-N Wikipedia:Estradiol [H][C@]12CC[C@]3(C)C(O)CC[C@@]3([H])[C@]1([H])CCc1cc(O)ccc21 chebi_ontology estra-1,3,5(10)-triene-3,17-diol oestradiol estrane 0 246.235 246.43080 Beilstein:3125721 C18H30 CHEBI:23966 GRXPVLPQNMUNNX-MHJRRCNVSA-N InChI=1S/C18H30/c1-18-11-4-7-17(18)16-9-8-13-5-2-3-6-14(13)15(16)10-12-18/h13-17H,2-12H2,1H3/t13?,14-,15+,16+,17-,18-/m0/s1 LIPID_MAPS_instance:LMST02010000 Oestran [H][C@]12CCCCC1CC[C@]1([H])[C@]2([H])CC[C@]2(C)CCC[C@@]12[H] chebi_ontology estrane oestrane ethanolamines CHEBI:23981 chebi_ontology ethanolamine ethanols Any primary alcohol based on an ethanol skeleton. CHEBI:23982 chebi_ontology ethyl methanesulfonate 0 124.019 124.15900 A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with ethanol. C3H8O3S CAS:62-50-0 CCOS(C)(=O)=O CHEBI:23994 EMS InChI=1S/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3 KEGG:C19239 PLUBXMRUUVWRLT-UHFFFAOYSA-N PMID:16039156 PMID:19797863 PMID:20102787 PMID:24475756 PMID:24524729 PMID:24531730 PMID:24728647 PMID:6936603 PMID:7285888 Reaxys:773969 Wikipedia:Ethyl_methanesulfonate chebi_ontology ethyl mesylate ethyl methanesulphonate methylsulfonic acid ethyl ester methylsulfonic acid, ethyl ester fat-soluble vitamin CHEBI:24020 Vitamins like A, D, E and K that dissolve in fats and are stored in body tissues. Unlike the water-soluble vitamins, these are stored in the body for long periods of time and generally pose a greater risk for toxicity when consumed in excess. chebi_ontology fat-soluble vitamins fettloesliche Vitamine fatty alcohol An aliphatic alcohol consisting of a chain of 8 to 22 carbon atoms. Fatty alcohols may be saturated or unsaturated and may be branched or unbranched. CHEBI:24026 Fettalkohol Fettalkohole LIPID_MAPS_class:LMFA05 alcool gras chebi_ontology fatty alcohol fatty alcohols fluorine atom 0 18.998 18.99840 9F CAS:7782-41-4 CHEBI:24061 F F Fluor InChI=1S/F WebElements:F YCKRFDGAMUMZLT-UHFFFAOYSA-N [F] chebi_ontology fluor fluorine fluorine fluorum fluorine molecular entity CHEBI:24062 chebi_ontology fluorine compounds fluorine molecular entities fluorine molecular entity fluoroalkane A haloalkane that is an alkane in which at least one hydrogen atom has been replaced by a fluorine atom. CHEBI:24067 chebi_ontology fluoroalkane fluoroalkanes fructosamine CHEBI:24103 chebi_ontology fructosamine fructosamines galactonate C6H11O7 CHEBI:24148 chebi_ontology galactonic acid A hexonic acid that has been found to increase in red blood cells of galactosemic patients. C6H12O7 CHEBI:24149 PMID:14680973 chebi_ontology galactoside CHEBI:24163 chebi_ontology galactoside galactosides glucocorticoid CHEBI:24261 Glucocorticoids are a class of steroid hormones that regulate a variety of physiological processes, in particular control of the concentration of glucose in blood. chebi_ontology glucocorticoids glucosamines Any hexosamine that is glucose in which at least one of the hydroxy groups has been replaced by an amino group. CHEBI:24271 chebi_ontology glutamic acid derivative An amino acid derivative resulting from reaction of glutamic acid at the amino group or either of the carboxy groups, or from the replacement of any hydrogen by a heteroatom. The definition normally excludes peptides containing glutamic acid residues. CHEBI:24315 chebi_ontology glutamine family amino acid An L-alpha-amino acid which is L-glutamic acid or any of the essential amino acids biosynthesised from it (glutamine, proline and arginine). A closed class. CHEBI:24318 PMID:20716061 chebi_ontology glutamine family amino acids EC 6.3.1.2 (glutamate--ammonia ligase) inhibitor An EC 6.3.* (C-N bond-forming ligase) inhibitor that interferes with the action of glutamate--ammonia ligase (EC 6.3.1.2). CHEBI:24319 EC 6.3.1.2 (glutamate--ammonia ligase) inhibitors EC 6.3.1.2 inhibitor EC 6.3.1.2 inhibitors L-glutamate:ammonia ligase (ADP-forming) inhibitor L-glutamate:ammonia ligase (ADP-forming) inhibitors L-glutamine synthetase inhibitor L-glutamine synthetase inhibitors Wikipedia:Glutamine_synthetase chebi_ontology glutamate--ammonia ligase (EC 6.3.1.2) inhibitor glutamate--ammonia ligase (EC 6.3.1.2) inhibitors glutamate--ammonia ligase inhibitor glutamate--ammonia ligase inhibitors glutamine synthetase inhibitor glutamine synthetase inhibitors glutamylhydroxamic synthetase inhibitor glutamylhydroxamic synthetase inhibitors glutarate A dicarboxylic acid anion obtained by deprotonation of at least one of the carboxy groups of glutaric acid. CHEBI:24329 chebi_ontology glutarate anion glutarates glutaric acid anion glycerol ether Any ether having glyceryl as at least one of the O-substituents. CHEBI:24353 chebi_ontology glycine derivative A proteinogenic amino acid derivative resulting from reaction of glycine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. CHEBI:24373 chebi_ontology glycogens CHEBI:24384 chebi_ontology glycopeptide Any carbohydrate derivative that consists of glycan moieties covalently attached to the side chains of the amino acid residues that constitute the peptide. CHEBI:24395 CHEBI:24396 CHEBI:5478 chebi_ontology glycopeptides glycoside A glycosyl compound resulting from the attachment of a glycosyl group to a non-acyl group RO-, RS-, RSe-, etc. The bond between the glycosyl group and the non-acyl group is called a glycosidic bond. By extension, the terms N-glycosides and C-glycosides are used as class names for glycosylamines and for compounds having a glycosyl group attached to a hydrocarbyl group respectively. These terms are misnomers and should not be used. The preferred terms are glycosylamines and C-glycosyl compounds, respectively. CHEBI:24400 O-glycoside O-glycosides chebi_ontology glycosides glycosides glycosphingolipid A glycosphingolipid is a glycolipid that is a carbohydrate-containing derivative of a sphingoid or ceramide. It is understood that the carbohydrate residue is attached by a glycosidic linkage to O-1 of the sphingoid. CHEBI:24402 CHEBI:5498 PMID:18845618 PMID:19303901 PMID:26954668 PMID:26976737 PMID:27253729 PMID:27325407 Wikipedia:Glycosphingolipid chebi_ontology glycosphingolipids chemical entity A chemical entity is a physical entity of interest in chemistry including molecular entities, parts thereof, and chemical substances. CHEBI:24431 chebi_ontology chemical entity biological role A role played by the molecular entity or part thereof within a biological context. CHEBI:24432 biological function chebi_ontology group A defined linked collection of atoms or a single atom within a molecular entity. CHEBI:24433 Gruppe Rest chebi_ontology group groupe grupo grupos guanidines Any organonitrogen compound containing a carbamimidamido (guanidino) group. Guanidines have the general structure (R(1)R(2)N)(R(3)R(4)N)C=N-R(5) and are related structurally to amidines and ureas. CHEBI:24436 chebi_ontology haloalkane An organohalogen compound that is an alkane in which at least one hydrogen atom has been replaced by with a halogen atom. CHEBI:24469 alkyl halide alkyl halides chebi_ontology haloalkanes haloamino acid Any non-proteinogenic amino acid carrying at least one halo group. CHEBI:24470 chebi_ontology haloamino acids halogen molecular entity CHEBI:24471 chebi_ontology halogen compounds halogen molecular entities halogen molecular entity halohydrocarbon A compound derived from a hydrocarbon by replacing a hydrogen atom with a halogen atom. CHEBI:24472 chebi_ontology halogenated hydrocarbons halohydrocarbons halogen CHEBI:24473 Halogene chebi_ontology group 17 elements group VII elements halogen halogene halogenes halogeno halogenos halogens heparan CHEBI:24500 chebi_ontology heparans herbicide A substance used to destroy plant pests. CHEBI:24527 Herbizid Unkrautbekaempfungsmittel Unkrautvertilgungsmittel Wikipedia:Herbicide Wildkrautbekaempfungsmittel chebi_ontology herbicides organic heterocyclic compound A cyclic compound having as ring members atoms of carbon and at least of one other element. CHEBI:24532 chebi_ontology organic heterocycle organic heterocyclic compounds heterodetic cyclic peptide A heterodetic cyclic peptide is a peptide consisting only of amino-acid residues, but in which the linkages forming the ring are not solely peptide bonds; one or more is an isopeptide, disulfide, ester, or other bond. CHEBI:24533 chebi_ontology heterodetic cyclic peptide heterodetic cyclic peptides peptide cyclique heterodetique peptido ciclico heterodetico hexitol CHEBI:24583 chebi_ontology hexitol hexitols hexosamine Any 6-carbon amino monosaccharide with at least one alcoholic hydroxy group replaced by an amino group. CHEBI:24586 chebi_ontology hexosamine hexosamines homocysteines CHEBI:24610 chebi_ontology homocystines A non-proteinogenic alpha-amino acid obtained by oxidative dimerisation of homocysteine and its derivatives. CHEBI:24612 chebi_ontology hormone CHEBI:24621 Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds. chebi_ontology endocrine hormones imidazolidine-2,4-dione An imidazolidinone with oxo groups at position 2 and 4. CHEBI:24628 chebi_ontology hydrocarbon A compound consisting of carbon and hydrogen only. CHEBI:24632 Kohlenwasserstoff Kohlenwasserstoffe chebi_ontology hidrocarburo hidrocarburos hydrocarbon hydrocarbons hydrocarbure hydroxides CHEBI:24651 Hydroxides are chemical compounds containing a hydroxy group or salts containing hydroxide (OH(-)). chebi_ontology hydroxy fatty acid Any fatty acid carrying one or more hydroxy substituents. CHEBI:24654 LIPID_MAPS_class:LMFA0105 PMID:18296335 PMID:6419288 PMID:8274032 chebi_ontology hydroxy fatty acids hydroxy-amino acid A non-proteinogenic alpha-amino acid bearing one or more hydroxy groups at unspecified positions. CHEBI:24662 chebi_ontology hydroxy-5beta-cholanic acid Any member of the class of 5beta-cholanic acids carrying at least one hydroxy group at unspecified position. CHEBI:24663 chebi_ontology hydroxy-5beta-cholanic acids hydroxy carboxylic acid Any carboxylic acid with at least one hydroxy group. CHEBI:24669 chebi_ontology hydroxy carboxylic acids hydroxycarboxylic acid hydroxycarboxylic acids hydroxybutyric acid Any compound comprising a butyric acid core carrying at least one hydroxy substituent. C4H8O3 CHEBI:24684 chebi_ontology hydroxybutanoic acid hydroxybutanoic acids hydroxybutyric acids hydroxymethyl group -CH3-OH 0 31.018 31.03392 CH3O CHEBI:24712 chebi_ontology hydroxymethyl serine side-chain hydroxyproline A proline derivative that is proline substituted by at least one hydroxy group. CHEBI:24741 chebi_ontology imidazoles A five-membered organic heterocycle containing two nitrogen atoms at positions 1 and 3, or any of its derivatives; compounds containing an imidazole skeleton. CHEBI:24780 chebi_ontology indoles Any compound containing an indole skeleton. CHEBI:24828 chebi_ontology oxoacid A compound which contains oxygen, at least one other element, and at least one hydrogen bound to oxygen, and which produces a conjugate base by loss of positive hydrogen ion(s) (hydrons). CHEBI:24833 chebi_ontology oxacids oxiacids oxo acid oxoacid oxoacids oxy-acids oxyacids inorganic anion CHEBI:24834 chebi_ontology inorganic anions inorganic molecular entity A molecular entity that contains no carbon. CHEBI:24835 anorganische Verbindungen chebi_ontology inorganic compounds inorganic entity inorganic molecular entities inorganics inorganic oxide CHEBI:24836 chebi_ontology inorganic oxides inorganic peroxide CHEBI:24837 Compounds of structure ROOR' in which R and R' are inorganic groups. chebi_ontology inorganic peroxide inorganic peroxides inorganic salt CHEBI:24839 anorganisches Salz chebi_ontology inorganic salts insecticide CHEBI:24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. Wikipedia:Insecticide chebi_ontology insecticides iodide salt CHEBI:24858 chebi_ontology iodide salts iodides iodine atom 0 126.904 126.90447 53I CHEBI:24859 Chemical element with atomic number 53. I I InChI=1S/I Iod J Jod WebElements:I ZCYVEMRRCGMTRW-UHFFFAOYSA-N [I] chebi_ontology iode iodine iodine iodium yodo iodine molecular entity CHEBI:24860 chebi_ontology iodine compounds iodine molecular entities iodine molecular entity iodoamino acid An amino acid containing at least one iodo substituent. CHEBI:24862 chebi_ontology iodophenol C6H5IO CHEBI:24863 chebi_ontology iodophenol iodothyronine An iodoamino acid in which the amino acid specified is thyronine. CHEBI:24864 chebi_ontology iodothyronines salt A salt is an assembly of cations and anions. CHEBI:24866 Salz Salze chebi_ontology ionic compound ionic compounds sal sales salt salts sel sels monoatomic ion CHEBI:24867 chebi_ontology monoatomic ions organic salt CHEBI:24868 chebi_ontology organic salts organisches Salz ion A molecular entity having a net electric charge. CHEBI:24870 Ion Ionen chebi_ontology ion iones ions iron molecular entity CHEBI:24873 chebi_ontology iron compounds iron molecular entities iron molecular entity iron cation CHEBI:24875 Fe Fe cation chebi_ontology iron cation iron cations isoleucine A 2-amino-3-methylpentanoic acid having either (2R,3R)- or (2S,3S)-configuration. Beilstein:1721790 CAS:443-79-8 CHEBI:24898 Hile PMID:17190852 Reaxys:1721790 chebi_ontology isoleucine rel-(2R,3R)-2-amino-3-methylpentanoic acid isoprenoid Any lipid formally derived from isoprene (2-methylbuta-1,3-diene), the skeleton of which can generally be discerned in repeated occurrence in the molecule. The skeleton of isoprenoids may differ from strict additivity of isoprene units by loss or shift of a fragment, commonly a methyl group. The class includes both hydrocarbons and oxygenated derivatives. CHEBI:24913 LIPID_MAPS_class:LMPR01 PMID:12769708 PMID:19219049 chebi_ontology isoprenoid isoprenoids isoprenoids isoquinoline alkaloid Any alkaloid that has a structure based on an isoquinoline nucleus. They are derived from the amino acids like tyrosine and phenylalanine. CHEBI:24921 chebi_ontology isoquinoline alkaloids isoquinolines A class of organic heteropolycyclic compound consisting of isoquinoline and its substitution derivatives. CHEBI:24922 chebi_ontology ketoaldonate CHEBI:24961 chebi_ontology ketoaldonate ketoaldonates ketoaldonic acid CHEBI:24963 Oxo carboxylic acids formally derived from aldonic acids by replacement of a secondary CHOH group by a carbonyl group. chebi_ontology ketoaldonic acid ketoaldonic acids ketohexose Any hexose containing a single ketone group. CHEBI:24973 chebi_ontology ketohexose ketohexoses ketose CHEBI:24978 CHEBI:6131 chebi_ontology ketose ketoses lactam CHEBI:24995 Cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Laktam Laktame chebi_ontology lactam lactams lactams lactate -1 2-hydroxypropanoate 2-hydroxypropanoic acid, ion(1-) 2-hydroxypropionate 89.024 89.07000 A hydroxy monocarboxylic acid anion that is the conjugate base of lactic acid, arising from deprotonation of the carboxy group. Beilstein:3587719 C3H5O3 CAS:113-21-3 CC(O)C([O-])=O CHEBI:24996 Gmelin:240074 InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/p-1 JVTAAEKCZFNVCJ-UHFFFAOYSA-M KEGG:C01432 MeCH(OH)CO2 anion MetaCyc:Lactate b-lactate beta-lactate chebi_ontology lactate leucine (+-)-Leucine (RS)-Leucine 0 131.095 131.17296 2-amino-4-methylpentanoic acid A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group. Beilstein:636005 C6H13NO2 CAS:328-39-2 CC(C)CC(N)C(O)=O CHEBI:25017 DL-Leucine Gmelin:50203 Hleu InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9) KEGG:C16439 L LIPID_MAPS_instance:LMFA01100048 Leu Leucin Leuzin PMID:17439666 ROHFNLRQFUQHCH-UHFFFAOYSA-N Reaxys:636005 Wikipedia:Leucine chebi_ontology leucine leukotriene Any icosanoid from that family of C20 polyunsaturated fatty acids and their derivatives generated by leukocytes from arachidonic acid, each member having four double bonds of which three are conjugated. CHEBI:25029 LIPID_MAPS_class:LMFA0302 Leukotrien Leukotriene PMID:10922142 PMID:15794321 PMID:3001504 PMID:6129158 PMID:6293196 PMID:6311078 PMID:8842590 PMID:9526099 PMID:9561094 chebi_ontology leucotriene leucotrienes leukotriene leukotrienes leukotrienes linear tetrapyrrole CHEBI:25046 chebi_ontology lysine 0 146.106 146.18764 2,6-diaminohexanoic acid A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6. Beilstein:1616991 C6H14N2O2 CAS:70-54-2 CHEBI:25094 Gmelin:279284 InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10) K KDXKERNSBIXSRK-UHFFFAOYSA-N KEGG:C16440 LYS Lysin NCCCCC(N)C(O)=O PMID:17439666 PMID:22264337 Reaxys:1616991 Wikipedia:Lysine alpha,epsilon-diaminocaproic acid chebi_ontology lysine magnesium atom 0 12Mg 23.985 24.30500 CAS:7439-95-4 CHEBI:25107 DrugBank:DB01378 FYYHWMGAXLPEAU-UHFFFAOYSA-N Gmelin:16207 InChI=1S/Mg KEGG:C00305 Magnesium Mg Mg WebElements:Mg [Mg] chebi_ontology magnesio magnesium magnesium mandelate -1 151.040 151.13938 2-hydroxy-2-(4-hydroxyphenyl)acetate Beilstein:3905858 Beilstein:4135334 C8H7O3 CAS:769-61-9 CHEBI:25147 Gmelin:328159 IWYDHOAUDWTVEP-UHFFFAOYSA-M InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/p-1 OC(C([O-])=O)c1ccccc1 alpha-hydroxybenzeneacetate alpha-hydroxybenzeneacetic acid, ion(1-) chebi_ontology hydroxy(phenyl)acetate mandelate ion menaquinones 0 Any prenylnaphthoquinone having a prenyl or polyprenyl group at position 3 and a methyl group at position 2 on the naphthoquinone ring. C11H4O2R4(C5H8)n CHEBI:25185 chebi_ontology metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. CHEBI:25212 CHEBI:26619 CHEBI:35220 chebi_ontology metabolite metabolites primary metabolites secondary metabolites metal cation CHEBI:25213 a metal cation chebi_ontology metal cations metalloporphyrin CHEBI:25216 chebi_ontology metalloporphyrins metaloporphyrins methanesulfonate ester 0 94.980 95.099 An organosulfonic ester resulting from the formal condensation of methanesulfonic acid with the hydroxy group of an alcohol, phenol, heteroarenol, or enol. CH3O3SR CHEBI:25223 CS(O*)(=O)=O chebi_ontology mesylate ester mesylate esters methanesulfonic acid esters methanesulfonate -1 94.980 95.09872 A 1,1-diunsubstituted alkanesulfonate that is the conjugate base of methanesulfonic acid. AFVFQIVMOAPDHO-UHFFFAOYSA-M CH3O3S CHEBI:25224 CS([O-])(=O)=O InChI=1S/CH4O3S/c1-5(2,3)4/h1H3,(H,2,3,4)/p-1 MetaCyc:CPD-3746 UM-BBD_compID:c0347 chebi_ontology methanesulfonate methylsulfonate monomethoxybenzene CHEBI:25235 Compounds containing a benzene skeleton substituted with one methoxy group. chebi_ontology monomethoxybenzenes methyl methanesulfonate 0 110.004 110.13200 A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with methanol. C2H6O3S CAS:66-27-3 CB1540 CHEBI:25255 COS(C)(=O)=O InChI=1S/C2H6O3S/c1-5-6(2,3)4/h1-2H3 KEGG:C19181 MBABOKRGFJTBAE-UHFFFAOYSA-N MMS MetaCyc:CPD-7038 Methanesulfonic acid methyl ester Methyl mesylate PMID:11016630 PMID:14761437 PMID:16764919 PMID:21353429 PMID:21860482 PMID:22907509 PMID:23117069 PMID:23384783 PMID:23483329 Reaxys:1098586 Wikipedia:Methyl_methanesulfonate as-Dimethyl sulfite chebi_ontology methyl methanesulfonate methylamines CHEBI:25274 chebi_ontology methylated amines methyltetrahydrofolate A group of heterocyclic compounds based on the N-methylated 5,6,7,8-tetrahydropteroic acid skeleton conjugated with one or more L-glutamic acid or L-glutamate units. CHEBI:25345 chebi_ontology methyltetrahydrofolates methylxanthine CHEBI:25348 chebi_ontology methylxanthines mineralocorticoid CHEBI:25354 Mineralocorticoids are a class of steroid hormones that regulate water and electrolyte metabolism. chebi_ontology mineralocorticoids mitochondrial respiratory-chain inhibitor CHEBI:25355 chebi_ontology mitochondrial electron transport chain inhibitors mitochondrial electron-transport chain inhibitor mitochondrial respiratory chain inhibitors elemental molecule A molecule all atoms of which have the same atomic number. CHEBI:25362 chebi_ontology homoatomic molecule homoatomic molecules molecule Any polyatomic entity that is an electrically neutral entity consisting of more than one atom. CHEBI:25367 Molekuel chebi_ontology molecula molecule molecules neutral molecular compounds molybdenum molecular entity CHEBI:25370 chebi_ontology molybdenum compounds molybdenum molecular entities molybdopterin cofactor A molybdopterin to which a metal or metal oxide is coordinated, and that acts as a prosthetic group. CHEBI:25372 COMe:MOL000127 chebi_ontology molybdopterin cofactors monoamine molecular messenger A group of neurotransmitters and neuromodulators that contain one amino group that is connected to an aromatic ring by ethylene group (-CH2-CH2-). Monoamines are derived from the aromatic amino acids phenylalanine, tyrosine, histidine and tryptophan. CHEBI:25375 chebi_ontology monamines monoamine monoamines monocarboxylic acid An oxoacid containing a single carboxy group. CHEBI:25384 chebi_ontology monocarboxylic acid monocarboxylic acids monounsaturated fatty acid Any fatty acid with one double or triple bond in the fatty acid chain and singly bonded carbon atoms in the rest of the chain. MUFAs have positive effects on the cardiovascular system, and in diabetes treatment. CHEBI:25413 MUFA MUFAs PMID:10584045 PMID:12936956 chebi_ontology monounsaturated fatty acids monoatomic monocation +1 0.00000 CHEBI:25414 [*+] chebi_ontology monoatomic monocations monovalent cation monovalent inorganic cations mutagen An agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution. CHEBI:25435 Wikipedia:Mutagen chebi_ontology mutagene mutagenes mutagenic agent mutageno mutagenos mutagens mycotoxin CHEBI:25442 Poisonous substance produced by fungi. chebi_ontology fungal toxins mycotoxins naphthoquinone A polycyclic aromatic ketone metabolite of naphthalene. CHEBI:25481 chebi_ontology naphthoquinones nematicide A substance used to destroy pests of the phylum Nematoda (roundworms). CHEBI:25491 Wikipedia:Nematicide chebi_ontology nematicides nematocide nematocides neopterins CHEBI:25500 chebi_ontology neuraminates CHEBI:25506 chebi_ontology neuraminic acids CHEBI:25508 chebi_ontology neurotransmitter An endogenous compound that is used to transmit information across the synapse between a neuron and another cell. CHEBI:25512 Wikipedia:Neurotransmitter chebi_ontology neurotransmitters neutral glycosphingolipid Any glycosphingolipid containing unsubstituted glycosyl moieties. CHEBI:25513 CHEBI:7543 chebi_ontology neutral glycosphingolipids aldicarb 0 190.078 190.26300 2-Methyl-2-(methylthio)propanal, O-((methylamino)carbonyl)oxime 2-Methyl-2-(methylthio)propionaldehyde O-(methylcarbamoyl)oxime 2-Methyl-2-methylthio-propionaldehyd-O-(N-methyl-carbamoyl)-oxim 2-methyl-N-[(methylcarbamoyl)oxy]-2-(methylsulfanyl)propan-1-imine Aldicarb Beilstein:2046931 C7H14N2O2S CAS:116-06-3 CHEBI:2555 InChI=1S/C7H14N2O2S/c1-7(2,12-4)5-9-11-6(10)8-3/h5H,1-4H3,(H,8,10) KEGG:C11015 LINCS:LSM-20978 PPDB:19 Patent:US3217037 QGLZXHRNAYXIBU-UHFFFAOYSA-N The oxime carbamate resulting from the addition of 2-methyl-2-(methylsulfanyl)propanaldoxime to methyl isocyanate. A member of the class of oxime carbamate insecticides, aldicarb is a mixture of E and Z isomers; it is not known which isomer is more active. [H]C(=NOC(=O)NC)C(C)(C)SC aldicarbe chebi_ontology nitrogen atom 7N CHEBI:25555 N N Stickstoff WebElements:N azote chebi_ontology nitrogen nitrogen nitrogeno nitrous acid 0 47.001 47.01348 CAS:7782-77-6 CHEBI:25567 Gmelin:983 HNO2 HNO2 IOVCWXUNBOPUCH-UHFFFAOYSA-N InChI=1S/HNO2/c2-1-3/h(H,2,3) KEGG:C00088 PDBeChem:NO2 [H]ON=O [NO(OH)] chebi_ontology dioxonitric acid hydrogen dioxonitrate(1-) hydroxidooxidonitrogen nitrosyl hydroxide nitrous acid nonanone Any ketone that is nonane substituted by an oxo group at unspecified position. CHEBI:25579 chebi_ontology nonanones nonmetal atom CHEBI:25585 Nichtmetall Nichtmetalle chebi_ontology no metal no metales non-metal non-metaux nonmetal nonmetal nonmetals nucleoside phosphate A nucleobase-containing molecular entity that is a nucleoside in which one or more of the sugar hydroxy groups has been converted into a mono- or poly-phosphate. The term includes both nucleotides and non-nucleotide nucleoside phosphates. CHEBI:25608 KEGG:C01329 NMP Nucleoside monophosphate chebi_ontology nucleoside phosphates oligopeptide A peptide containing a relatively small number of amino acids. CHEBI:25676 CHEBI:7755 Oligopeptid Wikipedia:Oligopeptide chebi_ontology oligopeptides oligopeptido organic heteromonocyclic compound CHEBI:25693 chebi_ontology organic heteromonocyclic compounds organic anion Any organic ion with a net negative charge. CHEBI:25696 chebi_ontology organic anions organic cation Any organic ion with a net positive charge. CHEBI:25697 chebi_ontology organic cations ether 0 15.995 15.99940 An organooxygen compound with formula ROR, where R is not hydrogen. CHEBI:25698 OR2 [*]O[*] chebi_ontology ether ethers ethers organic ion CHEBI:25699 chebi_ontology organic ions organic oxide An oxide in which the oxygen atom is bonded to a carbon atom. CHEBI:25701 chebi_ontology organic oxides organic phosphate CHEBI:25703 chebi_ontology organic phosphate organic phosphate ester organic phosphate esters organic phosphates organophosphate ester organophosphate esters organic sulfate CHEBI:25704 Compounds of the general formula SO3HOR where R is an organyl group chebi_ontology organic sulfates aliphatic alcohol 0 17.003 17.007 Aliphatic alcohol An alcohol derived from an aliphatic compound. CHEBI:2571 HOR KEGG:C02525 O* aliphatic alcohols an aliphatic alcohol chebi_ontology organophosphorus compound An organophosphorus compound is formally a compound containing at least one carbon-phosphorus bond, but the term is often extended to include esters and thioesters. CHEBI:25710 chebi_ontology organophosphorus compound organophosphorus compounds osmolyte A solute used by a cell under water stress to maintain cell volume. CHEBI:25728 chebi_ontology osmolytes oxide An oxide is a chemical compound of oxygen with other chemical elements. CHEBI:25741 chebi_ontology oxide oxides oxime 0 43.006 43.02470 CHEBI:25750 CHNOR2 Compounds of structure R2C=NOH derived from condensation of aldehydes or ketones with hydroxylamine. Oximes from aldehydes may be called aldoximes; those from ketones may be called ketoximes. O\N=C(\[*])[*] chebi_ontology oxime oximes oximes oxo carboxylic acid Any compound that has an aldehydic or ketonic group as well as a carboxylic acid group in the same molecule. CHEBI:25754 chebi_ontology oxo acids oxo carboxylic acids oxo carboxylic acids oxopentanoates C5H7O3 CHEBI:25798 The conjugate base of any oxopentanoic acid. chebi_ontology oxopentanoate oxopentanoic acid A C5 fatty acid carrying an oxo group at any position. C5H8O3 CHEBI:25799 chebi_ontology oxopentanoic acid oxovaleric acid unsaturated fatty acid anion Any fatty acid anion containing at least one C-C unsaturated bond; formed by deprotonation of the carboxylic acid moiety. CHEBI:2580 an unsaturated fatty acid chebi_ontology oxoproline A pyrrolidinemonocarboxylic acid consisting of proline bearing a single oxo substituent. C5H7NO3 CHEBI:25801 chebi_ontology oxoproline oxygen atom 0 15.995 15.99940 8O CHEBI:25805 InChI=1S/O KEGG:C00007 O O QVGXLLKOCUKJST-UHFFFAOYSA-N Sauerstoff WebElements:O [O] chebi_ontology oxigeno oxygen oxygen oxygene oxygen molecular entity CHEBI:25806 chebi_ontology oxygen molecular entities oxygen molecular entity oxopurine CHEBI:25810 chebi_ontology oxopurines p-quinones A quinone in which the two oxo groups of the quinone are located para to each other on the 6-membered quinonoid ring. CHEBI:25830 chebi_ontology p-quinone para-quinones pentanone Any ketone that is pentane substituted by an oxo group at unspecified position. CHEBI:25892 chebi_ontology pentanones pentenoic acid Any C5, straight-chain, monounsaturated fatty acid. C5:1 C5H8O2 CHEBI:25897 chebi_ontology pentenoic acid pentenoic acids pentitol An alditol obtained by reduction of any pentose. CHEBI:25899 chebi_ontology pentitol pentitols aldopentose phosphate CHEBI:25900 aldopentose phosphate aldopentose phosphates chebi_ontology pentose A five-carbon monosaccharide which in its linear form contains either an aldehyde group at position 1 (aldopentose) or a ketone group at position 2 (ketopentose). CHEBI:25901 chebi_ontology pentose pentoses peptide hormone Any peptide with hormonal activity in animals, whether endocrine, neuroendocrine, or paracrine. CHEBI:25905 chebi_ontology peptide hormones polypeptide hormone peroxides 0 31.990 CHEBI:25940 Compounds of structure ROOR'. O2R2 [*]OO[*] a peroxide chebi_ontology pesticide CHEBI:25944 Pestizid Pestizide Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. Wikipedia:Pesticide chebi_ontology pesticide pesticides phenylalanine derivative An amino acid derivative resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of phenylalanine by a heteroatom. The definition normally excludes peptides containing phenylalanine residues. CHEBI:25985 chebi_ontology phenylethanolamines An ethanolamine compound having a phenyl (substituted or unsubstituted) group on the carbon bearing the hydroxy substituent. CHEBI:25990 chebi_ontology pheromone A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour. CHEBI:26013 PMID:23988175 Wikipedia:Pheromone chebi_ontology ectohormone feromone pheromone pheromones phosphate CHEBI:26020 Salts and esters of phosphoric and oligophosphoric acids and their chalcogen analogues. In inorganic chemistry, the term is also used to describe anionic coordination entities with phosphorus as central atom. chebi_ontology phosphates phosphates phosphoric acid 0 97.977 97.99520 A phosphorus oxoacid that consits of one oxo and three hydroxy groups joined covalently to a central phosphorus atom. Beilstein:1921286 CAS:7664-38-2 CHEBI:26078 Drug_Central:4478 Gmelin:2000 H3O4P H3PO4 HMDB:HMDB0002142 InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4) KEGG:C00009 KEGG:D05467 KNApSAcK:C00007408 NBIIXXVUZAFLBC-UHFFFAOYSA-N Orthophosphoric acid PMID:11455380 PMID:15630224 PMID:17439666 PMID:17518491 PMID:22282755 PMID:22333268 PMID:22381614 PMID:22401268 Phosphate Phosphoric acid Phosphorsaeure Phosphorsaeureloesungen Reaxys:1921286 Wikipedia:Phosphoric_Acid [H]OP(=O)(O[H])O[H] [PO(OH)3] acide phosphorique acidum phosphoricum chebi_ontology orthophosphoric acid phosphoric acid tetraoxophosphoric acid trihydrogen tetraoxophosphate(3-) trihydroxidooxidophosphorus phosphoric acid derivative CHEBI:26079 chebi_ontology phosphorus molecular entity CHEBI:26082 chebi_ontology phosphorus molecular entities phylloquinones CHEBI:26106 chebi_ontology phytosteroid CHEBI:26124 chebi_ontology phytosteroids phytosterols CHEBI:26125 Sterols similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond. Wikipedia:Phytosterol chebi_ontology phytylnaphthoquinone CHEBI:26127 chebi_ontology biological pigment An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light. CHEBI:26130 chebi_ontology pigments piperazines CHEBI:26144 chebi_ontology plant growth regulator A chemical, natural or artificial, that can affect the rate of growth of a plant. CHEBI:26155 chebi_ontology plant growth regulators polar amino acid CHEBI:26167 CHEBI:8283 chebi_ontology polyol A compound that contains two or more hydroxy groups. CHEBI:26191 chebi_ontology polyols porphyrins CHEBI:26214 Natural pigments containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure. Wikipedia:Porphyrin chebi_ontology porphyrins potassium atom 0 19K 38.964 39.09830 CAS:7440-09-7 CHEBI:26216 DrugBank:DB01345 InChI=1S/K K K KEGG:C00238 Kalium WebElements:K ZLMJMSJWJFRBEC-UHFFFAOYSA-N [K] chebi_ontology kalium potasio potassium potassium potassium molecular entity CHEBI:26217 chebi_ontology potassium molecular entities potassium molecular entity prenylnaphthoquinone CHEBI:26254 chebi_ontology prenylquinone A quinone substituted by a polyprenyl-derived side-chain. Prenylquinones occur in all living cells. Due to their amphiphilic character, they are mainly located in biological membranes where they function as electron and proton carriers in the photosynthetic and respiratory electron transport chains. Some prenylquinones also perform more specialised roles sucy as antioxidants and enzyme cofactors. Prenylquinones are classified according to ring structure: the main classes are menaquinones, phylloquinones, ubiquinones and plastoquinones. CHEBI:26255 CHEBI:72751 PMID:19928587 PMID:21777468 PMID:21844348 PMID:22371323 PMID:3985624 chebi_ontology polyprenylquinone polyprenylquinones prenylquinones proline 0 115.063 115.13050 An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2. Beilstein:80809 C5H9NO2 CAS:609-36-9 CHEBI:26271 DL-Proline Gmelin:26927 Hpro InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8) KEGG:C16435 OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N PMID:16534801 PMID:21400017 PMID:21903295 PMID:22264337 PMID:22280966 PMID:22770225 Prolin Reaxys:80809 Wikipedia:Proline chebi_ontology prolina proline pyrrolidine-2-carboxylic acid proline derivative An amino acid derivative resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of proline by a heteroatom. The definition normally excludes peptides containing proline residues. CHEBI:26273 chebi_ontology proline derivatives propane-1,2-diols CHEBI:26284 chebi_ontology propanediol CHEBI:26288 chebi_ontology propanones A ketone that is propane carrying at least one oxo substituent. CHEBI:26292 chebi_ontology prostaglandin CAS:11000-26-3 CHEBI:26333 LIPID_MAPS_class:LMFA0301 Naturally occurring compounds derived from the parent C20 acid, prostanoic acid. chebi_ontology prostaglandin prostaglandins prostaglandins prostaglandins E 0 98.037 98.09990 C5H6O2R2 CHEBI:26338 O[C@@H]1CC(=O)[C@H]([*])[C@H]1[*] PGE chebi_ontology prostanoid CHEBI:26347 The family of natural prostaglandins and prostaglandin-like compounds including prostacyclins and thromboxanes. chebi_ontology prostanoid prostanoids prostanoids prosthetic group A tightly bound, specific nonpolypeptide unit in a protein determining and involved in its biological activity. CHEBI:26348 chebi_ontology groupe prosthetique prosthetic group prosthetic groups protoporphyrins CHEBI:26361 chebi_ontology pteridines CHEBI:26373 chebi_ontology pterins CHEBI:26375 chebi_ontology purine alkaloid CHEBI:26385 chebi_ontology purine alkaloids purine nucleobase 0 119.036 119.104 A nucleobase whose skeleton is derived from purine. C1(NC(=NC=2NC=NC12)*)=* C5H3N4R2 CHEBI:26386 KEGG:C15587 a purine nucleobase chebi_ontology purine bases purine nucleobase purine nucleobases purine nucleoside diphosphate CHEBI:26391 chebi_ontology purine nucleoside diphosphates purine nucleoside monophosphate CHEBI:26392 chebi_ontology purine nucleoside monophosphates purine nucleoside triphosphate CHEBI:26393 chebi_ontology purine nucleoside triphosphates purine nucleoside CHEBI:26394 chebi_ontology purine nucleoside purine nucleosides purine nucleotide Any nucleotide that has a purine nucleobase. CHEBI:26395 chebi_ontology purine nucleotides purine ribonucleoside diphosphate CHEBI:26396 chebi_ontology purine ribonucleoside diphosphates purine ribonucleoside monophosphate CHEBI:26397 chebi_ontology purine ribonucleoside monophosphates purine ribonucleoside triphosphate CHEBI:26398 chebi_ontology purine ribonucleoside triphosphates purine ribonucleoside *[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O 0 133.050 133.123 A ribonucleoside that has a purine moiety as the nucleobase (the R group in the illustration). C5H9O4R CHEBI:26399 chebi_ontology purine ribonucleosides purine ribonucleotide Any ribonucleotide that has a purine nucleobase. CHEBI:26400 chebi_ontology purine ribonucleotides purines 0 116.012 116.080 A class of imidazopyrimidines that consists of purine and its substituted derivatives. C5N4R7 CHEBI:13678 CHEBI:26401 chebi_ontology pyridine alkaloid CHEBI:26416 chebi_ontology pyridine alkaloids pyridines Any organonitrogen heterocyclic compound based on a pyridine skeleton and its substituted derivatives. CHEBI:26421 chebi_ontology pyrimidine nucleobase 0 77.014 77.064 A nucleobase whose skeleton is derived from pyrimidine. C4HN2R4 CHEBI:26432 N1C(=C(C(=NC1=*)*)*)* a pyrimidine nucleobase chebi_ontology pyrimidine bases pyrimidine nucleobase pyrimidine nucleobases pyrimidinemonocarboxylic acid CHEBI:26447 chebi_ontology pyrimidinemonocarboxylic acids pyrroles An azole that includes only one N atom and no other heteroatom as a part of the aromatic skeleton. CHEBI:26455 chebi_ontology pyrrolidine alkaloid CHEBI:26456 chebi_ontology pyrrolidine alkaloids quaternary nitrogen compound A nitrogen molecular entity that is electronically neutral but which contains a quaternary nitrogen. CHEBI:26469 chebi_ontology quinoline alkaloid CHEBI:26509 chebi_ontology quinoline alkaloids quinolines A class of aromatic heterocyclic compounds each of which contains a benzene ring ortho fused to carbons 2 and 3 of a pyridine ring. CHEBI:26513 chebi_ontology reactive oxygen species CHEBI:26523 Molecules or ions formed by the incomplete one-electron reduction of oxygen. They contribute to the microbicidal activity of phagocytes, regulation of signal transduction and gene expression, and the oxidative damage to biopolymers. ROS Wikipedia:Reactive_oxygen_species chebi_ontology retinals CHEBI:26534 chebi_ontology retinoic acid 0 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid 300.209 300.43512 A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified). C20H28O2 CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC(O)=O CHEBI:26536 InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22) LINCS:LSM-2135 PMID:24506204 SHGAZHPCJJPHSC-UHFFFAOYSA-N chebi_ontology retinoid CHEBI:26537 Oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. chebi_ontology retinoid retinoids retinoids ribonucleoside monophosphate CHEBI:26558 chebi_ontology ribonucleoside monophosphates ribonucleotide CHEBI:26561 chebi_ontology ribonucleotides ribose phosphate CHEBI:26562 chebi_ontology ribose phosphate ribose phosphates saturated fatty acid Any fatty acid containing no carbon to carbon multiple bonds. Known to produce adverse biological effects when ingested to excess. CHEBI:26607 PMID:16492686 PMID:19763019 PMID:20237329 SFA SFAs chebi_ontology saturated fatty acid saturated fatty acids semiochemical A molecular messenger released by an organism that affects the behaviour within or between species. CHEBI:26645 Wikipedia:Semiochemical chebi_ontology semiochemicals serine family amino acid 3-phosphoglycerate family amino acid 3-phosphoglycerate family amino acids An L-alpha-amino acid which is biosynthesised from 3-phosphoglycerate (i.e. serine, glycine, cysteine and homocysteine). A closed class. CHEBI:26650 PMID:20709681 chebi_ontology serine family amino acids short-chain fatty acid 0 30.011 An aliphatic monocarboxylic acid with a chain length of less than C6. If any non-hydrocarbon substituent is present, the compound is not normally regarded as a short-chain fatty acid. CH2OR CHEBI:26666 OC([*])=O PMID:16633129 PMID:16870803 PMID:18203540 PMID:20148677 SCFA SCFAs chebi_ontology short-chain fatty acids sialic acid Any of the N-acylneuraminic acids and their esters and other derivatives of the alcoholic hydroxy groups. CHEBI:26667 Sialsaeure Sialsaeuren acide sialique acides sialique chebi_ontology sialic acids sodium atom 0 11Na 22.98977 22.990 CAS:7440-23-5 CHEBI:26708 Gmelin:16221 InChI=1S/Na KEAYESYHFKHZAL-UHFFFAOYSA-N KEGG:C01330 Na Na Natrium WebElements:Na [Na] chebi_ontology natrium sodio sodium sodium sodium chloride 0 57.959 58.44247 An inorganic chloride salt having sodium(1+) as the counterion. Beilstein:3534976 CAS:7647-14-5 CHEBI:26710 ClNa FAPWRFPIFSIZLT-UHFFFAOYSA-M Gmelin:13673 InChI=1S/ClH.Na/h1H;/q;+1/p-1 KEGG:C13563 KEGG:D02056 Kochsalz MetaCyc:NACL NaCl Natriumchlorid PPDB:595 Reaxys:3534976 Wikipedia:Sodium_Chloride [Na+].[Cl-] chebi_ontology chlorure de sodium cloruro sodico common salt halite natrii chloridum rock salt salt sodium chloride table salt sodium molecular entity CHEBI:26712 chebi_ontology sodium compounds sodium molecular entities sodium salt Any alkali metal salt having sodium(1+) as the cation. CHEBI:26714 Natriumsalz Natriumsalze chebi_ontology sodium salts sphingenine A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration. C18H37NO2 CHEBI:26738 chebi_ontology sphingenines sphingolipid CHEBI:26739 Sphingolipids are a complex family of compounds that share a common structural feature, a sphingoid base backbone. chebi_ontology sphingolipids sphing-4-enine (2S,3R)-2-aminooctadec-4-ene-1,3-diol 0 299.282 299.49192 4-sphingenine A sphingenine in which the C=C double bond is located at the 4-position. Beilstein:7794904 C18H37NO2 CHEBI:26743 InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/t17-,18+/m0/s1 LINCS:LSM-5718 WWUZIQQURGPMPG-ZWKOTPCHSA-N [H]C(CCCCCCCCCCCCC)=C([H])[C@@H](O)[C@@H](N)CO chebi_ontology sphing-4-enine steroid hormone Any steroid that acts as hormone. CHEBI:26764 Steroidhormon Steroidhormone chebi_ontology hormona esteroide hormonas esteroideas hormone steroide hormones steroides steroid hormones carbohydrate phosphate CHEBI:26816 carbohydrate phosphates chebi_ontology sulfuric ester 0 95.952 96.06300 An ester of an alcohol and sulfuric acid. CHEBI:26819 O4SR2 [*]OS(=O)(=O)O[*] chebi_ontology sulfate ester sulfuric acid ester sulfuric acid esters sulfates CHEBI:26820 Salts and esters of sulfuric acid chebi_ontology sulfates sulfuric acid derivative sulphates sulfide Any sulfur molecular entity that involves either covalently bonded or anionic sulfur. CHEBI:26822 chebi_ontology sulphides sulfoglycolipid A sulfate ester of a glycolipid. CHEBI:26829 chebi_ontology sulfoglycolipids sulfonium compound CHEBI:26830 chebi_ontology sulfur atom 0 16S 31.972 32.06600 CAS:7704-34-9 CHEBI:26833 Elemental sulfur InChI=1S/S KEGG:C00087 KEGG:D06527 NINIDFKCEFEMDL-UHFFFAOYSA-N PPDB:605 S S Schwefel WebElements:S [S] azufre chebi_ontology soufre sulfur sulfur sulphur theion sulfur-containing amino acid CHEBI:26834 chebi_ontology sulfur-containing amino acids sulfur molecular entity CHEBI:26835 chebi_ontology sulfur molecular entities sulfur molecular entity sulfuric acid 0 97.967 98.07948 A sulfur oxoacid that consits of two oxo and two hydroxy groups joined covalently to a central sulfur atom. Acide sulfurique Acido sulfurico Acidum sulfuricum CAS:7664-93-9 CHEBI:26836 Gmelin:2122 H2O4S H2SO4 InChI=1S/H2O4S/c1-5(2,3)4/h(H2,1,2,3,4) KEGG:C00059 KEGG:D05963 KNApSAcK:C00007530 MolBase:4 PMID:13568755 PMID:16122922 PMID:19397353 PMID:22047659 PMID:22136045 PMID:22204399 PMID:22267186 PMID:22296037 PMID:22364556 PMID:22435616 PPDB:606 QAOWNCQODCNURD-UHFFFAOYSA-N Reaxys:2037554 Schwefelsaeureloesungen Sulfuric acid Wikipedia:Sulfuric_acid [H]OS(=O)(=O)O[H] [S(OH)2O2] [SO2(OH)2] chebi_ontology dihydrogen tetraoxosulfate dihydroxidodioxidosulfur hydrogen tetraoxosulfate(2-) hydrogen tetraoxosulfate(VI) sulfuric acid sulphuric acid tetraoxosulfuric acid terpenoid Any isoprenoid that is a natural product or related compound formally derived from isoprene units. Terpenoids may contain oxygen in various functional groups. This class is subdivided according to the number of carbon atoms in the parent terpene. The skeleton of terpenoids may differ from strict additivity of isoprene units by the loss or shift of a fragment, generally a methyl group. CHEBI:26873 Terpenoid Wikipedia:Terpenoid chebi_ontology terpenoide terpenoides terpenoids tertiary alcohol 0 71.050 71.09780 A tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it. C4H7OR3 CHEBI:26878 OC(C[*])(C[*])C[*] chebi_ontology tertiary alcohol tertiary alcohols tetrahydrofolic acid A group of heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with one or more L-glutamic acid units. CHEBI:26907 chebi_ontology tetrahydrofolate tetrahydrofolates tetrahydrofolic acids oxolanes Any oxacycle having an oxolane (tetrahydrofuran) skeleton. CHEBI:26912 chebi_ontology tetrapyrrole A natural pigment containing four pyrrole rings joined by one-carbon units linking position 2 of one pyrrole ring to position 5 of the next. CHEBI:26932 chebi_ontology tetrapyrrole tetrapyrroles tetraterpenoid Any terpenoid derived from a tetraterpene. The term includes compounds in which the C40 skeleton of the parent tetraterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups). C40 isoprenoids CHEBI:26935 LIPID_MAPS_class:LMPR0107 chebi_ontology tetraterpenoides tetraterpenoids thiamine CHEBI:26948 chebi_ontology thiamines thioacetic acid CHEBI:26952 KEGG:C01857 Thioessigsaeure chebi_ontology ethanethioic acid thiocarboxylic ester An ester in which one or both oxygens of an ester group have been replaced by divalent sulfur. CHEBI:26959 chebi_ontology thiocarboxylic esters organic heterotricyclic compound An organic tricyclic compound in which at least one of the rings of the tricyclic skeleton contains one or more heteroatoms. CHEBI:26979 chebi_ontology heterotricyclic compounds organic heterotricyclic compounds threitol (R*,R*)-1,2,3,4-butanetetrol C4H10O4 CAS:7493-90-5 CHEBI:26981 Gmelin:82500 PMID:20717558 chebi_ontology rel-(2R,3R)-butane-1,2,3,4-tetrol threo-tetritol threonine An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 1-hydroxyethyl group. Beilstein:8204750 C4H9NO3 CAS:80-68-2 CHEBI:26986 PMID:11379295 PMID:15221503 PMID:22264337 Threonin Wikipedia:Threonine chebi_ontology threonine thromboxane A class of oxygenated oxane derivatives, originally derived from prostaglandin precursors in platelets, that stimulate aggregation of platelets and constriction of blood vessels. CHEBI:26995 LIPID_MAPS_class:LMFA0303 Wikipedia:Thromboxane chebi_ontology thromboxane thromboxanes tocopherol A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain. CAS:1406-66-2 CHEBI:27013 Methyltocols Tocopherol Tocopherols Wikipedia:Tocopherol chebi_ontology tocoferol tocoferoles tocopherol tocopherols toluenes Any member of the class of benzenes that is a substituted benzene in which the substituents include one (and only one) methyl group. CHEBI:27024 chebi_ontology toxin CHEBI:27026 Poisonous substance produced by a biological organism such as a microbe, animal or plant. Wikipedia:Toxin chebi_ontology toxin toxins micronutrient Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions. CHEBI:27027 Wikipedia:Micronutrient chebi_ontology micronutrients trace elements transition element atom An element whose atom has an incomplete d sub-shell, or which can give rise to cations with an incomplete d sub-shell. CHEBI:27081 Uebergangselement Uebergangsmetalle chebi_ontology metal de transicion metal de transition metales de transicion metaux de transition transition element transition element transition elements transition metal transition metals tricarboxylic acid trianion CHEBI:27092 chebi_ontology tricarboxylate tricarboxylates tricarboxylic acid trianions tricarboxylic acid An oxoacid containing three carboxy groups. C3H3O6R CHEBI:27093 Tricarbonsaeure Trikarbonsaeure Wikipedia:Tricarboxylic_acid chebi_ontology tricarboxylic acids trimethylxanthine CHEBI:27134 chebi_ontology trimethylxanthines triol A chemical compound containing three hydroxy groups. CHEBI:27136 chebi_ontology triols tryptamines CHEBI:27162 Tryptamine and its substitution derivatives. chebi_ontology organic heterobicyclic compound CHEBI:27171 chebi_ontology heterobicyclic compounds organic heterobicyclic compounds tyramines Aralkylamino compounds which contain a tyramine skeleton. CHEBI:27175 chebi_ontology univalent carboacyl group A univalent carboacyl group is a group formed by loss of OH from the carboxy group of a carboxylic acid. CHEBI:27207 chebi_ontology univalent acyl group univalent carboacyl groups univalent carboxylic acyl groups unsaturated fatty acid Any fatty acid containing at least one C=C or C#C bond. CHEBI:27208 LIPID_MAPS_class:LMFA0103 PMID:5322381 alkene acid chebi_ontology olefinic acid unsaturated fatty acids urate(2-) -2 166.09454 C5H2N4O3 CHEBI:27216 chebi_ontology urate dianion uric acid 0 168.11042 An oxopurine that is the final oxidation product of purine metabolism. C5H4N4O3 CHEBI:27226 HMDB:HMDB0000289 Wikipedia:Uric_acid chebi_ontology uric acids urocanate -1 137.035 137.11618 3-(1H-imidazol-4-yl)prop-2-enoate An monocarboxylic acid anion that is the conjugate base of urocanic acid. C6H5N2O2 CHEBI:27247 ECMDB:ECMDB21396 InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/p-1 KEGG:C00785 LOIYMIARKYCTBW-UHFFFAOYSA-M MetaCyc:UROCANATE [H]C(=C([H])c1c[nH]cn1)C([O-])=O chebi_ontology urocanate urocanic acid 0 138.043 138.12412 3-(1H-imidazol-4-yl)-2-propenoic acid 3-(1H-imidazol-4-yl)prop-2-enoic acid 3-imidazol-4-ylacrylic acid An alpha,beta-unsaturated monocarboxylic acid that is prop-2-enoic acid substituted by a 1H-imidazol-4-yl group at position 3. It is a metabolite of hidtidine. Beilstein:8128219 C6H6N2O2 CAS:104-98-3 CHEBI:27248 ECMDB:ECMDB21396 HMDB:HMDB0000301 InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10) LOIYMIARKYCTBW-UHFFFAOYSA-N MetaCyc:UROCANATE PDBeChem:URO PMID:11669511 PMID:24397532 PMID:24627570 Reaxys:8128219 Wikipedia:Urocanic_acid [H]C(=C([H])c1c[nH]cn1)C(O)=O chebi_ontology valine 0 117.079 117.14638 2-amino-3-methylbutanoic acid A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group. Beilstein:506689 C5H11NO2 CAS:516-06-3 CC(C)C(N)C(O)=O CHEBI:27266 DL-valine Gmelin:49877 Hval InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8) KEGG:C16436 KZSNJWFQEVHDMF-UHFFFAOYSA-N PMID:17190852 PMID:22770225 Reaxys:506689 Valin Wikipedia:Valine chebi_ontology valina valine vitamin D CHEBI:27300 D vitamins Vitamin D is a group of fat-soluble prohormones, which can be obtained from sun exposure, food and supplements. Vitamin D is biologically inactive and converted to the biologically active calcitriol via double hydroxylation in the body. chebi_ontology volatile oil component Any metabolite that is found naturally as a component of a volatile oil. CHEBI:27311 Wikipedia:Essential_oil chebi_ontology essential oil component essential oil components ethereal oil component ethereal oil components volatile oil components water-soluble vitamin CHEBI:27314 chebi_ontology wasserloesliche Vitamine water-soluble vitamins xanthophyll A subclass of carotenoids consisting of the oxygenated carotenes. CHEBI:27325 DrugBank:DB00137 chebi_ontology xanthophylls xanthophylls zinc atom 0 30Zn 63.929 65.39000 CAS:7440-66-6 CHEBI:27363 Gmelin:16321 HCHKCACWOHOZIP-UHFFFAOYSA-N InChI=1S/Zn KEGG:C00038 PDBeChem:ZN WebElements:Zn Zink Zn Zn Zn(II) Zn2+ [Zn] chebi_ontology cinc zinc zinc zincum zinc molecular entity CHEBI:27364 chebi_ontology zinc compounds zinc molecular entities zwitterion A neutral compound having formal unit electrical charges of opposite sign on non-adjacent atoms. Sometimes referred to as inner salts, dipolar ions (a misnomer). CHEBI:27369 chebi_ontology compose zwitterionique compuestos zwitterionicos zwitterion zwitteriones zwitterionic compounds zwitterions methanesulfonic acid 0 95.988 96.10666 AFVFQIVMOAPDHO-UHFFFAOYSA-N An alkanesulfonic acid in which the alkyl group directly linked to the sulfo functionality is methyl. Beilstein:1446024 CAS:75-75-2 CH4O3S CHEBI:27376 CHEBI:6813 CS(O)(=O)=O Gmelin:1681 InChI=1S/CH4O3S/c1-5(2,3)4/h1H3,(H,2,3,4) KEGG:C11145 MetaCyc:CPD-3746 Methanesulfonic acid Methansulfonsaeure PMID:24304088 PMID:24593036 Reaxys:1446024 Wikipedia:Methanesulfonic_acid chebi_ontology methanesulfonic acid methylsulfonic acid 3-aminoisobutyric acid 0 103.063 103.11980 2-(aminomethyl)propionic acid 2-Methyl-beta-alanine 3-Amino-2-methylpropanoate 3-Aminoisobutanoate 3-Aminoisobutanoic acid 3-amino-2-methylpropanoic acid 3-aminoisobutyric acid A beta-amino-acid that is isobutyric acid in which one of the methyl hydrogens is substituted by an amino group. BAIB Beilstein:1720958 Beilstein:1745458 C4H9NO2 CAS:10569-72-9 CAS:144-90-1 CC(CN)C(O)=O CHEBI:18712 CHEBI:19959 CHEBI:27389 CHEBI:359 DL-beta-aminoisobutyric acid Gmelin:1520758 HMDB:HMDB0003911 InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7) KEGG:C05145 MetaCyc:3-AMINO-ISOBUTYRATE PMID:11785300 PMID:14576092 PMID:18299183 PMID:18600547 PMID:19186330 PMID:19735301 PMID:22735334 PMID:2274753 PMID:5776546 PMID:639325 PMID:8307374 QCHPKSFMDHPSNR-UHFFFAOYSA-N Reaxys:1720958 Wikipedia:3-Aminoisobutyric_acid alpha-Methyl-beta-alanine bAib beta-aminoisobutyric acid chebi_ontology folic acid 0 441.140 441.39750 An N-acyl-amino acid that is a form of the water-soluble vitamin B9. Its biologically active forms (tetrahydrofolate and others) are essential for nucleotide biosynthesis and homocysteine remethylation. Beilstein:100781 C19H19N7O6 CAS:59-30-3 CHEBI:24075 CHEBI:27470 CHEBI:42610 CHEBI:5140 CHEBI:569217 DrugBank:DB00158 Drug_Central:1231 FOLIC ACID Folate Folic acid Folsaeure InChI=1S/C19H19N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/t12-/m0/s1 KEGG:C00504 KEGG:D00070 KNApSAcK:C00001539 LINCS:LSM-5355 MetaCyc:CPD-12826 N-(4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamic acid N-pteroyl-L-glutamic acid Nc1nc2ncc(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)nc2c(=O)[nH]1 OVBPIULPVIDEAO-LBPRGKRZSA-N PDBeChem:FOL PGA PMID:11261364 PMID:11451208 PMID:14387833 PMID:15754725 PMID:17784727 PMID:18788725 PMID:19355913 PMID:24650098 PMID:9040515 PteGlu Pteroylglutamic acid Reaxys:100781 Wikipedia:Folic_Acid chebi_ontology pteroyl-L-glutamic acid pteroyl-L-monoglutamic acid vitamin Bc vitamin M zeaxanthin (3R,3'R)-beta,beta-carotene-3,3'-diol (3R,3'R)-dihydroxy-beta,beta-carotene 0 568.428 568.87144 Beilstein:2068416 C40H56O2 CAS:144-68-3 CC(\C=C\C=C(C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C CHEBI:10108 CHEBI:27361 CHEBI:27547 InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-24,35-36,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36-/m1/s1 JKQXZKUSFCKOGQ-QAYBQHTQSA-N KEGG:C06098 KNApSAcK:C00000931 LIPID_MAPS_instance:LMPR01070261 MetaCyc:CPD1F-130 Wikipedia:Zeaxanthin Zeaxanthin all-trans-beta-carotene-3,3'-diol all-trans-zeaxanthin anchovyxanthin beta,beta-carotene-3,3'-diol chebi_ontology selenium atom 0 34Se 78.96000 79.917 BUGBHKTXTAQXES-UHFFFAOYSA-N CAS:7782-49-2 CHEBI:26627 CHEBI:27568 CHEBI:9091 InChI=1S/Se KEGG:C01529 Se Se Selen Selenium WebElements:Se [Se] chebi_ontology selenio selenium selenium histidine 0 155.069 155.15468 2-amino-3-(1H-imidazol-4-yl)propanoic acid An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3. Beilstein:84087 C6H9N3O2 CAS:4998-57-6 CHEBI:24598 CHEBI:27570 CHEBI:43118 CHEBI:5733 DL-Histidine Gmelin:3656 HNDVDQJCIGZPNO-UHFFFAOYSA-N Histidin Histidine InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11) KEGG:C00768 KNApSAcK:C00001363 NC(Cc1c[nH]cn1)C(O)=O PMID:17190852 PMID:22264337 PMID:22770225 PMID:29286160 Reaxys:84087 Wikipedia:Histidine alpha-Amino-1H-imidazole-4-propionic acid chebi_ontology histidina histidine aldosterone (+)-aldosterone (11beta)-11,21-dihydroxy-3,20-dioxopregn-4-en-18-al 0 11beta,21-Dihydroxy-3,20-dioxo-4-pregnen-18-al 11beta,21-dihydroxy-3,20-dioxopregn-4-en-18-al 360.194 360.44400 A pregnane-based steroidal hormone produced by the outer-section (zona glomerulosa) of the adrenal cortex in the adrenal gland, and acts on the distal tubules and collecting ducts of the kidney to cause the conservation of sodium, secretion of potassium, increased water retention, and increased blood pressure. The overall effect of aldosterone is to increase reabsorption of ions and water in the kidney. ALDOSTERONE Aldosterone Beilstein:3224996 C21H28O5 CAS:52-39-1 CHEBI:22306 CHEBI:2563 CHEBI:27584 CHEBI:40919 DrugBank:DB04630 Drug_Central:111 HMDB:HMDB0000037 InChI=1S/C21H28O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h8,11,14-17,19,22,25H,2-7,9-10H2,1H3/t14-,15-,16+,17-,19+,20-,21+/m0/s1 KEGG:C01780 LINCS:LSM-42770 LIPID_MAPS_instance:LMST02030026 PDBeChem:AS4 PMID:10438974 PQSUYGKTWSAVDQ-ZVIOFETBSA-N Reaxys:3224996 Wikipedia:Aldosterone [H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])[C@@H](O)C[C@]12C=O)C(=O)CO aldosterone chebi_ontology carbon atom 0 12.000 12.01070 6C C C CAS:7440-44-0 CHEBI:23009 CHEBI:27594 CHEBI:3399 Carbon InChI=1S/C KEGG:C06265 Kohlenstoff OKTJSMMVPCPJKN-UHFFFAOYSA-N WebElements:C [C] carbon carbon carbone carbonium carbono chebi_ontology hydantoin 0 100.027 100.07614 2,4(3H,5H)-imidazoledione 2,4-imidazolidinedione Beilstein:110598 C3H4N2O2 CAS:461-72-3 CHEBI:24625 CHEBI:27612 CHEBI:5773 Glycolylurea Gmelin:101266 Hydantoin InChI=1S/C3H4N2O2/c6-2-1-4-3(7)5-2/h1H2,(H2,4,5,6,7) KEGG:C05146 O=C1CNC(=O)N1 PDBeChem:HYN WJRBRSLFGCUECM-UHFFFAOYSA-N chebi_ontology imidazole-2,4(3H,5H)-dione imidazolidine-2,4-dione vanillylmandelate -1 197.045 197.16480 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetate 3-Methoxy-4-hydroxymandelate A hydroxy monocarboxylic acid anion that is the conjugate base of vanillylmandelic acid. C9H9O5 CGQCWMIAEPEHNQ-UHFFFAOYSA-M CHEBI:1573 CHEBI:20105 CHEBI:27622 COc1cc(ccc1O)C(O)C([O-])=O InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)/p-1 KEGG:C05584 chebi_ontology vanilmandelate cobalt atom 0 27Co 58.933 58.93320 A cobalt group element atom that has atomic number 27. CAS:7440-48-4 CHEBI:23335 CHEBI:27638 CHEBI:3788 Co Co Cobalt GUTLYIVDDKVIGB-UHFFFAOYSA-N InChI=1S/Co KEGG:C00175 KEGG:C19171 Kobalt PDBeChem:3CO WebElements:Co [Co] chebi_ontology cobalt cobalt cobalto cobaltum 3',5'-cyclic dGMP CHEBI:1330 CHEBI:19832 CHEBI:27682 chebi_ontology caffeine 0 1,3,7-Trimethylxanthine 1,3,7-trimethyl-2,6-dioxopurine 1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione 1,3,7-trimethylpurine-2,6-dione 1,3,7-trimethylxanthine 1-methyltheobromine 194.080 194.19076 3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion 7-methyltheophylline A trimethylxanthine in which the three methyl groups are located at positions 1, 3, and 7. A purine alkaloid that occurs naturally in tea and coffee. Beilstein:17705 C8H10N4O2 CAFFEINE CAS:58-08-2 CHEBI:22982 CHEBI:27732 CHEBI:3295 CHEBI:41472 Caffeine Cn1cnc2n(C)c(=O)n(C)c(=O)c12 Coffein DrugBank:DB00201 Drug_Central:463 Gmelin:103040 HMDB:HMDB0001847 InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3 KEGG:C07481 KEGG:D00528 KNApSAcK:C00001492 Koffein LINCS:LSM-2026 MetaCyc:1-3-7-TRIMETHYLXANTHINE PDBeChem:CFF PMID:10510174 PMID:10796597 PMID:10803761 PMID:10822912 PMID:10884512 PMID:10924888 PMID:10983026 PMID:11014293 PMID:11022879 PMID:11209966 PMID:11312039 PMID:11410911 PMID:11431501 PMID:11815511 PMID:11949272 PMID:12397877 PMID:12457274 PMID:12574990 PMID:12915014 PMID:12943586 PMID:14521986 PMID:14607010 PMID:15257305 PMID:15280431 PMID:15681408 PMID:15718055 PMID:15840517 PMID:16143823 PMID:16391865 PMID:16528931 PMID:16644114 PMID:16709440 PMID:16805851 PMID:16856769 PMID:17132260 PMID:17387608 PMID:17508167 PMID:17724925 PMID:17932622 PMID:17957400 PMID:18068204 PMID:18258404 PMID:18421070 PMID:18625110 PMID:18647558 PMID:19007524 PMID:19047957 PMID:19084078 PMID:19088793 PMID:19418355 PMID:19879252 PMID:20164568 PMID:20470411 PMID:22770225 PMID:7441110 PMID:7689104 PMID:8332255 PMID:8347173 PMID:8679661 PMID:9063686 PMID:9067318 PMID:9132918 PMID:9218278 RYYVLZVUVIJVGH-UHFFFAOYSA-N Reaxys:17705 Thein Wikipedia:Caffeine anhydrous caffeine cafeina cafeine caffeine chebi_ontology guaranine mateina methyltheobromine teina theine detergent A surfactant (or a mixture containing one or more surfactants) having cleaning properties in dilute solutions. CHEBI:23648 CHEBI:27780 CHEBI:4456 Detergents KEGG:C01689 chebi_ontology detergent (S)-colchicine (S)-N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide 0 399.168 399.43700 7alphaH-colchicine Beilstein:2228813 C22H25NO6 CAS:64-86-8 CHEBI:27882 CHEBI:3811 COc1cc2CC[C@H](NC(C)=O)c3cc(=O)c(OC)ccc3-c2c(OC)c1OC Colchicin Colchicine DrugBank:DB01394 Drug_Central:726 IAKHMKGGTNLKSZ-INIZCTEOSA-N InChI=1S/C22H25NO6/c1-12(24)23-16-8-6-13-10-19(27-3)21(28-4)22(29-5)20(13)14-7-9-18(26-2)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m0/s1 KEGG:C07592 KEGG:D00570 KNApSAcK:C00002327 LINCS:LSM-5199 N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide PDBeChem:LOC Wikipedia:Colchicine chebi_ontology colchicina colchicinum tryptophan 0 2-amino-3-(1H-indol-3-yl)propanoic acid 204.090 204.22526 An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3. Beilstein:86196 C11H12N2O2 CAS:54-12-6 CHEBI:27163 CHEBI:27897 CHEBI:9769 Gmelin:4532 Htrp InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15) KEGG:C00806 KNApSAcK:C00001396 LINCS:LSM-36836 NC(Cc1c[nH]c2ccccc12)C(O)=O PMID:17439666 PMID:22264337 QIVBCDIJIAJPQS-UHFFFAOYSA-N Reaxys:86196 Trp Tryptophan W Wikipedia:Tryptophan alpha-Amino-beta-(3-indolyl)-propionic acid alpha-amino-beta-3-indolepropionic acid beta-3-indolylalanine chebi_ontology triptofano tryptophan tryptophane cyanic acid 0 43.006 43.02478 Beilstein:1732479 CAS:420-05-3 CAS:71000-82-3 CHEBI:23422 CHEBI:28024 CHEBI:3968 CHNO Cyanic acid Cyansaeure Gmelin:839 HOCN InChI=1S/CHNO/c2-1-3/h3H KEGG:C01417 OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N Zyansaeure [C(N)OH] chebi_ontology hydrogen nitridooxocarbonate hydroxidonitridocarbon nitridooxocarbonic acid phenylalanine 0 165.079 165.18918 2-amino-3-phenylpropanoic acid An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group. Beilstein:1910407 C9H11NO2 CAS:150-30-1 CHEBI:25984 CHEBI:28044 CHEBI:8089 COLNVLDHVKWLRT-UHFFFAOYSA-N DL-Phenylalanine F Gmelin:50836 InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12) KEGG:C02057 NC(Cc1ccccc1)C(O)=O PHE PMID:17439666 PMID:22264337 Phenylalanin Phenylalanine Reaxys:1910407 Wikipedia:Phenylalanine alpha-Amino-beta-phenylpropionic acid chebi_ontology fenilalanina phenylalanine glycogen A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues. CAS:9005-79-2 CHEBI:24379 CHEBI:28087 CHEBI:5466 Glycogen KEGG:C00182 animal starch chebi_ontology liver starch methylcobalamin 0 1343.588 1344.38230 C63H91CoN13O14P CAS:13422-55-4 CHEBI:25291 CHEBI:28115 CHEBI:48831 CHEBI:6869 CO-METHYLCOBALAMIN COMe:MOL000085 Coalpha-[alpha-(5,6-dimethylbenzimidazolyl)]-Cobeta-methylcobamide DrugBank:DB03614 Gmelin:124528 InChI=1S/C62H90N13O14P.CH3.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);1H3;/q;;+2/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;/m1../s1 JEWJRMKHSMTXPP-WZHZPDAFSA-L KEGG:C06453 KEGG:D03246 MeCbl Methylcobalamin PDBeChem:COB [H][C@]12[C@H](CC(N)=O)[C@@]3(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]4[C@@H](O)[C@H](O[C@@H]4CO)n4c[n+](c5cc(C)c(C)cc45)[Co-3]456(C)N1C3=C(C)C1=[N+]4C(=CC3=[N+]5C(=C(C)C4=[N+]6[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]3CCC(N)=O)C(C)(C)[C@@H]1CCC(N)=O chebi_ontology mecobalamin methylcob(III)alamin methylcobalamin galactose An aldohexose that is the C-4 epimer of glucose. C6H12O6 CAS:26566-61-0 CHEBI:24162 CHEBI:28260 CHEBI:33933 CHEBI:5256 Gal Galactose Galaktose KEGG:C01582 Wikipedia:Galactose chebi_ontology galacto-hexose galactose glutamine 0 146.069 146.14458 2,5-diamino-5-oxopentanoic acid 2-Aminoglutaramic acid 2-amino-4-carbamoylbutanoic acid An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4. Beilstein:1723795 C5H10N2O3 CAS:585-21-7 CAS:6899-04-3 CHEBI:24316 CHEBI:28300 CHEBI:5432 Glutamin Glutamine Glutaminsaeure-5-amid Gmelin:27318 Hgln InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10) KEGG:C00303 KNApSAcK:C00001359 NC(CCC(N)=O)C(O)=O Reaxys:1723795 Wikipedia:Glutamine ZDXPYRJPNDTMRX-UHFFFAOYSA-N chebi_ontology glutamic acid gamma-amide glutamine rac-lactic acid (+-)-2-hydroxypropanoic acid 0 2-Hydroxypropanoic acid 2-Hydroxypropionic acid A racemate comprising equimolar amounts of (R)- and (S)-lactic acid. Beilstein:1209341 C(=O)([C@@H](O)C)O.C(=O)([C@H](O)C)O C3H6O3 CAS:50-21-5 CHEBI:24998 CHEBI:28358 CHEBI:6351 DrugBank:DB04398 E270 InChI=1S/2C3H6O3/c2*1-2(4)3(5)6/h2*2,4H,1H3,(H,5,6)/t2*2-/m10/s1 KEGG:C01432 KEGG:D00111 KVZLHPXEUGJPAH-QNDGGIRCSA-N LIPID_MAPS_instance:LMFA01050002 Lactic acid Milchsaeure PMID:17190852 PMID:29079364 Reaxys:1209341 Wikipedia:Lactic_acid alpha-hydroxypropanoic acid alpha-hydroxypropionic acid chebi_ontology rac-2-hydroxypropanoic acid alpha,omega-dicarboxylic acid CHEBI:10197 CHEBI:13780 CHEBI:22361 CHEBI:28383 KEGG:C04025 alpha(omega)-Dicarboxylic acid alpha,omega-Dicarboxylic acid alpha,omega-dicarboxylic acids chebi_ontology vitamin K A fat-soluble vitamin required for the synthesis of prothrombin and certain other blood coagulation factors. CAS:12001-79-5 CHEBI:10009 CHEBI:27301 CHEBI:27307 CHEBI:28384 KEGG:C01628 Vitamin K chebi_ontology vitamine K alpha-carotene 0 536.438 536.87264 A cyclic carotene with a beta- and an epsilon-ring at opposite ends respectively. ANVAOWXLWRTKGA-JLTXGRSLSA-N Beilstein:2067408 Beilstein:3227599 C40H56 CAS:432-70-2 CC(\C=C\C=C(C)\C=C\C1C(C)=CCCC1(C)C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C CHEBI:10215 CHEBI:22447 CHEBI:28425 HMDB:HMDB0003993 InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-23,25-28,37H,15-16,24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+ KEGG:C05433 KNApSAcK:C00003765 LIPID_MAPS_instance:LMPR01070258 PMID:23620017 PMID:24169341 PMID:9408998 Reaxys:2682045 all-trans-alpha-carotene alpha-Carotene alpha-carotene beta,epsilon-carotene chebi_ontology carbamic acid 0 61.016 61.04006 A one-carbon compound that is ammonia in which one of the hydrogens is replaced by a carboxy group. Although carbamic acid derivatives are common, carbamic acid itself has never been synthesised. Aminoameisensaeure Aminoformic acid Beilstein:1734754 CARBAMIC ACID CAS:463-77-4 CH3NO2 CHEBI:22504 CHEBI:23002 CHEBI:28616 CHEBI:3386 CHEBI:44573 Carbamate Carbamic acid Carbamidsaeure DrugBank:DB04261 Gmelin:130345 InChI=1S/CH3NO2/c2-1(3)4/h2H2,(H,3,4) KEGG:C01563 KXDHJXZQYSOELW-UHFFFAOYSA-N NC(O)=O PDBeChem:OUT Wikipedia:Carbamic_acid carbamic acid chebi_ontology phosphorus atom 0 15P 30.97376 30.974 CAS:7723-14-0 CHEBI:26080 CHEBI:28659 CHEBI:8168 Gmelin:16235 InChI=1S/P KEGG:C06262 OAICVXFJPJFONN-UHFFFAOYSA-N P P Phosphor Phosphorus WebElements:P [P] chebi_ontology fosforo phosphore phosphorus phosphorus neopterin CHEBI:25499 CHEBI:28670 CHEBI:44294 CHEBI:7511 chebi_ontology molybdenum atom 0 42Mo 95.94000 97.905 CAS:7439-98-7 CHEBI:25369 CHEBI:28685 CHEBI:49750 CHEBI:6968 Gmelin:16205 InChI=1S/Mo KEGG:C00150 Mo Mo Molybdaen Molybdenum WebElements:Mo ZOKXTWBITQBERF-UHFFFAOYSA-N [Mo] chebi_ontology molibdeno molybdene molybdenum molybdenum dehydroepiandrosterone 0 288.209 288.42440 3-BETA-HYDROXY-5-ANDROSTEN-17-ONE 3beta-Hydroxyandrost-5-en-17-one 3beta-hydroxyandrost-5-en-17-one 3beta-hydroxyandrost-5-en-17-one An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands. C19H28O2 CAS:53-43-0 CHEBI:11911 CHEBI:1723 CHEBI:20246 CHEBI:28689 CHEBI:40738 CHEBI:86953 DHA DHEA Dehydroepiandrosterone Dehydroisoandrosterone DrugBank:DB01708 Drug_Central:795 FMGSKLZLMKYGDP-USOAJAOKSA-N HMDB:HMDB0000077 InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1 Intrarosa KEGG:C01227 KEGG:D08409 LIPID_MAPS_instance:LMST02020021 MetaCyc:3-BETA-HYDROXYANDROST-5-EN-17-ONE PDBeChem:AND PMID:14662261 PMID:18634257 PMID:24256992 PMID:24424045 Prasterone Reaxys:2058110 Wikipedia:Dehydroepiandrosterone [H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)C(=O)CC[C@@]21[H] chebi_ontology copper atom 0 29Cu 62.930 63.54600 CAS:7440-50-8 CHEBI:23376 CHEBI:28694 CHEBI:3874 Copper Cu Cu Gmelin:16269 InChI=1S/Cu KEGG:C00070 Kupfer RYGMFSIKBFXOCR-UHFFFAOYSA-N WebElements:Cu [Cu] chebi_ontology cobre copper copper cuivre cuprum fructose A ketohexose that is an isomer of glucose. CAS:30237-26-4 CHEBI:24104 CHEBI:24110 CHEBI:28757 CHEBI:5172 DrugBank:DB04173 Fru Fruchtzucker Fructose Fruktose KEGG:C01496 Wikipedia:Fructose arabino-Hexulose arabino-hex-2-ulose chebi_ontology fructose L-glucitol (2R,3S,4S,5S)-hexane-1,2,3,4,5,6-hexol 0 182.079 182.17176 Beilstein:1721906 C6H14O6 CAS:6706-59-8 CHEBI:21394 CHEBI:28789 CHEBI:6223 D-Gulitol D-gulitol ECMDB:ECMDB00247 FBPFZTCFMRRESA-FSIIMWSLSA-N Gmelin:648560 InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m0/s1 KEGG:C01722 L-Glucitol L-Sorbitol L-glucitol L-sorbitol MetaCyc:CPD-12810 OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO PMID:19695255 Reaxys:1721906 The L-enantiomer of glucitol. YMDB:YMDB00724 chebi_ontology serotonin 0 176.095 176.215 3-(2-Aminoethyl)-1H-indol-5-ol 3-(2-aminoethyl)-1H-indol-5-ol 5-HT 5-Hydroxytryptamine A primary amino compound that is the 5-hydroxy derivative of tryptamine. Beilstein:143524 C10H12N2O C1=CC(=CC=2C(=CNC12)CCN)O CAS:50-67-9 CHEBI:1420 CHEBI:26652 CHEBI:28790 CHEBI:49894 Enteramine Gmelin:1861995 HMDB:HMDB0000259 InChI=1S/C10H12N2O/c11-4-3-7-6-12-10-2-1-8(13)5-9(7)10/h1-2,5-6,12-13H,3-4,11H2 KEGG:C00780 KNApSAcK:C00001429 LINCS:LSM-6589 MetaCyc:SEROTONIN PDBeChem:SRO PMID:18593914 PMID:22770225 PMID:24136337 QZAYGJVTTNCVMB-UHFFFAOYSA-N Reaxys:143524 SEROTONIN Serotonin Wikipedia:Serotonin chebi_ontology serotonine thrombocytin thrombotonin heparan sulfate (C12H19NO20S3)n 0 A linear polysaccharide in which the backbone consists of a variably sulfated repeating disaccharide unit. Beilstein:8186767 CAS:9050-30-0 CHEBI:24502 CHEBI:24507 CHEBI:28815 CHEBI:5661 Heparan N-sulfate Heparan sulfate Heparan sulphate Heparatan sulfate Heparin monosulfate Heparin sulfate Heparitin monosulfate Heparitin sulfate KEGG:C00925 KEGG:D08536 N-Acetylheparan sulfate PMID:8713797 chebi_ontology lutein (3R,3'R,6'R)-beta,epsilon-carotene-3,3'-diol (3R,3'R,6S)-4,5-DIDEHYDRO-5,6-DIHYDRO-BETA,BETA-CAROTENE-3,3'-DIOL 0 568.428 568.87144 Beilstein:2068550 Bo-Xan C40H56O2 CAS:127-40-2 CC(\C=C\C=C(C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C CHEBI:27324 CHEBI:28838 CHEBI:43817 CHEBI:6576 DrugBank:DB00137 Drug_Central:4145 E 161b HMDB:HMDB0003233 InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36+,37-/m0/s1 KBPHJBAIARWVSC-RGZFRNHPSA-N KEGG:C08601 KNApSAcK:C00003776 LIPID_MAPS_instance:LMPR01070274 Lutein MetaCyc:CPD1F-119 PDBeChem:LUT PMID:10714278 PMID:14670087 PMID:23543147 PMID:24451312 Reaxys:2068550 Wikipedia:Lutein Xanthophyll chebi_ontology lutein 5alpha-androstane 0 260.250 260.45738 5alpha-Androstane 5alpha-androstane Androstane Beilstein:2043119 C19H32 CAS:438-22-2 CHEBI:20638 CHEBI:2712 CHEBI:28859 InChI=1S/C19H32/c1-18-11-5-7-16(18)15-9-8-14-6-3-4-12-19(14,2)17(15)10-13-18/h14-17H,3-13H2,1-2H3/t14-,15+,16+,17+,18+,19+/m1/s1 KEGG:C01554 LIPID_MAPS_instance:LMST02020056 PMID:13749674 QZLYKIGBANMMBK-UGCZWRCOSA-N The 5alpha-stereoisomer of androstane. [H][C@]12CCCC[C@]1(C)[C@@]1([H])CC[C@]3(C)CCC[C@@]3([H])[C@]1([H])CC2 chebi_ontology fatty acid anion -1 43.990 44.00950 Alkanate CHEBI:13634 CHEBI:24022 CHEBI:28868 CHEBI:4985 CO2R Fatty acid anion Fettsaeureanion Fettsaeureanionen KEGG:C02403 PMID:18628202 The conjugate base of a fatty acid, arising from deprotonation of the carboxylic acid group of the corresponding fatty acid. [O-]C([*])=O a fatty acid acido graso anionico acidos grasos anionicos anion de l'acide gras chebi_ontology fatty acid anions menadione 0 172.052 172.18002 2-Methyl-1,4-naphthochinon 2-Methyl-1,4-naphthoquinone 2-methyl-1,4-naphthalenedione 2-methylnaphthalene-1,4-dione A member of the class of 1,4-naphthoquinones that is 1,4-naphthoquinone which is substituted at position 2 by a methyl group. It is used as a nutritional supplement and for the treatment of hypoprothrombinemia. C11H8O2 CAS:58-27-5 CC1=CC(=O)c2ccccc2C1=O CHEBI:27304 CHEBI:28869 CHEBI:46306 CHEBI:6747 DrugBank:DB00170 Drug_Central:1683 HMDB:HMDB0001892 InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 KEGG:C05377 KEGG:D02335 LINCS:LSM-3755 MENADIONE MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione PDBeChem:VK3 PMID:13779073 PMID:15052609 PMID:16469140 PMID:1650428 PMID:28166217 PMID:9380028 Reaxys:1908453 Vitamin K3 Wikipedia:Menadione chebi_ontology menadione tetradecanoic acid 0 1-tetradecanecarboxylic acid 14 14:0 14:00 228.209 228.37090 A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat. Beilstein:508624 C14 C14H28O2 CAS:544-63-8 CCCCCCCCCCCCCC(O)=O CH3-[CH2]12-COOH CHEBI:26897 CHEBI:278516 CHEBI:28875 CHEBI:44232 CHEBI:7056 CHEBI:73168 DrugBank:DB08231 Gmelin:242115 HMDB:HMDB0000806 InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16) KEGG:C06424 KNApSAcK:C00001228 LIPID_MAPS_instance:LMFA01010014 MYRISTIC ACID MetaCyc:CPD-7836 Myristic acid Myristinsaeure PDBeChem:MYR PMID:13129458 PMID:15149689 PMID:16509590 PMID:16554156 PMID:19154695 PMID:19761868 PMID:19786012 PMID:19902021 PMID:19955401 PMID:20634506 PMID:20920594 PMID:21955528 PMID:22030224 PMID:27206979 PMID:28600633 PMID:6802973 Reaxys:508624 TUNFSRHWOTWDNC-UHFFFAOYSA-N Tetradecanoic acid Wikipedia:Myristic_acid acide tetradecanoique chebi_ontology myristic acid n-Tetradecan-1-oic acid n-Tetradecoic acid n-tetradecanoic acid tetradecoic acid ganglioside A molecule composed of a glycosphingolipid (ceramide and oligosaccharide) with one or more sialic acids linked on the sugar chain. CHEBI:26669 CHEBI:28892 CHEBI:36525 CHEBI:5274 Ganglioside KEGG:C01808 LIPID_MAPS_class:LMSP0601 PMID:16158191 PMID:2088646 Wikipedia:Ganglioside chebi_ontology gangliosides sialoglycosphingolipids ammonium +1 18.034 18.03850 AMMONIUM ION Ammonium(1+) An onium cation obtained by protonation of ammonia. CAS:14798-03-9 CHEBI:22534 CHEBI:28938 CHEBI:49783 CHEBI:7435 Gmelin:84 H4N InChI=1S/H3N/h1H3/p+1 KEGG:C01342 MetaCyc:AMMONIUM MolBase:929 NH4(+) NH4+ PDBeChem:NH4 PMID:11319011 PMID:11341317 PMID:12096804 PMID:14512268 PMID:14879753 PMID:16345391 PMID:16903292 PMID:17392693 PMID:18515490 PMID:19199063 PMID:19596600 PMID:19682559 PMID:19716251 PMID:21993530 PMID:22265469 PMID:22524020 PMID:22562341 PMID:22631217 QGZKDVFQNNGYKY-UHFFFAOYSA-O Reaxys:16093784 Wikipedia:Ammonium [H][N+]([H])([H])[H] [NH4](+) ammonium azanium chebi_ontology calciol (+)-vitamin D3 (1S,3Z)-3-[(2E)-2-[(1R,3AR,7AS)-7A-METHYL-1-[(2R)-6-METHYLHEPTAN-2-YL]-2,3,3A,5,6,7-HEXAHYDRO-1H-INDEN-4-YLIDENE]ETHYLIDENE]-4-METHYLIDENE-CYCLOHEXAN-1-OL (3S,5Z,7E)-9,10-secocholesta-5,7,10(19)-trien-3-ol (3beta,5Z,7E)-9,10-secocholesta-5,7,10(19)-trien-3-ol (5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-trien-3-ol 0 384.339 384.63766 A hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group. It is the inactive form of vitamin D3, being hydroxylated in the liver to calcidiol (25-hydroxyvitamin D3), which is then further hydroxylated in the kidney to give calcitriol (1,25-dihydroxyvitamin D3), the active hormone. Beilstein:2339331 C27H44O CAS:67-97-0 CC CHEBI:10008 CHEBI:23170 CHEBI:28940 CHEBI:46283 Cholecalciferol Delta-D DrugBank:DB00169 Drug_Central:2840 Gmelin:1267613 HMDB:HMDB0000876 InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26+,27-/m1/s1 KEGG:C05443 KEGG:D00188 LIPID_MAPS_instance:LMST03020000 LIPID_MAPS_instance:LMST03020001 PDBeChem:VD3 PMID:15876428 PMID:17156784 PMID:19817701 PMID:23964472 PMID:9627702 PPDB:160 QYSXJUFSXHHAJI-YRZJJWOYSA-N Reaxys:2339331 Vitamin D3 Wikipedia:Cholecalciferol [H][C@@]1(CC[C@]2([H])[C@]1(C)CCC\C2=C/C=C1/C[C@@H](O)CCC1=C)[C@H](C)CCCC(C)C activated 7-dehydrocholesterol calciol chebi_ontology colecalciferol oleovitamin D3 vitamin D3 amino sugar Aminosugars Any sugar having one or more alcoholic hydroxy groups replaced by substituted or unsubstituted amino groups. CHEBI:22481 CHEBI:22530 CHEBI:2662 CHEBI:28963 KEGG:C05383 PMID:18424273 PMID:9056391 amino sugars aminosugar chebi_ontology dicarboxylic acid dianion -2 87.980 A carboxylic acid dianion obtained by deprotonation of both carboxy groups of any dicarboxylic acid. C2O4R CHEBI:13632 CHEBI:23688 CHEBI:23689 CHEBI:28965 CHEBI:38711 [O-]C(=O)[*]C([O-])=O a dicarboxylate chebi_ontology dicarboxylate dicarboxylates dicarboxylic acid dianion dicarboxylic acid dianions carbonic acid 0 62.000 62.02478 BVKZGUZCCUSVTD-UHFFFAOYSA-N CAS:463-79-6 CH2O3 CHEBI:13351 CHEBI:23017 CHEBI:23744 CHEBI:28976 CHEBI:3401 Carbonic acid Dihydrogen carbonate Gmelin:25554 H2CO3 InChI=1S/CH2O3/c2-1(3)4/h(H2,2,3,4) KEGG:C01353 Koehlensaeure OC(O)=O PDBeChem:CO3 [CO(OH)2] carbonic acid chebi_ontology dihydroxidooxidocarbon arginine 0 174.112 174.20112 2-Amino-5-guanidinovaleric acid 2-amino-5-(carbamimidamido)pentanoic acid 2-amino-5-guanidinopentanoic acid An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group. Arginin Arginine Beilstein:1725411 C6H14N4O2 CAS:7200-25-1 CHEBI:22616 CHEBI:2643 CHEBI:29016 Harg InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10) KEGG:C02385 NC(CCCNC(N)=N)C(O)=O ODKSFYDXXFIFQN-UHFFFAOYSA-N PMID:10848923 Reaxys:1725411 Wikipedia:L-Arginine arginine chebi_ontology keratan CHEBI:14490 CHEBI:24954 CHEBI:29057 chebi_ontology carboxylic acid anion -1 43.990 44.00950 CHEBI:13626 CHEBI:13945 CHEBI:23026 CHEBI:29067 CHEBI:58657 CO2R The conjugate base formed when the carboxy group of a carboxylic acid is deprotonated. [O-]C([*])=O a carboxylate carboxylic acid anions carboxylic anions chebi_ontology L-ascorbic acid (5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one 0 176.032 176.12410 ASCORBIC ACID Ascoltin Ascorbic acid Ascorbicap Ascorbinsaeure BPDB:2405 Beilstein:84272 C6H8O6 CAS:50-81-7 CHEBI:21240 CHEBI:2868 CHEBI:29073 CHEBI:40892 CHEBI:43473 CIWBSHSKHKDKBQ-JLAZNSOCSA-N DrugBank:DB00126 Drug_Central:4072 E 300 E-300 E300 Gmelin:4087 HMDB:HMDB0000044 InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1 KEGG:C00072 KEGG:D00018 KNApSAcK:C00001179 L-(+)-ascorbic acid L-Ascorbate L-Ascorbic acid L-threo-hex-2-enono-1,4-lactone MetaCyc:ASCORBATE PDBeChem:ASC PMID:12569111 PMID:15949874 PMID:17253561 PMID:17636648 PMID:18813862 PMID:19273781 PMID:19692922 PMID:22770225 PMID:491997 PMID:9506998 Reaxys:84272 The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate. Vitamin C Wikipedia:Ascorbic_Acid [H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO acide ascorbique acido ascorbico acidum ascorbicum acidum ascorbinicum ascorbic acid chebi_ontology mononucleotide 0 213.016 213.103 C5H10O7PR CHEBI:14616 CHEBI:25404 CHEBI:29075 CHEBI:6983 KEGG:C02171 Mononucleotide chebi_ontology mononucleotides sodium(1+) +1 22.98977 22.990 A monoatomic monocation obtained from sodium. CAS:17341-25-2 CHEBI:26717 CHEBI:29101 CHEBI:49766 CHEBI:9175 FKNQFGJONOIPTF-UHFFFAOYSA-N Gmelin:15196 InChI=1S/Na/q+1 KEGG:C01330 Na Na(+) Na+ PDBeChem:NA SODIUM ION [Na+] chebi_ontology sodium cation sodium(1+) sodium(1+) ion sodium(I) cation potassium(1+) +1 38.964 39.09830 A monoatomic monocation obtained from potassium. CAS:24203-36-9 CHEBI:26219 CHEBI:29103 CHEBI:49685 CHEBI:8345 Gmelin:15203 InChI=1S/K/q+1 K K(+) K+ KEGG:C00238 KEGG:D08403 NPYPAHLBTDXSSS-UHFFFAOYSA-N PDBeChem:K POTASSIUM ION [K+] chebi_ontology potassium cation potassium(1+) potassium(1+) ion potassium(I) cation calcium(2+) +2 39.963 40.07800 BHPQYMZQTOCNFJ-UHFFFAOYSA-N CALCIUM ION CAS:14127-61-8 CHEBI:22988 CHEBI:29108 CHEBI:3308 CHEBI:48760 Ca Ca(2+) Ca2+ Gmelin:6850 InChI=1S/Ca/q+2 KEGG:C00076 PDBeChem:CA [Ca++] calcium(2+) calcium(2+) ion calcium(II) cation calcium, doubly charged positive ion chebi_ontology hydrogenperoxide(1-) -1 32.998 33.00674 CAS:14691-59-9 CHEBI:29192 Gmelin:507 HO2 HO2(-) HOO anion HOO(-) InChI=1S/H2O2/c1-2/h1-2H/p-1 MHAJPDPJQMAIIY-UHFFFAOYSA-M [HO2](-) [H]O[O-] chebi_ontology dioxidanide hydrogen(peroxide)(1-) hydrogendioxide(1-) hydrogenperoxide(1-) cyanate -1 41.998 42.01684 CAS:661-20-1 CAS:71000-82-3 CHEBI:14037 CHEBI:23419 CHEBI:29195 CNO Cyanat InChI=1S/CHNO/c2-1-3/h3H/p-1 KEGG:C01417 OCN(-) UM-BBD_compID:c0568 XLJMAIOERFSOGZ-UHFFFAOYSA-M Zyanat [C(N)O](-) [O-]C#N chebi_ontology cyanate cyanate ion nitridooxidocarbonate(1-) isocyanic acid 0 43.006 43.02478 A colourless, volatile, poisonous inorganic compound with the formula HNCO; the simplest stable chemical compound that contains carbon, hydrogen, nitrogen, and oxygen, the four most commonly-found elements in organic chemistry and biology. Beilstein:1616281 CAS:75-13-8 CHEBI:29202 CHNO Gmelin:840 HN=C=O HNCO ICA InChI=1S/CHNO/c2-1-3/h2H N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N PMID:19494520 PMID:26124058 PMID:26760716 PMID:977566 Reaxys:1616281 [C(NH)O] carbimide chebi_ontology hydrogen isocyanate isocyanate isocyanic acid isocyansaeure isozyansaeure methenamide oxidoazanediidocarbon sulfonic acid 0 81.972 82.08008 BDHFUVZGWQCTTF-UHFFFAOYSA-N CHEBI:29214 Gmelin:1404640 H2O3S HSHO3 InChI=1S/H2O3S/c1-4(2)3/h4H,(H,1,2,3) Sulfonsaeure [H]S(O)(=O)=O [SHO2(OH)] acide sulfonique chebi_ontology hydridohydroxidodioxidosulfur sulfonic acid sulphonic acid thiol 0 32.980 33.07300 An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety. CHEBI:13443 CHEBI:13696 CHEBI:17366 CHEBI:26969 CHEBI:29256 CHEBI:8766 CHEBI:9556 HSR KEGG:C00145 Mercaptan Merkaptan RSH S[*] Thiol Wikipedia:Thiol a thiol chebi_ontology mercaptans thiols thiols calcium(0) 0 39.963 40.07800 Beilstein:4241647 CAS:7440-70-2 CHEBI:29320 Ca Ca(0) Can Gmelin:16277 InChI=1S/Ca OYPRJOBELJOOCE-UHFFFAOYSA-N [Ca] calcium calcium(0) chebi_ontology azanide -1 16.019 16.02262 CHEBI:29337 H2N HYGWNUKOUCZBND-UHFFFAOYSA-N InChI=1S/H2N/h1H2/q-1 NH2(-) [H][N-][H] amide azanide chebi_ontology dihydridonitrate(1-) hydridonitrate(2-) -2 15.011 15.01468 A divalent inorganic anion resulting from the removal of two protons from ammonia. CHEBI:29340 DZQYTNGKSBCIOE-UHFFFAOYSA-N HN InChI=1S/HN/h1H/q-2 NH(2-) [N--][H] azanediide chebi_ontology hydridonitrate(2-) imide monocarboxylic acid amide 0 41.998 42.01680 A carboxamide derived from a monocarboxylic acid. CHEBI:13211 CHEBI:22207 CHEBI:25383 CHEBI:29347 CHEBI:6977 CNOR3 [*]N([*])C([*])=O chebi_ontology monocarboxylic acid amides methanediide -2 14.016 14.02658 Beilstein:5915711 CH2 CH2(2-) CHEBI:29360 Gmelin:322698 InChI=1S/CH2/h1H2/q-2 PZPOWPOFQLSNJO-UHFFFAOYSA-N [CH2](2-) [H][C--][H] chebi_ontology dihydridocarbonate(2-) methanediide peroxy group -OO- 0 31.990 31.99880 CHEBI:29369 O2 chebi_ontology peroxy oxonium +1 19.018 19.02322 CAS:13968-08-6 CHEBI:29412 Gmelin:141 H3O H3O(+) Hydronium cation Hydronium ion InChI=1S/H2O/h1H2/p+1 MolBase:1646 XLYOFNOQVPJJNP-UHFFFAOYSA-O [H][O+]([H])[H] [OH3](+) aquahydrogen(1+) chebi_ontology oxidanium oxonium trihydridooxygen(1+) methylidyne group #CH 0 13.008 13.01864 CH CHEBI:29429 chebi_ontology methylidyne methanide -1 15.023 15.03452 Beilstein:1813938 CAS:15194-58-8 CH3 CH3(-) CHEBI:29438 Gmelin:259263 InChI=1S/CH3/h1H3/q-1 LGRLWUINFJPLSH-UHFFFAOYSA-N [CH3](-) [H][C-]([H])[H] chebi_ontology lambda(2)-methanuide methanide methyl anion trihydridocarbonate(1-) hydridodioxygen(1+) +1 32.998 33.00674 CHEBI:29793 Gmelin:508 HO2 HO2(+) HOO(+) InChI=1S/O2/c1-2/p+1 MYMOFIZGZYHOMD-UHFFFAOYSA-O [HO2](+) [H][O+]=O chebi_ontology dioxidenium hydridodioxygen(1+) diphosphoric acid 0 1,5-dihydrido-2,4-dihydroxido-2,4-dioxido-1,3,5-trioxy-2,4-diphosphy-[5]catena 177.943 177.97508 An acyclic phosphorus acid anhydride obtained by condensation of two molecules of phosphoric acid. CAS:2466-09-3 CHEBI:29888 CHEBI:45067 CHEBI:8683 Diphosphoric acid Diphosphorsaeure DrugBank:DB04160 ECMDB:ECMDB04142 Gmelin:82619 H4O7P2 H4P2O7 InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6) KEGG:C00013 KNApSAcK:C00019561 OP(O)(=O)OP(O)(O)=O PDBeChem:PPV PMID:6291941 PYROPHOSPHATE Pyrophosphate Pyrophosphoric acid Pyrophosphorsaeure Reaxys:3942075 XPPKVPWEQAFLFU-UHFFFAOYSA-N [(HO)2P(O)OP(O)(OH)2] acide diphosphorique chebi_ontology diphosphoric acid mu-oxido-bis(dihydroxidooxidophosphorus) thiol group -SH 0 32.980 33.07394 CHEBI:26821 CHEBI:29916 CHEBI:29917 HS HS- Mercaptogruppe Merkaptogruppe Sulfhydrylgruppe Thiolgruppe chebi_ontology mercapto group sulfanyl sulfhydryl group sulphydryl group thiol thiol group hydrosulfide -1 32.980 33.07394 CAS:15035-72-0 CHEBI:29919 Gmelin:24766 HS HS anion HS(-) InChI=1S/H2S/h1H2/p-1 RWSOTUBLDIXVET-UHFFFAOYSA-M [S-][H] chebi_ontology hydrogen sulfide hydrogen(sulfide)(1-) hydrosulfide sulfanide sulfo group -S(O)2(OH) 0 80.965 81.07214 CHEBI:29922 HO3S PDBeChem:SFO SULFO GROUP chebi_ontology hydroxydioxo-lambda(6)-sulfanyl hydroxysulfonyl sulfo L-glutamate(1-) (2S)-2-ammoniopentanedioate -1 146.045 146.12136 An alpha-amino-acid anion that is the conjugate base of L-glutamic acid, having anionic carboxy groups and a cationic amino group C5H8NO4 CAS:11070-68-1 CHEBI:13107 CHEBI:21301 CHEBI:29985 Gmelin:936654 InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/p-1/t3-/m0/s1 L-glutamate L-glutamate(1-) L-glutamic acid monoanion L-glutamic acid, ion(1-) MetaCyc:GLT WHUUTDBJXJRKMK-VKHMYHEASA-M [NH3+][C@@H](CCC([O-])=O)C([O-])=O chebi_ontology hydrogen L-glutamate D-glutamate(1-) (2R)-2-ammoniopentanedioate -1 146.045 146.12136 An alpha-amino-acid anion that is the conjugate base of D-glutamic acid, having anionic carboxy groups and a cationic amino group Beilstein:8319427 C5H8NO4 CHEBI:12979 CHEBI:21022 CHEBI:29986 D-glutamate D-glutamate(1-) D-glutamic acid monoanion InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/p-1/t3-/m1/s1 MetaCyc:D-GLT WHUUTDBJXJRKMK-GSVOUGTGSA-M [NH3+][C@H](CCC([O-])=O)C([O-])=O chebi_ontology hydrogen D-glutamate glutamate(2-) -2 145.038 145.11342 2-aminopentanedioate A dicarboxylic acid dianion that is the conjugate base of glutamate(1-). Beilstein:4134100 C5H7NO4 CHEBI:29987 Gmelin:327903 InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/p-2 NC(CCC([O-])=O)C([O-])=O Reaxys:4134100 WHUUTDBJXJRKMK-UHFFFAOYSA-L chebi_ontology glutamate glutamate(2-) glutamic acid dianion L-glutamate(2-) (2S)-2-aminopentanedioate -2 145.038 145.11342 An L-alpha-amino acid anion that is the dianion obtained by the deprotonation of the both the carboxy groups of L-glutamic acid. C5H7NO4 CHEBI:29988 Gmelin:327905 InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/p-2/t3-/m0/s1 L-glutamate L-glutamate(2-) L-glutamic acid dianion N[C@@H](CCC([O-])=O)C([O-])=O WHUUTDBJXJRKMK-VKHMYHEASA-L chebi_ontology D-glutamate(2-) (2R)-2-aminopentanedioate -2 145.038 145.11342 Beilstein:8143000 C5H7NO4 CHEBI:29989 D-glutamate D-glutamate(2-) D-glutamic acid dianion Gmelin:327904 InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/p-2/t3-/m1/s1 N[C@H](CCC([O-])=O)C([O-])=O WHUUTDBJXJRKMK-GSVOUGTGSA-L chebi_ontology copper(0) 0 62.930 63.54600 CAS:7440-50-8 CHEBI:30052 Cu Cu(0) Cun InChI=1S/Cu RYGMFSIKBFXOCR-UHFFFAOYSA-N [Cu] chebi_ontology copper copper(0) acetate -1 59.013 59.04402 A monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of acetic acid. ACETATE ION Azetat Beilstein:1901470 C2H3O2 CAS:71-50-1 CC([O-])=O CH3-COO(-) CHEBI:13704 CHEBI:22165 CHEBI:30089 CHEBI:40480 DrugBank:DB03166 Ethanoat Gmelin:1379 InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)/p-1 KEGG:C00033 MeCO2 anion MetaCyc:ACET PDBeChem:ACT PMID:17190852 PMID:22211106 PMID:22371380 QTBSBXVTEAMEQO-UHFFFAOYSA-M Reaxys:1901470 UM-BBD_compID:c0050 Wikipedia:Acetate acetate acetic acid, ion(1-) chebi_ontology ethanoate lithium atom 0 3Li 6.94100 7.016 CAS:7439-93-2 CHEBI:30145 InChI=1S/Li Li Li Lithium WHXSMMKQMYFTQS-UHFFFAOYSA-N WebElements:Li [Li] chebi_ontology lithium lithium litio zinc(0) 0 63.929 65.39000 CAS:7440-66-6 CHEBI:30185 DrugBank:DB01593 HCHKCACWOHOZIP-UHFFFAOYSA-N InChI=1S/Zn Zn Zn(0) Znn [Zn] chebi_ontology zinc zinc(0) thioacetate -1 74.990 75.11062 Beilstein:1848542 Beilstein:3903387 C2H3OS CAS:29632-72-2 CC([S-])=O CHEBI:15233 CHEBI:26951 CHEBI:30320 DUYAAUVXQSMXQP-UHFFFAOYSA-M Gmelin:323277 InChI=1S/C2H4OS/c1-2(3)4/h1H3,(H,3,4)/p-1 Thioacetat chebi_ontology ethanethioate thioacetate isopropyl group (CH3)2CH- -CH(CH3)2 0 1-methylethyl 43.055 43.08768 C3H7 CHEBI:30353 chebi_ontology iPr isopropyl propan-2-yl valine side-chain isobutyl group (CH3)2CH-CH2- -CH2-CH(CH3)2 0 2-methylpropan-1-ido 2-methylpropyl 57.070 57.11426 C4H9 CHEBI:30356 chebi_ontology iBu isobutyl leucine side-chain isopentane (CH3)2CH-CH2-CH3 0 1,1,2-trimethylethane 1,1-dimethylpropane 2-methylbutane 72.094 72.14878 An alkane that is butane substituted by a methyl group at position 2. Beilstein:1730723 C5H12 CAS:78-78-4 CCC(C)C CHEBI:30362 Gmelin:49318 InChI=1S/C5H12/c1-4-5(2)3/h5H,4H2,1-3H3 PMID:21481069 PMID:23904008 PMID:24833189 PMID:24932627 QWTDNUCVQCZILF-UHFFFAOYSA-N R-601a Reaxys:1730723 Wikipedia:Isopentane chebi_ontology dimethylethylmethane iso-C5H12 iso-pentane isoamylhydride isopentane isobutane (CH3)2CH-CH3 0 2-methylpropane 58.078 58.12220 An alkane that is propane substituted by a methyl group at position 2. Beilstein:1730720 C4H10 CAS:75-28-5 CC(C)C CHEBI:30363 E943b Gmelin:1301 InChI=1S/C4H10/c1-4(2)3/h4H,1-3H3 KEGG:D04623 NNPPMTNAJDCUHE-UHFFFAOYSA-N PMID:24179026 PMID:24464945 R-600a Reaxys:1730720 Wikipedia:Isobutane chebi_ontology isobutane cobalamin A cobalt-corrinoid hexaamide that is cobalamin with the oxidation state of the central cobalt atom unspecified. CHEBI:30411 COBALAMIN COMe:MOL000036 Coalpha-[alpha-(5,6-dimethylbenzimidazolyl)]-cobamide PDBeChem:B12 PMID:11371572 PMID:15181872 chebi_ontology cobalamin monoatomic dication +2 0.00000 CHEBI:23856 CHEBI:30412 CHEBI:4665 Divalent cation KEGG:C00572 [*++] chebi_ontology divalent cation divalent inorganic cations monoatomic dications heme A heme is any tetrapyrrolic chelate of iron. CHEBI:14386 CHEBI:24491 CHEBI:30413 COMe:MOL000025 DrugBank:DB03014 Haem KEGG:C00032 chebi_ontology haem haeme hem heme hemes hemos sulfonium +1 34.996 35.08982 CAS:18155-21-0 CHEBI:30488 Gmelin:307 H3S H3S(+) H3S+ InChI=1S/H2S/h1H2/p+1 RWSOTUBLDIXVET-UHFFFAOYSA-O [H][S+]([H])[H] [SH3](+) chebi_ontology sulfanium sulfonium sulphonium trihydridosulfur(1+) gamma-aminobutyrate -1 102.056 102.11186 4-Amino-butyrat 4-Aminobutylate 4-aminobutanoate 4-aminobutanoic acid ion (1-) 4-aminobutyrate An gamma-amino acid anion resulting from the deprotonation of the carboxy group of gamma-aminobutyric acid. BTCSSZJGUNDROE-UHFFFAOYSA-M Beilstein:3536873 C4H8NO2 CHEBI:11961 CHEBI:20317 CHEBI:30566 Gmelin:559138 InChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)/p-1 KEGG:C00334 NCCCC([O-])=O PMID:12509893 Reaxys:3536873 chebi_ontology gamma-aminobutanoate gamma-aminobutyrate anion thyroxine zwitterion (2S)-2-azaniumyl-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate 0 2-Amino-3-[4-(4-hydroxy-3,5-diiodo-phenoxy)-3,5-diiodo-phenyl]-propionate 776.687 776.87000 C15H11I4NO4 CHEBI:305790 InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23) The amino acid zwitterion formed from thyroxine by transfer of a proton from the carboxy group to the amino group. Major species at pH 7.3. XUIIKFGFIJCVMT-UHFFFAOYSA-N [NH3+]C(Cc1cc(I)c(Oc2cc(I)c(O)c(I)c2)c(I)c1)C([O-])=O chebi_ontology thyroxine ATP(4-) -4 502.964 503.14946 A nucleoside triphosphate(4-) obtained by global deprotonation of the triphosphate OH groups of ATP; major species present at pH 7.3. ATP Beilstein:3581767 C10H12N5O13P3 CHEBI:30616 Gmelin:342798 InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/p-4/t4-,6-,7-,10-/m1/s1 Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J adenosine 5'-triphosphate(4-) atp chebi_ontology oxalate(2-) -2 87.980 88.01900 A dicarboxylic acid dianion obtained by deprotonation of both carboxy groups of oxalic acid. Beilstein:1905970 C2O4 CAS:338-70-5 CHEBI:14702 CHEBI:25729 CHEBI:30623 CHEBI:44820 Gmelin:2207 InChI=1S/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6)/p-2 KEGG:C00209 MUBZPKHOEPUJKR-UHFFFAOYSA-L OXALATE ION PDBeChem:OXL Reaxys:1905970 UM-BBD_compID:c0017 [O-]C(=O)C([O-])=O chebi_ontology ethanedioate ethanedioic acid, ion(2-) ox oxalate thyroxine 0 2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid 776.687 776.87006 An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions. Beilstein:2228514 C15H11I4NO4 CAS:300-30-1 CHEBI:30660 DL-Thyroxine InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23) NC(Cc1cc(I)c(Oc2cc(I)c(O)c(I)c2)c(I)c1)C(O)=O O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-DL-tyrosine PMID:15206581 PMID:24375501 PMID:9824273 Thx XUIIKFGFIJCVMT-UHFFFAOYSA-N chebi_ontology thyroxine thyronine 0 2-amino-3-[4-(4-hydroxyphenoxy)phenyl]propanoic acid 273.100 273.28394 A tyrosine derivative where the phenolic hydrogen of tyrosine is substituted by 4-hydroxyphenyl. Beilstein:2947040 C15H15NO4 CAS:1034-10-2 CHEBI:30661 Gmelin:419747 InChI=1S/C15H15NO4/c16-14(15(18)19)9-10-1-5-12(6-2-10)20-13-7-3-11(17)4-8-13/h1-8,14,17H,9,16H2,(H,18,19) KKCIOUWDFWQUBT-UHFFFAOYSA-N NC(Cc1ccc(Oc2ccc(O)cc2)cc1)C(O)=O O-(4-hydroxyphenyl)-DL-tyrosine PMID:15643926 Reaxys:2947040 chebi_ontology thyronine phenylacetic acid 0 136.052 136.14792 2-PHENYLACETIC ACID 2-Phenylethanoic acid A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group. Beilstein:1099647 Benzeneacetic acid Benzylformic acid C8H8O2 CAS:103-82-2 CHEBI:25977 CHEBI:30745 CHEBI:44686 CHEBI:8085 Drug_Central:4624 ECMDB:ECMDB04128 Gmelin:68976 HMDB:HMDB0000209 InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10) KEGG:C07086 KNApSAcK:C00000750 MetaCyc:PHENYLACETATE OC(=O)Cc1ccccc1 Omega-Phenylacetic acid PA PDBeChem:PAC PMID:12147706 PMID:12569987 PMID:15057459 PMID:15506622 PMID:15646820 PMID:17622769 PMID:2083978 PMID:24587751 PMID:24631718 PMID:7544181 PMID:7716788 Phenylacetic acid Reaxys:1099647 WLJVXDMOQOGPHL-UHFFFAOYSA-N Wikipedia:Phenylacetic_acid YMDB:YMDB00891 alpha-toluic acid benzeneacetic acid chebi_ontology omega-phenylacetic acid phenylacetic acid formic acid 0 46.005 46.02538 Acide formique Ameisensaeure BDAGIHXWWSANSR-UHFFFAOYSA-N BPDB:1749 Beilstein:1209246 CAS:64-18-6 CH2O2 CHEBI:24082 CHEBI:30751 CHEBI:42460 CHEBI:5145 DrugBank:DB01942 FORMIC ACID Formic acid Gmelin:1008 H-COOH HCO2H HCOOH HMDB:HMDB0000142 InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3) KEGG:C00058 KNApSAcK:C00001182 LIPID_MAPS_instance:LMFA01010040 MetaCyc:FORMATE Methanoic acid PDBeChem:FMT PMID:12591956 PMID:14637377 PMID:15811469 PMID:16120414 PMID:16185830 PMID:16222862 PMID:16230297 PMID:16445901 PMID:16465784 PMID:18034701 PMID:18397576 PMID:22080171 PMID:22280475 PMID:22304812 PMID:22385261 PMID:22447125 PMID:22483350 PMID:22499553 PMID:22540994 PMID:22606986 PMID:22622393 PMID:3946945 PMID:7361809 Patent:CN101481304 Reaxys:1209246 The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects. Wikipedia:Formic_acid [H]C(O)=O aminic acid bilorin chebi_ontology formic acid formylic acid hydrogen carboxylic acid methoic acid propionic acid 0 74.037 74.07850 A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group. Beilstein:506071 C3H6O2 CAS:79-09-4 CCC(O)=O CH3-CH2-COOH CHEBI:26304 CHEBI:30768 CHEBI:45227 CHEBI:8476 DrugBank:DB03766 Gmelin:1821 InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5) KEGG:C00163 KEGG:D02310 LIPID_MAPS_instance:LMFA01010003 PA PDBeChem:PPI PMID:15868474 PMID:1628870 PMID:16763906 PPDB:1341 PROPANOIC ACID Propanoic acid Propionic acid Propionsaeure XBDQKXXYIPTUBI-UHFFFAOYSA-N acide propanoique acide propionique carboxyethane chebi_ontology ethanecarboxylic acid ethylformic acid metacetonic acid methylacetic acid propanoic acid propioic acid propionic acid propoic acid pseudoacetic acid citric acid 0 192.027 192.12350 2-Hydroxy-1,2,3-propanetricarboxylic acid 2-Hydroxytricarballylic acid 2-hydroxypropane-1,2,3-tricarboxylic acid 3-Carboxy-3-hydroxypentane-1,5-dioic acid A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms. BPDB:1359 Beilstein:782061 C6H8O7 CAS:77-92-9 CHEBI:23322 CHEBI:30769 CHEBI:3727 CHEBI:41523 CITRIC ACID Citric acid Citronensaeure DrugBank:DB04272 Drug_Central:666 E330 Gmelin:4240 H3cit HMDB:HMDB0000094 InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12) KEGG:C00158 KEGG:D00037 KNApSAcK:C00007619 KRKNYBCHXYNGOX-UHFFFAOYSA-N MetaCyc:CIT OC(=O)CC(O)(CC(O)=O)C(O)=O PDBeChem:CIT PMID:11762832 PMID:11782123 PMID:11857437 PMID:14537820 PMID:15311880 PMID:15934243 PMID:16232627 PMID:17190852 PMID:17357118 PMID:17604395 PMID:18298573 PMID:18960216 PMID:19288211 PMID:22115968 PMID:22192423 PMID:22264346 PMID:22373571 PMID:22509852 Reaxys:782061 Wikipedia:Citric_Acid chebi_ontology citric acid butyric acid 0 1-butanoic acid 1-butyric acid 1-propanecarboxylic acid 4:0 88.052 88.10510 A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group. BUTANOIC ACID Beilstein:906770 Butanoate Butanoic acid Buttersaeure Butyric acid C4:0 C4H8O2 CAS:107-92-6 CCCC(O)=O CH3-[CH2]2-COOH CHEBI:113450 CHEBI:22948 CHEBI:30772 CHEBI:3234 CHEBI:41208 DrugBank:DB03568 FERIUCNNQQJTOY-UHFFFAOYSA-N Gmelin:26242 HMDB:HMDB0000039 InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6) KEGG:C00246 KNApSAcK:C00001180 LIPID_MAPS_instance:LMFA01010004 MetaCyc:BUTYRIC_ACID PDBeChem:BUA PMID:10736622 PMID:10956204 PMID:11201044 PMID:11208715 PMID:11238216 PMID:11305323 PMID:12068484 PMID:13678314 PMID:14962641 PMID:1542095 PMID:15809727 PMID:15810631 PMID:15938880 PMID:19318247 PMID:19366864 PMID:19703412 PMID:21699495 PMID:22038864 PMID:22194341 PMID:22322557 PMID:22339023 PMID:22466881 Reaxys:906770 Wikipedia:Butyric_acid acide butanoique acide butyrique butanic acid butanoic acid butanoic acid butoic acid butyric acid chebi_ontology ethylacetic acid n-butanoic acid n-butyric acid propanecarboxylic acid propylformic acid hexanoic acid 0 1-hexanoic acid 1-pentanecarboxylic acid 116.084 116.15830 6:0 A C6, straight-chain saturated fatty acid. Beilstein:773837 C6:0 C6H12O2 CAS:142-62-1 CCCCCC(O)=O CH3-[CH2]4-COOH CHEBI:24571 CHEBI:30776 CHEBI:40213 CHEBI:5702 ECMDB:ECMDB21229 FUZZWVXGSFPDMH-UHFFFAOYSA-N Gmelin:185066 HEXANOIC ACID HMDB:HMDB0000535 Hexanoate Hexanoic acid Hexylic acid InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8) KEGG:C01585 KNApSAcK:C00001218 LIPID_MAPS_instance:LMFA01010006 MetaCyc:HEXANOATE PDBeChem:6NA PMID:10685018 PMID:1556177 PMID:24357269 PMID:24924750 Pentanecarboxylic acid Reaxys:773837 Wikipedia:Hexanoic_acid YMDB:YMDB01424 butylacetic acid caproic acid capronic acid chebi_ontology hexanoic acid hexoic acid n-Caproic acid n-hexanoic acid n-hexoic acid n-hexylic acid pentiformic acid pentylformic acid malonic acid 0 104.011 104.06146 An alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group. Beilstein:1751370 C3H4O4 CAS:141-82-2 CHEBI:25132 CHEBI:30794 CHEBI:44060 CHEBI:6660 DrugBank:DB02175 Gmelin:2550 H2malo HMDB:HMDB0000691 HOOC-CH2-COOH InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7) KEGG:C00383 KNApSAcK:C00001193 LIPID_MAPS_instance:LMFA01170041 MALONIC ACID Malonic acid MetaCyc:MALONATE OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N PDBeChem:MLA PMID:22770225 Propanedioic acid Reaxys:1751370 Wikipedia:Malonic_acid chebi_ontology propanedioic acid malonate(1-) -1 103.003 103.05352 Beilstein:3904186 C3H3O4 CHEBI:30795 Gmelin:324637 HOOC-CH2-COO(-) Hmalo InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)/p-1 Malonic acid, conjugate base OC(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-M carboxyacetate chebi_ontology tetradecanoate -1 1-tetradecanecarboxylate 227.201 227.364 A long-chain fatty acid anion that is the conjugate base of myristic acid; major species at pH 7.3. Beilstein:3589340 C(CCCCCCCC)CCCCC([O-])=O C14H27O2 CH3-[CH2]12-COO(-) CHEBI:30807 CHEBI:35292 Gmelin:335122 InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)/p-1 KEGG:C06424 Reaxys:3589340 TUNFSRHWOTWDNC-UHFFFAOYSA-M Tetradecanoate chebi_ontology myristate n-tetradecan-1-oate n-tetradecoate tetradecanoate tetradecoate orotate -1 155.009 155.08830 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate Beilstein:3651747 C5H3N2O4 CAS:73-97-2 CHEBI:14698 CHEBI:25719 CHEBI:30839 Gmelin:464718 InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)/p-1 PXQPEWDEAKTCGB-UHFFFAOYSA-M [O-]C(=O)c1cc(=O)[nH]c(=O)[nH]1 chebi_ontology orotate urate(1-) -1 167.10248 7,9-dihydro-1H-purine-2,6,8(3H)-trione, ion(1-) C5H3N4O3 CAS:3106-08-9 CHEBI:15290 CHEBI:30848 chebi_ontology uric acid monoanion uric acid, ion(1-) methylmalonic acid 0 1,1-Ethanedicarboxylic acid 118.027 118.08804 2-methylmalonic acid A dicarboxylic acid that is malonic acid in which one of the methylene hydrogens is substituted by a methyl group. Beilstein:1756084 C4H6O4 CAS:516-05-2 CC(C(O)=O)C(O)=O CHEBI:25319 CHEBI:30860 CHEBI:42270 CHEBI:6881 DrugBank:DB04183 Gmelin:50008 HMDB:HMDB0000202 InChI=1S/C4H6O4/c1-2(3(5)6)4(7)8/h2H,1H3,(H,5,6)(H,7,8) Isosuccinic acid KEGG:C02170 LIPID_MAPS_instance:LMFA01170118 METHYLMALONIC ACID MetaCyc:CPD-546 Methylmalonic acid PDBeChem:DXX PMID:11673368 PMID:15770414 PMID:17190852 PMID:21478039 PMID:21652239 PMID:21687976 PMID:21748409 PMID:21802231 PMID:21896502 PMID:22104738 PMID:22233538 PMID:22301932 PMID:22332180 PMID:22377700 PMID:22422209 PMID:22424943 PMID:22509143 PMID:22537172 PMID:22770225 Reaxys:1756084 Wikipedia:Methylmalonic_acid ZIYVHBGGAOATLY-UHFFFAOYSA-N alpha-methylmalonic acid chebi_ontology methylpropanedioic acid methylmalonate(1-) -1 117.019 117.08010 2-carboxypropanoate A dicarboxylic acid monoanion resulting from the removal of a proton from one of the carboxylic acid groups of methylmalonic acid. Beilstein:5499681 C4H5O4 CC(C(O)=O)C([O-])=O CHEBI:30861 Gmelin:142213 InChI=1S/C4H6O4/c1-2(3(5)6)4(7)8/h2H,1H3,(H,5,6)(H,7,8)/p-1 Reaxys:5499681 ZIYVHBGGAOATLY-UHFFFAOYSA-M chebi_ontology alcohol 0 17.003 A compound in which a hydroxy group, -OH, is attached to a saturated carbon atom. Alcohol CHEBI:13804 CHEBI:22288 CHEBI:2553 CHEBI:30879 HOR KEGG:C00069 O[*] alcohols an alcohol chebi_ontology glucitol Beilstein:1721909 C6H14O6 CHEBI:15093 CHEBI:26724 CHEBI:26726 CHEBI:30911 CHEBI:33795 CHEBI:33796 CHEBI:9201 Gmelin:83165 Sorbitol Wikipedia:Sorbitol chebi_ontology glucitol gulitol rel-(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol sorbitol 2-oxoglutaric acid 0 146.022 146.09810 2-Ketoglutaric acid 2-oxopentanedioic acid An oxo dicarboxylic acid that consists of glutaric acid bearing an oxo substituent at position 2. It is an intermediate metabolite in Krebs cycle. Beilstein:1705689 C5H6O5 CAS:328-50-7 CHEBI:1253 CHEBI:19749 CHEBI:30915 CHEBI:40661 DrugBank:DB02926 Gmelin:602480 HMDB:HMDB0000208 InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10) KEGG:C00026 KNApSAcK:C00000769 KPGXRSRHYNQIFN-UHFFFAOYSA-N MetaCyc:2-KETOGLUTARATE OC(=O)CCC(=O)C(O)=O Oxoglutaric acid PDBeChem:AKG PMID:17439666 PMID:18990406 PMID:20155414 PMID:20200292 PMID:20583149 PMID:20636327 PMID:21964641 Reaxys:1705689 Wikipedia:Alpha-Ketoglutaric_acid alpha-Ketoglutaric acid alpha-ketoglutaric acid chebi_ontology 2-oxoglutarate(1-) -1 145.014 145.09020 2-ketoglutarate 4-carboxy-2-oxobutanoate A dicarboxylic acid monoanion resulting from selective deprotonation of the 1-carboxy group of 2-oxoglutaric acid. Beilstein:4132418 C5H5O5 CHEBI:30916 Gmelin:2159365 InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)/p-1 KPGXRSRHYNQIFN-UHFFFAOYSA-M OC(=O)CCC(=O)C([O-])=O Reaxys:4132418 chebi_ontology 3-hydroxy-3-methylglutarate(1-) -1 161.045 161.13270 4-carboxy-3-hydroxy-3-methylbutanoate A dicarboxylic acid monoanion resulting from the removal of a proton from one of the carboxylic acid groups of 3-hydroxy-3-methylglutaric acid. C6H9O5 CC(O)(CC(O)=O)CC([O-])=O CHEBI:30920 InChI=1S/C6H10O5/c1-6(11,2-4(7)8)3-5(9)10/h11H,2-3H2,1H3,(H,7,8)(H,9,10)/p-1 NPOAOTPXWNWTSH-UHFFFAOYSA-M chebi_ontology glutarate(2-) -2 130.027 130.09874 A dicarboxylic acid dianion obtained by deprotonation of both the carboxy groups of glutaric acid. Beilstein:3904695 C5H6O4 CHEBI:14322 CHEBI:24327 CHEBI:30921 Gmelin:240388 InChI=1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9)/p-2 JFCQEDHGNNZCLN-UHFFFAOYSA-L Reaxys:3904695 [O-]C(=O)CCCC([O-])=O chebi_ontology glutarate pentanedioate pyrazine 0 1,4-Diazin 1,4-diazine 80.037 80.08804 A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms. Beilstein:103905 C4H4N2 CAS:290-37-9 CHEBI:30953 Gmelin:1733 HMDB:HMDB0034176 InChI=1S/C4H4N2/c1-2-6-4-3-5-1/h1-4H KYQCOXFCLRTKLS-UHFFFAOYSA-N PMID:24964033 Pyrazin Reaxys:103905 Wikipedia:Pyrazine c1cnccn1 chebi_ontology p-diazine paradiazine pyrazine pyz bile acid 5beta-bile acid 5beta-bile acids Any member of a group of hydroxy-5beta-cholanic acids occuring in bile, where they are present as the sodium salts of their amides with glycine or taurine. In mammals bile acids almost invariably have 5beta-configuration. Bile acid Bile salt CHEBI:3098 Gallensaeure Gallensaeuren KEGG:C01558 bile acids chebi_ontology 4,4'-bipyridine 0 156.069 156.18400 4,4'-bipyridine 4,4'-bipyridyl 4,4'-bpy 4,4'-dipyridine 4,4'-dipyridyl 4,4-Bipyridin 4-(4-pyridyl)pyridine A bipyridine in which the two pyridine moieties are linked by a bond between positions C-4 and C-4'. Beilstein:113176 C10H8N2 CAS:553-26-4 CHEBI:30985 Gmelin:3759 InChI=1S/C10H8N2/c1-5-11-6-2-9(1)10-3-7-12-8-4-10/h1-8H MWVTWFVJZLCBMC-UHFFFAOYSA-N PMID:24022647 PMID:24358992 PMID:24446585 Reaxys:113176 Wikipedia:4,4%27-Bipyridine c1cc(ccn1)-c1ccncc1 chebi_ontology gamma,gamma'-bipyridyl gamma,gamma'-dipyridyl valerate -1 101.060 101.12376 A short-chain fatty acid anion that is the conjugate base of valeric acid; present in ester form as component of many steroid-based pharmaceuticals. Beilstein:3903735 C5H9O2 CAS:10023-74-2 CCCCC([O-])=O CH3-[CH2]3-COO(-) CHEBI:14751 CHEBI:25890 CHEBI:31011 Gmelin:325619 InChI=1S/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7)/p-1 NQPDZGIKBAWPEJ-UHFFFAOYSA-M PMID:17314444 PMID:18783570 Reaxys:3903735 chebi_ontology n-propylacetate pentanoate pentanoate pentanoic acid, ion(1-) ammonium chloride 0 53.003 53.49120 Ammonium chloride Ammoniumchlorid An inorganic chloride having ammonium as the counterion. CAS:12125-02-9 CHEBI:31206 Cl.H4N ClH4N Gmelin:10120 InChI=1S/ClH.H3N/h1H;1H3 KEGG:C12538 KEGG:D01139 NH4Cl NLXLAEXVIDQMFP-UHFFFAOYSA-N Wikipedia:Ammonium_Chloride [Cl-].[H][N+]([H])([H])[H] [NH4]Cl ammonium chloride azanium chloride chebi_ontology bradykinin 0 1059.561 1060.20850 A linear nonapeptide messenger belonging to the kinin group of proteins, with amino acid sequence RPPGFSPFR. Enzymatically produced from kallidin in the blood, it is a powerful vasodilator that causes smooth muscle contraction, and may mediate inflammation. Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg BK C50H73N15O11 CAS:58-82-2 CHEBI:3165 InChI=1S/C50H73N15O11/c51-32(16-7-21-56-49(52)53)45(72)65-25-11-20-39(65)47(74)64-24-9-18-37(64)43(70)58-28-40(67)59-34(26-30-12-3-1-4-13-30)41(68)62-36(29-66)46(73)63-23-10-19-38(63)44(71)61-35(27-31-14-5-2-6-15-31)42(69)60-33(48(75)76)17-8-22-57-50(54)55/h1-6,12-15,32-39,66H,7-11,16-29,51H2,(H,58,70)(H,59,67)(H,60,69)(H,61,71)(H,62,68)(H,75,76)(H4,52,53,56)(H4,54,55,57)/t32-,33-,34-,35-,36-,37-,38-,39-/m0/s1 L-Arg-L-Pro-L-Pro-Gly-L-Phe-L-Ser-L-Pro-L-Phe-L-Arg L-arginyl-L-prolyl-L-prolylglycyl-L-phenylalanyl-L-seryl-L-prolyl-L-phenylalanyl-L-arginine L-bradykinin N[C@@H](CCCNC(N)=N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O PMID:11799074 PMID:11975815 PMID:13446366 PMID:13811230 PMID:14597148 PMID:15105283 PMID:16680069 PMID:18127230 PMID:27318425 PMID:27328010 PMID:27432758 PMID:27445816 PMID:7859389 PMID:8723398 PMID:9403361 QXZGBUJJYSLZLT-FDISYFBBSA-N RPPGFSPFR Reaxys:24162492 Reaxys:2801232 Wikipedia:Bradykinin chebi_ontology alaninate -1 2-aminopropanoate 88.040 88.08528 An alpha-amino-acid anion that is the conjugate base of alanine, arising from deprotonation of the carboxy group. Beilstein:3903719 C3H6NO2 CC(N)C([O-])=O CHEBI:32439 Gmelin:101040 InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/p-1 QNAYBMKLOCPYGJ-UHFFFAOYSA-M alaninate alanine anion chebi_ontology alaninium +1 1-carboxyethanaminium 90.056 90.10116 An alpha-amino-acid cation that is the conjugate acid of alanine. C3H8NO2 CC([NH3+])C(O)=O CHEBI:32440 Gmelin:362663 InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/p+1 QNAYBMKLOCPYGJ-UHFFFAOYSA-O alanine cation alaninium chebi_ontology L-cysteinate(1-) (2R)-2-amino-3-mercaptopropanoate (2R)-2-amino-3-sulfanylpropanoate -1 120.012 120.15128 Beilstein:4128886 C3H6NO2S CHEBI:32442 Gmelin:325857 InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/p-1/t2-/m0/s1 L-cysteinate(1-) L-cysteine anion L-cysteine monoanion N[C@@H](CS)C([O-])=O Reaxys:4128886 The L-enantiomer of cysteinate(1-). XUJNEKJLAYXESH-REOHCLBHSA-M chebi_ontology hydrogen L-cysteinate L-cysteinate(2-) (2R)-2-amino-3-sulfidopropanoate -2 119.004 119.14334 Beilstein:5921923 C3H5NO2S CHEBI:32443 Gmelin:325856 InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/p-2/t2-/m0/s1 L-cysteinate L-cysteinate(2-) L-cysteine dianion N[C@@H](C[S-])C([O-])=O Reaxys:5921923 The L-enantiomer of cysteinate(2-). XUJNEKJLAYXESH-REOHCLBHSA-L chebi_ontology L-cysteinium (1R)-1-carboxy-2-mercaptoethanaminium (1R)-1-carboxy-2-sulfanylethanaminium +1 122.028 122.16716 C3H8NO2S CHEBI:32445 Gmelin:325860 InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/p+1/t2-/m0/s1 L-cysteine cation L-cysteinium L-cysteinium(1+) The L-enantiomer of cysteinium. XUJNEKJLAYXESH-REOHCLBHSA-O [NH3+][C@@H](CS)C(O)=O chebi_ontology D-cysteinate(1-) (2S)-2-amino-3-mercaptopropanoate (2S)-2-amino-3-sulfanylpropanoate -1 120.012 120.15128 C3H6NO2S CHEBI:32449 D-cysteinate(1-) D-cysteine monoanion Gmelin:1006156 InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/p-1/t2-/m1/s1 N[C@H](CS)C([O-])=O The D-enantiomer of cysteinate(1-). XUJNEKJLAYXESH-UWTATZPHSA-M chebi_ontology hydrogen D-cysteinate D-cysteinate(2-) (2S)-2-amino-3-sulfidopropanoate -2 119.004 119.14334 C3H5NO2S CHEBI:32450 D-cysteinate D-cysteinate(2-) D-cysteine dianion Gmelin:1342792 InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/p-2/t2-/m1/s1 N[C@H](C[S-])C([O-])=O The D-enantiomer of cysteinate(2-). XUJNEKJLAYXESH-UWTATZPHSA-L chebi_ontology D-cysteinium (1S)-1-carboxy-2-mercaptoethanaminium (1S)-1-carboxy-2-sulfanylethanaminium +1 122.028 122.16716 C3H8NO2S CHEBI:32451 D-cysteine cation D-cysteinium Gmelin:363237 InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/p+1/t2-/m1/s1 The D-enantiomer of cysteinium. XUJNEKJLAYXESH-UWTATZPHSA-O [NH3+][C@H](CS)C(O)=O chebi_ontology cysteinate(1-) -1 120.012 120.15128 2-amino-3-mercaptopropanoate 2-amino-3-sulfanylpropanoate A sulfur-containing amino-acid anion that is the conjugate base of cysteine, obtained by deprotonation of the carboxy group. Beilstein:4128885 C3H6NO2S CHEBI:32456 Gmelin:363235 InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/p-1 NC(CS)C([O-])=O Reaxys:4128885 XUJNEKJLAYXESH-UHFFFAOYSA-M chebi_ontology cys(-) cysteinate(1-) cysteine monoanion hydrogen cysteinate cysteinate(2-) -2 119.004 119.14334 2-amino-3-sulfidopropanoate C3H5NO2S CHEBI:32457 Gmelin:49990 InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/p-2 NC(C[S-])C([O-])=O XUJNEKJLAYXESH-UHFFFAOYSA-L chebi_ontology cysteinate cysteinate(2-) cysteine dianion cysteinium +1 1-carboxy-2-mercaptoethanaminium 1-carboxy-2-sulfanylethanaminium 122.028 122.16716 C3H8NO2S CHEBI:32458 Gmelin:325859 H2cys(+) InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/p+1 XUJNEKJLAYXESH-UHFFFAOYSA-O [NH3+]C(CS)C(O)=O chebi_ontology cysteine cation cysteinium phenylalaninate -1 164.071 164.18120 2-amino-3-phenylpropanoate An aromatic amino-acid anion that is the conjugate base of phenylalanine, arising from deprotonation of the carboxy group. C9H10NO2 CHEBI:32504 COLNVLDHVKWLRT-UHFFFAOYSA-M Gmelin:329083 InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/p-1 NC(Cc1ccccc1)C([O-])=O chebi_ontology phenylalaninate phenylalanine anion phenylalaninium +1 1-carboxy-2-phenylethanaminium 166.087 166.19710 An alpha-amino-acid cation that is the conjugate acid of phenylalanine, arising from protonation of the amino group. C9H12NO2 CHEBI:32505 COLNVLDHVKWLRT-UHFFFAOYSA-O InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/p+1 [NH3+]C(Cc1ccccc1)C(O)=O chebi_ontology phenylalanine cation phenylalaninium glycinium +1 76.040 76.07458 An alpha-amino-acid cation that is the conjugate acid of glycine, arising from protonation of the amino. C2H6NO2 CHEBI:32507 DHMQDGOQFOQNFH-UHFFFAOYSA-O Gmelin:323509 H2gly(+) InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)/p+1 NH3(+)-CH2-COOH [NH3+]CC(O)=O carboxymethanaminium chebi_ontology glycine cation glycinium glycinate -1 74.024 74.05870 An alpha-amino-acid anion that is the conjugate base of glycine, arising from deprotonation of the carboxy group. Beilstein:1852023 C2H4NO2 CHEBI:32508 DHMQDGOQFOQNFH-UHFFFAOYSA-M Gmelin:81890 H2N-CH2-COO(-) InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)/p-1 NCC([O-])=O Reaxys:1852023 UM-BBD_compID:c0559 aminoacetate chebi_ontology gly(-) glycinate glycine anion histidinate(1-) -1 154.062 154.14660 2-amino-3-(1H-imidazol-4-yl)propanoate Beilstein:3959092 C6H8N3O2 CHEBI:32529 Gmelin:364417 HNDVDQJCIGZPNO-UHFFFAOYSA-M InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/p-1 NC(Cc1c[nH]cn1)C([O-])=O chebi_ontology histidinate(1-) histidine anion hydrogen histidinate histidinate(2-) -2 153.054 153.13880 2-amino-3-imidazol-1-id-4-ylpropanoate C6H7N3O2 CHEBI:32530 InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H2,8,9,10,11)/p-2 NC(Cc1c[n-]cn1)C([O-])=O TWRZMXZXJKNOLO-UHFFFAOYSA-L chebi_ontology histidinate histidinate(2-) histidine dianion histidinium(1+) +1 156.077 156.16262 2-ammonio-3-(1H-imidazol-3-ium-4-yl)propanoate C6H10N3O2 CHEBI:32531 HNDVDQJCIGZPNO-UHFFFAOYSA-O InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/p+1 [NH3+]C(Cc1c[nH]c[nH+]1)C([O-])=O chebi_ontology histidine monocation histidinium histidinium(1+) histidinium(2+) +2 157.085 157.17056 4-(2-ammonio-2-carboxyethyl)-1H-imidazol-3-ium C6H11N3O2 CHEBI:32532 Gmelin:1151904 HNDVDQJCIGZPNO-UHFFFAOYSA-P InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/p+2 [NH3+]C(Cc1c[nH]c[nH+]1)C(O)=O chebi_ontology histidine dication histidinediium histidinium(2+) lysinate -1 145.098 145.17970 2,6-diaminohexanoate An alpha-amino-acid anion that is the conjugate base of lysine, arising from deprotonation of the carboxy group. C6H13N2O2 CHEBI:32563 Gmelin:815095 InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/p-1 KDXKERNSBIXSRK-UHFFFAOYSA-M NCCCCC(N)C([O-])=O chebi_ontology lys(-) lysinate lysinate(1-) lysine anion lysinium(1+) +1 147.113 147.19558 2,6-diammoniohexanoate An alpha-amino-acid cation that is the conjugate acid of lysine, having two cationic amino groups and an anionic carboxy group. C6H15N2O2 CHEBI:32564 InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/p+1 KDXKERNSBIXSRK-UHFFFAOYSA-O [NH3+]CCCCC([NH3+])C([O-])=O chebi_ontology lysine monocation lysinium lysinium(1+) lysinium(2+) +2 1-carboxypentane-1,5-diaminium 148.121 148.20352 An alpha-amino-acid cation obtained by protonation of both amino groups of lysine. C6H16N2O2 CHEBI:32565 InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/p+2 KDXKERNSBIXSRK-UHFFFAOYSA-P [NH3+]CCCCC([NH3+])C(O)=O chebi_ontology lysine dication lysinediium lysinium(2+) isoleucinate CHEBI:32612 Gmelin:101585 chebi_ontology ile(-) isoleucinate isoleucine anion rel-(2R,3R)-2-amino-3-methylpentanoate isoleucinium CHEBI:32613 Gmelin:1651827 H2ile(+) chebi_ontology isoleucine cation isoleucinium rel-(1R,2R)-1-carboxy-2-methylbutan-1-aminium leucinate -1 130.087 130.16502 2-amino-4-methylpentanoate An alpha-amino-acid anion that is the conjugate base of leucine, arising from deprotonation of the carboxy group. C6H12NO2 CC(C)CC(N)C([O-])=O CHEBI:32627 InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/p-1 ROHFNLRQFUQHCH-UHFFFAOYSA-M Reaxys:5245805 chebi_ontology leu(-) leucinate leucine anion leucinium +1 1-carboxy-3-methylbutan-1-aminium 132.102 132.18090 An alpha-amino-acid cation that is the conjugate acid of leucine, arising from protonation of the amino group. C6H14NO2 CC(C)CC([NH3+])C(O)=O CHEBI:32628 Gmelin:1651836 H2leu(+) InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/p+1 ROHFNLRQFUQHCH-UHFFFAOYSA-O chebi_ontology leucine cation leucinium methioninate -1 148.043 148.20444 2-amino-4-(methylsulfanyl)butanoate A sulfur-containing amino-acid anion that is the conjugate base of methionine, arising from deprotonation of the carboxy group. Beilstein:3937270 C5H10NO2S CHEBI:32644 CSCCC(N)C([O-])=O FFEARJCKVFRZRR-UHFFFAOYSA-M Gmelin:326565 InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/p-1 Reaxys:3937270 chebi_ontology met(-) methioninate methionine anion methioninium +1 1-carboxy-3-(methylsulfanyl)propan-1-aminium 150.059 150.22032 A sulfur-containing amino-acid anion that is the conjugate acid of methionine, arising from protonation of the amino group. C5H12NO2S CHEBI:32646 CSCCC([NH3+])C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-O Gmelin:326567 H2met(+) InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/p+1 chebi_ontology methionine cation methioninium asparaginate -1 131.046 131.11006 2,4-diamino-4-oxobutanoate An alpha-amino-acid anion that is the conjugate base of asparagine, arising from deprotonation of the carboxy group. C4H7N2O3 CHEBI:32660 DCXYFEDJOCDNAF-UHFFFAOYSA-M Gmelin:327370 InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/p-1 NC(CC(N)=O)C([O-])=O asp(-) asparaginate asparagine anion chebi_ontology asparaginium +1 133.061 133.12594 3-amino-1-carboxy-3-oxopropan-1-aminium C4H9N2O3 CHEBI:32661 DCXYFEDJOCDNAF-UHFFFAOYSA-O H2asp(+) InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/p+1 NC(=O)CC([NH3+])C(O)=O asparagine cation asparaginium chebi_ontology glutaminate -1 145.061 145.13664 2,5-diamino-5-oxopentanoate An alpha-amino-acid anion that is the conjugate base of glutamine, arising from deprotonation of the carboxy group. C5H9N2O3 CHEBI:32678 Gmelin:464703 InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/p-1 NC(CCC(N)=O)C([O-])=O ZDXPYRJPNDTMRX-UHFFFAOYSA-M chebi_ontology gln(-) glutaminate glutamine anion glutaminium +1 147.077 147.15252 4-amino-1-carboxy-4-oxobutan-1-aminium An alpha-amino-acid cation that is the conjugate acid of glutamine, arising from protonation of the amino group. C5H11N2O3 CHEBI:32679 H2gln(+) InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/p+1 NC(=O)CCC([NH3+])C(O)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-O chebi_ontology glutamine cation glutaminium argininate -1 173.104 173.19318 2-amino-5-(carbamimidamido)pentanoate 2-amino-5-guanidinopentanoate C6H13N4O2 CHEBI:32695 Gmelin:603497 InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/p-1 NC(CCCNC(N)=N)C([O-])=O ODKSFYDXXFIFQN-UHFFFAOYSA-M arg(-) argininate arginine anion chebi_ontology argininium(1+) +1 175.120 175.20906 2-ammonio-5-guanidiniopentanoate C6H15N4O2 CHEBI:32696 Gmelin:1345599 H2arg(+) InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/p+1 NC(=[NH2+])NCCCC([NH3+])C([O-])=O ODKSFYDXXFIFQN-UHFFFAOYSA-O arginine arginine monocation argininium argininium(1+) chebi_ontology argininium(2+) (1-carboxy-4-guanidiniobutyl)ammonium +2 176.127 176.21700 C6H16N4O2 CHEBI:32697 H3arg(2+) InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/p+2 NC(=[NH2+])NCCCC([NH3+])C(O)=O ODKSFYDXXFIFQN-UHFFFAOYSA-P arginine dication argininediium argininium(2+) chebi_ontology tryptophanate -1 2-amino-3-(1H-indol-3-yl)propanoate 203.082 203.21732 An alpha-amino-acid anion that is the conjugate base of tryptophan, arising from deprotonation of the carboxy group. Beilstein:4144997 C11H11N2O2 CHEBI:32727 Gmelin:331342 InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/p-1 NC(Cc1c[nH]c2ccccc12)C([O-])=O QIVBCDIJIAJPQS-UHFFFAOYSA-M Reaxys:4144998 chebi_ontology trp(-) tryptophan anion tryptophanate tryptophanium +1 1-carboxy-2-(1H-indol-3-yl)ethanaminium 205.098 205.23320 An alpha-amino-acid cation that is the conjugate acid of tryptophan, arising from protonation of the alpha-amino group. C11H13N2O2 CHEBI:32728 Htrp(+) InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/p+1 QIVBCDIJIAJPQS-UHFFFAOYSA-O [NH3+]C(Cc1c[nH]c2ccccc12)C(O)=O chebi_ontology tryptophan cation tryptophanium tyrosinate(1-) -1 180.066 180.18064 2-amino-3-(4-hydroxyphenyl)propanoate An alpha-amino-acid anion that is the conjugate base of tyrosine, arising from deprotonation of the carboxy group. Beilstein:3548387 Beilstein:4139515 C9H10NO3 CHEBI:32784 Gmelin:329372 InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/p-1 NC(Cc1ccc(O)cc1)C([O-])=O OUYCCCASQSFEME-UHFFFAOYSA-M chebi_ontology hydrogen tyrosinate tyrosinate(1-) tyrosine anion tyrosinate(2-) -2 179.058 179.17270 2-amino-3-(4-oxidophenyl)propanoate C9H9NO3 CHEBI:32785 InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/p-2 NC(Cc1ccc([O-])cc1)C([O-])=O OUYCCCASQSFEME-UHFFFAOYSA-L chebi_ontology tyrosinate tyrosinate(2-) tyrosine dianion tyrosinium +1 1-carboxy-2-(4-hydroxyphenyl)ethanaminium 182.082 182.19652 An alpha-amino-acid cation that is the conjugate acid of tyrosine, arising from protonation of the amino group. C9H12NO3 CHEBI:32786 InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/p+1 OUYCCCASQSFEME-UHFFFAOYSA-O [NH3+]C(Cc1ccc(O)cc1)C(O)=O chebi_ontology tyrosine cation tyrosinium (R)-2-hydroxyglutaric acid (2R)-2-hydroxypentanedioic acid (R)-2-Hydroxyglutarate (R)-Hydroxyglutarate 0 148.037 148.11402 Beilstein:1723806 C5H8O5 CHEBI:18651 CHEBI:310 CHEBI:32796 CHEBI:339 HWXBTNAVRSUOJR-GSVOUGTGSA-N InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/t3-/m1/s1 KEGG:C01087 KEGG:C02911 MetaCyc:R-2-HYDROXYGLUTARATE O[C@H](CCC(O)=O)C(O)=O Reaxys:1723806 The (R)-enantiomer of 2-hydroxyglutaric acid. chebi_ontology (S)-2-hydroxyglutaric acid (2S)-2-hydroxypentanedioic acid (S)-2-Hydroxyglutarate 0 148.037 148.11402 Beilstein:1723807 C5H8O5 CAS:13095-48-2 CHEBI:18739 CHEBI:32797 CHEBI:380 Gmelin:1218919 HWXBTNAVRSUOJR-VKHMYHEASA-N InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/t3-/m0/s1 KEGG:C03196 MetaCyc:CPD-381 O[C@@H](CCC(O)=O)C(O)=O Reaxys:1723807 chebi_ontology pyruvic acid 0 2-Oxopropanoic acid 2-Oxopropansaeure 2-Oxopropionsaeure 2-ketopropionic acid 2-oxopropanoic acid 2-oxopropanoic acid 88.016 88.06206 A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis. Acetylformic acid BTS Beilstein:506211 Brenztraubensaeure C3H4O3 CAS:127-17-3 CC(=O)C(O)=O CH3COCOOH CHEBI:26466 CHEBI:32816 CHEBI:45253 CHEBI:8685 DrugBank:DB00119 ECMDB:ECMDB00243 Gmelin:101087 HMDB:HMDB0000243 InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6) KEGG:C00022 KNApSAcK:C00001200 LCTONWCANYUPML-UHFFFAOYSA-N LIPID_MAPS_instance:LMFA01060077 MetaCyc:PYRUVATE PDBeChem:PYR PMID:11762589 PMID:19260671 PMID:22150460 PMID:22233273 PMID:22735334 PMID:22770225 PYRUVIC ACID Pyroracemic acid Pyruvic acid Reaxys:506211 Wikipedia:Pyruvic_acid YMDB:YMDB00175 acetylformic acid acide pyruvique alpha-Oxopropionsaeure alpha-ketopropionic acid chebi_ontology pyruvic acid threoninate C4H8NO3 CHEBI:32832 chebi_ontology rel-(2R,3S)-2-amino-3-hydroxybutanoate threoninate threonine anion threoninium C4H10NO3 CHEBI:32833 chebi_ontology rel-(1R,2S)-1-carboxy-2-hydroxypropan-1-aminium threonine cation threoninium serinate -1 104.035 104.08468 2-amino-3-hydroxypropanoate An alpha-amino-acid anion that is the conjugate base of serine. C3H6NO3 CHEBI:32845 Gmelin:324692 InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/p-1 MTCFGRXMJLQNBG-UHFFFAOYSA-M NC(CO)C([O-])=O chebi_ontology serinate serine anion serinium +1 1-carboxy-2-hydroxyethanaminium 106.050 106.10056 An alpha-amino-acid cation that is the conjugate acid of serine. C3H8NO3 CHEBI:32846 Gmelin:1925675 InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/p+1 MTCFGRXMJLQNBG-UHFFFAOYSA-O [NH3+]C(CO)C(O)=O chebi_ontology serine cation serinium valinate -1 116.071 116.13844 2-amino-3-methylbutanoate C5H10NO2 CC(C)C(N)C([O-])=O CHEBI:32859 Gmelin:49876 InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/p-1 KZSNJWFQEVHDMF-UHFFFAOYSA-M chebi_ontology val(-) valinate valine anion valinium +1 1-carboxy-2-methylpropan-1-aminium 118.087 118.15432 C5H12NO2 CC(C)C([NH3+])C(O)=O CHEBI:32860 Gmelin:1651060 H2val(+) InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/p+1 KZSNJWFQEVHDMF-UHFFFAOYSA-O chebi_ontology valine cation valinium L-prolinate (2S)-pyrrolidine-2-carboxylate -1 114.056 114.12250 An optically active form of prolinate having L-configuration. Beilstein:4307988 C5H8NO2 CHEBI:32862 Gmelin:82610 InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/p-1/t4-/m0/s1 L-prolinate L-proline anion ONIBWKKTOPOVIA-BYPYZUCNSA-M Reaxys:4307988 [O-]C(=O)[C@@H]1CCCN1 chebi_ontology L-prolinium (2S)-2-carboxypyrrolidinium +1 116.071 116.13840 An optically active form of prolinium having L-configuration. C5H10NO2 CHEBI:32864 Gmelin:363493 InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/p+1/t4-/m0/s1 L-proline cation L-prolinium OC(=O)[C@@H]1CCC[NH2+]1 ONIBWKKTOPOVIA-BYPYZUCNSA-O chebi_ontology D-prolinate (2R)-pyrrolidine-2-carboxylate -1 114.056 114.12250 An optically active form of prolinate having D-configuration. C5H8NO2 CHEBI:32867 D-prolinate D-proline anion Gmelin:533350 InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/p-1/t4-/m1/s1 ONIBWKKTOPOVIA-SCSAIBSYSA-M [O-]C(=O)[C@H]1CCCN1 chebi_ontology D-prolinium (2R)-2-carboxypyrrolidinium +1 116.071 116.13840 An optically active form of prolinium having D-configuration. C5H10NO2 CHEBI:32868 D-proline cation D-prolinium Gmelin:363492 InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/p+1/t4-/m1/s1 OC(=O)[C@H]1CCC[NH2+]1 ONIBWKKTOPOVIA-SCSAIBSYSA-O chebi_ontology prolinate -1 114.056 114.12256 An alpha-amino-acid anion that is the conjugate base of proline, arising from deprotonation of the carboxy group. Beilstein:5387795 C5H8NO2 CHEBI:32871 Gmelin:50151 InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/p-1 ONIBWKKTOPOVIA-UHFFFAOYSA-M Reaxys:5387795 [O-]C(=O)C1CCCN1 chebi_ontology pro(-) prolinate proline anion pyrrolidine-2-carboxylate prolinium +1 116.071 116.13840 2-carboxypyrrolidinium An alpha-amino-acid cation that is the conjugate acid of proline, arising from protonation of the amino group. C5H10NO2 CHEBI:32872 H2pro(+) InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/p+1 OC(=O)C1CCC[NH2+]1 ONIBWKKTOPOVIA-UHFFFAOYSA-O chebi_ontology proline cation prolinium tertiary amine 0 14.003 14.00670 A compound formally derived from ammonia by replacing three hydrogen atoms by hydrocarbyl groups. CHEBI:26879 CHEBI:32876 CHEBI:9458 KEGG:C02196 NR3 R3N Tertiary amine [*]N([*])[*] chebi_ontology tertiaeres Amin tertiary amines primary amine 0 16.019 16.02260 A compound formally derived from ammonia by replacing one hydrogen atom by a hydrocarbyl group. CHEBI:26263 CHEBI:26265 CHEBI:32877 CHEBI:8407 CHEBI:8409 H2NR KEGG:C00375 KEGG:C00893 KEGG:C02580 N[*] Primary amine Primary monoamine R-NH2 RCH2NH2 chebi_ontology primaeres Amin primary amines propane 0 44.063 44.09562 ATUOYWHBWRKTHZ-UHFFFAOYSA-N Beilstein:1730718 C3H8 CAS:74-98-6 CCC CH3-CH2-CH3 CHEBI:32879 E944 Gmelin:25044 InChI=1S/C3H8/c1-3-2/h3H2,1-2H3 Propan chebi_ontology propane amine A compound formally derived from ammonia by replacing one, two or three hydrogen atoms by hydrocarbyl groups. Amin Amine CHEBI:13814 CHEBI:22474 CHEBI:2641 CHEBI:32952 KEGG:C00706 Substituted amine amines chebi_ontology sodium acetate 0 82.003 82.03379 Beilstein:3595639 C2H3NaO2 CAS:127-09-3 CHEBI:32954 Gmelin:20502 InChI=1S/C2H4O2.Na/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1 Natriumazetat VMHLLURERBWHNL-UHFFFAOYSA-M Wikipedia:Sodium_Acetate [Na+].CC([O-])=O acetic acid, sodium salt anhydrous sodium acetate chebi_ontology sodium acetate sodium acetate anhydrous ornithinate -1 131.082 131.15312 2,5-diaminopentanoate 2,5-diaminopentanoate AHLPHDHHMVZTML-UHFFFAOYSA-M C5H11N2O2 CHEBI:11448 CHEBI:19370 CHEBI:32964 Gmelin:1242186 InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/p-1 NCCCC(N)C([O-])=O chebi_ontology ornithinate ornithine anion 2-aminoethanesulfonate -1 124.007 124.13998 2-aminoethanesulfonate A 1,1-diunsubstituted alkanesulfonate that is ethanesulfonate substituted by an amino group at position 2. Beilstein:3588289 C2H6NO3S CHEBI:32970 InChI=1S/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6)/p-1 NCCS([O-])(=O)=O Reaxys:3588289 XOAAWQZATWQOTB-UHFFFAOYSA-M chebi_ontology amide Amide An amide is a derivative of an oxoacid RkE(=O)l(OH)m (l =/= 0) in which an acidic hydroxy group has been replaced by an amino or substituted amino group. CHEBI:22473 CHEBI:2633 CHEBI:32988 KEGG:C00241 amides chebi_ontology diphosphate(1-) -1 176.935 176.96714 A monovalent inorganic anion obtained by deprotonation of one of the phosphate OH groups in diphosphoric acid. CHEBI:33017 Gmelin:185086 H3O7P2 H3P2O7(-) InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-1 OP(O)(=O)OP(O)([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-M chebi_ontology trihydrogen diphosphate diphosphate(3-) -3 174.920 174.95126 A trivalent inorganic anion obtained by removal of all three protons from diphosphoric acid. Beilstein:185088 CHEBI:33019 HO7P2 HP2O7(3-) InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-3 OP([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-K chebi_ontology diphosphate hydrogen diphosphate calcium carbonate 0 100.087 99.947 A calcium salt with formula CCaO3. BPDB:108 CAS:471-34-1 CCaO3 CHEBI:3311 CO3.Ca CaCO3 Calcium carbonate Calciumcarbonat DrugBank:DB06724 E 170 InChI=1S/CH2O3.Ca/c2-1(3)4;/h(H2,2,3,4);/q;+2/p-2 KEGG:C08129 KEGG:D00932 Kalziumkarbonat PPDB:108 Precipitated calcium carbonate Reaxys:8008338 VTYYLEPIZMXCLO-UHFFFAOYSA-L Wikipedia:Calcium_carbonate [Ca+2].C(=O)([O-])[O-] calcium carbonate calcium carbonate (1:1) calcium trioxidocarbonate carbonate de calcium carbonato de calcio carbonic acid calcium salt (1:1) chebi_ontology kohlensaurer Kalk bisphenol A 0 2, 2-Bis(4-hydroxyphenyl)propane 2,2-Bis(4'-hydroxyphenyl)propane 2,2-Bis(4-Hydroxyphenyl)propane 2,2-Bis(p-hydroxyphenyl)propane 2,2-Di(4-hydroxyphenyl)propane 2,2-Di(4-phenylol)propane 228.115 228.28634 4,4'-(1-Methylethane-1,1-diyl)diphenol 4,4'-(1-Methylethylidene)bisphenol 4,4'-(Propane-2,2-diyl)diphenol 4,4'-(propane-2,2-diyl)diphenol 4,4'-Bisphenol A 4,4'-Isopropylidenediphenol A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups. BPA Bisphenol A C15H16O2 CAS:80-05-7 CC(C)(c1ccc(O)cc1)c1ccc(O)cc1 CHEBI:22900 CHEBI:31295 CHEBI:33216 CHEBI:47094 Dianin's compound DrugBank:DB06973 HMDB:HMDB0032133 IISBACLAFKSPIT-UHFFFAOYSA-N InChI=1S/C15H16O2/c1-15(2,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h3-10,16-17H,1-2H3 KEGG:C13624 LINCS:LSM-37080 PMID:10593191 PMID:11361040 PMID:12860292 PMID:15936980 PMID:16904728 PMID:24471646 PMID:25042713 PMID:25148994 PMID:25524584 PMID:25569640 PMID:25637671 PMID:25663485 Reaxys:1107700 UM-BBD_compID:c0764 Wikipedia:Bisphenol_A bisphenol A bisphenol-A chebi_ontology chromane 0 134.073 134.17510 3,4-dihydro-2H-1-benzopyran 3,4-dihydro-2H-chromene 3,4-dihydrobenzo[b]pyran A benzopyran consisting of a pyran ring having a benzene ring ortho-fused across positions 2 and 3. Beilstein:116150 C1COc2ccccc2C1 C9H10O CAS:493-08-3 CHEBI:33224 Chroman Gmelin:122981 InChI=1S/C9H10O/c1-2-6-9-8(4-1)5-3-7-10-9/h1-2,4,6H,3,5,7H2 Reaxys:116150 VZWXIQHBIQLMPN-UHFFFAOYSA-N chebi_ontology chromane vitamin Any micronutrient that is an organic compound. The term "vitamines" (from vita + amines) was coined in 1912 by Casimir Funk, who believed that these compounds were amines. CHEBI:10004 CHEBI:27305 CHEBI:33229 Vitamin Wikipedia:Vitamin chebi_ontology vitamina vitaminas vitamine vitamines vitamins vitaminum application CHEBI:33232 Intended use of the molecular entity or part thereof by humans. chebi_ontology fundamental particle A particle not known to have substructure. CHEBI:33233 chebi_ontology elementary particle elementary particles vitamin E A chromanol that is chroman-6-ol which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. CAS:59-02-9 CHEBI:33234 MetaCyc:Vitamin-E PMID:7898412 PMID:7901680 Wikipedia:Vitamin_E chebi_ontology vitamin E monoatomic entity A monoatomic entity is a molecular entity consisting of a single atom. CHEBI:33238 atomic entity chebi_ontology monoatomic entities coordination entity An assembly consisting of a central atom (usually metallic) to which is attached a surrounding array of other groups of atoms (ligands). CHEBI:33240 chebi_ontology coordination compounds coordination entities coordination entity oxoacid derivative CHEBI:33241 chebi_ontology oxoacid derivatives inorganic hydride CHEBI:33242 chebi_ontology inorganic hydrides organic fundamental parent An organic fundamental parent is a structure used as a basis for substitutive names in organic nomenclature, containing, in addition to one or more hydrogen atoms, a single atom of an element, a number of atoms (alike or different) linked together to form an unbranched chain, a monocyclic or polycyclic ring system, or a ring assembly or ring/chain system. CHEBI:33245 chebi_ontology organic fundamental parents organic parent hydrides inorganic group Any substituent group which does not contain carbon. CHEBI:33246 chebi_ontology inorganic groups organic group Any substituent group or skeleton containing carbon. CHEBI:33247 chebi_ontology organic groups hydrocarbyl group A univalent group formed by removing a hydrogen atom from a hydrocarbon. CHEBI:33248 chebi_ontology groupe hydrocarbyle grupo hidrocarbilo grupos hidrocarbilo hydrocarbyl group hydrocarbyl groups organyl group Any organic substituent group, regardless of functional type, having one free valence at a carbon atom. CHEBI:33249 chebi_ontology groupe organyle grupo organilo grupos organilo organyl group organyl groups atom A chemical entity constituting the smallest component of an element having the chemical properties of the element. CHEBI:22671 CHEBI:23907 CHEBI:33250 atom atome atomo atoms atomus chebi_ontology element elements atomic nucleus A nucleus is the positively charged central portion of an atom, excluding the orbital electrons. Atomkern CHEBI:33252 Kern chebi_ontology noyau noyau atomique nuclei nucleo nucleo atomico nucleus nucleus atomi nucleon CHEBI:33253 Heavy nuclear particle: proton or neutron. Nukleon Nukleonen chebi_ontology nucleon nucleons primary amide A derivative of an oxoacid RkE(=O)l(OH)m (l =/= 0) in which an acidic hydroxy group has been replaced by an amino or substituted amino group. CHEBI:33256 chebi_ontology primary amide primary amides elemental molecular entity A molecular entity all atoms of which have the same atomic number. CHEBI:33259 chebi_ontology homoatomic entity homoatomic molecular entities homoatomic molecular entity elemental hydrogen CHEBI:33260 chebi_ontology organosulfur compound An organosulfur compound is a compound containing at least one carbon-sulfur bond. CHEBI:23010 CHEBI:25714 CHEBI:33261 Wikipedia:Organosulfur_compounds chebi_ontology organosulfur compound organosulfur compounds elemental oxygen CHEBI:33262 chebi_ontology diatomic oxygen CHEBI:33263 O2 chebi_ontology polyatomic anion An anion consisting of more than one atom. CHEBI:33273 chebi_ontology polyatomic anions molecular messenger CHEBI:33280 chebi_ontology chemical messenger antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Antibiotika Antibiotikum CHEBI:22582 CHEBI:33281 PMID:12964249 PMID:22117953 PMID:22439833 PMID:22849268 PMID:22849276 PMID:22958833 antibiotic antibiotics antibiotique antimicrobial antimicrobial agents antimicrobials chebi_ontology microbicide microbicides antibacterial agent A substance that kills or slows the growth of bacteria. CHEBI:33282 antibacterial agents antibacterials bactericide bactericides chebi_ontology nutrient A nutrient is a food component that an organism uses to survive and grow. CHEBI:33284 chebi_ontology nutrients heteroorganic entity A heteroorganic entity is an organic molecular entity in which carbon atoms or organic groups are bonded directly to one or more heteroatoms. CHEBI:33285 chebi_ontology heteroorganic entities organoelement compounds agrochemical An agrochemical is a substance that is used in agriculture or horticulture. CHEBI:33286 Wikipedia:Agrochemical agrichemical agrichemicals agricultural chemicals agrochemicals chebi_ontology fertilizer A fertilizer is any substance that is added to soil or water to assist the growth of plants. CHEBI:33287 chebi_ontology fertiliser fertilizers food Any material that can be ingested by an organism. CHEBI:33290 chebi_ontology foods foodstuff foodstuffs fuel An energy-rich substance that can be transformed with release of usable energy. CHEBI:33292 chebi_ontology diagnostic agent A substance administered to aid diagnosis of a disease. CHEBI:33295 chebi_ontology diagnostic aid alkali metal molecular entity A molecular entity containing one or more atoms of an alkali metal. CHEBI:33296 alkali metal molecular entities chebi_ontology alkaline earth molecular entity An alkaline earth molecular entity is a molecular entity containing one or more atoms of an alkaline earth metal. CHEBI:33299 alkaline earth compounds alkaline earth molecular entities alkaline earth molecular entity alkaline-earth compounds chebi_ontology pnictogen Any p-block element atom that is in group 15 of the periodic table: nitrogen, phosphorus, arsenic, antimony and bismuth. CHEBI:33300 chebi_ontology group 15 elements group V elements nitrogenoideos nitrogenoides pnictogene pnictogenes pnictogens pnictogen molecular entity A p-block molecular entity containing any pnictogen. CHEBI:33302 chebi_ontology pnictogen molecular entities pnictogen molecular entity chalcogen Any p-block element belonging to the group 16 family of the periodic table. CHEBI:33303 Chalkogen Chalkogene PMID:17084588 anfigeno anfigenos calcogeno calcogenos chalcogen chalcogene chalcogenes chalcogens chebi_ontology group 16 elements group VI elements chalcogen molecular entity Any p-block molecular entity containing a chalcogen. CHEBI:33304 chalcogen compounds chalcogen molecular entities chalcogen molecular entity chebi_ontology carbon group element atom CHEBI:33306 carbon group element carbon group elements carbonoides chebi_ontology cristallogene cristallogenes group 14 elements group IV elements thiocarboxylic acid An organic acid in which one or both oxygens of a carboxy group have been replaced by divalent sulfur. CHEBI:33307 carbothioic acids chebi_ontology thiocarboxylic acid thiocarboxylic acids thiocarboxylic acids carboxylic ester 0 43.990 An ester of a carboxylic acid, R(1)C(=O)OR(2), where R(1) = H or organyl and R(2) = organyl. CHEBI:13204 CHEBI:23028 CHEBI:33308 CHEBI:3408 CO2R2 Carboxylic ester KEGG:C02391 Wikipedia:Ester [*]C(=O)O[*] a carboxylic ester carboxylic acid esters carboxylic esters chebi_ontology main group element atom An atom belonging to one of the main groups (found in the s- and p- blocks) of the periodic table. CHEBI:33318 Hauptgruppenelement Hauptgruppenelemente chebi_ontology main group element main group elements zinc group element atom CHEBI:33340 chebi_ontology group 12 elements zinc group element zinc group elements chromium group element atom CHEBI:33350 chebi_ontology chromium group element chromium group elements group 6 elements iron group element atom CHEBI:33356 chebi_ontology group 8 elements iron group element iron group elements cobalt group element atom CHEBI:33358 chebi_ontology cobalt group element cobalt group elements group 9 elements copper group element atom CHEBI:33366 chebi_ontology coinage metals copper group element copper group elements group 11 elements sulfur oxoacid CHEBI:33402 chebi_ontology oxoacids of sulfur sulfur oxoacids hydracid A hydracid is a compound which contains hydrogen that is not bound to oxygen, and which produces a conjugate base by loss of positive hydrogen ion(s) (hydrons). CHEBI:33405 chebi_ontology hydracid hydracids pnictogen oxoacid CHEBI:33408 chebi_ontology pnictogen oxoacids sulfur oxoacid derivative CHEBI:33424 chebi_ontology sulfur oxoacid derivative sulfur oxoacid derivatives monoatomic monoanion -1 0.00000 CHEBI:33429 [*-] chebi_ontology monoatomic monoanions elemental chlorine CHEBI:33431 chebi_ontology monoatomic chlorine CHEBI:33432 Cl atomic chlorine chebi_ontology monoatomic halogen CHEBI:33433 chebi_ontology monoatomic halogens elemental halogen CHEBI:33434 chebi_ontology elemental halogen elemental halogens phospho sugar Any monosaccharide containing an alcoholic hydroxy group esterified with phosphoric acid. CHEBI:15132 CHEBI:25406 CHEBI:26086 CHEBI:33447 CHEBI:9320 KEGG:C00934 PMID:18186488 chebi_ontology monosaccharide phosphates phospho sugar phospho sugars phosphorylated sugar phosphorylated sugars phosphosugar phosphosugars benzylic group Arylmethyl groups and derivatives formed by substitution: ArCR2-. CHEBI:33452 benzylic group benzylic groups benzylic groups chebi_ontology groupe benzylique nitrogen oxoacid CHEBI:33455 chebi_ontology nitrogen oxoacids oxoacids of nitrogen phosphorus oxoacid A pnictogen oxoacid which contains phosphorus and oxygen, at least one hydrogen atom bound to oxygen, and forms an ion by the loss of one or more protons. CHEBI:33457 Oxosaeure des Phosphors chebi_ontology oxoacids of phosphorus phosphorus oxoacid phosphorus oxoacids nitrogen oxoanion CHEBI:33458 chebi_ontology nitrogen oxoanion nitrogen oxoanions oxoanions of nitrogen pnictogen oxoanion CHEBI:33459 chebi_ontology pnictogen oxoanion pnictogen oxoanions phosphorus oxoanion CHEBI:33461 chebi_ontology oxoanions of phosphorus phosphorus oxoanion phosphorus oxoanions hydrocarbylidyne group CHEBI:33474 RC# Trivalent groups, RC#, formed by removing three hydrogen atoms from the same carbon atom of a hydrocarbon, the free valencies of which are engaged in a triple bond. chebi_ontology groupe hydrocarbylidyne hydrocarbylidyne group hydrocarbylidyne groups hydrocarbylidyne groups sulfur oxoanion CHEBI:33482 chebi_ontology oxoanions of sulfur sulfur oxoanion sulfur oxoanions chalcogen oxoacid CHEBI:33484 chalcogen oxoacid chalcogen oxoacids chebi_ontology chalcogen oxoanion CHEBI:33485 chalcogen oxoanion chalcogen oxoanions chebi_ontology transition element molecular entity A molecular entity containing one or more atoms of a transition element. CHEBI:33497 chebi_ontology transition element molecular entities transition metal molecular entity alkali metal cation CHEBI:33504 alkali metal cations chebi_ontology alkaline earth cation CHEBI:33513 alkaline earth cations alkaline earth metal cation alkaline-earth metal cations chebi_ontology transition element cation CHEBI:33515 chebi_ontology transition element cations transition metal cation metal atom An atom of an element that exhibits typical metallic properties, being typically shiny, with high electrical and thermal conductivity. CHEBI:25217 CHEBI:33521 CHEBI:6788 KEGG:C00050 PMID:21784043 Wikipedia:Metal chebi_ontology elemental metal elemental metals metal element metal elements metals sulfur hydride CHEBI:33535 chebi_ontology hydrides of sulfur sulfur hydride sulfur hydrides sulphur hydrides thiosulfuric acid CHEBI:33540 H2O3S2 chebi_ontology sulfurothioic acid thiosulfuric acid thiosulfate(1-) CHEBI:33541 HO3S2 HS2O3(-) KEGG:C00320 chebi_ontology hydrogen sulfurothioate sulfonate -1 80.965 81.07214 BDHFUVZGWQCTTF-UHFFFAOYSA-M CHEBI:33543 Gmelin:971569 HO3S InChI=1S/H2O3S/c1-4(2)3/h4H,(H,1,2,3)/p-1 SHO3(-) The sulfur oxoanion formed by deprotonation of sulfonic acid. [H]S([O-])(=O)=O [SHO3](-) chebi_ontology hydridotrioxidosulfate(1-) sulfonates organosulfonic acid 0 80.965 81.07100 An organic derivative of sulfonic acid in which the sulfo group is linked directly to carbon. CHEBI:33551 HO3SR OS([*])(=O)=O chebi_ontology organosulfonic acids sulfonic acids sulfonic acid derivative CHEBI:33552 chebi_ontology derivatives of sulfonic acid sulfonic acid derivative sulfonic acid derivatives organosulfonate oxoanion *S([O-])(=O)=O -1 79.957 80.064 An organic anion obtained by deprotonation of the sufonate group(s) of any organosulfonic acid. CHEBI:33554 O3SR chebi_ontology organosulfonate organosulfonate oxoanions organosulfonates alpha-amino-acid anion An amino-acid anion obtained by deprotonation of any alpha-amino acid. CHEBI:33558 alpha-amino acid anions alpha-amino-acid anion alpha-amino-acid anions chebi_ontology s-block element atom CHEBI:33559 chebi_ontology s-block element s-block elements p-block element atom Any main group element atom belonging to the p-block of the periodic table. CHEBI:33560 chebi_ontology p-block element p-block elements d-block element atom CHEBI:33561 chebi_ontology d-block element d-block elements glycolipid Any member of class of 1,2-di-O-acylglycerols joined at oxygen 3 by a glycosidic linkage to a carbohydrate part (usually a mono-, di- or tri-saccharide). Some substances classified as bacterial glycolipids have the sugar part acylated by one or more fatty acids and the glycerol part may be absent. CHEBI:24393 CHEBI:33563 CHEBI:5476 Glycolipid KEGG:C05005 Wikipedia:Glycolipids chebi_ontology glycolipids catechols 0 1,2-benzenediols 106.005 106.079 Any compound containing an o-diphenol component. C6H2O2R4 CHEBI:134187 CHEBI:13628 CHEBI:18862 CHEBI:33566 KEGG:C15571 OC1=C(O)C(*)=C(*)C(*)=C1* a catechol benzene-1,2-diols chebi_ontology catecholamine 0 151.063 151.163 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] and derivatives formed by substitution. C8H9NO2R2 CHEBI:23056 CHEBI:33567 CHEBI:3468 Catecholamine KEGG:C02012 catecholamines catecholamines chebi_ontology adrenaline (+-)-adrenaline (+-)-epinephrine 0 183.090 183.20446 2-(methylamino)-1-(3,4-dihydroxyphenyl)ethanol 4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol A catecholamine in which the aminoethyl side-chain is hydroxy-substituted at C-1 and methylated on nitrogen. Beilstein:2212160 C9H13NO3 CAS:329-65-7 CHEBI:33568 CNCC(O)c1ccc(O)c(O)c1 Drug_Central:4508 Gmelin:51559 InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3 LINCS:LSM-4958 PMID:10052027 PMID:24252294 PMID:24719616 Reaxys:2212160 UCTWMZQNUQWSLP-UHFFFAOYSA-N chebi_ontology dl-adrenaline epinephrine racemic racepinefrina racepinefrine racepinefrinum noradrenaline 0 169.074 169.17788 4-(2-amino-1-hydroxyethyl)benzene-1,2-diol A catecholamine in which C-1 of the aminoethyl side-chain is hydroxy-substituted. Beilstein:2210994 C8H11NO3 CAS:138-65-8 CHEBI:33569 Gmelin:863925 InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2 LINCS:LSM-5181 NCC(O)c1ccc(O)c(O)c1 SFLSHLFXELFNJZ-UHFFFAOYSA-N chebi_ontology noradrenalina norepinephrine benzenediols CHEBI:22705 CHEBI:22711 CHEBI:33570 chebi_ontology carboxylic acid 0 44.998 45.01740 A carbon oxoacid acid carrying at least one -C(=O)OH group and having the structure RC(=O)OH, where R is any any monovalent functional group. Carboxylic acids are the most common type of organic acid. CHEBI:13428 CHEBI:13627 CHEBI:23027 CHEBI:33575 CHO2R Carbonsaeure Carbonsaeuren Karbonsaeure OC([*])=O PMID:17147560 PMID:18433345 RC(=O)OH Wikipedia:Carboxylic_acid acide carboxylique acides carboxyliques acido carboxilico acidos carboxilicos carboxylic acid carboxylic acids chebi_ontology sulfur-containing carboxylic acid Any carboxylic acid having a sulfur substituent. CHEBI:33576 S-containing carboxylic acid S-containing carboxylic acids chebi_ontology sulfur-containing carboxylic acids main group molecular entity A molecular entity containing one or more atoms from any of groups 1, 2, 13, 14, 15, 16, 17, and 18 of the periodic table. CHEBI:33579 chebi_ontology main group compounds main group molecular entities carbon group molecular entity CHEBI:33582 carbon group molecular entities carbon group molecular entity chebi_ontology cyclic compound Any molecule that consists of a series of atoms joined together to form a ring. CHEBI:33595 Wikipedia:Cyclic_compound chebi_ontology cyclic compounds homocyclic compound A cyclic compound having as ring members atoms of the same element only. CHEBI:33597 chebi_ontology homocyclic compound homocyclic compounds isocyclic compounds carbocyclic compound A homocyclic compound in which all of the ring members are carbon atoms. CHEBI:33598 carbocycle carbocyclic compound carbocyclic compounds chebi_ontology hydrogen molecular entity CHEBI:33608 chebi_ontology hydrogen compounds hydrogen molecular entities polycyclic compound CHEBI:33635 chebi_ontology polycyclic compounds bicyclic compound A molecule that features two fused rings. CHEBI:33636 bicyclic compounds chebi_ontology aliphatic compound Any acyclic or cyclic, saturated or unsaturated carbon compound, excluding aromatic compounds. CHEBI:33653 aliphatic compounds chebi_ontology aromatic compound A cyclically conjugated molecular entity with a stability (due to delocalization) significantly greater than that of a hypothetical localized structure (e.g. Kekule structure) is said to possess aromatic character. CHEBI:33655 aromatic compounds aromatic molecular entity aromatics aromatische Verbindungen chebi_ontology arene Any monocyclic or polycyclic aromatic hydrocarbon. CHEBI:33658 arene arenes aromatic hydrocarbons chebi_ontology organic aromatic compound CHEBI:33659 chebi_ontology organic aromatic compounds monocyclic compound CHEBI:33661 chebi_ontology monocyclic compounds annulene A mancude monocyclic hydrocarbon without side chains of the general formula CnHn (n is an even number) or CnHn+1 (n is an odd number). In systematic nomenclature an annulene with seven or more carbon atoms may be named [n]annulene, where n is the number of carbon atoms. CHEBI:33662 annulene annulenes chebi_ontology cyclic hydrocarbon CHEBI:33663 chebi_ontology cyclic hydrocarbon cyclic hydrocarbons monocyclic hydrocarbon CHEBI:33664 chebi_ontology monocyclic hydrocarbon monocyclic hydrocarbons monocyclic hydrocarbons heteromonocyclic compound CHEBI:33670 chebi_ontology heteromonocyclic compound heteromonocyclic compounds heteropolycyclic compound A polycyclic compound in which at least one of the rings contains at least one non-carbon atom. CHEBI:33671 chebi_ontology heteropolycyclic compounds polyheterocyclic compounds heterobicyclic compound A bicyclic compound in which at least one of the rings contains at least one skeletal heteroatom. CHEBI:33672 chebi_ontology heterobicyclic compounds zinc group molecular entity CHEBI:33673 chebi_ontology zinc group molecular entities s-block molecular entity An s-block molecular entity is a molecular entity containing one or more atoms of an s-block element. CHEBI:33674 chebi_ontology s-block compounds s-block molecular entities s-block molecular entity p-block molecular entity A main group molecular entity that contains one or more atoms of a p-block element. CHEBI:33675 chebi_ontology p-block compounds p-block molecular entities p-block molecular entitiy d-block molecular entity A d-block molecular entity is a molecular entity containing one or more atoms of a d-block element. CHEBI:33676 chebi_ontology d-block compounds d-block molecular entities d-block molecular entity hydrides CHEBI:33692 Hydrides are chemical compounds of hydrogen with other chemical elements. chebi_ontology oxygen hydride CHEBI:33693 chebi_ontology hydrides of oxygen oxygen hydride oxygen hydrides biomacromolecule A macromolecule formed by a living organism. Biopolymere CHEBI:33694 biomacromolecules biopolymer biopolymers chebi_ontology information biomacromolecule CHEBI:33695 chebi_ontology genetically encoded biomacromolecules genetically encoded biopolymers information biomacromolecules information biopolymers information macromolecule information macromolecules nucleic acid A macromolecule made up of nucleotide units and hydrolysable into certain pyrimidine or purine bases (usually adenine, cytosine, guanine, thymine, uracil), D-ribose or 2-deoxy-D-ribose and phosphoric acid. CHEBI:33696 NA Nukleinsaeure Nukleinsaeuren acide nucleique acides nucleiques acido nucleico acidos nucleicos chebi_ontology nucleic acids ribonucleic acid CAS:63231-63-0 CHEBI:33697 High molecular weight, linear polymers, composed of nucleotides containing ribose and linked by phosphodiester bonds; RNA is central to the synthesis of proteins. RNA RNS Ribonukleinsaeure chebi_ontology pentosenucleic acids ribonucleic acid ribonucleic acids ribonucleic acids ribose nucleic acid yeast nucleic acid proteinogenic amino-acid residue CHEBI:33700 canonical amino-acid residue canonical amino-acid residues chebi_ontology common amino acid residues proteinogenic amino-acid residues standard amino acid residues standard amino-acid residues polyatomic cation A cation consisting of more than one atom. CHEBI:33702 chebi_ontology polyatomic cations amino-acid cation CHEBI:33703 amino acid cation amino-acid cation amino-acid cations chebi_ontology alpha-amino acid 0 74.024 74.05870 Amino acid Amino acids An amino acid in which the amino group is located on the carbon atom at the position alpha to the carboxy group. C2H4NO2R CHEBI:10208 CHEBI:13779 CHEBI:22442 CHEBI:2642 CHEBI:33704 KEGG:C00045 KEGG:C05167 NC([*])C(O)=O alpha-amino acid alpha-amino acids alpha-amino carboxylic acids chebi_ontology beta-amino acid A non-proteinogenic amino acid in which the amino group is located on the carbon atom at the position beta to the carboxy group. CHEBI:33706 beta-amino acid beta-amino acids chebi_ontology gamma-amino acid A non-proteinogenic amino-acid in which the amino group is located on the carbon atom at the position gamma to the carboxy group. CHEBI:33707 chebi_ontology gamma-amino acid gamma-amino acids amino-acid residue CHEBI:33708 When two or more amino acids combine to form a peptide, the elements of water are removed, and what remains of each amino acid is called an amino-acid residue. amino acid residue amino-acid residue amino-acid residues chebi_ontology amino acid A carboxylic acid containing one or more amino groups. Aminocarbonsaeure Aminokarbonsaeure Aminosaeure CHEBI:13815 CHEBI:22477 CHEBI:33709 Wikipedia:Amino_acid amino acids chebi_ontology alpha-amino-acid residue CHEBI:33710 alpha-amino-acid residues chebi_ontology alpha-amino-acid cation CHEBI:33719 alpha-amino acid cations alpha-amino-acid cation alpha-amino-acid cations chebi_ontology carbohydrate acid CHEBI:33720 carbohydrate acid carbohydrate acids chebi_ontology carbohydrate acid anion CHEBI:33721 carbohydrate acid anion carbohydrate acid anions chebi_ontology tetritol CHEBI:33729 chebi_ontology tetritol tetritols chromium group molecular entity CHEBI:33741 chebi_ontology chromium group molecular entities chromium group molecular entity iron group molecular entity CHEBI:33744 chebi_ontology iron group molecular entities iron group molecular entity copper group molecular entity CHEBI:33745 chebi_ontology copper group molecular entities copper group molecular entity hexonic acid Any aldonic acid formed by oxidising the aldehyde group of an aldohexose to a carboxylic acid group. CHEBI:33752 aldohexonic acids chebi_ontology hexonic acid hexonic acids hexonate CHEBI:33760 aldohexonates chebi_ontology hexonate hexonates cobalt group molecular entity CHEBI:33767 chebi_ontology cobalt group molecular entities cobalt group molecular entity galactonates CHEBI:33778 chebi_ontology canonical nucleoside residue CHEBI:33791 canonical nucleoside residues chebi_ontology common nucleoside residues nucleoside residue standard nucleoside residues canonical ribonucleoside residue CHEBI:33792 N Nuc canonical ribonucleoside residues chebi_ontology common ribonucleoside residue common ribonucleoside residues standard ribonucleoside residues organic hydroxy compound An organic compound having at least one hydroxy group attached to a carbon atom. CHEBI:33822 CHEBI:64710 chebi_ontology hydroxy compounds organic alcohol organic hydroxy compounds organic cyclic compound Any organic molecule that consists of atoms connected in the form of a ring. CHEBI:33832 chebi_ontology organic cyclic compounds heteroarene A heterocyclic compound formally derived from an arene by replacement of one or more methine (-C=) and/or vinylene (-CH=CH-) groups by trivalent or divalent heteroatoms, respectively, in such a way as to maintain the continuous pi-electron system characteristic of aromatic systems and a number of out-of-plane pi-electrons corresponding to the Hueckel rule (4n+2). CHEBI:33833 chebi_ontology hetarenes heteroarenes benzenoid aromatic compound CHEBI:33836 benzenoid aromatic compounds benzenoid compound chebi_ontology conjugated protein CHEBI:33837 COMe:PRX000001 Conjugated protein is a protein that contains a non-peptide component, usually in stoichiometric proportion. chebi_ontology complex protein conjugated proteins nucleoside 0 116.047 116.115 An N-glycosyl compound that has both a nucleobase, normally adenine, guanine, xanthine, thymine, cytosine or uracil, and either a ribose or deoxyribose as functional parents. C5H8O3R2 CHEBI:13661 CHEBI:25611 CHEBI:33838 CHEBI:7647 KEGG:C00801 Nucleoside [C@H]1([C@H]([C@@H](*)[C@@H](O1)*)O)CO a nucleoside chebi_ontology nucleosides nucleosides macromolecule A macromolecule is a molecule of high relative molecular mass, the structure of which essentially comprises the multiple repetition of units derived, actually or conceptually, from molecules of low relative molecular mass. CHEBI:33839 Wikipedia:Macromolecule chebi_ontology macromolecule macromolecules polymer polymer molecule polymers aromatic annulene CHEBI:33842 aromatic annulenes chebi_ontology monocyclic arene A monocyclic aromatic hydrocarbon. CHEBI:33847 chebi_ontology monocyclic arenes phenols 0 89.003 89.072 Aryl alcohol C1(=C(C(=C(C(=C1*)*)*)*)*)O C6HOR5 CHEBI:13664 CHEBI:13825 CHEBI:25969 CHEBI:2857 CHEBI:33853 KEGG:C15584 MetaCyc:Phenols Organic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring. Wikipedia:Phenols a phenol arenols chebi_ontology phenols arenecarbaldehyde *C(=O)[H] 0 29.003 29.018 Any aldehyde in which the carbonyl group is attached to an aromatic moiety. Aromatic aldehyde CHEBI:13819 CHEBI:22621 CHEBI:2832 CHEBI:33855 CHEBI:87908 CHOR KEGG:C00193 MetaCyc:Aryl-Aldehyde an aromatic aldehyde arenecarbaldehyde arenecarbaldehydes aryl aldehyde aryl aldehydes chebi_ontology aromatic amino acid 0 74.024 88.085 An amino acid whose structure includes an aromatic ring. Aromatic amino acid C2H4NO2R CHEBI:13820 CHEBI:22623 CHEBI:2835 CHEBI:33856 KEGG:C01021 Wikipedia:Aromatic_amino_acid aromatic amino acid aromatic amino acids chebi_ontology aromatic carboxylic acid Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring. CHEBI:13817 CHEBI:13821 CHEBI:2830 CHEBI:33859 aromatic carboxylic acids chebi_ontology aromatic amine An amino compound in which the amino group is linked directly to an aromatic system. CHEBI:13827 CHEBI:22622 CHEBI:22646 CHEBI:2834 CHEBI:2863 CHEBI:33860 aromatic amines aryl amine aryl amines arylamine arylamines chebi_ontology transition element coordination entity CHEBI:33861 chebi_ontology transition element coordination entities transition metal coordination compounds transition metal coordination entities cobalt molecular entity CHEBI:33888 chebi_ontology cobalt compounds cobalt molecular entities cobalt molecular entity cobalt coordination entity CHEBI:33890 chebi_ontology cobalt coordination compounds cobalt coordination entities cobalt coordination entity iron coordination entity CHEBI:33892 chebi_ontology iron coordination compounds iron coordination entities iron coordination entity reagent A substance used in a chemical reaction to detect, measure, examine, or produce other substances. CHEBI:33893 chebi_ontology reactif reactivo reagent reagents cobalt corrinoid CHEBI:33906 chebi_ontology cobalt corrinoids cobalt-corrinoids metallotetrapyrrole CHEBI:33909 chebi_ontology metal-tetrapyrrole metal-tetrapyrrole complex metallotetrapyrroles corrinoid 285.020 A derivative of the corrin nucleus, which contains four reduced or partly reduced pyrrole rings joined in a macrocycle by three =C- groups and one direct carbon-carbon bond linking alpha positions. C19HN4R21 CHEBI:23391 CHEBI:33913 CHEBI:3890 Corrinoid Corrinoid protein Corrinoid protein Co+ KEGG:C06021 Korrinoid chebi_ontology corrinoid corrinoide corrinoides corrinoids aldopentose A pentose with a (potential) aldehyde group at one end. CHEBI:33916 PMID:10723607 aldopentose aldopentoses chebi_ontology aldohexose A hexose with a (potential) aldehyde group at one end. CHEBI:2558 CHEBI:33917 aldohexose aldohexoses chebi_ontology macronutrient CHEBI:33937 chebi_ontology ribose Any aldopentose where the open-chain form has all the hydroxy groups on the same side in the Fischer projection. Occurrs in two enantiomeric forms, D- and L-ribose, of which only the former is found in nature. C5H10O5 CHEBI:26564 CHEBI:33942 Rib chebi_ontology ribo-pentose ribose halide salt CHEBI:33958 chebi_ontology halide salts halides fucose 6-Deoxygalactose 6-deoxygalactose Any deoxygalactose that is deoxygenated at the 6-position. CAS:7724-73-4 CHEBI:24118 CHEBI:33984 CHEBI:5182 Fuc Fucose KEGG:C00382 PMID:12651883 chebi_ontology fucose carnitinium +1 162.113 162.20688 3-carboxy-2-hydroxy-N,N,N-trimethylpropan-1-aminium 3-hydroxy-4-(trimethylammonio)butanoic acid A quaternary ammonium ion that is the the conjugate acid of carnitine. C7H16NO3 CAS:406-76-8 CAS:461-06-3 CHEBI:3424 C[N+](C)(C)CC(O)CC(O)=O Carnitine InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/p+1 KEGG:C00487 PHIQHXFUZVPYII-UHFFFAOYSA-O chebi_ontology paraquat +2 1,1'-Dimethyl-4,4'-bipyridinium 1,1'-dimethyl-4,4'-bipyridyldiylium 1,1'-dimethyl-[4,4'-bipyridin]-1,1'-diium 186.116 186.25304 An organic cation that consists of 4,4'-bipyridine bearing two N-methyl substituents loctated at the 1- and 1'-positions. Beilstein:3590305 C12H14N2 CAS:4685-14-7 CHEBI:34905 C[n+]1ccc(cc1)-c1cc[n+](C)cc1 Gmelin:51125 INFDPOAKFNIJBF-UHFFFAOYSA-N InChI=1S/C12H14N2/c1-13-7-3-11(4-8-13)12-5-9-14(2)10-6-12/h3-10H,1-2H3/q+2 KEGG:C14701 N,N'-dimethyl-4,4'-bipyridinium N,N'-dimethyl-4,4'-bipyridinium dication PMID:11349957 PMID:18620719 PMID:20377249 PMID:20582739 PMID:21236547 PMID:21300143 PMID:21318114 PMID:21429624 PMID:21493003 PMID:21598522 PMID:21616728 PMID:21619794 PMID:21619822 PMID:21750730 PMID:21777615 PMID:21787677 PMID:21802509 PPDB:505 Paraquat Reaxys:3590305 chebi_ontology dimethyl viologen methyl viologen ion(2+) paraquat dication paraquat ion serotonin(1+) +1 177.103 177.22250 2-(5-hydroxy-1H-indol-3-yl)ethanaminium An ammonium ion that is the conjugate acid of serotonin; major species at pH 7.3. C10H13N2O CHEBI:350546 InChI=1S/C10H12N2O/c11-4-3-7-6-12-10-2-1-8(13)5-9(7)10/h1-2,5-6,12-13H,3-4,11H2/p+1 QZAYGJVTTNCVMB-UHFFFAOYSA-O [NH3+]CCc1c[nH]c2ccc(O)cc12 chebi_ontology serotonin serotonin cation nitrogen hydride CHEBI:35106 chebi_ontology nitrogen hydrides azane CHEBI:35107 Saturated acyclic nitrogen hydrides having the general formula NnHn+2. azanes chebi_ontology aldose phosphate CHEBI:35131 aldose phosphates chebi_ontology metalloprotein CHEBI:35134 COMe:PRX000002 chebi_ontology metalloprotein metalloproteine metalloproteins iron protein CHEBI:35136 COMe:PRX000004 chebi_ontology iron protein iron proteins iron-containing proteins hemoprotein CHEBI:35137 COMe:PRX000008 Conjugated proteins containing heme as the prosthetic group. Haemoprotein Haemprotein chebi_ontology haem protein haemoprotein heme protein hemeproteins hemoprotein hemoproteins hemoglobin CHEBI:35143 COMe:PRX000321 chebi_ontology haemoglobin hemoglobin vertebrate haemoglobin (6'R)-beta,epsilon-carotene (+)-alpha-carotene (6'R)-beta,epsilon-carotene 0 536.438 536.87264 ANVAOWXLWRTKGA-NTXLUARGSA-N Beilstein:2067409 C40H56 CAS:7488-99-5 CC(\C=C\C=C(C)\C=C\[C@H]1C(C)=CCCC1(C)C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C CHEBI:35147 InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-23,25-28,37H,15-16,24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+/t37-/m0/s1 LIPID_MAPS_instance:LMPR01070011 alpha-carotene (natural) chebi_ontology (6'S)-beta,epsilon-carotene (6'S)-beta,epsilon-carotene 0 536.438 536.87264 ANVAOWXLWRTKGA-QTRZAOAUSA-N Beilstein:2682045 C40H56 CC(\C=C\C=C(C)\C=C\[C@@H]1C(C)=CCCC1(C)C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C CHEBI:35148 InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-23,25-28,37H,15-16,24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+/t37-/m1/s1 chebi_ontology elemental calcium CHEBI:35155 chebi_ontology calcium salt CHEBI:35156 Kalziumsalz Kalziumsalze calcium salts chebi_ontology cyclic carotene CHEBI:35163 chebi_ontology cyclic carotene cyclic carotenes 2-oxo monocarboxylic acid anion -1 2-oxo monocarboxylate 2-oxo monocarboxylic acid anions 71.985 An oxo monocarboxylic acid anion in which the oxo group is located at the 2-position. C2O3R CHEBI:35179 CHEBI:70795 MetaCyc:2-Oxo-carboxylates PMID:10850983 [O-]C(=O)C([*])=O a 2-oxocarboxylate chebi_ontology terpene A hydrocarbon of biological origin having carbon skeleton formally derived from isoprene [CH2=C(CH3)CH=CH2]. CHEBI:35186 Terpen chebi_ontology terpene terpenes terpenes terpeno terpenos diterpene A C20 terpene. CHEBI:35190 Diterpen chebi_ontology diterpenes diterpenes diterpeno diterpenos triterpene A C30 terpene. CHEBI:35191 Triterpen chebi_ontology triterpenes triterpenes triterpeno triterpenos tetraterpene A C40 terpene. CHEBI:35193 chebi_ontology tetraterpenes tetraterpenes tetraterpeno tetraterpenos surfactant A substance which lowers the surface tension of the medium in which it is dissolved, and/or the interfacial tension with other phases, and, accordingly, is positively adsorbed at the liquid/vapour and/or at other interfaces. CHEBI:35195 chebi_ontology surface active agent surfactant surfactants molybdenum coordination entity CHEBI:35202 chebi_ontology molybdenum coordination compounds molybdenum coordination entities molybdopterins CHEBI:35203 Wikipedia:Molybdopterin chebi_ontology plant growth retardant CHEBI:26154 CHEBI:26156 CHEBI:35219 chebi_ontology plant growth inhibitor plant growth inhibitors plant growth retardants antimetabolite A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization. CHEBI:35221 Wikipedia:Antimetabolite antimetabolite antimetabolites chebi_ontology inhibitor A substance that diminishes the rate of a chemical reaction. CHEBI:35222 chebi_ontology inhibidor inhibiteur inhibitor inhibitors catalyst A substance that increases the rate of a reaction without modifying the overall standard Gibbs energy change in the reaction. CHEBI:35223 Katalysator catalizador catalyseur catalyst chebi_ontology fossil fuel A fuel such as coal, oil and natural gas which has formed over many years through the decomposition of deposited vegetation which was under extreme pressure of an overburden of earth. CHEBI:35230 chebi_ontology fossil fuel L-cysteine zwitterion (2R)-2-ammonio-3-mercaptopropanoate (2R)-2-ammonio-3-sulfanylpropanoate 0 121.020 121.15922 C3H7NO2S CHEBI:35235 Gmelin:49993 InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1 L-cysteine L-cysteine zwitterion XUJNEKJLAYXESH-REOHCLBHSA-N [NH3+][C@@H](CS)C([O-])=O chebi_ontology D-cysteine zwitterion (2S)-2-ammonio-3-mercaptopropanoate (2S)-2-ammonio-3-sulfanylpropanoate 0 121.020 121.15922 C3H7NO2S CHEBI:35236 D-cysteine D-cysteine zwitterion Gmelin:2352354 InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m1/s1 XUJNEKJLAYXESH-UWTATZPHSA-N [NH3+][C@H](CS)C([O-])=O chebi_ontology cysteine zwitterion (+)H3N-CH(CH2SH)-COO(-) 0 121.020 121.15922 2-ammonio-3-mercaptopropanoate 2-ammonio-3-sulfanylpropanoate C3H7NO2S CHEBI:35237 Gmelin:49992 InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6) XUJNEKJLAYXESH-UHFFFAOYSA-N [NH3+]C(CS)C([O-])=O chebi_ontology cysteine zwitterion amino acid zwitterion CHEBI:35238 The zwitterionic form of an amino acid having a negatively charged carboxyl group and a positively charged amino group. amino acid zwitterion chebi_ontology serine zwitterion 0 105.043 105.09262 2-ammonio-3-hydroxypropanoate An amino acid zwitterion obtained by transfer of a proton from the carboxy to the amnio group of serine. Beilstein:3935647 C3H7NO3 CHEBI:35243 Gmelin:2060272 InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7) MTCFGRXMJLQNBG-UHFFFAOYSA-N [NH3+]C(CO)C([O-])=O chebi_ontology serine zwitterion quaternary ammonium ion +1 14.003 14.00670 A derivative of ammonium, NH4(+), in which all four of the hydrogens bonded to nitrogen have been replaced with univalent (usually organyl) groups. CHEBI:26470 CHEBI:35267 CHEBI:8693 KEGG:C06703 NR4 Quaternary amine [*][N+]([*])([*])[*] chebi_ontology quaternary ammonium quaternary ammonium ion quaternary ammonium ions quaternary ammonium salt CHEBI:26468 CHEBI:35268 CHEBI:35273 Derivatives of ammonium compounds, (NH4(+))Y(-), in which all four of the hydrogens bonded to nitrogen have been replaced with univalent (usually organyl) groups. chebi_ontology quaternary ammonium compound quaternary ammonium compounds quaternary ammonium salt quaternary ammonium salts ammonium ion Ammonium, NH4(+), and derivatives formed by substitution by univalent groups. CHEBI:35274 ammonium ions azanium ions chebi_ontology ammonium compound CHEBI:35276 Compounds (NH4(+))Y(-) and derivatives, in which one or more of the hydrogens bonded to nitrogen have been replaced with univalent groups. ammonium compounds azanium compounds chebi_ontology onium betaine CHEBI:35281 Neutral molecules having charge-separated forms with an onium atom which bears no hydrogen atoms and that is not adjacent to the anionic atom. betaines chebi_ontology onium betaines ammonium betaine Any neutral molecule having charge-separated forms with a quaternary ammonium atom which bears no hydrogen atoms and that is not adjacent to the anionic atom. CHEBI:35284 ammonium betaines chebi_ontology acylcholine +1 131.095 131.17290 A choline ester formed from choline and a carboxylic acid. C6H13NO2R CHEBI:13245 CHEBI:22227 CHEBI:2463 CHEBI:35287 C[N+](C)(C)CCOC([*])=O KEGG:C01777 acylcholines an acylcholine chebi_ontology all-trans-retinoate (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate -1 299.201 299.42718 A retinoate that is the conjugate base of all-trans-retinoic acid. C20H27O2 CC(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(C)=C/C([O-])=O CHEBI:26535 CHEBI:35291 InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/p-1/b9-6+,12-11+,15-8+,16-14+ KEGG:C00777 Retinoate SHGAZHPCJJPHSC-YCNIQYBTSA-M all-trans-Retinoate all-trans-retinoate chebi_ontology carbopolycyclic compound A polyclic compound in which all of the ring members are carbon atoms. CHEBI:35294 carbopolycyclic compounds chebi_ontology homopolycyclic compound CHEBI:35295 chebi_ontology homopolycyclic compounds hexoside CHEBI:35313 chebi_ontology hexoside hexosides cephaeline 0 466.283 466.61240 7',10,11-trimethoxyemetan-6'-ol A pyridoisoquinoline comprising emetam having a hydroxy group at the 6'-position and methoxy substituents at the 7'-, 10- and 11-positions. Beilstein:100615 C28H38N2O4 CAS:483-17-0 CHEBI:3533 Cephaelin Cephaeline DTGZHCFJNDAHEN-OZEXIGSWSA-N InChI=1S/C28H38N2O4/c1-5-17-16-30-9-7-19-13-27(33-3)28(34-4)15-22(19)24(30)11-20(17)10-23-21-14-26(32-2)25(31)12-18(21)6-8-29-23/h12-15,17,20,23-24,29,31H,5-11,16H2,1-4H3/t17-,20-,23+,24-/m0/s1 KEGG:C09390 KNApSAcK:C00001835 LINCS:LSM-3808 PMID:11411558 PMID:11913711 PMID:11996324 PMID:12880315 PMID:13437707 PMID:18327911 PMID:20061395 PMID:20495341 PMID:21228475 PMID:2715231 PMID:6716976 Reaxys:100615 [H][C@]1(C[C@@]2([H])NCCc3cc(O)c(OC)cc23)C[C@]2([H])N(CCc3cc(OC)c(OC)cc23)C[C@@H]1CC chebi_ontology central nervous system stimulant Any drug that enhances the activity of the central nervous system. CHEBI:35337 CNS stimulant Wikipedia:Central_nervous_system_stimulants analeptic analeptic agent analeptic drug analeptics central nervous system stimulant central stimulant chebi_ontology steroid 0 259.243 259.450 Any of naturally occurring compounds and synthetic analogues, based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred. Natural steroids are derived biogenetically from squalene, so may be considered as triterpenoids. C12C(C3C(C(CC3)*)(C)CC1)CCC4C2(CCCC4)C C19H31R CHEBI:13687 CHEBI:26768 CHEBI:35341 CHEBI:9263 KEGG:C00377 MetaCyc:Steroids Steroid a steroid chebi_ontology steroids 17alpha-hydroxy steroid 17-alpha-Hydroxysteroid 17alpha-hydroxy steroids CHEBI:13585 CHEBI:19174 CHEBI:35342 CHEBI:782 KEGG:C03336 The alpha-stereoisomer of 17-hydroxy steroid. chebi_ontology 17beta-hydroxy steroid 17beta-Hydroxysteroid 17beta-hydroxy steroids A 17-hydroxy steroid in which the hydroxy group at position 17 has a beta-configuration. CHEBI:19176 CHEBI:35343 CHEBI:794 KEGG:C03051 chebi_ontology 21-hydroxy steroid 21-Hydroxysteroid 21-hydroxy steroids 21-hydroxysteroids CHEBI:1300 CHEBI:13596 CHEBI:19803 CHEBI:35344 KEGG:C02506 chebi_ontology 11beta-hydroxy steroid 0 11beta-Hydroxysteroid 11beta-hydroxy steroids 11beta-hydroxysteroids 275.237 275.450 Any 11-hydroxy steroid in which the hydroxy group at position 11 has beta- configuration. C12(CCCCC1CCC3C2[C@H](CC4(C3CCC4*)C)O)C C19H31OR CHEBI:13774 CHEBI:19134 CHEBI:35346 CHEBI:738 KEGG:C01058 an 11beta-hydroxysteroid chebi_ontology 3beta-sterol 0 275.237 275.450 3beta-hydroxysteroids 3beta-sterols A sterol in which the hydroxy group at position 3 has beta- configuration. C12C(C3C(C(CC3)*)(C)CC1)CCC4C2(CC[C@@H](C4)O)C C19H31OR CHEBI:13609 CHEBI:1725 CHEBI:1726 CHEBI:20248 CHEBI:35348 a 3beta-hydroxysterol chebi_ontology hydroxy steroid CHEBI:24748 CHEBI:35350 CHEBI:5814 Hydroxysteroid KEGG:C02159 chebi_ontology hydroxy steroids hydroxysteroids organonitrogen compound Any heteroorganic entity containing at least one carbon-nitrogen bond. CHEBI:35352 chebi_ontology organonitrogen compounds organonitrogens fatty acid 0 44.998 45.01740 Any aliphatic monocarboxylic acid derived from or contained in esterified form in an animal or vegetable fat, oil or wax. CHEBI:13633 CHEBI:24024 CHEBI:35366 CHEBI:4984 CHO2R Fatty acid Fettsaeure Fettsaeuren KEGG:C00162 OC([*])=O PMID:14287444 PMID:14300208 PMID:14328676 Wikipedia:Fatty_acid acide gras acides gras acido graso acidos grasos chebi_ontology fatty acids fatty acids thiocarboxylic acid anion CHEBI:35367 chebi_ontology thiocarboxylates thiocarboxylic acid anions monosaccharide CHEBI:25407 CHEBI:35381 CHEBI:6984 KEGG:C06698 Monosaccharid Monosaccharide Monosacharid Parent monosaccharides are polyhydroxy aldehydes H[CH(OH)]nC(=O)H or polyhydroxy ketones H-[CHOH]n-C(=O)[CHOH]m-H with three or more carbon atoms. The generic term 'monosaccharide' (as opposed to oligosaccharide or polysaccharide) denotes a single unit, without glycosidic connection to other such units. It includes aldoses, dialdoses, aldoketoses, ketoses and diketoses, as well as deoxy sugars, provided that the parent compound has a (potential) carbonyl group. chebi_ontology monosacarido monosacaridos monosaccharide monosaccharides oxoanion An oxoanion is an anion derived from an oxoacid by loss of hydron(s) bound to oxygen. CHEBI:33274 CHEBI:33436 CHEBI:35406 chebi_ontology oxoacid anions oxoanion oxoanions N-acetylneuraminate -1 308.098 308.26196 5-acetamido-3,5-dideoxy-D-galacto-non-2-ulopyranosonate 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-non-2-ulosonate A ketoaldonate that is the conjugate base of N-acetylneuraminic acid, obtained by deprotonation of the carboxy group. C11H18NO9 CHEBI:12471 CHEBI:12579 CHEBI:21617 CHEBI:33987 CHEBI:35418 InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/p-1/t5-,6+,7+,8+,9+,11?/m0/s1 MetaCyc:N-ACETYLNEURAMINATE N-acetylneuraminate Reaxys:9227329 SQVRNKJHWKZAKO-LUWBGTNYSA-M [H][C@]1(OC(O)(C[C@H](O)[C@H]1NC(C)=O)C([O-])=O)[C@H](O)[C@H](O)CO chebi_ontology sialate antiinfective agent A substance used in the prophylaxis or therapy of infectious diseases. CHEBI:35441 anti-infective agents anti-infective drugs antiinfective agents antiinfective drug chebi_ontology antiparasitic agent A substance used to treat or prevent parasitic infections. CHEBI:35442 Wikipedia:Antiparasitic antiparasitic drugs antiparasitics chebi_ontology parasiticides antidepressant Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. CHEBI:35469 antidepressant drugs antidepressants chebi_ontology thymoanaleptics thymoleptic drugs thymoleptics central nervous system drug A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. CHEBI:35470 CNS agent CNS drugs central nervous system agents chebi_ontology psychotropic drug A loosely defined grouping of drugs that have effects on psychological function. CHEBI:35471 Wikipedia:Psychotropic_drug chebi_ontology psychoactive agent psychoactive drugs psychopharmaceuticals psychotropic drugs anti-inflammatory drug A substance that reduces or suppresses inflammation. CHEBI:35472 anti-inflammatory drugs antiinflammatory agent antiinflammatory drug antiinflammatory drugs chebi_ontology tranquilizing drug A traditional grouping of drugs said to have a soothing or calming effect on mood, thought or behaviour. CHEBI:35473 ataractics chebi_ontology tranquilising drug tranquilizing drugs tranquillising agent tranquillizing agents anxiolytic drug Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. CHEBI:35474 anti-anxiety agents anti-anxiety drugs anxiolytic agents anxiolytics chebi_ontology minor tranquilisers minor tranquilizers minor tranquilizing agents alkali metal salt CHEBI:35479 alkali metal salts chebi_ontology analgesic An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. CHEBI:35480 chebi_ontology non-narcotic analgesic A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors. CHEBI:35481 chebi_ontology central nervous system depressant A loosely defined group of drugs that tend to reduce the activity of the central nervous system. CHEBI:35488 CNS depressants central nervous system depressants chebi_ontology organic disulfide 0 63.944 64.13000 CHEBI:35489 Compounds of structure RSSR in which R and R' are organic groups. S2R2 [*]SS[*] an organic disulfide chebi_ontology disulfides organic disulfides cystine zwitterion 0 240.024 240.30256 3,3'-disulfanediylbis(2-ammoniopropanoate) 3,3'-dithiobis(2-ammoniopropanoate) An amino acid zwitterion that is the tautomer of cystine. C6H12N2O4S2 CHEBI:35492 Gmelin:51007 InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12) LEVWYRKDKASIDU-UHFFFAOYSA-N [NH3+]C(CSSCC([NH3+])C([O-])=O)C([O-])=O chebi_ontology diuretic An agent that promotes the excretion of urine through its effects on kidney function. CHEBI:35498 chebi_ontology diuretics alkaloid fundamental parent CHEBI:35506 alkaloid fundamental parents chebi_ontology natural product fundamental parent CHEBI:35507 chebi_ontology natural product fundamental parents steroid fundamental parent CHEBI:35508 chebi_ontology steroid fundamental parents androstane 0 260.250 260.45738 Beilstein:5247532 C19H32 CAS:24887-75-0 CHEBI:35509 InChI=1S/C19H32/c1-18-11-5-7-16(18)15-9-8-14-6-3-4-12-19(14,2)17(15)10-13-18/h14-17H,3-13H2,1-2H3/t14?,15-,16-,17-,18-,19-/m0/s1 LIPID_MAPS_instance:LMST02020000 QZLYKIGBANMMBK-FZFXZXLVSA-N [H][C@@]12CCC3CCCC[C@]3(C)[C@@]1([H])CC[C@]1(C)CCC[C@@]21[H] androstane chebi_ontology 5alpha-cholestane (5alpha)-cholestane 0 372.376 372.67002 5alpha-cholestane Beilstein:2051806 C27H48 CAS:481-21-0 CHEBI:20650 CHEBI:35515 HMDB:HMDB0041632 InChI=1S/C27H48/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h19-25H,6-18H2,1-5H3/t20-,21-,22+,23-,24+,25+,26+,27-/m1/s1 Reaxys:2051806 The 5alpha-stereoisomer of cholestane. XIIAYQZJNBULGD-XWLABEFZSA-N [H][C@]12CCCC[C@]1(C)[C@@]1([H])CC[C@]3(C)[C@]([H])(CC[C@@]3([H])[C@]1([H])CC2)[C@H](C)CCCC(C)C alpha-cholestane chebi_ontology cholestane 0 372.376 372.67002 Beilstein:5334741 C27H48 CAS:14982-53-7 CHEBI:35516 InChI=1S/C27H48/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h19-25H,6-18H2,1-5H3/t20-,21?,22+,23-,24+,25+,26+,27-/m1/s1 LIPID_MAPS_instance:LMST01010000 Wikipedia:Cholestane XIIAYQZJNBULGD-LDHZKLTISA-N [H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4CCCC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C chebi_ontology cholestane cholane 0 330.329 330.59028 C24H42 CHEBI:35519 InChI=1S/C24H42/c1-5-8-17(2)20-12-13-21-19-11-10-18-9-6-7-15-23(18,3)22(19)14-16-24(20,21)4/h17-22H,5-16H2,1-4H3/t17-,18?,19+,20-,21+,22+,23+,24-/m1/s1 QSHQKIURKJITMZ-BRPMRXRMSA-N [H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4CCCC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC chebi_ontology cholane beta-adrenergic agonist An agent that selectively binds to and activates beta-adrenergic receptors. CHEBI:35522 beta-adrenergic agonists beta-adrenergic receptor agonist beta-adrenoceptor agonists chebi_ontology sympathomimetic agent A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. CHEBI:35524 chebi_ontology sympathomimetic sympathomimetics hypoglycemic agent A drug which lowers the blood glucose level. CHEBI:35526 antidiabetic antihyperglycemic antihyperglycemic agent antihyperglycemic agents antihyperglycemic drug antihyperglycemic drugs antihyperglycemics chebi_ontology hypoglycemic agents hypoglycemic drug hypoglycemic drugs bipyridine Bipyridin C10H8N2 CHEBI:35545 bipyridine bipyridyl chebi_ontology heterocyclic organic fundamental parent CHEBI:35552 chebi_ontology heterocyclic fundamental parent heterocyclic organic fundamental parents heterocyclic parent hydrides organic heterocyclic fundamental parents cardiovascular drug A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume. CHEBI:35554 cardiovascular agent cardiovascular drugs chebi_ontology mancude organic heteromonocyclic parent CHEBI:35555 chebi_ontology mancude organic heteromonocyclic parents mancude-ring organic heteromonocyclic parents mancude ring Any molecular entity that consists of a ring having (formally) the maximum number of noncumulative double bonds. CHEBI:35568 chebi_ontology mancude rings mancude-ring systems mancunide-ring systems mancude organic heterobicyclic parent CHEBI:35570 chebi_ontology mancude organic heterobicyclic parents mancude-ring organic heterobicyclic parents mancude organic heterocyclic parent CHEBI:35571 chebi_ontology mancude organic heterocyclic parents mancude-ring organic heterocyclic parents organic mancude parent CHEBI:35573 chebi_ontology organic mancude parents organic mancude-ring parents purine A heterobicyclic aromatic organic compound comprising a pyrimidine ring fused to an imidazole ring; the parent compound of the purines. C5H4N4 CHEBI:35584 HMDB:HMDB0001366 KEGG:C15587 MetaCyc:PURINE PMID:12865945 PMID:24088627 chebi_ontology purine 1H-purine 0 120.044 120.11210 1H-purine C5H4N4 CHEBI:35586 Gmelin:2379911 InChI=1S/C5H4N4/c1-4-5(8-2-6-1)9-3-7-4/h1-3H,(H,6,7,8,9) KDCGOANMDULRCW-UHFFFAOYSA-N The 1H-tautomer of purine. c1nc2c[nH]cnc2n1 chebi_ontology 3H-purine 0 120.044 120.11222 3H-purine C5H4N4 CHEBI:35588 InChI=1S/C5H4N4/c1-4-5(8-2-6-1)9-3-7-4/h1-3H,(H,6,7,8,9) KDCGOANMDULRCW-UHFFFAOYSA-N PMID:6149478 PMID:7178185 PMID:7296170 Reaxys:1210196 The 3H-tautomer of purine. c1nc2cnc[nH]c2n1 chebi_ontology 9H-purine 0 120.044 120.11222 9H-purine Beilstein:606899 C5H4N4 CAS:120-73-0 CHEBI:35589 Gmelin:3120 InChI=1S/C5H4N4/c1-4-5(8-2-6-1)9-3-7-4/h1-3H,(H,6,7,8,9) KDCGOANMDULRCW-UHFFFAOYSA-N The 9H-tautomer of purine. Wikipedia:Purine c1ncc2nc[nH]c2n1 chebi_ontology carbon oxoanion A negative ion consisting solely of carbon and oxygen atoms, and therefore having the general formula CxOy(n-) for some integers x, y and n. CHEBI:35604 carbon oxoanion carbon oxoanions chebi_ontology oxocarbon anion oxocarbon anions carbon oxoacid CHEBI:35605 carbon oxoacids chebi_ontology oxoacids of carbon antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. CHEBI:35610 anticancer agent anticancer agents antineoplastic antineoplastic agents chebi_ontology cytostatic flavouring agent A food additive that is used to added improve the taste or odour of a food. CHEBI:35617 chebi_ontology flavoring agent flavoring agents flavour enhancer flavour enhancers flavouring agents aromatic ether Any ether in which the oxygen is attached to at least one aryl substituent. CHEBI:35618 chebi_ontology vasodilator agent A drug used to cause dilation of the blood vessels. CHEBI:35620 chebi_ontology vasodilator vasodilator agents anticonvulsant A drug used to prevent seizures or reduce their severity. Antiepileptika Antiepileptikum Antikonvulsiva Antikonvulsivum CHEBI:35623 anti-convulsant anti-convulsants anti-convulsive agent anti-convulsive agents anticonvulsants anticonvulsive agent anticonvulsive agents antiepileptic antiepileptics antiepileptique antiepileptiques chebi_ontology adrenergic uptake inhibitor ARI Adrenergic uptake inhibitors are drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin. CHEBI:35640 NERI NRI adrenergic reuptake inhibitor adrenergic reuptake inhibitors adrenergic uptake inhibitors chebi_ontology norepinephrine reuptake inhibitor norepinephrine reuptake inhibitors 5-ammoniolevulinate 0 131.058 131.12990 5-aminolevulinate 5-ammonio-4-oxopentanoate 5-ammonio-4-oxovalerate 5-azaniumyl-4-oxopentanoate C5H9NO3 CHEBI:356416 InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9) PMID:14667225 The zwitterion formed from 5-aminolevulinic acid by transfer of a proton from the carboxy group to the amino group. It is the major species present at physiological pH. ZGXJTSGNIOSYLO-UHFFFAOYSA-N [NH3+]CC(=O)CCC([O-])=O chebi_ontology EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor Any EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that inhibits HMG-CoA reductases. Hydroxymethylglutaryl-CoA reductase inhibitors have been shown to lower directly cholesterol synthesis. The Enzyme Commission designation is EC 1.1.1.34 for the NADPH-dependent enzyme and EC 1.1.1.88 for an NADH-dependent enzyme. CHEBI:35664 HMG-CoA reductase inhibitor HMG-CoA reductase inhibitors PMID:1464741 PMID:15531285 PMID:20467214 Wikipedia:HMG-CoA_reductase chebi_ontology hydroxymethylglutaryl-CoA reductase inhibitor hydroxymethylglutaryl-CoA reductase inhibitors histamine agonist A drug that binds to and activates histamine receptors. Although they have been suggested for a variety of clinical applications, histamine agonists have so far been more widely used in research than therapeutically. CHEBI:35678 chebi_ontology histamine agonists antilipemic drug A substance used to treat hyperlipidemia (an excess of lipids in the blood). CHEBI:35679 Wikipedia:Hypolipidemic_agent antihyperlipemic antihyperlipemics antihyperlipidemic antihyperlipidemic agent antihyperlipidemic agents antihyperlipidemic drug antihyperlipidemic drugs antihyperlipidemics antilipemic antilipemic drugs antilipemics chebi_ontology hypolipidemic agent hypolipidemic agents secondary alcohol 0 30.011 30.02600 58.07910 A secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it. CH2OR2 CHEBI:13425 CHEBI:13686 CHEBI:26617 CHEBI:35681 CHEBI:58662 CHEBI:8741 CHEBI:9077 KEGG:C00432 KEGG:C01612 OC([*])[*] R-CHOH-R' Secondary alcohol a secondary alcohol chebi_ontology secondary alcohols dicarboxylic acid Any carboxylic acid containing two carboxy groups. CHEBI:23692 CHEBI:35692 CHEBI:36172 CHEBI:4501 Dicarboxylic acid KEGG:C02028 chebi_ontology dicarboxylic acids dicarboxylic acid anion CHEBI:35693 chebi_ontology dicarboxylic acid anion dicarboxylic acid anions dicarboxylic acid monoanion Any dicarboxylic acid anion that is a monoanion obtained by the deprotonation of only one of the carboxy groups of the dicarboxylic acid. CHEBI:35695 chebi_ontology dicarboxylic acid monoanions ester A compound formally derived from an oxoacid RkE(=O)l(OH)m (l > 0) and an alcohol, phenol, heteroarenol, or enol by linking with formal loss of water from an acidic hydroxy group of the former and a hydroxy group of the latter. CHEBI:23960 CHEBI:35701 CHEBI:4859 Ester KEGG:C00287 Wikipedia:Ester chebi_ontology esters diethyl ether 0 1,1'-oxybisethane 1,1'-oxydiethane 3-oxapentane 74.073 74.12160 Aether An ether in which the oxygen atom is linked to two ethyl groups. Anesthetic ether Beilstein:1696894 C4H10O CAS:60-29-7 CCOCC CHEBI:23991 CHEBI:31565 CHEBI:35702 Diethyl ether Diethylaether Drug_Central:4417 Ether Gmelin:25444 InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3 KEGG:C13240 KEGG:D01772 PMID:24443836 Pronarcol R-610 RTZKZFJDLAIYFH-UHFFFAOYSA-N Reaxys:1696894 Wikipedia:Diethyl_ether aether aether pro narcosi chebi_ontology diethyl oxide ethoxyethane ethyl ether ethyl oxide xenobiotic A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means. CHEBI:10074 CHEBI:27333 CHEBI:35703 KEGG:C06708 Wikipedia:Xenobiotic Xenobiotic chebi_ontology xenobiotic xenobiotic compounds xenobiotics immunosuppressive agent An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response. CHEBI:35705 chebi_ontology immunosuppressant immunosuppressive agents inmunosupresor sedative A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. CHEBI:35717 chebi_ontology hypnotics hypnotics and sedatives sedative drug sedatives sedatives and hypnotics antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. CHEBI:35718 antifungal antifungal agents antifungal drug antifungal drugs antifungals chebi_ontology heparan sulfates CHEBI:35721 chebi_ontology sulfated glycosaminoglycan CHEBI:35722 chebi_ontology glycosaminoglycan sulfate glycosaminoglycan sulfates sulfated glycosaminoglycans carbohydrate sulfate CHEBI:35724 carbohydrate sulfates carbohydrate sulphates chebi_ontology dicarboxylic acid monoamide CHEBI:13210 CHEBI:23691 CHEBI:35735 CHEBI:6976 chebi_ontology dicarboxylic acid monoamide dicarboxylic acid monoamides monothiocarboxylic acid CHEBI:35737 Compounds in which one oxygen of a carboxy group has been replaced by divalent sulfur; RC(=O)SH or RC(=S)OH. chebi_ontology monothiocarboxylic acid monothiocarboxylic acids monothiocarboxylic acids thio acid liposaccharide CHEBI:35740 chebi_ontology liposaccharides glycerolipid Any member of the group of lipids containing a common glycerol backbone to which at least one fatty acid-derived group is attached. CHEBI:35741 PMID:18606873 chebi_ontology glycerolipids carbocyclic fatty acid Any fatty acid containing a ring composed of carbon atoms. CHEBI:35744 carbocyclic fatty acids chebi_ontology tricarboxylic acid anion Any anion of a tricarboxylic acid formed by deprotonation of at least one carboxy group. CHEBI:35753 chebi_ontology tricarboxylic acid anion tricarboxylic acid anions monocarboxylic acid anion -1 43.990 44.01000 A carboxylic acid anion formed when the carboxy group of a monocarboxylic acid is deprotonated. CHEBI:13657 CHEBI:25382 CHEBI:3407 CHEBI:35757 CO2R Carboxylate KEGG:C00060 Monocarboxylate [O-]C([*])=O a monocarboxylate chebi_ontology monocarboxylates monocarboxylic acid anions phosphate ion A phosphorus oxoanion that is the conjugate base of phosphoric acid. CHEBI:35780 Pi chebi_ontology phosphate phosphate ions diphosphate ion CHEBI:14177 CHEBI:35781 CHEBI:35782 PPi chebi_ontology diphosphate ions sphingoid CHEBI:35785 LIPID_MAPS_class:LMSP01 Spd Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds. chebi_ontology sphingoid sphingoid base sphingoid bases sphingoids phosphosphingolipid CHEBI:35786 chebi_ontology phosphosphingolipids sphingophospholipid sphingophospholipids seco-steroid CHEBI:35788 chebi_ontology seco-steroids oxo steroid CHEBI:24979 CHEBI:25804 CHEBI:35789 chebi_ontology keto steroids ketosteroids oxo steroids oxosteroids tetrapyrrole fundamental parent CHEBI:35794 chebi_ontology tetrapyrrole fundamental parents citrate(1-) -1 191.11558 A tricarboxylic acid monoanion that is the conjugate base of citric acid, obtained by deprotonation of one of the three carboxy groups. C6H7O7 CHEBI:35804 H2cit H2cit(-) chebi_ontology dihydrogen citrate citrate(2-) -2 190.10764 A tricarboxylic acid dianion obtained by deprotonation of two of the three carboxy groups of citric acid. C6H6O7 CHEBI:35808 Hcit Hcit(2-) chebi_ontology hydrogen citrate branched-chain fatty acid Any fatty acid in which the parent hydrocarbon chain has one or more alkyl substituents; a common component in animal and bacterial lipids. The fatty acyl chain is usually saturated and the substituent a methyl group; however, unsaturated BCFAs are found in marine animals, and branches other than methyl are found in microbial lipids. BCFA BCFAs Branched chain fatty acid CHEBI:22919 CHEBI:3166 CHEBI:35819 KEGG:C05996 PMID:18318842 branched fatty acid branched fatty acids branched-chain fatty acids chebi_ontology antiprotozoal drug Any antimicrobial drug which is used to treat or prevent protozoal infections. CHEBI:35820 Wikipedia:Antiprotozoal_agent antiprotozoal agent antiprotozoal agents antiprotozoal drugs chebi_ontology anticholesteremic drug A substance used to lower plasma cholesterol levels. CHEBI:35821 CHEBI:64906 anticholesteremic anticholesteremic agent anticholesteremic drugs antihypercholesterolemic antihypercholesterolemic agent antihypercholesterolemic agents antihypercholesterolemic drug antihypercholesterolemic drugs antihypercholesterolemics chebi_ontology cholesterol inhibitor hypocholesteremic agent mandelic acid (RS)-Mandelic acid 0 152.047 152.14732 2-Hydroxy-2-phenylacetic acid 2-Hydroxy-2-phenylethanoic acid A 2-hydroxy monocarboxylic acid that is acetic acid in which two of the methyl hydrogens are substituted by phenyl and hydroxyl groups. Beilstein:510011 C8H8O3 CAS:90-64-2 CHEBI:25149 CHEBI:32801 CHEBI:35825 DL-Mandelic acid Drug_Central:1629 Gmelin:218213 HMDB:HMDB0000703 IWYDHOAUDWTVEP-UHFFFAOYSA-N InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11) Mandelsaeure OC(C(O)=O)c1ccccc1 PMID:22770225 PMID:24278065 PMID:4813698 Reaxys:510011 Wikipedia:Mandelic_acid alpha-hydroxybenzeneacetic acid chebi_ontology hydroxy(phenyl)acetic acid hydroxy monocarboxylic acid Any monocarboxylic acid which also contains a separate (alcoholic or phenolic) hydroxy substituent. CHEBI:35868 chebi_ontology hydroxy acid hydroxy monocarboxylic acids oxo monocarboxylic acid Any monocarboxylic acid having at least one additional oxo functional group. CHEBI:35871 chebi_ontology oxo monocarboxylic acids imidazopyrimidine CHEBI:35875 chebi_ontology imidazopyrimidines pnictogen hydride CHEBI:35881 chebi_ontology pnictogen hydride pnictogen hydrides oxo monocarboxylic acid anion CHEBI:35178 CHEBI:35901 CHEBI:35902 chebi_ontology oxo monocarboxylic acid anions oxo carboxylic acid anion Any carboxylic acid anion containing at least one oxo group. CHEBI:35903 chebi_ontology oxo carboxylic acid anions glutarate(1-) -1 131.034 131.10668 4-carboxybutanoate A dicarboxylic acid monoanion that is the conjugate base of glutaric acid. Beilstein:3904478 C5H7O4 CHEBI:30922 CHEBI:35906 CHEBI:35907 Gmelin:326031 InChI=1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9)/p-1 JFCQEDHGNNZCLN-UHFFFAOYSA-M OC(=O)CCCC([O-])=O Reaxys:3904478 chebi_ontology hydrogen glutarate 2-oxo monocarboxylic acid 0 2-Oxo acid 2-Oxocarboxylate 2-oxo acid 2-oxo carboxylic acids 2-oxo monocarboxylic acids 72.993 73.02750 Any monocarboxylic acid having a 2-oxo substituent. C2HO3R CHEBI:11634 CHEBI:1238 CHEBI:13195 CHEBI:13594 CHEBI:19736 CHEBI:35909 CHEBI:35910 KEGG:C00161 OC(=O)C([*])=O chebi_ontology sterol ester 0 3-hydroxysteroid ester 3-hydroxysteroid esters 302.225 302.452 A steroid ester obtained by formal condensation of the carboxy group of any carboxylic acid with the 3-hydroxy group of a sterol. C12C(C3C(C(CC3)*)(C)CC1)CCC4C2(CCC(C4)OC(*)=O)C C20H30O2R2 CHEBI:13220 CHEBI:15115 CHEBI:26770 CHEBI:26772 CHEBI:35915 CHEBI:9268 CHEBI:9269 KEGG:C01958 Sterol ester Steryl ester a steryl ester chebi_ontology delta-amino acid A non-proteinogenic amino acid in which the amino group is located on the carbon atom at the position delta to the carboxy group. CHEBI:35931 chebi_ontology delta-amino acids pent-2-enoic acid 0 100.052 100.11582 2-pentenoic acid A pentenoic acid having the double bond at position 2. C5:1, n-3 C5H8O2 CAS:626-98-2 CHEBI:35939 InChI=1S/C5H8O2/c1-2-3-4-5(6)7/h3-4H,2H2,1H3,(H,6,7) LIPID_MAPS_instance:LMFA01030005 Pent-2-ensaeure Propylidenessigsaeure Reaxys:1720310 YIYBQIKDCADOSF-UHFFFAOYSA-N [H]C(CC)=CC(O)=O alpha-Butylen-alpha-carbonsaeure alpha-pentenoic acid alpha.beta-Pentensaeure beta-Aethyl-acrylsaeure beta-Aethylacrylsaeure beta-ethyl acrylic acid chebi_ontology pent-2-enoic acid neurotransmitter agent A substance used for its pharmacological action on any aspect of neurotransmitter systems. Neurotransmitter agents include agonists, antagonists, degradation inhibitors, uptake inhibitors, depleters, precursors, and modulators of receptor function. CHEBI:35942 chebi_ontology neurotransmitter agents 4-oxo monocarboxylic acid 4-oxo acid 4-oxo monocarboxylic acids CHEBI:35950 chebi_ontology 3-hydroxy monocarboxylic acid 3-hydroxy acid 3-hydroxy monocarboxylic acids A hydroxy monocarboxylic acid that has a hydroxy group beta to the carboxy group. CHEBI:35969 beta-hydroxy acid beta-hydroxy acids beta-hydroxy carboxylic acid beta-hydroxy carboxylic acids chebi_ontology dihydroxy monocarboxylic acid Any hydroxy monocarboxylic acid carrying at least two hydroxy groups. CHEBI:35972 chebi_ontology dihydroxy monocarboxylic acids diamino acid Any amino acid carrying two amino groups. CHEBI:35987 chebi_ontology antimicrobial drug A drug used to treat or prevent microbial infections. CHEBI:36043 antimicrobial drugs chebi_ontology antiviral drug A substance used in the prophylaxis or therapy of virus diseases. CHEBI:36044 anti-viral drug anti-virus drug antiviral drugs chebi_ontology hydroxy monocarboxylic acid anion Any monocarboxylic acid anion carrying at least one hydroxy substituent. CHEBI:36059 chebi_ontology hydroxy monocarboxylic acid anions hydroxymonocarboxylic acid anion hydroxymonocarboxylic acid anions oxytocic A drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients). CHEBI:36063 chebi_ontology oxytocic oxytocic agents oxytocic drugs uterine stimulants cholanoid CHEBI:22867 CHEBI:36078 CHEBI:50419 LIPID_MAPS_class:LMST04 bile acids and derivatives chebi_ontology cholanoids protein A biological macromolecule minimally consisting of one polypeptide chain synthesized at the ribosome. CHEBI:13677 CHEBI:14911 CHEBI:36080 chebi_ontology proteins inorganic chloride CHEBI:36093 chebi_ontology inorganic chloride salt inorganic chloride salts inorganic chlorides quinone CHEBI:13684 CHEBI:26517 CHEBI:36141 Chinon Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included). Wikipedia:Quinone chebi_ontology quinone quinones quinones oxo dicarboxylic acid Any dicarboxylic acid carrying one or more oxo groups. CHEBI:36145 chebi_ontology oxo dicarboxylic acids oxo dicarboxylate CHEBI:36147 chebi_ontology oxo dicarboxylates oxo-dicarboxylic acid dianion oxo-dicarboxylic acid dianions 2-hydroxyglutarate(1-) -1 147.029 147.10610 A dicarboxylic acid monoanion resulting from the removal of a proton from one of the carboxylic acid groups of 2-hydroxyglutaric acid. C5H7O5 CHEBI:36149 HWXBTNAVRSUOJR-UHFFFAOYSA-M InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/p-1 [H+].OC(CCC([O-])=O)C([O-])=O chebi_ontology hydrogen 2-hydroxypentanedioate disaccharide A compound in which two monosaccharides are joined by a glycosidic bond. CHEBI:23844 CHEBI:36233 CHEBI:4654 Disaccharid Disaccharide Disacharid KEGG:C01911 chebi_ontology disacarido disacaridos disaccharides cholanic acid 0 360.303 360.57320 A steroid acid that consists of cholane having a carboxy group in place of the methyl group at position 24. C24H40O2 CAS:25312-65-6 CHEBI:36237 InChI=1S/C24H40O2/c1-16(7-12-22(25)26)19-10-11-20-18-9-8-17-6-4-5-14-23(17,2)21(18)13-15-24(19,20)3/h16-21H,4-15H2,1-3H3,(H,25,26)/t16-,17?,18+,19-,20+,21+,23+,24-/m1/s1 Patent:JP2008069152 RPKLZQLYODPWTM-KBMWBBLPSA-N Reaxys:13246008 [H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4CCCC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O chebi_ontology cholan-24-oic acid 5beta-cholanic acid (5beta)-cholan-24-oic acid (5beta,17beta)-gamma-methylandrostane-17-butanoic acid 0 360.303 360.57320 5beta-cholan-24-oic acid 5beta-cholanic acid 5beta-cholanoic acid Beilstein:3214794 C24H40O2 CAS:546-18-9 CHEBI:36238 InChI=1S/C24H40O2/c1-16(7-12-22(25)26)19-10-11-20-18-9-8-17-6-4-5-14-23(17,2)21(18)13-15-24(19,20)3/h16-21H,4-15H2,1-3H3,(H,25,26)/t16-,17+,18+,19-,20+,21+,23+,24-/m1/s1 LIPID_MAPS_instance:LMST04010441 RPKLZQLYODPWTM-LVVAJZGHSA-N [H][C@@]12CCCC[C@]1(C)[C@@]1([H])CC[C@]3(C)[C@]([H])(CC[C@@]3([H])[C@]1([H])CC2)[C@H](C)CCC(O)=O chebi_ontology ursocholanic acid 3-(4-hydroxyphenyl)pyruvate -1 179.034 179.14950 3-(4-Hydroxyphenyl)pyruvate 3-(4-hydroxyphenyl)-2-oxopropanoate 3-(4-hydroxyphenyl)pyruvate 3-(p-hydroxyphenyl)pyruvate 4-Hydroxyphenylpyruvate A 2-oxo monocarboxylic acid anion obtained by removal of a proton from the carboxylic acid group of 3-(4-hydroxyphenyl)pyruvic acid. Beilstein:3950858 C9H7O4 CHEBI:11725 CHEBI:11727 CHEBI:12016 CHEBI:20425 CHEBI:36242 CHEBI:594665 HPP InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)/p-1 KEGG:C01179 KKADPXVIOXHVKN-UHFFFAOYSA-M Oc1ccc(CC(=O)C([O-])=O)cc1 PMID:11948155 PMID:14593448 Reaxys:3950858 UM-BBD_compID:c0235 chebi_ontology p-hydroxyphenylpyruvate 5beta-cholanic acids CHEBI:36248 Members of the class of cholanic acids based on a 5beta-cholane skeleton. chebi_ontology bile acid salt A salt of a bile acid. CHEBI:36277 bile acid salts chebi_ontology cholanic acids CHEBI:23166 CHEBI:23211 CHEBI:36278 chebi_ontology tricarboxylic acid monoanion CHEBI:36299 chebi_ontology tricarboxylic acid monoanions tricarboxylic acid dianion CHEBI:36300 chebi_ontology tricarboxylic acid dianions cyclic tetrapyrrole CHEBI:36309 chebi_ontology cyclic tetrapyrroles macrocyclic tetrapyrrole macrocyclic tetrapyrroles lepton CHEBI:36338 Lepton is a fermion that does not experience the strong force (strong interaction). The term is derived from the Greek lambdaepsilonpitauomicronsigma (small, thin). chebi_ontology leptons baryon Baryon is a fermion that does experience the strong force (strong interaction). The term is derived from the Greek betaalpharhoupsilonsigma (heavy). CHEBI:36339 baryons chebi_ontology fermion CHEBI:36340 Particle of half-integer spin quantum number following Fermi-Dirac statistics. Fermions are named after Enrico Fermi. chebi_ontology fermion fermions subatomic particle A particle smaller than an atom. CHEBI:36342 chebi_ontology subatomic particles composite particle A subatomic particle known to have substructure (i.e. consisting of smaller particles). CHEBI:36343 chebi_ontology composite particles hadron CHEBI:36344 Hadron is a subatomic particle which experiences the strong force. chebi_ontology hadrons nuclear particle A nucleus or any of its constituents in any of their energy states. CHEBI:36347 chebi_ontology nuclear particle polyatomic entity Any molecular entity consisting of more than one atom. CHEBI:36357 chebi_ontology polyatomic entities polyatomic ion An ion consisting of more than one atom. CHEBI:36358 chebi_ontology polyatomic ions phosphorus oxoacid derivative CHEBI:36359 chebi_ontology phosphorus oxoacid derivative phosphorus oxoacids and derivatives CHEBI:36360 chebi_ontology alkaline earth salt CHEBI:36364 alkaline earth salts chebi_ontology emetan 0 360.257 360.53506 C25H32N2 CHEBI:36380 InChI=1S/C25H32N2/c1-2-18-17-27-14-12-20-8-4-6-10-23(20)25(27)16-21(18)15-24-22-9-5-3-7-19(22)11-13-26-24/h3-10,18,21,24-26H,2,11-17H2,1H3/t18-,21-,24+,25-/m0/s1 KSQYVPHTTWSOHG-CKBKHPSWSA-N [H][C@]1(C[C@@]2([H])NCCc3ccccc23)C[C@]2([H])N(CCc3ccccc23)C[C@@H]1CC chebi_ontology emetan mancude organic heterotricyclic parent CHEBI:36416 chebi_ontology mancude organic heterotricyclic parents mancude-ring organic heterotricyclic parents sulfoglycosphingolipid CHEBI:36477 chebi_ontology sulfoglycosphingolipids galactosylceramide 0 279.095 279.244 Any of the cerebrosides in which the monosaccharide head group is galactose. C10H17NO8R2 CHEBI:13641 CHEBI:36498 Cerebroside D-Galactosyl-N-acylsphingosine D-Galactosylceramide Galactocerebroside KEGG:C02686 KEGG:G11121 PMID:16758576 PMID:2088646 PMID:23065187 PMID:23446636 PMID:23650721 PMID:25947378 PMID:26058499 PMID:26907993 PMID:27786470 [C@H]([C@@H](*)O)(NC(=O)*)COC1O[C@@H]([C@@H]([C@@H]([C@H]1O)O)O)CO a D-galactosylceramide chebi_ontology galactocerebroside galactocerebrosides galactosylceramides acidic glycosphingolipid CHEBI:22208 CHEBI:2428 CHEBI:36526 chebi_ontology carbonyl compound Any compound containing the carbonyl group, C=O. The term is commonly used in the restricted sense of aldehydes and ketones, although it actually includes carboxylic acids and derivatives. CHEBI:36586 carbonyl compounds chebi_ontology organic oxo compound CHEBI:36587 Organic compounds containing an oxygen atom, =O, doubly bonded to carbon or another element. chebi_ontology organic oxo compounds oxo compounds acid anhydride CHEBI:36606 Compounds consisting of two acyl groups bonded to the same oxygen atom acyl-O-acyl. acid anhydride acid anhydrides acid anhydrides anhydride d'acide chebi_ontology acyclic acid anhydride CHEBI:36608 acyclic acid anhydride acyclic acid anhydrides acyclic acid anhydrides acyclic anhydrides chebi_ontology organochlorine compound An organochlorine compound is a compound containing at least one carbon-chlorine bond. CHEBI:36683 Wikipedia:Organochloride chebi_ontology chloroorganic compounds chlororganische Verbindungen organochloride compound organochloride compounds organochlorine compound organochlorine compounds organohalogen compound A compound containing at least one carbon-halogen bond. CHEBI:36684 chebi_ontology organohalogen compounds heterotricyclic compound CHEBI:36688 chebi_ontology heterotricyclic compound heterotricyclic compounds heterotricyclic compounds corticosteroid hormone Any of a class of steroid hormones that are produced in the adrenal cortex. CHEBI:36699 adrenal cortex hormones chebi_ontology corticosteroid hormones phosphocholines Any compound having phosphocholine as part of its structure. CHEBI:36700 O-phosphocholines chebi_ontology choline phosphates phosphorylcholines phosphoethanolamine CHEBI:36711 chebi_ontology phosphoethanolamines biladienes CHEBI:36735 Compounds based on a biladiene skeleton. chebi_ontology (trifluoromethyl)benzene (trifluoromethyl)benzene 0 146.034 146.10980 A fluorohydrocarbon that is fluoroform in which the hydrogen is substituted by a phenyl group. Beilstein:1906908 C6H5CF3 C7H5F3 CAS:98-08-8 CF3Ph CHEBI:36810 FC(F)(F)c1ccccc1 GETTZEONDQJALK-UHFFFAOYSA-N Gmelin:3670 InChI=1S/C7H5F3/c8-7(9,10)6-4-2-1-3-5-6/h1-5H PMID:11671431 PMID:20958547 PMID:24267073 PMID:24669762 PhCF3 Reaxys:1906908 alpha,alpha,alpha-trifluorotoluene benzotrifluoride chebi_ontology omega-trifluorotoluene phenylfluoroform trifluoromethylbenzene seco-cholestane CHEBI:36818 chebi_ontology seco-cholestanes ring assembly CHEBI:36820 Two or more cyclic systems (single rings or fused systems) which are directly joined to each other by double or single bonds are named ring assemblies when the number of such direct ring junctions is one less than the number of cyclic systems involved. chebi_ontology ring assemblies ring assembly pseudohalide anion CHEBI:36828 chebi_ontology pseudohalide anions pseudohalide ions pseudohalides pseudohalogen anion pseudohalogen ion polyatomic monoanion CHEBI:36829 chebi_ontology polyatomic monoanions monoanion -1 CHEBI:36830 chebi_ontology monoanions 3-hydroxy steroid 3-hydroxy steroids Any hydroxy steroid carrying a hydroxy group at position 3. CHEBI:36834 chebi_ontology 3beta-hydroxy steroid 0 275.237 275.450 3beta-hydroxy steroids A 3-hydroxy steroid in which the 3-hydroxy substituent is in the beta-position. C12C(C3C(C(CC3)*)(C)CC1)CCC4C2(CC[C@@H](C4)O)C C19H31OR CHEBI:36836 CHEBI:71195 KEGG:C02945 MetaCyc:3-Beta-Hydroxysterols PMID:10535978 PMID:12829805 a 3beta-hydroxysteroid chebi_ontology 17-hydroxy steroid 17-hydroxy steroids A hydroxy steroid carrying a hydroxy group at position 17. CHEBI:36838 chebi_ontology 11-hydroxy steroid 11-hydroxy steroids CHEBI:36841 chebi_ontology hydroxy seco-steroid CHEBI:36853 chebi_ontology hydroxy seco-steroids 20-oxo steroid 20-oxo steroids An oxo steroid carrying an oxo group at position 20. CHEBI:36885 chebi_ontology 18-oxo steroid 18-oxo steroids CHEBI:36887 chebi_ontology elemental iodine CHEBI:36893 chebi_ontology elemental bromine CHEBI:36894 chebi_ontology monoatomic bromine Br CHEBI:36896 atomic bromine chebi_ontology monoatomic iodine CHEBI:36897 I atomic iodine chebi_ontology chalcogen hydride CHEBI:36902 chalcogen hydride chalcogen hydrides chebi_ontology inorganic ion CHEBI:36914 chebi_ontology inorganic ions inorganic cation CHEBI:36915 chebi_ontology inorganic cations cation A monoatomic or polyatomic species having one or more elementary charges of the proton. CHEBI:23058 CHEBI:3473 CHEBI:36916 Cation KEGG:C01373 Kation Kationen cation cationes cations chebi_ontology chalcocarbonic acid CHEBI:36961 chalcocarbonic acid chalcocarbonic acids chalcocarbonic acids chebi_ontology organochalcogen compound An organochalcogen compound is a compound containing at least one carbon-chalcogen bond. CHEBI:36962 chebi_ontology organochalcogen compound organochalcogen compounds organooxygen compound An organochalcogen compound containing at least one carbon-oxygen bond. CHEBI:36963 PMID:17586126 chebi_ontology organooxygen compound organooxygen compounds nucleotide A nucleotide is a nucleoside phosphate resulting from the condensation of the 3 or 5 hydroxy group of a nucleoside with phosphoric acid. CHEBI:13215 CHEBI:13663 CHEBI:36976 CHEBI:7656 KEGG:C00215 Nucleotide a nucleotide chebi_ontology nucleotides cyclic purine nucleotide CHEBI:36982 chebi_ontology cyclic purine nucleotides ribonucleoside 5'-monophosphate CHEBI:1976 CHEBI:1977 CHEBI:20500 CHEBI:36996 CHEBI:37010 chebi_ontology ribonucleoside 5'-monophosphates ribonucleoside 5'-phosphate CHEBI:37015 chebi_ontology ribonucleoside 5'-phosphates purine ribonucleoside 5'-monophosphate CHEBI:37021 chebi_ontology purine ribonucleoside 5'-monophosphates amino-acid anion CHEBI:37022 amino acid anions amino-acid anion amino-acid anions chebi_ontology purine ribonucleoside 5'-diphosphate CHEBI:37038 chebi_ontology purine ribonucleoside 5'-diphosphates purine ribonucleoside 5'-triphosphate CHEBI:37045 chebi_ontology purine ribonucleoside 5'-triphosphates 3-hydroxybutyrate -1 103.040 103.09658 3-OH butyrate 3-OH-butyrate 3-hydroxybutanoate A hydroxy fatty acid anion that is the conjugate base of 3-hydroxybutyric acid, obtained by deprotonation of the carboxy group; major species at pH 7.3. Beilstein:4127635 C4H7O3 CC(O)CC([O-])=O CHEBI:37054 DL-3-hydroxybutyrate InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/p-1 Reaxys:4127635 WHBMMWSBFZVSSR-UHFFFAOYSA-M beta-hydroxy-n-butyrate beta-hydroxybutanoate chebi_ontology ribonucleoside 5'-diphosphate CHEBI:37075 chebi_ontology ribonucleoside 5'-diphosphates ribonucleoside 5'-triphosphate CHEBI:37076 chebi_ontology ribonucleoside 5'-triphosphates adenosine 5'-phosphate CHEBI:37096 adenosine 5'-phosphates chebi_ontology organobromine compound A compound containing at least one carbon-bromine bond. CHEBI:37141 bromoorganic compound chebi_ontology organobromine compounds organoiodine compound An organoiodine compound is a compound containing at least one carbon-iodine bond. CHEBI:37142 chebi_ontology organoiodine compound organoiodine compounds organofluorine compound An organofluorine compound is a compound containing at least one carbon-fluorine bond. CHEBI:37143 chebi_ontology fluoroorganic compound fluoroorganic compounds fluoroorganics fluororganische Verbindungen organofluorine compound organofluorine compounds glucan A polysaccharide composed of glucose residues. C12H22O11(C6H10O5)n CAS:9037-91-6 CHEBI:24255 CHEBI:37163 CHEBI:5392 Glucan KEGG:C01379 chebi_ontology glucan glucans homopolysaccharide CHEBI:37164 Glycans composed of a single type of monosaccharide residue. They are named by replacing the ending '-ose' of the sugar by '-an'. chebi_ontology homoglycan homopolysaccharide homopolysaccharides organic hydride CHEBI:37175 chebi_ontology organic hydrides mononuclear parent hydride CHEBI:37176 chebi_ontology mononuclear hydride mononuclear hydrides mononuclear parent hydrides elemental sodium CHEBI:37246 chebi_ontology elemental potassium CHEBI:37247 chebi_ontology elemental zinc CHEBI:37253 chebi_ontology phytanate -1 3,7,11,15-tetramethylhexadecanoate 3,7,11,15-tetramethylhexadecanoate 3,7,11,15-tetramethylpalmitate 311.295 311.52246 A branched-chain saturated fatty acid anion that is the conjugate base of phytanic acid, arising from deprotonation of the carboxylic acid group. Beilstein:3669982 C20H39O2 CC(C)CCCC(C)CCCC(C)CCCC(C)CC([O-])=O CHEBI:14834 CHEBI:26109 CHEBI:37257 InChI=1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22)/p-1 KEGG:C01607 PMID:5130448 RLCKHJSFHOZMDR-UHFFFAOYSA-M Reaxys:3669982 chebi_ontology phytanate anion mucopolysaccharide Any of the group of polysaccharides composed of alternating units from uronic acids and glycosamines, and commonly partially esterified with sulfuric acid. CHEBI:25425 CHEBI:37395 CHEBI:7011 KEGG:C05114 Mucopolysaccharid Mucopolysaccharide Mukopolysaccharid chebi_ontology mucopolisacarido mucopolisacaridos mucopolysaccharides chondroitin sulfate Any of a class of 10--60 kDa glycosaminoglycan sulfates, widely distributed in cartilage and other mammalian connective tissues. CAS:9007-28-7 CHEBI:23224 CHEBI:3676 CHEBI:37397 Chondroitin sulfate Chondroitinsulfat KEGG:C00607 PMID:11514091 PMID:7538297 chebi_ontology chondroitin polysulfate chondroitin sulfates chondroitin sulfuric acid chondroitin sulphate elemental copper CHEBI:37404 chebi_ontology alpha-amanitin 0 1,8-anhydro-S(1),C(2.5)-cyclo[L-cysteinyl-L-asparaginyl-trans-4-hydroxy-L-prolyl-(R)-4,5-dihydroxy-L-isoleucyl-6-hydroxy-L-tryptophylglycyl-L-isoleucylglycine] (R)-S(1)-oxide 918.354 918.97106 A heterodetic cyclic peptide consisting of eight amino acid residues and containing a thioether bridge between a cysteine and a tryptophan residue. It is found in a number of poisonous mushrooms, including Amanita phalloides (the death cap), Galerina marginata, and and Conocybe filaris. Beilstein:1071138 C39H54N10O14S CAS:23109-05-9 CHEBI:10207 CHEBI:37414 CHEBI:37415 CIORWBWIBBPXCG-SXZCQOKQSA-N InChI=1S/C39H54N10O14S/c1-4-16(2)31-36(60)42-11-29(55)43-25-15-64(63)38-21(20-6-5-18(51)7-22(20)46-38)9-23(33(57)41-12-30(56)47-31)44-37(61)32(17(3)27(53)14-50)48-35(59)26-8-19(52)13-49(26)39(62)24(10-28(40)54)45-34(25)58/h5-7,16-17,19,23-27,31-32,46,50-53H,4,8-15H2,1-3H3,(H2,40,54)(H,41,57)(H,42,60)(H,43,55)(H,44,61)(H,45,58)(H,47,56)(H,48,59)/t16-,17-,19+,23-,24-,25-,26-,27-,31-,32-,64+/m0/s1 KEGG:C08438 KNApSAcK:C00001516 PMID:109306 PMID:17525082 PMID:19556115 PMID:20529816 PMID:23763309 PMID:6208374 PMID:6630208 PMID:9093889 Reaxys:1071138 Wikipedia:Alpha-amanitin [H][C@]12Cc3c([nH]c4cc(O)ccc34)[S@](=O)C[C@]([H])(NC(=O)CNC(=O)[C@@]([H])(NC(=O)CNC1=O)[C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N1C[C@H](O)C[C@@]1([H])C(=O)N[C@@]([H])([C@@H](C)[C@@H](O)CO)C(=O)N2 alpha-Amanitin alpha-Amanitine alpha-Amatoxin chebi_ontology EC 2.7.7.6 (RNA polymerase) inhibitor An EC 2.7.7.* (nucleotidyltransferase) inhibitor that interferes with the action of RNA polymerase (EC 2.7.7.6). C RNA formation factors inhibitor C RNA formation factors inhibitors C ribonucleic acid formation factors inhibitor C ribonucleic acid formation factors inhibitors CHEBI:37416 DNA-dependent RNA nucleotidyltransferase inhibitor DNA-dependent RNA nucleotidyltransferase inhibitors DNA-dependent RNA polymerase inhibitor DNA-dependent RNA polymerase inhibitors DNA-dependent ribonucleate nucleotidyltransferase inhibitor DNA-dependent ribonucleate nucleotidyltransferase inhibitors DNA-directed RNA polymerase inhibitor DNA-directed RNA polymerase inhibitors DNA-directed nucleoside-triphosphate:RNA nucleotidyltransferase inhibitor DNA-directed nucleoside-triphosphate:RNA nucleotidyltransferase inhibitors EC 2.7.7.6 (RNA polymerase) inhibitors EC 2.7.7.6 inhibitor EC 2.7.7.6 inhibitors RNA nucleotidyltransferase (DNA-directed) inhibitor RNA nucleotidyltransferase (DNA-directed) inhibitors RNA nucleotidyltransferase inhibitor RNA nucleotidyltransferase inhibitors RNA polymerase (EC 2.7.7.6) inhibitor RNA polymerase (EC 2.7.7.6) inhibitors RNA polymerase I inhibitor RNA polymerase I inhibitors RNA polymerase II inhibitor RNA polymerase II inhibitors RNA polymerase III inhibitor RNA polymerase III inhibitors RNA polymerase inhibitor RNA polymerase inhibitors RNA transcriptase inhibitor RNA transcriptase inhibitors Wikipedia:RNA_polymerase chebi_ontology deoxyribonucleic acid-dependent ribonucleic acid polymerase inhibitor deoxyribonucleic acid-dependent ribonucleic acid polymerase inhibitors directed RNA polymerase inhibitor nucleoside-triphosphate:RNA nucleotidyltransferase (DNA-directed) inhibitor nucleoside-triphosphate:RNA nucleotidyltransferase (DNA-directed) inhibitors ribonucleate nucleotidyltransferase inhibitor ribonucleate nucleotidyltransferase inhibitors ribonucleate polymerase inhibitor ribonucleate polymerase inhibitors ribonucleic acid nucleotidyltransferase inhibitor ribonucleic acid nucleotidyltransferase inhibitors ribonucleic acid polymerase inhibitor ribonucleic acid polymerase inhibitors ribonucleic acid transcriptase inhibitor ribonucleic acid transcriptase inhibitors ribonucleic polymerase inhibitor ribonucleic polymerase inhibitors ribonucleic transcriptase inhibitor ribonucleic transcriptase inhibitors transcriptase inhibitor transcriptase inhibitors folic acids A group of heterocyclic compounds based on the pteroic acid skeleton conjugated with one or more L-glutamic acid units. CHEBI:24074 CHEBI:24076 CHEBI:37445 chebi_ontology folate folates folates acid Acid An acid is a molecular entity capable of donating a hydron (Bronsted acid) or capable of forming a covalent bond with an electron pair (Lewis acid). CHEBI:13800 CHEBI:13801 CHEBI:22209 CHEBI:2426 CHEBI:37527 KEGG:C00174 Saeure Saeuren acid acide acido acids an acid chebi_ontology heteroatomic molecular entity A molecular entity consisting of two or more chemical elements. CHEBI:37577 chebi_ontology chemical compound heteroatomic molecular entities halide Any heteroatomic molecular entity that is a chemical compound of halogen with other chemical elements. CHEBI:37578 Wikipedia:Halide chebi_ontology halides carboxamide 0 41.998 42.01680 An amide of a carboxylic acid, having the structure RC(=O)NR2. The term is used as a suffix in systematic name formation to denote the -C(=O)NH2 group including its carbon atom. CHEBI:35354 CHEBI:35355 CHEBI:37622 CNOR3 [*]C(=O)N([*])[*] carboxamides carboxamides chebi_ontology primary carboxamide mannose An aldohexose that is the C-2 epimer of glucose. C6H12O6 CHEBI:14575 CHEBI:33930 CHEBI:37684 Man PMID:16180318 PMID:24407290 chebi_ontology manno-hexose mannose protein kinase inhibitor An EC 2.7.* (P-containing group transferase) inhibitor that interferes with the action of protein kinases. CHEBI:37699 chebi_ontology protein kinase inhibitors EC 3.1.1.8 (cholinesterase) inhibitor An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8). BChE inhibitor BChE inhibitors BtChoEase inhibitor BtChoEase inhibitors CHEBI:37733 EC 3.1.1.8 (cholinesterase) inhibitors EC 3.1.1.8 inhibitor EC 3.1.1.8 inhibitors anticholineesterase inhibitor anticholineesterase inhibitors anticholinesterase anticholinesterases benzoylcholinesterase inhibitor benzoylcholinesterase inhibitors butyrylcholine esterase inhibitor butyrylcholine esterase inhibitors butyrylcholinesterase inhibitor butyrylcholinesterase inhibitors chebi_ontology choline esterase II (unspecific) inhibitor choline esterase II (unspecific) inhibitors choline esterase inhibitor choline esterase inhibitors cholinesterase (EC 3.1.1.8) inhibitor cholinesterase (EC 3.1.1.8) inhibitors cholinesterase inhibitor non-specific cholinesterase inhibitor non-specific cholinesterase inhibitors propionylcholinesterase inhibitor propionylcholinesterase inhibitors pseudocholinesterase inhibitor pseudocholinesterase inhibitors phosphoric ester CHEBI:26019 CHEBI:37734 chebi_ontology acyclic phosphorus acid anhydride CHEBI:37786 acyclic phosphorus acid anhydrides chebi_ontology amino sulfonic acid An organosulfonic acid containing one or more amino groups. CHEBI:37793 amino sulfonic acids aminosulfonic acid aminosulfonic acids chebi_ontology butane 0 58.078 58.12220 A straight chain alkane composed of 4 carbon atoms. Beilstein:969129 C4H10 CAS:106-97-8 CCCC CHEBI:22945 CHEBI:25462 CHEBI:37808 CHEBI:44430 E 943a E-943a E943a Gmelin:1148 IJDNQMDRQITEOD-UHFFFAOYSA-N InChI=1S/C4H10/c1-3-4-2/h3-4H2,1-2H3 N-BUTANE PDBeChem:NBU PMID:24179026 R-600 Reaxys:969129 Wikipedia:Butane butane chebi_ontology n-Butan n-C4H10 n-butane sulfuric acid derivative CHEBI:37826 chebi_ontology sulfuric acid derivative sulfuric acid derivatives carboacyl group A carboacyl group is a group formed by loss of at least one OH from the carboxy group of a carboxylic acid. CHEBI:37838 carboacyl groups carboxylic acyl group carboxylic acyl groups chebi_ontology growth hormone A hormone that specifically regulates growth. CAS:9002-72-6 CHEBI:37845 GH KEGG:C18181 Somatotropin Wachstumshormon chebi_ontology growth hormones plant hormone A plant growth regulator that modulates the formation of stems, leaves and flowers, as well as the development and ripening of fruit. The term includes endogenous and non-endogenous compounds (e.g. active compounds produced by bacteria on the leaf surface) as well as semi-synthetic and fully synthetic compounds. CHEBI:26158 CHEBI:37848 Wikipedia:Phytohormone chebi_ontology phytohormone phytohormones plant growth factor plant growth factors plant growth hormone plant growth hormones plant hormones octanol A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of eight carbon atoms. C8H18O CAS:29063-28-3 CHEBI:37868 Oktanol Oktylalkohol chebi_ontology n-octanol octanol octyl alcohol adrenergic agonist An agent that selectively binds to and activates adrenergic receptors. CHEBI:37886 adrenergic agonists adrenergic receptor agonist adrenoceptor agonists adrenomimetic adrenomimetics chebi_ontology adrenergic antagonist An agent that binds to but does not activate adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists. CHEBI:37887 adrenergic antagonists adrenergic blockaders adrenergic blocker adrenergic blockers adrenergic receptor blockaders adrenoceptor antagonists chebi_ontology alpha-adrenergic antagonist An agent that binds to but does not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma. CHEBI:37890 alpha-adrenergic antagonists alpha-adrenergic blocker alpha-adrenergic blockers alpha-adrenergic receptor blockaders alpha-adrenoceptor antagonists chebi_ontology H1-receptor antagonist CHEBI:37955 H1 antihistaminics H1 receptor antagonists H1 receptor blockaders H1-receptor antagonists H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. H1-receptor blocker H1-receptor blockers PMID:22035879 chebi_ontology classical antihistamines classical antihistaminics histamine antagonist CHEBI:37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. PMID:22035879 Wikipedia:Antihistamines antihistamine antihistamines antihistaminico antihistaminics chebi_ontology histamine receptor blocker histamine receptor blockers histaminergic drug CHEBI:37957 Drugs used for their actions on histaminergic systems. chebi_ontology histamine agents histamine drugs histaminergic agent histaminergic agents histaminergic drugs adrenergic agent Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter. CHEBI:37962 adrenergic agents adrenergic drug adrenergic drugs adrenergic neuron agents adrenergics chebi_ontology carbotricyclic compound A carbopolyclic compound comprising of three carbocyclic rings. CHEBI:38032 carbotricyclic compounds chebi_ontology antimalarial A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human. CHEBI:38068 antimalarials chebi_ontology anti-arrhythmia drug A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. CHEBI:38070 antiarrhythmic agent chebi_ontology polypyrrole A compound composed of two or more pyrrole units. Beilstein:8538310 CHEBI:38077 PPys chebi_ontology poly(pyrrole)s polypyrroles organonitrogen heterocyclic compound Any organonitrogen compound containing a cyclic component with nitrogen and at least one other element as ring member atoms. CHEBI:38101 chebi_ontology heterocyclic organonitrogen compounds organonitrogen heterocyclic compounds oxacycle Any organic heterocyclic compound containing at least one ring oxygen atom. CHEBI:38104 PMID:17134300 chebi_ontology heterocyclic organooxygen compounds organooxygen heterocyclic compounds oxacycles organosulfur heterocyclic compound CHEBI:38106 chebi_ontology heterocyclic organosulfur compounds organosulfur heterocyclic compounds cardiotonic drug A drug that has a strengthening effect on the heart or that can increase cardiac output. CHEBI:38147 cardiotonic drugs chebi_ontology chelator A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate. CHEBI:23090 CHEBI:3585 CHEBI:38161 CHEBI:6789 Chelating agent KEGG:C00917 KEGG:C02169 Metal chelator chebi_ontology chelating agents chelators complexon organic heteropolycyclic compound CHEBI:25429 CHEBI:38075 CHEBI:38166 chebi_ontology organic heteropolycyclic compounds monocyclic heteroarene CHEBI:38179 chebi_ontology monocyclic heteroarenes polycyclic heteroarene CHEBI:38180 chebi_ontology polycyclic heteroarenes hydrocarbyl anion CHEBI:38222 chebi_ontology pyrrolidines Any of a class of heterocyclic amines having a saturated five-membered ring. CHEBI:26922 CHEBI:38191 CHEBI:38260 chebi_ontology imidazolidines CHEBI:38261 chebi_ontology 2-amino-3-hydroxybutanoic acid 0 119.058 119.11920 2-amino-3-hydroxybutanoic acid AYFVYJQAPQTCCC-UHFFFAOYSA-N An alpha-amino acid that is butanoic acid substituted by an amino group at position 2 and a hydroxy group at position 3. Beilstein:1098902 C4H9NO3 CC(O)C(N)C(O)=O CHEBI:38263 InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8) chebi_ontology 2-amino-3-methylpentanoic acid 0 131.095 131.17296 2-amino-3-methylpentanoic acid A branched chain amino acid that consists of 3-methylpentanoic acid bearing an amino substituent at position 2. AGPKZVBTJJNPAG-UHFFFAOYSA-N C6H13NO2 CAS:443-79-8 CCC(C)C(N)C(O)=O CHEBI:38264 InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9) KEGG:C16434 PMID:10944265 Reaxys:1721790 chebi_ontology pyrrolidinone CHEBI:38275 chebi_ontology pyrrolidinones L-ascorbate (2R)-2-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate -1 175.024 175.11618 Ascorbate Beilstein:3549814 C6H7O6 CAS:299-36-5 CHEBI:13082 CHEBI:13861 CHEBI:38290 CIWBSHSKHKDKBQ-JLAZNSOCSA-M Gmelin:506552 InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/p-1/t2-,5+/m0/s1 KEGG:C00072 L-Ascorbate L-ascorbate L-ascorbate(1-) L-ascorbic acid, ion(1-) PMID:18450228 PMID:18678913 PMID:19162177 PMID:9506998 The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants. Vitamin C [H][C@@]1(OC(=O)C(O)=C1[O-])[C@@H](O)CO chebi_ontology diazolidine CHEBI:38304 chebi_ontology diazolidines imidazolyl carboxylic acid Any member of the class of imidazoles in which the imidazole ring is substituted by one (or more) carboxy group(s). CHEBI:38307 chebi_ontology imidazolyl carboxylic acids diazines Any organic heterocyclic compound containing a benzene ring in which two of the C-H fragments have been replaced by isolobal nitrogens (the diazine parent structure). CHEBI:38313 chebi_ontology pyrazines CHEBI:38314 chebi_ontology pyrimidinecarboxylate anion CHEBI:38316 chebi_ontology pyrimidinecarboxylate anions cholinergic drug Any drug used for its actions on cholinergic systems. Included here are agonists and antagonists, drugs that affect the life cycle of acetylcholine, and drugs that affect the survival of cholinergic neurons. CHEBI:38323 chebi_ontology cholinergic agent cholinergic drugs cholinomimetic cholinergic agonist Any drug that binds to and activates cholinergic receptors. CHEBI:38324 acetylcholine agonist acetylcholine agonists acetylcholine receptor agonist chebi_ontology cholinergic agonists cholinomimetic cholinomimetics muscarinic agonist Any drug that binds to and activates a muscarinic cholinergic receptor. CHEBI:38325 chebi_ontology muscarinic acetylcholine receptor agonist muscarinic agonists muscarinic cholinergic agonist muscarinic cholinergic agonists pyrimidone A pyrimidine carrying one or more oxo substituents. CHEBI:38337 chebi_ontology pyrimidones aminopyrimidine A member of the class of pyrimidines that is pyrimidine substituted by at least one amino group and its derivatives. CHEBI:38338 aminopyrimidines chebi_ontology trans-pent-2-enoic acid (2E)-2-pentenoic acid (2E)-pent-2-enoic acid (E)-2-pentenic acid (E)-2-pentenoic acid (E)-pent-2-en-1-oic acid 0 100.052 100.11582 5:1, n-3 trans A pent-3-enoic acid in trans- configuration. C5:1, n-3 trans C5H8O2 CAS:13991-37-2 CC\C=C\C(O)=O CHEBI:38366 E-2-Pentencarbonsaeure InChI=1S/C5H8O2/c1-2-3-4-5(6)7/h3-4H,2H2,1H3,(H,6,7)/b4-3+ LIPID_MAPS_instance:LMFA01030005 Pent-2t-ensaeure Reaxys:1720312 YIYBQIKDCADOSF-ONEGZZNKSA-N chebi_ontology trans-2-pentenic acid trans-2-pentenoic acid trans-Pent-2-ensaeure trans-alpha,beta-penteneoic acid 1,3-thiazoles 1,3-thiazoles CHEBI:26949 CHEBI:38417 CHEBI:38418 chebi_ontology 1-benzopyran 1-benzopyrans CHEBI:38443 chebi_ontology carbamate insecticide CHEBI:38461 Derivatives of carbamic acid with insecticidal properties of general formula ROC(=O)NR(1)R(2), where ROH is an alcohol, oxime, or phenol and R(1) is hydrogen or methyl. Like organophosphate insecticides, they are cholinesterase inhibitors, but carbamate insecticides differ in action from the organophosphates in that the inhibitory effect on cholinesterase is generally brief. carbamate insecticides chebi_ontology EC 3.1.1.7 (acetylcholinesterase) inhibitor AChEI AcCholE inhibitor AcCholE inhibitors An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid. CHEBI:38462 EC 3.1.1.7 (acetylcholinesterase) inhibitors EC 3.1.1.7 inhibitor EC 3.1.1.7 inhibitors Wikipedia:Acetylcholinesterase_inhibitor acetyl.beta-methylcholinesterase inhibitor acetyl.beta-methylcholinesterase inhibitors acetylcholine acetylhydrolase inhibitor acetylcholine acetylhydrolase inhibitors acetylcholine esterase inhibitor acetylcholine hydrolase inhibitor acetylcholine hydrolase inhibitors acetylcholinesterase (EC 3.1.1.7) inhibitor acetylcholinesterase (EC 3.1.1.7) inhibitors acetylcholinesterase inhibitor acetylcholinesterase inhibitors acetylthiocholinesterase inhibitor acetylthiocholinesterase inhibitors chebi_ontology choline esterase I inhibitor choline esterase I inhibitors cholinesterase inhibitor cholinesterase inhibitors true cholinesterase inhibitor true cholinesterase inhibitors imidazolyl carboxylic acid anion A monocarboxylic acid anion resulting from the deprotonation of the carboxy group of an imidazolyl carboxylic acid. CHEBI:38466 chebi_ontology imidazolyl carboxylic acid anions electron-transport chain inhibitor CHEBI:38496 chebi_ontology respiratory-chain inhibitor CHEBI:38497 chebi_ontology isoquinoline alkaloid fundamental parent CHEBI:38515 chebi_ontology isoquinoline alkaloid fundamental parents 1-(methylsulfanyl)acetaldoxime 0 1-(Methylthio)acetaldehyde oxime 1-(Methylthio)acetaldoxime 105.025 105.15982 Beilstein:1901214 C3H7NOS CAS:13749-94-5 CHEBI:38534 CSC(C)=NO InChI=1S/C3H7NOS/c1-3(4-5)6-2/h5H,1-2H3 Methomyl oxime Methyl N-hydroxyacetimidothioate Methyl N-hydroxyethanimidothioate Methyl thioacetohydroxamate TYEVWCPZVQACAE-UHFFFAOYSA-N chebi_ontology methyl N-hydroxyethanimidothioate simple protein CHEBI:38560 chebi_ontology simple proteins diazine C4H4N2 CHEBI:38627 Diazin The parent structure of the diazines. chebi_ontology aminoalkylindole CHEBI:22503 CHEBI:24792 CHEBI:38631 aminoalkylindoles chebi_ontology membrane transport modulator Any agent that affects the transport of molecular entities across a biological membrane. CHEBI:38632 chebi_ontology membrane transport modulators organic sodium salt CHEBI:38700 chebi_ontology organic sodium salt organic sodium salts inorganic sodium salt CHEBI:38702 chebi_ontology inorganic sodium salts carboxylic acid dianion Any dianion containing at least one carboxy group. CHEBI:38716 carboxylic acid dianion carboxylic acid dianions chebi_ontology carboxylic acid trianion A trianion containing at least one carboxy group. CHEBI:38717 carboxylic acid trianion carboxylic acid trianions chebi_ontology pteroate C14H11N6O3 CHEBI:37074 CHEBI:38793 chebi_ontology pteroic acid C14H12N6O3 CAS:119-24-4 CHEBI:26378 CHEBI:38794 DrugBank:DB04196 Pteroic acid Pteroinsaeure chebi_ontology pteroic acids CHEBI:38795 chebi_ontology pteroates CHEBI:38796 chebi_ontology calcium channel agonist Agents that increase calcium influx into calcium channels of excitable tissues. CHEBI:38807 calcium channel activator calcium channel activators calcium channel agonists chebi_ontology calcium channel modulator A membrane transport modulator that is able to regulate intracellular calcium levels. CHEBI:38808 calcium channel modulators chebi_ontology ryanodine receptor modulator CHEBI:38809 RyR modulator chebi_ontology ryanodine receptor modulators ryanodine-sensitive calcium channel modulator ryanodine-sensitive calcium-release channel modulator fluorocarbon CHEBI:38824 Compounds consisting wholly of fluorine and carbon. chebi_ontology fluorocarbon fluorocarbons fluorocarbons tetrafluoromethane 0 87.994 88.00431 Beilstein:1697288 CAS:75-73-0 CF4 CF4 CHEBI:38825 FC(F)(F)F Freon 14 Gmelin:2016 Halon 14 InChI=1S/CF4/c2-1(3,4)5 TXEYQDLBPFQVAA-UHFFFAOYSA-N Tetrafluorkohlenstoff Tetrafluormethan carbon tetrafluoride chebi_ontology perfluoromethane tetrafluoridocarbon tetrafluorocarbon tetrafluoromethane halophenol CHEBI:38856 chebi_ontology halophenol halophenols anaesthetic Anaesthetika Anaesthetikum CHEBI:38867 Substance which produces loss of feeling or sensation. anaesthetic anaesthetics anesthetic agent anesthetic drug anesthetics chebi_ontology general anaesthetic Allgemeinanaesthetika Allgemeinanaesthetikum CHEBI:38869 Substance that produces loss of consciousness. chebi_ontology general anaesthetic general anaesthetics general anesthetics inhalation anaesthetic CHEBI:38870 Inhalationsanaesthetika Inhalationsanaesthetikum Inhalationsnarkotika Inhalationsnarkotikum anesthetic gases chebi_ontology inhalation anesthetics corticotropin 0 4538.259 4541.06600 A polypeptide hormone produced and secreted by the pituitary gland comprising 39 amino acid residues coupled in a linear sequence. The N-terminal 24-amino acid segment is identical in all species and contains the adrenocorticotrophic activity. Corticotropin stimulates the cortex of the adrenal gland and boosts the synthesis of corticosteroids, mainly glucocorticoids but also sex steroids (androgens). It is used in the treatment of certain neurological disorders such as infantile spasms and multiple sclerosis, and diagnostically to investigate adrenocortical insufficiency. ACTH Adrenocorticotropic hormone C207H308N56O58S CAS:9002-60-2 CHEBI:3892 CSCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](N)CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](Cc1ccccc1)C(O)=O Corticotropin DrugBank:DB01285 Drug_Central:4931 IDLFZVILOHSSID-OVLDLUHVSA-N InChI=1S/C207H308N56O58S/c1-108(2)89-140(186(302)240-135(69-74-163(279)280)182(298)254-149(204(320)321)94-117-43-20-15-21-44-117)250-193(309)152-54-35-86-262(152)202(318)147(92-116-41-18-14-19-42-116)252-171(287)114(11)230-175(291)132(66-71-160(273)274)234-170(286)113(10)231-191(307)150(105-265)255-183(299)136(70-75-164(281)282)241-190(306)146(98-165(283)284)249-180(296)133(67-72-161(275)276)235-169(285)112(9)229-157(270)101-225-174(290)145(97-156(213)269)251-194(310)153-55-36-87-263(153)203(319)148(93-119-60-64-123(268)65-61-119)253-199(315)167(110(5)6)257-185(301)129(49-26-30-79-210)243-198(314)168(111(7)8)259-196(312)155-57-38-85-261(155)201(317)139(53-34-83-223-207(218)219)244-178(294)130(51-32-81-221-205(214)215)237-177(293)128(48-25-29-78-209)236-176(292)127(47-24-28-77-208)232-158(271)103-227-197(313)166(109(3)4)258-195(311)154-56-37-84-260(154)200(316)138(50-27-31-80-211)233-159(272)102-226-173(289)143(95-120-99-224-126-46-23-22-45-124(120)126)247-179(295)131(52-33-82-222-206(216)217)238-187(303)142(90-115-39-16-13-17-40-115)246-189(305)144(96-121-100-220-107-228-121)248-181(297)134(68-73-162(277)278)239-184(300)137(76-88-322-12)242-192(308)151(106-266)256-188(304)141(245-172(288)125(212)104-264)91-118-58-62-122(267)63-59-118/h13-23,39-46,58-65,99-100,107-114,125,127-155,166-168,224,264-268H,24-38,47-57,66-98,101-106,208-212H2,1-12H3,(H2,213,269)(H,220,228)(H,225,290)(H,226,289)(H,227,313)(H,229,270)(H,230,291)(H,231,307)(H,232,271)(H,233,272)(H,234,286)(H,235,285)(H,236,292)(H,237,293)(H,238,303)(H,239,300)(H,240,302)(H,241,306)(H,242,308)(H,243,314)(H,244,294)(H,245,288)(H,246,305)(H,247,295)(H,248,297)(H,249,296)(H,250,309)(H,251,310)(H,252,287)(H,253,315)(H,254,298)(H,255,299)(H,256,304)(H,257,301)(H,258,311)(H,259,312)(H,273,274)(H,275,276)(H,277,278)(H,279,280)(H,281,282)(H,283,284)(H,320,321)(H4,214,215,221)(H4,216,217,222)(H4,218,219,223)/t112-,113-,114-,125-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,142-,143-,144-,145-,146-,147-,148-,149-,150-,151-,152-,153-,154-,155-,166-,167-,168-/m0/s1 KEGG:C02017 KEGG:D00146 L-seryl-L-tyrosyl-L-seryl-L-methionyl-L-alpha-glutamyl-L-histidyl-L-phenylalanyl-L-arginyl-L-tryptophylglycyl-L-lysyl-L-prolyl-L-valylglycyl-L-lysyl-L-lysyl-L-arginyl-L-arginyl-L-prolyl-L-valyl-L-lysyl-L-valyl-L-tyrosyl-L-prolyl-L-alpha-aspartylglycyl-L-alanyl-L-alpha-glutamyl-L-alpha-aspartyl-L-alpha-glutamyl-L-seryl-L-alanyl-L-alpha-glutamyl-L-alanyl-L-phenylalanyl-L-prolyl-L-leucyl-L-alpha-glutamyl-L-phenylalanine SYSMEHFRWGKPVGKKRRPVKVYPDGAEDQLAEAFPLEF adrenocorticotropin chebi_ontology corticotrofina corticotrophine corticotrophinum corticotropin cortrophin indole alkaloid An alkaloid containing an indole skeleton. CHEBI:24795 CHEBI:38958 CHEBI:5901 Indole alkaloid KEGG:C06073 Wikipedia:Indole_alkaloid chebi_ontology indole alkaloids methylbenzene Any alkylbenzene that is benzene substituted with one or more methyl groups. CHEBI:38975 chebi_ontology methylbenzenes alkylbenzene A monocyclic arene that is benzene substituted with one or more alkyl groups. Alkylbenzol CHEBI:38976 alkylbenzene alkylbenzenes chebi_ontology apolipoprotein CHEBI:39015 Protein component on the surface of lipoprotein. apolipoproteins chebi_ontology inclusion compound A complex in which one component (the host) forms a cavity or, in the case of a crystal, a crystal lattice containing spaces in the shape of long tunnels or channels in which molecular entities of a second chemical species (the guest) are located. There is no covalent bonding between guest and host, the attraction being generally due to van der Waals forces. CHEBI:39022 chebi_ontology compose d'inclusion compuesto de inclusion compuestos de inclusion inclusion complex inclusion compound inclusion compounds clathrate compound CHEBI:39024 Clathrat Clathratverbindung Inclusion compound in which the guest molecule is in a cage formed by the host molecule or by a lattice of host molecules. Klathrat Klathratverbindung cage compound chebi_ontology clathrate clathrate compounds clathrates clatrato clatratos compuesto de clatrato low-density lipoprotein A class of lipoproteins of small size (18-25 nm) and low density (1.019-1.063 g/ml) particles with a core composed mainly of cholesterol esters and smaller amounts of triglycerides. The surface monolayer consists mostly of phospholipids, a single copy of apolipoprotein B-100, and free cholesterol molecules. The main function of LDL is to transport cholesterol and cholesterol esters from the liver. Excessive levels are associated with cardiovascular disease. CHEBI:39026 LDL PMID:11082530 PMID:15583011 PMID:15913955 PMID:19349632 PMID:28401639 PMID:28432662 PMID:28792690 PMID:28827781 PMID:28847800 PMID:28859941 PMID:28870972 Wikipedia:Low-density_lipoprotein beta-lipoproteins chebi_ontology low-density lipoproteins calcium cation CHEBI:39123 Ca calcium cation calcium cations chebi_ontology calcium ion CHEBI:39124 Ca calcium ion calcium ions chebi_ontology Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). Bronsted acid Bronsted-Saeure CHEBI:39141 acide de Bronsted chebi_ontology donneur d'hydron hydron donor Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). Bronsted base Bronsted-Base CHEBI:39142 accepteur d'hydron base de Bronsted chebi_ontology hydron acceptor Lewis base A molecular entity able to provide a pair of electrons and thus capable of forming a covalent bond with an electron-pair acceptor (Lewis acid), thereby producing a Lewis adduct. CHEBI:39144 Lewis base Lewis-Base base de Lewis chebi_ontology donneur d'une paire d'electrons electron donor 4-oxopentanoate -1 115.040 115.10728 3-acetylpropionate 4-ketovalerate 4-oxopentanoate 4-oxovalerate A member of the class of oxopentanoates that is the conjugate base of 4-oxopentanoic acid. Beilstein:3537533 C5H7O3 CC(=O)CCC([O-])=O CHEBI:39150 Gmelin:325844 InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)/p-1 JOOXCMJARBKPKM-UHFFFAOYSA-M Reaxys:3537533 beta-acetylpropionate chebi_ontology gamma-ketovalerate laevulinate levulate levulinate (R)-nicotine (+)-nicotine (R)-3-(1-methyl-2-pyrrolidinyl)pyridine 0 162.116 162.23160 3-[(2R)-1-methylpyrrolidin-2-yl]pyridine A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has R-configuration. Beilstein:4666243 Beilstein:82110 C10H14N2 CAS:25162-00-9 CHEBI:39162 CN1CCC[C@@H]1c1cccnc1 InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-/m1/s1 KEGG:C16386 SNICXCGAKADSCV-SNVBAGLBSA-N chebi_ontology d-nicotine pseudonicotine halomethane A haloalkane that is methane in which one (or more) of the hydrogens have been replaced by a halogen atom/halogen atoms. CHEBI:39279 chebi_ontology halomethane halomethanes fluoromethanes A halomethane that is methane in which one or more hydrogens has been replaced by fluorine. CHEBI:39281 chebi_ontology growth regulator Any chemical substance that inhibits the life-cycle of an organism. CHEBI:39317 chebi_ontology growth regulators branched-chain saturated fatty acid Any saturated fatty acid with a carbon side-chain or isopropyl termination. CHEBI:39417 branched saturated fatty acid branched saturated fatty acids branched-chain saturated fatty acid branched-chain saturated fatty acids chebi_ontology straight-chain saturated fatty acid Any saturated fatty acid lacking a side-chain. CHEBI:39418 PMID:15644336 chebi_ontology straight-chain saturated fatty acid straight-chain saturated fatty acids tocol 2-methyl-2-phytyl-6-chromanol A chromanol with a chroman-6-ol skeleton that is substituted at position 2 by a saturated or triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. CAS:119-98-2 CHEBI:27010 CHEBI:27011 CHEBI:39437 Reaxys:1436460 chebi_ontology tocols pyrimidines Any compound having a pyrimidine as part of its structure. CHEBI:13681 CHEBI:26448 CHEBI:39447 chebi_ontology dihydrogenphosphate -1 96.969 96.98724 A monovalent inorganic anion that consists of phosphoric acid in which one of the three OH groups has been deprotonated. CHEBI:29137 CHEBI:39739 CHEBI:39745 DIHYDROGENPHOSPHATE ION DrugBank:DB02831 Gmelin:1999 H2O4P H2PO4(-) InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-1 NBIIXXVUZAFLBC-UHFFFAOYSA-M PDBeChem:2HP [H]OP([O-])(=O)O[H] [PO2(OH)2](-) chebi_ontology dihydrogen(tetraoxidophosphate)(1-) dihydrogenphosphate dihydrogentetraoxophosphate(1-) dihydrogentetraoxophosphate(V) dihydroxidodioxidophosphate(1-) methoxyethane 0 1-methoxyethane 60.058 60.09500 Aethylmethylaether An ether that is the methyl ether derivative of ethanol. Beilstein:1730785 C2H5OCH3 C3H8O CAS:540-67-0 CCOC CHEBI:39832 Gmelin:163978 InChI=1S/C3H8O/c1-3-4-2/h3H2,1-2H3 METHOXYETHANE Methoxyethan Methylaethylaether PDBeChem:2ME PMID:12662033 Patent:KR20080019002 Reaxys:1730785 Wikipedia:Methoxyethane XOBKSJJDNFUZPF-UHFFFAOYSA-N chebi_ontology methoxyethane methyl ethyl ether cyclic ketone CHEBI:3992 Cyclic ketone KEGG:C02019 chebi_ontology cyclic ketones fluoroform 0 70.003 70.01385 Beilstein:1731035 CAS:75-46-7 CHEBI:24073 CHEBI:41543 CHEBI:41550 CHF3 CHF3 Freon 23 Freon F-23 Gmelin:1543 InChI=1S/CHF3/c2-1(3)4/h1H PDBeChem:CFT TRIFLUOROMETHANE UM-BBD_compID:c0802 XPDWGBQVDMORPB-UHFFFAOYSA-N [H]C(F)(F)F carbon trifluoride chebi_ontology fluoroform methyl trifluoride carbonate -2 59.985 60.00890 BVKZGUZCCUSVTD-UHFFFAOYSA-L Beilstein:3600898 CARBONATE ION CAS:3812-32-6 CHEBI:29201 CHEBI:41605 CHEBI:41609 CO3 CO3(2-) Gmelin:1559 InChI=1S/CH2O3/c2-1(3)4/h(H2,2,3,4)/p-2 Karbonat PDBeChem:CO3 [CO3](2-) [O-]C([O-])=O carbonate chebi_ontology trioxidocarbonate(2-) D-hexose A hexose that has D-configuration at position 5. C6H12O6 CHEBI:4194 D-Hexose D-hexopyranose D-hexose D-hexoses KEGG:C00738 chebi_ontology (3,4-dihydroxyphenyl)acetic acid (3,4-dihydroxyphenyl)acetic acid 0 168.042 168.14672 2-(3,4-DIHYDROXYPHENYL)ACETIC ACID 3,4-Dihydroxyphenyl acetic acid 3,4-Dihydroxyphenylacetic acid 3,4-dihydroxyphenylacetic acid A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine. Beilstein:2211017 C8H8O4 CAS:102-32-9 CFFZDZCDUFSOFZ-UHFFFAOYSA-N CHEBI:1386 CHEBI:41936 CHEBI:41941 DrugBank:DB01702 Gmelin:874810 HMDB:HMDB0001336 InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) KEGG:C01161 OC(=O)Cc1ccc(O)c(O)c1 PDBeChem:DHY PMID:11251641 PMID:11681538 PMID:11868042 PMID:15212971 PMID:15862791 PMID:18706927 PMID:19191673 PMID:22770225 PMID:4420192 Reaxys:2211017 Wikipedia:DOPAC chebi_ontology dopacetic acid homoprotocatechuic acid L-threitol (2S,3S)-butane-1,2,3,4-tetrol 0 122.058 122.11980 Beilstein:1719754 Beilstein:4652748 Beilstein:5725953 C4H10O4 CHEBI:42090 D-TREITOL DrugBank:DB03278 Gmelin:1971390 InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4-/m0/s1 L-threitol L-threo-tetritol OC[C@H](O)[C@@H](O)CO PDBeChem:DTL PMID:15639248 PMID:16671745 PMID:16901854 PMID:7925706 Reaxys:1719754 The L-enantiomer of threitol. UNXHWFMMPAWVPI-IMJSIDKUSA-N chebi_ontology (R)-lactic acid (-)-lactic acid (2R)-2-hydroxypropanoic acid (R)-(-)-lactic acid 0 90.032 90.07794 An optically active form of lactic acid having (R)-configuration. Beilstein:1720252 C3H6O3 CAS:10326-41-7 CHEBI:341 CHEBI:42105 CHEBI:42111 CHEBI:43701 C[C@@H](O)C(O)=O D-2-Hydroxypropanoic acid D-2-Hydroxypropionic acid D-Lactic acid D-Milchsaeure D-lactic acid DrugBank:DB03066 DrugBank:DB04398 Gmelin:362718 HMDB:HMDB0001311 InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1 JVTAAEKCZFNVCJ-UWTATZPHSA-N KEGG:C00256 KNApSAcK:C00019549 LACTIC ACID PDBeChem:LAC PMID:21842515 PMID:22127808 PMID:22277286 PMID:22344644 Reaxys:1720252 Wikipedia:Lactic_acid chebi_ontology (S)-lactic acid (+)-lactic acid (2S)-2-hydroxypropanoic acid (S)-(+)-lactic acid (S)-2-hydroxypropanoic acid (S)-2-hydroxypropionic acid 0 90.032 90.07794 An optically active form of lactic acid having (S)-configuration. Beilstein:1720251 C3H6O3 CAS:79-33-4 CHEBI:422 C[C@H](O)C(O)=O Gmelin:362717 HMDB:HMDB0000190 InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1 JVTAAEKCZFNVCJ-REOHCLBHSA-N KEGG:C00186 KNApSAcK:C00001191 L-(+)-alpha-hydroxypropionic acid L-(+)-lactic acid L-Lactic acid L-Milchsaeure PMID:21996028 PMID:22336740 PMID:22367529 PMID:22424924 PMID:22443585 PMID:22461545 PMID:22534372 PMID:22538963 PMID:22578598 Reaxys:1720251 Wikipedia:Lactic_Acid chebi_ontology formyl group -CH(O) -CHO 0 29.003 29.01804 CHEBI:24089 CHEBI:42480 CHEBI:42485 CHO FORMYL GROUP Fo H-CO- PDBeChem:FOR aldehyde group carbaldehyde chebi_ontology formyl methanoyl 1,1-dimethyl-4-phenylpiperazinium iodide 0 1,1-Dimethyl-4-phenylpiperazine iodide 1,1-Dimethyl-4-phenylpiperazinium Iodide 1,1-dimethyl-4-phenylpiperazinium iodide 318.059 318.19721 Beilstein:3746109 C12H19N2.I CAS:54-77-3 CHEBI:4290 DMPP DMPP iodide Dimethylphenylpiperazinium iodide InChI=1S/C12H19N2.HI/c1-14(2)10-8-13(9-11-14)12-6-4-3-5-7-12;/h3-7H,8-11H2,1-2H3;1H/q+1;/p-1 KEGG:C07488 N,N-Dimethyl-N'-phenylpiperazinium iodide XFZJGFIKQCCLGK-UHFFFAOYSA-M [I-].C[N+]1(C)CCN(CC1)c1ccccc1 chebi_ontology hydroxy group -OH 0 17.003 17.00734 CHEBI:24706 CHEBI:43171 CHEBI:43176 HO HYDROXY GROUP PDBeChem:HYD chebi_ontology hydroxy hydroxy group hydroxyl hydroxyl group oxidanyl (4S)-4-hydroxy-3,4-dihydropyrimidin-2(1H)-one CHEBI:43254 chebi_ontology hydrogen iodide 0 127.912 127.91241 A diatomic molecule containing covalently bonded hydrogen and iodine atoms. CAS:10034-85-2 CHEBI:43451 CHEBI:5591 Gmelin:814 HI HI Hydrogen iodide Hydrogeniodid Hydroiodic acid I[H] InChI=1S/HI/h1H Iodwasserstoff Jodwasserstoff KEGG:C05590 Wasserstoffiodid XMBWDFGMSWQBCA-UHFFFAOYSA-N [HI] chebi_ontology hydriodic acid hydrogen iodide hydroiodic acid iodane iodidohydrogen iodure d'hydrogene hydrogenphosphate -2 95.961 95.97930 A phosphate ion that is the conjugate base of dihydrogenphosphate. CHEBI:29139 CHEBI:43470 CHEBI:43474 Gmelin:1998 HO4P HPO4(2-) HYDROGENPHOSPHATE ION INORGANIC PHOSPHATE GROUP InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-2 MolBase:1628 NBIIXXVUZAFLBC-UHFFFAOYSA-L OP([O-])([O-])=O PDBeChem:IPS PDBeChem:PI [P(OH)O3](2-) [PO3(OH)](2-) chebi_ontology hydrogen phosphate hydrogen(tetraoxidophosphate)(2-) hydrogenphosphate hydrogentetraoxophosphate(2-) hydrogentetraoxophosphate(V) hydroxidotrioxidophosphate(2-) phosphate butan-1-amine 0 1-Aminobutan 1-aminobutane 1-butanamine 1-butylamine 73.089 73.13680 A primary aliphatic amine that is butane substituted by an amino group at position 1. BUTYLAMINE Beilstein:605269 C4H11N CAS:109-73-9 CCCCN CHEBI:43799 DrugBank:DB03659 Gmelin:1784 HQABUPZFAYXKJW-UHFFFAOYSA-N InChI=1S/C4H11N/c1-2-3-4-5/h2-5H2,1H3 MetaCyc:BUTYLAMINE PDBeChem:LYT PMID:16387436 PMID:23470444 PMID:23734590 Reaxys:605269 Wikipedia:N-Butylamine butan-1-amine butanamine butylamine chebi_ontology mono-n-butylamine monobutylamine n-Butylamin n-C4H9NH2 n-butylamine dermatan (C14H21NO11)n 0 A mucopolysaccharide consisting of repeating beta-(1->4)-linked L-iduronyl-(beta1->3)-N-acetyl-D-galactosamine units. CHEBI:4439 Dermatan Dermatan L-iduronate KEGG:C01490 chebi_ontology diphosphate(2-) -2 175.928 175.95920 A divalent inorganic anion obtained by removal of both protons from diphosphoric acid. CHEBI:33018 CHEBI:45208 CHEBI:45212 DrugBank:DB02212 Gmelin:185085 H2O7P2 H2P2O7(2-) InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-2 OP([O-])(=O)OP(O)([O-])=O PDBeChem:POP PYROPHOSPHATE 2- XPPKVPWEQAFLFU-UHFFFAOYSA-L chebi_ontology dihydrogen diphosphate methylcarbamic acid 0 75.032 75.06664 An amino acid consisting of carbamic acid having an N-methyl substituent. Beilstein:1738994 C2H5NO2 CAS:6414-57-9 CHEBI:38464 CHEBI:45374 CHEBI:45379 CNC(O)=O InChI=1S/C2H5NO2/c1-3-2(4)5/h3H,1H3,(H,4,5) Methylcarbamidsaeure Monomethyl carbamate N-Methylcarbamate N-methylcarbamic acid PDBeChem:RGI Reaxys:1738994 UFEJKYYYVXYMMS-UHFFFAOYSA-N chebi_ontology methylcarbamic acid 13-cis-retinol (13cis)-retinol (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol 0 13-cis-retinol 286.230 286.45160 Beilstein:1913943 C20H30O CAS:2052-63-3 CC(\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C)=C\CO CHEBI:45479 FPIPGXGPPPQFEQ-HWCYFHEPSA-N InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13- LIPID_MAPS_instance:LMPR01090011 PDBeChem:RTL RETINOL chebi_ontology sec-butyl group -CH(CH3)-CH2-CH3 0 1-methylpropyl 57.070 57.11426 C4H9 CH3-CH2-CH(CH3)- CHEBI:30352 CHEBI:45554 CHEBI:45557 PDBeChem:SBU SEC-BUTYL GROUP but-2-yl butan-2-ido butan-2-yl chebi_ontology isoleucine side-chain s-butyl sec-butyl ADP(3-) -3 424.006 424.17730 5'-O-[(phosphonatooxy)phosphinato]adenosine A nucleoside 5'-diphosphate(3-) arising from deprotonation of all three diphosphate OH groups of adenosine 5'-diphosphate (ADP); major species present at pH 7.3. ADP ADP trianion Beilstein:3783669 C10H12N5O10P2 CHEBI:456216 Gmelin:341336 InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/p-3/t4-,6-,7-,10-/m1/s1 Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-K adenosine 5'-diphosphate chebi_ontology 4-oxopentanoic acid 0 116.047 116.11522 3-acetylpropionic acid 3-ketobutane-1-carboxylic acid 4-ketovaleric acid 4-oxopentanoic acid 4-oxovaleric acid An oxopentanoic acid with the oxo group in the 4-position. Beilstein:506796 C5H8O3 CAS:123-76-2 CC(=O)CCC(O)=O CHEBI:39149 CHEBI:45628 CHEBI:45630 DrugBank:DB02239 Gmelin:164703 HMDB:HMDB0000720 InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8) JOOXCMJARBKPKM-UHFFFAOYSA-N LAEVULINIC ACID LEVA LIPID_MAPS_instance:LMFA01060006 Laevulinsaeure Levulinsaeure PDBeChem:SHF PMID:13215009 PMID:16662002 PMID:19246769 PMID:23627123 Reaxys:506796 Wikipedia:Levulinic_acid beta-acetylpropionic acid chebi_ontology gamma-ketovaleric acid levulic acid levulinic acid hydrogensulfate -1 96.960 97.07154 CHEBI:29199 CHEBI:45693 CHEBI:45696 Gmelin:2121 HO4S HSO4(-) HYDROGEN SULFATE InChI=1S/H2O4S/c1-5(2,3)4/h(H2,1,2,3,4)/p-1 PDBeChem:SOH QAOWNCQODCNURD-UHFFFAOYSA-M [H]OS([O-])(=O)=O [SO3(OH)](-) chebi_ontology hydrogen(tetraoxidosulfate)(1-) hydrogensulfate hydrogensulfate(1-) hydrogentetraoxosulfate(1-) hydrogentetraoxosulfate(VI) hydroxidotrioxidosulfate(1-) 5-fluorouracil 0 130.018 130.07730 5-FU 5-Fluoracil 5-Fluoropyrimidine-2,4-dione 5-Fluorouracil 5-fluoropyrimidine-2,4(1H,3H)-dione 5-fluorouracil A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth. Beilstein:127172 C4H3FN2O2 CAS:51-21-8 CHEBI:2054 CHEBI:46343 CHEBI:46345 DrugBank:DB00544 Drug_Central:26 Fc1c[nH]c(=O)[nH]c1=O Fluorouracil GHASVSINZRGABV-UHFFFAOYSA-N HMDB:HMDB0014684 InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9) KEGG:C07649 KEGG:D00584 LINCS:LSM-4261 PDBeChem:URF PMID:11356943 PMID:12520460 PMID:14769231 PMID:19023200 Reaxys:127172 Wikipedia:Fluorouracil chebi_ontology fluorouracil fluorouracilo fluorouracilum oxo group 0 15.995 15.99940 =O CHEBI:29353 CHEBI:44607 CHEBI:46629 O OXO GROUP PDBeChem:OXO chebi_ontology oxo diketone A compound that contains two ketone functionalities. CHEBI:46640 Wikipedia:Diketone chebi_ontology diketones mineral CHEBI:46662 In general, a mineral is a chemical substance that is normally crystalline formed and has been formed as a result of geological processes. The term also includes metamict substances (naturally occurring, formerly crystalline substances whose crystallinity has been destroyed by ionising radiation) and can include naturally occurring amorphous substances that have never been crystalline ('mineraloids') such as georgite and calciouranoite as well as substances formed by the action of geological processes on bigenic compounds ('biogenic minerals'). Minerale chebi_ontology mineral minerales minerals mineraux fluorohydrocarbon A compound derived from a hydrocarbon by replacing one or more hydrogen atoms with fluorine atoms. CHEBI:46695 FKW Fluorkohlenwasserstoffe HFC chebi_ontology fluorohydrocarbons pyrrolidinemonocarboxylic acid CHEBI:46701 chebi_ontology pyrrolidinemonocarboxylic acids carbonate salt CHEBI:46721 carbonate salts chebi_ontology phosphate mineral CHEBI:46723 chebi_ontology phosphate minerals dipeptide Any molecule that contains two amino-acid residues connected by peptide linkages. C4H6N2O3R2 CHEBI:23835 CHEBI:4634 CHEBI:46761 Dipeptid Dipeptide KEGG:C00107 chebi_ontology dipeptides pyrrolidinecarboxylic acid CHEBI:46767 chebi_ontology pyrrolidinecarboxylic acids hydroxypyrrolidine CHEBI:46773 chebi_ontology hydroxypyrrolidines N-alkylpyrrolidine CHEBI:46775 N-alkylpyrrolidines chebi_ontology solvent A liquid that can dissolve other substances (solutes) without any change in their chemical composition. CHEBI:46787 Loesungsmittel Wikipedia:Solvent chebi_ontology solvant solvents ethanethioic O-acid 0 75.998 76.11856 Beilstein:1733298 C2H4OS CC(O)=S CHEBI:46800 DUYAAUVXQSMXQP-UHFFFAOYSA-N Gmelin:1216872 InChI=1S/C2H4OS/c1-2(3)4/h1H3,(H,3,4) chebi_ontology ethanethioic O-acid urate anion An organic anion obtained by removal of at least one proton from any uric acid. CHEBI:46818 chebi_ontology urate anion urate salt CHEBI:46819 chebi_ontology sarcosinium +1 90.056 90.10116 An alpha-amino-acid cation that is the conjugate acid of sarcosine, arising from protonation of the amino group. C3H8NO2 CHEBI:46842 FSYKKLYZXJSNPZ-UHFFFAOYSA-O Gmelin:323778 InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6)/p+1 [H][N+]([H])(C)CC(O)=O carboxy-N-methylmethanaminium chebi_ontology N-arylpiperazine CHEBI:46848 N-arylpiperazines chebi_ontology piperazinium salt CHEBI:46849 chebi_ontology piperazinium salts organoammonium salt CHEBI:46850 chebi_ontology organoammonium salts carboxy group -C(O)OH -CO2H -COOH 0 44.998 45.01744 CARBOXY GROUP CHEBI:23025 CHEBI:41420 CHEBI:46883 CHO2 PDBeChem:CBX carboxy carboxyl group chebi_ontology oxalate(1-) -1 88.987 89.02694 A dicarboxylic acid monoanion that is the conjugate base of oxalic acid. Beilstein:3601755 C2HO4 CHEBI:46904 Gmelin:49515 Hox InChI=1S/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6)/p-1 MUBZPKHOEPUJKR-UHFFFAOYSA-M OC(=O)C([O-])=O carboxyformate chebi_ontology hydrogen ethanedioate hydrogen oxalate ornithinium(1+) +1 133.098 133.16900 2,5-diammoniopentanoate AHLPHDHHMVZTML-UHFFFAOYSA-O C5H13N2O2 CHEBI:46912 InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/p+1 [NH3+]CCCC([NH3+])C([O-])=O chebi_ontology ornithine ornithine monocation ornithinium ornithinium(1+) ornithinium(2+) +2 1-carboxybutane-1,4-diaminium 134.106 134.17694 AHLPHDHHMVZTML-UHFFFAOYSA-P C5H14N2O2 CHEBI:46913 InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/p+2 [NH3+]CCCC([NH3+])C(O)=O chebi_ontology ornithine dication ornithinediium ornithinium(2+) sarcosinate (methylamino)acetate -1 88.040 88.08528 An alpha-amino-acid anion that is the conjugate base of sarcosine, arising from deprotonation of the carboxy group. Beilstein:3536300 C3H6NO2 CHEBI:46915 CNCC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-M Gmelin:81987 InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6)/p-1 Reaxys:3536300 chebi_ontology sarcosinate 2-aminooctadecene-1,3-diol 2-aminooctadecene-1,3-diol 2-aminooctadecene-1,3-diols An aminodiol composed of any octadecene having hydroxy functional groups at positions 1 and 3 and an amino substituent at position 2. C18H37NO2 CHEBI:46963 chebi_ontology 2-aminooctadec-4-ene-1,3-diol 0 2-aminooctadec-4-ene-1,3-diol 2-aminooctadec-4-ene-1,3-diols 299.282 299.49192 A 2-aminooctadecene-1,3-diol having its double bond at position 4. C18H37NO2 CHEBI:46964 InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3 WWUZIQQURGPMPG-UHFFFAOYSA-N [H]C(CCCCCCCCCCCCC)=C([H])C(O)C(N)CO chebi_ontology (2R,3S)-2-aminooctadec-4-ene-1,3-diol (2R,3S)-2-aminooctadec-4-ene-1,3-diol 0 299.282 299.49192 A 2-aminooctadec-4-ene-1,3-diol having (2R,3S)-configuration. Beilstein:8112208 C18H37NO2 CHEBI:46965 InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/t17-,18+/m1/s1 Reaxys:8112208 WWUZIQQURGPMPG-MSOLQXFVSA-N [H]C(CCCCCCCCCCCCC)=C([H])[C@H](O)[C@H](N)CO chebi_ontology L-erythro-sphingosine (2R,3S,4E)-2-aminooctadec-4-ene-1,3-diol 0 299.282 299.49190 A (2R,3S)-2-aminooctadec-4-ene-1,3-diol in which the double bond has E geochemistry. Beilstein:4352185 C18H37NO2 CAS:6036-75-5 CCCCCCCCCCCCC\C=C\[C@H](O)[C@H](N)CO CHEBI:46967 CHEBI:78744 InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m1/s1 L-Erythro-c18-sphingosine L-erythro-sphing-4-enine Reaxys:10777443 WWUZIQQURGPMPG-MCXRAWCPSA-N chebi_ontology L-ribose A ribose in which the chiral carbon atom furthest away from the aldehyde group (C4') has the same configuration as in L-glyceraldehyde. C5H10O5 CHEBI:46997 L-Rib L-ribo-pentose L-ribose chebi_ontology ribofuranose 0 150.12990 A cyclic ribose having a 5-membered tetrahydrofuran ring; the predominant (C3'-endo) form of the two cyclic structures (the other is the "C2'-endo" form, having a 6-membered ring) adopted by ribose in aqueous solution. C5H10O5 CHEBI:46998 chebi_ontology rel-(3R,4S,5R)-5-(hydroxymethyl)tetrahydrofuran-2,3,4-triol ribofuranose D-ribofuranose (3R,4S,5R)-5-(hydroxymethyl)tetrahydrofuran-2,3,4-triol 0 150.053 150.12990 A ribofuranose having D-configuration. Beilstein:1904878 C5H10O5 CAS:50-69-1 CHEBI:4233 CHEBI:46999 CHEBI:47013 D-Ribose D-ribofuranose D-ribose Gmelin:364108 HMFHBZSHGGEWLO-SOOFDHNKSA-N InChI=1S/C5H10O5/c6-1-2-3(7)4(8)5(9)10-2/h2-9H,1H2/t2-,3-,4-,5?/m1/s1 KEGG:C00121 OC[C@H]1OC(O)[C@H](O)[C@@H]1O PMID:9506998 Patent:US2152662 Reaxys:1904878 chebi_ontology ribose tetrahydrofuranol CHEBI:47017 chebi_ontology tetrahydrofuranols dihydroxytetrahydrofuran CHEBI:47019 chebi_ontology dihydroxytetrahydrofurans hydroxycalciol CHEBI:47042 chebi_ontology hydroxycalciol hydroxycalciols hydroxycholecalciferol hydroxycholecalciferols hydrogen bromide 0 79.926 80.91194 A diatomic molecule containing covalently bonded hydrogen and bromine atoms. BrH Br[H] Bromwasserstoff CAS:10035-10-6 CHEBI:29134 CHEBI:31673 CHEBI:47266 CPELXLSAUQHCOX-UHFFFAOYSA-N Gmelin:620 HBr HBr Hydrobromic acid Hydrogenbromid InChI=1S/BrH/h1H KEGG:C13645 [HBr] bromane bromidohydrogen bromure d'hydrogene chebi_ontology hydrogen bromide imipramine 0 10,11-dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine 280.194 280.40734 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine 3-(5H-DIBENZO[B,F]AZEPIN-5-YL)-N,N-DIMETHYLPROPAN-1-AMINE 5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine A dibenzoazepine that is 5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom. Antideprin BCGWQEUPMDMJNV-UHFFFAOYSA-N Beilstein:256892 C19H24N2 CAS:50-49-7 CHEBI:47498 CHEBI:47499 CHEBI:5881 CN(C)CCCN1c2ccccc2CCc2ccccc12 DrugBank:DB00458 Drug_Central:1427 Gmelin:1572523 HMDB:HMDB0001848 Imipramin Imipramine InChI=1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3 Irmin KEGG:C07049 KEGG:D08070 LINCS:LSM-2852 Melipramine N-(gamma-dimethylaminopropyl)iminodibenzyl PDBeChem:IXX PMID:20825390 Patent:US2554736 Reaxys:256892 Wikipedia:Imipramine chebi_ontology imipramine imipraminum imizine acetate ester 0 59.013 59.04400 Acetic ester Acetyl ester Any carboxylic ester where the carboxylic acid component is acetic acid. C2H3O2R CC(=O)O[*] CHEBI:13244 CHEBI:13799 CHEBI:22189 CHEBI:2406 CHEBI:47622 KEGG:C01883 Wikipedia:Acetate#Esters acetate acetate esters acetates acetyl esters an acetyl ester chebi_ontology ammonium salt Ammoniumsalz Ammoniumsalze CHEBI:47704 ammonium salt ammonium salts chebi_ontology very-low-density lipoprotein cholesterol CHEBI:47773 Cholesterol esters and free cholesterol which are contained in or bound to very low density lipoproteins (VLDL). VLDL cholesterol VLDL-C chebi_ontology pre-beta-lipoprotein cholesterol low-density lipoprotein cholesterol CHEBI:47774 Cholesterol esters and free cholesterol which are contained in or bound to low-density lipoproteins (LDL). LDL cholesterol LDL-C beta-lipoprotein cholesterol chebi_ontology high-density lipoprotein cholesterol CHEBI:47775 Cholesterol esters and free cholesterol which are contained in or bound to high-density lipoproteins (HDL). HDL cholesterol HDL-C alpha-lipoprotein cholesterol chebi_ontology very-low-density lipoprotein triglyceride CHEBI:47776 Triglycerides which are contained in very low density lipoproteins (VLDL). VLDL triacylglycerol VLDL triglyceride chebi_ontology very-low-density lipoprotein triglycerides glyceride Any ester resulting from the condensation of one or more of the hydroxy groups of glycerol (propane-1,2,3-triol) with fatty acids. CHEBI:13730 CHEBI:22230 CHEBI:47778 acylglycerol acylglycerols chebi_ontology glyceride glycerides glycerides 3-oxo steroid 0 273.222 273.434 3-Oxosteroid 3-oxo steroids 3-oxosteroids Any oxo steroid where an oxo substituent is located at position 3. C12C(C3C(C(CC3)*)(C)CC1)CCC4C2(CCC(C4)=O)C C19H29OR CHEBI:13607 CHEBI:1653 CHEBI:20182 CHEBI:47788 CHEBI:71186 KEGG:C01876 MetaCyc:3-Oxosteroids PMID:9811880 a 3-oxosteroid chebi_ontology 5H-dibenzo[b,f]azepine 0 193.089 193.24388 2,2'-iminostilbene 2,3,6,7-dibenzazepine 5H-Dibenz[b,f]azepin 5H-dibenz[b,f]azepine 5H-dibenzazepine 5H-dibenzo[b,f]azepine A mancude organic heterotricyclic parent that consists of a seven-membered nitrogen hetrocycle fused with two benzene rings. Beilstein:1343358 C14H11N CAS:256-96-2 CHEBI:47802 InChI=1S/C14H11N/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)15-13/h1-10,15H LCGTWRLJTMHIQZ-UHFFFAOYSA-N N1c2ccccc2C=Cc2ccccc12 PMID:22322005 PMID:24358274 Reaxys:1343358 Wikipedia:Dibenzazepine chebi_ontology dibenz(b,f)azepine dibenzazepine iminostilbene o,o'-iminostilbene dibenzoazepine CHEBI:47804 chebi_ontology dibenzazepine dibenzoazepine dibenzoazepines emetine 0 480.299 480.63898 6',7',10,11-tetramethoxyemetan A pyridoisoquinoline comprising emetam having methoxy substituents at the 6'-, 7'-, 10- and 11-positions. AUVVAXYIELKVAI-CKBKHPSWSA-N Beilstein:100834 Beilstein:6253162 C29H40N2O4 CAS:483-18-1 CHEBI:4781 Drug_Central:1001 Emetan Emetin Emetine InChI=1S/C29H40N2O4/c1-6-18-17-31-10-8-20-14-27(33-3)29(35-5)16-23(20)25(31)12-21(18)11-24-22-15-28(34-4)26(32-2)13-19(22)7-9-30-24/h13-16,18,21,24-25,30H,6-12,17H2,1-5H3/t18-,21-,24+,25-/m0/s1 KEGG:C09421 KNApSAcK:C00001849 LINCS:LSM-2041 MetaCyc:CPD-14817 PMID:16109351 PMID:17094176 Reaxys:100834 Wikipedia:Emetine [H][C@]1(C[C@@]2([H])NCCc3cc(OC)c(OC)cc23)C[C@]2([H])N(CCc3cc(OC)c(OC)cc23)C[C@@H]1CC cephaeline methyl ether chebi_ontology methyl cephaeline ureas CHEBI:27220 CHEBI:36947 CHEBI:47857 chebi_ontology urea derivatives indicator Anything used in a scientific experiment to indicate the presence of a substance or quality, change in a body, etc. CHEBI:47867 Indikator chebi_ontology photosensitizing agent A chemical compound that can be excited by light of a specific wavelength and subsequently transfer energy to a chosen reactant. This is commonly molecular oxygen within a cancer tissue, which is converted to (highly rective) singlet state oxygen. This rapidly reacts with any nearby biomolecules, ultimately killing the cancer cells. CHEBI:47868 chebi_ontology photosensitising agent steroid ester CHEBI:26762 CHEBI:47880 KEGG:C15506 chebi_ontology steroid esters cyclic polypyrrole CHEBI:47882 chebi_ontology cyclic polypyrroles macrocyclic polypyrroles polypyrrole macrocycles steroid acid Any steroid substituted by at least one carboxy group. CHEBI:47891 chebi_ontology steroid acids alkanesulfonic acid CHEBI:13809 CHEBI:33553 CHEBI:47901 Organic derivatives of sulfonic acid in which the sulfo group is linked directly to carbon of an alkyl group. alkanesulfonic acid alkanesulfonic acids alkylsulfonic acids chebi_ontology 3-oxo-Delta(4) steroid 0 271.206 271.418 3-Oxo-delta4-steroid 3-oxo Delta(4)-steroid 3-oxo Delta(4)-steroids 3-oxo-Delta(4) steroids A 3-oxo steroid conjugated to a C=C double bond at the alpha,beta position. C12C(C3C(C(CC3)*)(C)CC1)CCC=4C2(CCC(C4)=O)C C19H27OR CHEBI:13604 CHEBI:1626 CHEBI:20157 CHEBI:47909 KEGG:C00619 MetaCyc:3-Oxo-Delta-4-Steroids a 3-oxo-Delta(4)-steroid chebi_ontology enflurane 0 183.971 184.49210 2-chloro-1,1,2-trifluoroethyl difluoromethyl ether 2-chloro-1-(difluoromethoxy)-1,1,2-trifluoroethane Alyrane An ether in which the oxygen atom is connected to 2-chloro-1,1,2-trifluoroethyl and difluoromethyl groups. Beilstein:1903921 C3H2ClF5O CAS:13838-16-9 CHEBI:4792 DrugBank:DB00228 Drug_Central:1009 Efrane Enflurane Ethrane FC(F)OC(F)(F)C(F)Cl HMDB:HMDB0014373 InChI=1S/C3H2ClF5O/c4-1(5)3(8,9)10-2(6)7/h1-2H JPGQOUSTVILISH-UHFFFAOYSA-N KEGG:C07516 KEGG:D00543 Methylflurether PMID:23934553 PMID:25386744 PMID:7457058 Patent:AU2014277860 Patent:US5783199 Reaxys:1903921 Wikipedia:Enflurane chebi_ontology tripeptide Any molecule that contains three amino-acid residues connected by peptide linkages. C6H8N3O4R3 CHEBI:27138 CHEBI:47923 CHEBI:9742 KEGG:C00316 Tripeptide chebi_ontology tripeptides nicotinic acetylcholine receptor agonist An agonist that selectively binds to and activates a nicotinic acetylcholine receptor. CHEBI:47958 CHEBI:82738 Wikipedia:Nicotinic_acetylcholine_receptor chebi_ontology muscarinic agonists nicotinic acetylcholine receptor agonists nicotinic agonist nicotinic agonists sulfur oxide CHEBI:48154 Schwefeloxide chebi_ontology oxides of sulfur sulfur oxides fucopyranose 6-deoxygalactopyranose C6H12O5 CHEBI:48206 chebi_ontology fucopyranose antiseptic drug A substance used locally on humans and other animals to destroy harmful microorganisms or to inhibit their activity (cf. disinfectants, which destroy microorganisms found on non-living objects, and antibiotics, which can be transported through the lymphatic system to destroy bacteria within the body). CHEBI:48218 Wikipedia:Antiseptic antiseptic antiseptic agent antiseptic agents antiseptics chebi_ontology local antiinfective agents local microbicides topical antiinfective agents topical microbicides disinfectant An antimicrobial agent that is applied to non-living objects to destroy harmful microorganisms or to inhibit their activity. CHEBI:48219 Desinfektionsmittel chebi_ontology desinfectant disinfectants disinfecting agent serotonergic drug CHEBI:48278 chebi_ontology serotonergic agents serotonergic drugs serotonin drugs serotonergic antagonist 5-HT antagonists 5-hydroxytryptamine antagonists CHEBI:48279 Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists. antiserotonergic agents chebi_ontology serotonin antagonists serotonin blockaders butane-1,2,3,4-tetrol 0 1,2,3,4-tetrahydroxybutane 122.058 122.11980 A tetritol that is butane substituted by hydroxy groups at positions 1, 2, 3 and 4. Beilstein:1735878 C4H10O4 CAS:149-32-6 CAS:7541-59-5 CHEBI:48299 Erythrite Erythrol InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2 KEGG:C00503 KEGG:D08915 KNApSAcK:C00001161 OCC(O)C(O)CO Phycite Phycitol Reaxys:1735878 UNXHWFMMPAWVPI-UHFFFAOYSA-N butane-1,2,3,4-tetrol chebi_ontology D-threitol (2R,3R)-butane-1,2,3,4-tetrol 0 122.058 122.11980 Beilstein:1719752 Beilstein:5725952 C4H10O4 CAS:2418-52-2 CAS:7493-90-5 CHEBI:48300 D-threitol D-threo-tetritol DrugBank:DB03278 Gmelin:1782960 HMDB:HMDB0004136 InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4-/m1/s1 KEGG:C16884 MetaCyc:CPD-12825 OC[C@@H](O)[C@H](O)CO PDBeChem:DTL PMID:1596913 PMID:16748290 PMID:16901854 PMID:17577890 PMID:17979222 PMID:18863753 PMID:22735334 PMID:24643482 PMID:25108762 PMID:5855592 PMID:6368527 PMID:908147 Reaxys:1719752 The D-enantiomer of threitol. UNXHWFMMPAWVPI-QWWZWVQMSA-N Wikipedia:Threitol chebi_ontology disulfide CHEBI:48343 Compounds of structure RSSR'. chebi_ontology disulfides polar solvent A solvent that is composed of polar molecules. Polar solvents can dissolve ionic compounds or ionisable covalent compounds. CHEBI:48354 chebi_ontology polar solvent polar solvents non-polar solvent CHEBI:48355 chebi_ontology protic solvent A polar solvent that is capable of acting as a hydron (proton) donor. CHEBI:48356 chebi_ontology protogenic solvent aprotic solvent CHEBI:48357 chebi_ontology polar aprotic solvent A solvent with a comparatively high relative permittivity (or dielectric constant), greater than ca. 15, and a sizable permanent dipole moment, that cannot donate suitably labile hydrogen atoms to form strong hydrogen bonds. CHEBI:48358 chebi_ontology dipolar aprotic solvent protophilic solvent CHEBI:48359 chebi_ontology amphiprotic solvent CHEBI:48360 chebi_ontology carbamimidic acid 0 60.032 60.05534 Beilstein:773698 CAS:4744-36-9 CH4N2O CHEBI:48376 H2N-C(=NH)-OH H2N-C(OH)=NH HO-C(=NH)-NH2 InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4) Isoharnstoff NC(O)=N XSQUKJJJFZCRTK-UHFFFAOYSA-N carbamimic acid carbamimidic acid carbonamidimidic acid chebi_ontology isourea pseudourea imidic acid CHEBI:48377 Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing =O by =NR; thus tautomers of amides. In organic chemistry an unspecified imidic acid is generally a carboximidic acid, RC(=NR)(OH). chebi_ontology imidic acid imidic acids imidic acids imino acids carboximidic acid CHEBI:48378 carboximidic acid carboximidic acids carboximidic acids chebi_ontology isourea A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives. CHEBI:48379 chebi_ontology isoureas isoureas true alpha-adrenergic drug Any drug that acts on an alpha-adrenergic receptor. CHEBI:48539 alpha-adrenergic drugs chebi_ontology beta-adrenergic drug Any of the drugs that act on beta-adrenergic receptors. CHEBI:48540 beta-adrenergic drugs chebi_ontology methanesulfonates CHEBI:48544 Esters or salts of methanesulfonic acid. chebi_ontology dopaminergic agent A drug used for its effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons. CHEBI:48560 chebi_ontology dopamine agent dopamine agents dopamine drug dopamine drugs dopaminergic agents radical scavenger A role played by a substance that can react readily with, and thereby eliminate, radicals. CHEBI:48578 chebi_ontology free radical scavengers free-radical scavenger agonist CHEBI:48705 Substance which binds to cell receptors normally responding to naturally occurring substances and which produces a response of its own. agonist agonista agoniste agonists chebi_ontology antagonist CHEBI:48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances. antagonist antagonista antagoniste antagonists chebi_ontology sulfurous acid 0 81.972 82.08008 CAS:7782-99-2 CHEBI:26837 CHEBI:48854 CHEBI:9344 Gmelin:1458 H2O3S H2SO3 InChI=1S/H2O3S/c1-4(2)3/h(H2,1,2,3) KEGG:C00094 KNApSAcK:C00019662 LSNNMFCWUKXFEE-UHFFFAOYSA-N OS(O)=O PDBeChem:SO3 S(O)(OH)2 Sulfite Sulfurous acid UM-BBD_compID:c0348 [SO(OH)2] acide sulfureux acido sulfuroso chebi_ontology dihydrogen trioxosulfate dihydroxidooxidosulfur schweflige Saeure sulfurous acid sulphurous acid trioxosulfuric acid cholinergic antagonist Anticholinergika Anticholinergikum Any drug that binds to but does not activate cholinergic receptors, thereby blocking the actions of acetylcholine or cholinergic agonists. CHEBI:48873 acetylcholine antagonists acetylcholine receptor antagonist agent anticholinergique agente anticolinergico agentes anticolinergicos anticholinergic agents anticholinergics anticholinergiques anticolinergicos chebi_ontology cholinergic-blocking agents thiazoles An azole in which the five-membered heterocyclic aromatic skeleton contains a N atom and one S atom. CHEBI:48901 chebi_ontology thiazole N-acyl-L-alpha-amino acid 0 101.011 101.061 Any L-alpha-amino acid carrying an N-acyl substituent. C3H3NO3R2 CHEBI:13240 CHEBI:48927 CHEBI:7232 KEGG:C02850 N-Acyl-L-amino acid chebi_ontology phytane 0 2,6,10,14-tetramethylhexadecane 282.329 282.54748 Beilstein:1744639 C20H42 CAS:638-36-8 CCC(C)CCCC(C)CCCC(C)CCCC(C)C CHEBI:48937 GGYKPYDKXLHNTI-UHFFFAOYSA-N InChI=1S/C20H42/c1-7-18(4)12-9-14-20(6)16-10-15-19(5)13-8-11-17(2)3/h17-20H,7-16H2,1-6H3 Phytan chebi_ontology isobutyrate -1 2-methylpropanoate 2-methylpropanoate 2-methylpropanoic acid, ion(1-) 2-methylpropionate 87.045 87.09718 A branched, short-chain, saturated fatty acid anion; the conjugate base of isobutyric acid, formed by deprotonation of the carboxylic acid group. Beilstein:3903644 C4H7O2 CAS:5711-69-3 CC(C)C([O-])=O CHEBI:11627 CHEBI:25334 CHEBI:48944 Gmelin:324364 InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)/p-1 Isobutyrat KQNPFQTWMSNSAP-UHFFFAOYSA-M MetaCyc:ISOBUTYRATE Reaxys:3903644 UM-BBD_compID:c0383 chebi_ontology i-butyrate iPrCO2 anion isobutanoate isobutyric acid anion methylpropanoate 4-hydroxyphenylacetate (4-hydroxyphenyl)acetate (p-hydroxyphenyl)acetate -1 151.040 151.13938 2-(4-hydroxyphenyl)ethanoate 4-hydroxybenzeneacetate 4-hydroxyphenylacetate A monocarboxylic acid anion that is obtained by removal of a proton from the carboxylic acid group of 4-hydroxyphenylacetic acid. C8H7O3 CHEBI:48999 InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)/p-1 MetaCyc:4-HYDROXYPHENYLACETATE Oc1ccc(CC([O-])=O)cc1 Reaxys:3905591 XQXPVVBIMDBYFF-UHFFFAOYSA-M chebi_ontology beta-amino-acid anion CHEBI:49095 chebi_ontology 3-aminoisobutyrate -1 102.056 102.11186 3-amino-2-methylpropanoate A beta-amino acid anion that is the conjugate base of 3-aminoisobutyric acid, arising from deprotonation of the carboxy group. C4H8NO2 CC(CN)C([O-])=O CHEBI:49096 InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/p-1 PMID:17190852 QCHPKSFMDHPSNR-UHFFFAOYSA-M beta-aminoisobutyrate chebi_ontology peripheral nervous system drug A drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system. CHEBI:49110 chebi_ontology peripheral nervous system agent peripheral nervous system drugs anti-asthmatic drug A drug used to treat asthma. CHEBI:49167 anti-asthmatic agent anti-asthmatic agents anti-asthmatic drugs chebi_ontology 2-hydroxy monocarboxylic acid 2-hydroxy acid 2-hydroxy monocarboxylic acids CHEBI:19626 CHEBI:35967 CHEBI:49302 chebi_ontology contraceptive drug A chemical substance that prevents or reduces the probability of conception. CHEBI:49323 chebi_ontology contraceptive agent contraceptive drugs hydrogen atom 0 1.00794 1.008 1H CHEBI:24634 CHEBI:49636 CHEBI:49637 H H InChI=1S/H Wasserstoff WebElements:H YZCKVEUIGOORGS-UHFFFAOYSA-N [H] chebi_ontology hidrogeno hydrogen hydrogen hydrogene organic amino compound A compound formally derived from ammonia by replacing one, two or three hydrogen atoms by organyl groups. CHEBI:50047 chebi_ontology organic amino compounds excitatory amino acid agonist An agent that binds to and activates excitatory amino acid receptors. CHEBI:50103 chebi_ontology excitatory amino acid agonists excitatory amino acid receptor agonist excitatory amino acid receptor agonists sex hormone Any hormone that is responsible for controlling sexual characteristics and reproductive function. CHEBI:50112 Geschlechtshormon Geschlechtshormone Sexualhormon Sexualhormone chebi_ontology hormone sexuelle hormones sexuelles sex hormones androgen A sex hormone that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors. Androgen Androgene CHEBI:50113 androgene androgenes androgeno androgenos androgens chebi_ontology estrogen A hormone that stimulates or controls the development and maintenance of female sex characteristics in mammals by binding to oestrogen receptors. The oestrogens are named for their importance in the oestrous cycle. The oestrogens that occur naturally in the body, notably estrone, estradiol, estriol, and estetrol are steroids. Other compounds with oestrogenic activity are produced by plants (phytoestrogens) and fungi (mycoestrogens); synthetic compounds with oestrogenic activity are known as xenoestrogens. CHEBI:50114 Estrogene Oestrogen Oestrogene Wikipedia:Estrogen chebi_ontology estrogene estrogenes estrogenes Hormon estrogeno estrogenos estrogens oestrogen oestrogene oestrogenes oestrogens trifluoromethyl group -CF3 0 68.995 69.00591 CF3 CHEBI:50127 chebi_ontology trifluoromethyl keratolytic drug A drug that softens, separates, and causes desquamation of the cornified epithelium or horny layer of skin. Keratolytic drugs are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases. CHEBI:50176 chebi_ontology desquamating agent keratolytic agent keratolytic drugs skin-peeling agent dermatologic drug A drug used to treat or prevent skin disorders or for the routine care of skin. CHEBI:50177 chebi_ontology dermatologic agent dermatologic drugs dermatological agent provitamin A substance that can be converted into a vitamin by animal tissues. CHEBI:50188 Wikipedia:Provitamin chebi_ontology provitamins retinol 0 286.230 286.45160 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified). C20H30O CC(C=CC=C(C)C=CC1=C(C)CCCC1(C)C)=CCO CHEBI:15037 CHEBI:26538 CHEBI:50211 FPIPGXGPPPQFEQ-UHFFFAOYSA-N InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3 LINCS:LSM-5317 MetaCyc:Retinols chebi_ontology retinol EC 3.1.4.* (phosphoric diester hydrolase) inhibitor An EC 3.1.* (ester hydrolase) inhibitor that interferes with the action of a phosphoric diester hydrolase (EC 3.1.4.*). CHEBI:50218 CHEBI:76774 EC 3.1.4.* (phosphoric diester hydrolase) inhibitors chebi_ontology phosphodiesterase inhibitor phosphodiesterase inhibitors phosphoric diester hydrolase (EC 3.1.4.*) inhibitor phosphoric diester hydrolase (EC 3.1.4.*) inhibitors phosphoric diester hydrolase inhibitor phosphoric diester hydrolase inhibitors hematologic agent CHEBI:50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system. chebi_ontology hematologic agents anticoagulant An agent that prevents blood clotting. CHEBI:50249 anticoagulante anticoagulants chebi_ontology 2-hydroxydicarboxylic acid 2-Hydroxydicarboxylic acid 2-hydroxydicarboxylic acids Any dicarboxylic acid carrying a hydroxy group on the carbon atom at position alpha to the carboxy group. C3H4O5(CH2)n CHEBI:1154 CHEBI:19636 CHEBI:50263 KEGG:C03668 chebi_ontology prodrug A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug. CHEBI:50266 PMID:23993918 PMID:23998799 PMID:24329110 PMID:24628402 PMID:24709544 PMID:25144792 PMID:25157234 PMID:25269430 PMID:25391982 PMID:25591121 PMID:25620096 PMID:25795057 PMID:26028253 PMID:26184144 PMID:28070577 PMID:28215138 PMID:28219047 PMID:28259775 PMID:28319647 PMID:28329729 PMID:28334528 Prodrugs Wikipedia:Prodrug chebi_ontology protective agent CHEBI:50267 Synthetic or natural substance which is given to prevent a disease or disorder or are used in the process of treating a disease or injury due to a poisonous agent. chebi_ontology chemoprotectant chemoprotectants chemoprotective agent chemoprotective agents protective agents canonical nucleotide residue CHEBI:50297 canonical nucleotide residues chebi_ontology canonical ribonucleotide residue CHEBI:50299 canonical ribonucleotide residues chebi_ontology onium compound CHEBI:50312 chebi_ontology onium cation CHEBI:50313 Mononuclear cations derived by addition of a hydron to a mononuclear parent hydride of the pnictogen, chalcogen and halogen families. chebi_ontology onium cations onium cations onium ion onium ions chloronium +1 36.985 37.46858 CHEBI:50315 ClH2 Gmelin:331 H2Cl(+) IGJWHVUMEJASKV-UHFFFAOYSA-N InChI=1S/ClH2/h1H2/q+1 [ClH2](+) [H][Cl+][H] chebi_ontology chloranium chloronium bromonium +1 80.934 81.91988 BrH2 CHEBI:50316 Gmelin:719134 H2Br(+) IWNNBBVLEFUBNE-UHFFFAOYSA-N InChI=1S/BrH2/h1H2/q+1 [BrH2](+) [H][Br+][H] bromanium bromonium chebi_ontology iodonium +1 128.920 128.92035 CHEBI:50317 Gmelin:1425841 H2I H2I(+) InChI=1S/H2I/h1H2/q+1 MGFYSGNNHQQTJW-UHFFFAOYSA-N [H][I+][H] [IH2](+) chebi_ontology iodanium iodonium nucleotide residue CHEBI:50319 chebi_ontology nucleotide residues nucleoside residue CHEBI:50320 chebi_ontology nucleoside residues proteinogenic amino-acid side-chain group A univalent organyl group obtained by cleaving the bond from C-2 to the side chain of a proteinogenic amino-acid. CHEBI:50325 canonical amino-acid side-chain canonical amino-acid side-chains chebi_ontology proteinogenic amino-acid side-chain proteinogenic amino-acid side-chain groups proteinogenic amino-acid side-chains sulfanylmethyl group -CH2-SH 0 46.996 47.10052 CH3S CHEBI:50326 HS-CH2- chebi_ontology cysteine side-chain sulfanylmethyl 2-carboxyethyl group 0 2-carboxyethyl 73.029 73.07060 C3H5O2 CHEBI:50329 chebi_ontology glutamic acid side-chain 2-amino-2-oxoethyl group 0 2-amino-2-oxoethyl 58.029 58.05930 C2H4NO CHEBI:50330 asparagine side-chain chebi_ontology 3-amino-3-oxopropyl group 0 3-amino-3-oxopropyl 72.045 72.08588 C3H6NO CHEBI:50331 chebi_ontology glutamine side-chain 4-hydroxybenzyl group 0 107.050 107.12988 4-hydroxybenzyl C7H7O CHEBI:50336 chebi_ontology tyrosine side-chain 1H-indol-3-ylmethyl group 0 130.066 130.16656 1H-indol-3-ylmethyl C9H8N CHEBI:50337 chebi_ontology tryptophan side-chain 1H-imidazol-4-ylmethyl group 0 1H-imidazol-4-ylmethyl 81.045 81.09598 C4H5N2 CHEBI:50338 chebi_ontology histidine side-chain 4-aminobutyl group 0 4-aminobutyl 72.081 72.12894 C4H10N CHEBI:50339 chebi_ontology lysine side-chain 3-carbamimidamidopropyl group 0 100.087 100.14242 3-(carbamimidoylamino)propyl 3-carbamimidamidopropyl 3-guanidinopropyl C4H10N3 CHEBI:50340 arginine side-chain chebi_ontology 1-hydroxyethyl group 0 1-hydroxyethyl 45.034 45.06050 C2H5O CHEBI:50341 chebi_ontology threonine side-chain organic iodide salt CHEBI:50356 chebi_ontology organic iodide salts cholestanoid Any steroid based on a cholestane skeleton and its derivatives. CHEBI:50401 chebi_ontology cholestanoids androstanoid Any steroid based on an androstane skeleton and its derivatives. CHEBI:50402 androstanoids chebi_ontology lipoprotein cholesterol CHEBI:50404 Cholesterol esters and free cholesterol which are contained in or bound to lipoproteins. chebi_ontology haloalkyl group A group derived from a haloalkane by removal of a hydrogen atom. CHEBI:50491 chebi_ontology haloalkyl groups laxative An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic. CHEBI:50503 aperient aperients chebi_ontology laxante laxatives purgative purgatives sweetening agent CHEBI:50505 Substance that sweeten food, beverages, medications, etc. chebi_ontology sweetener sweeteners bipyridines CHEBI:50511 Compounds containing a bipyridine group. bipyridyls chebi_ontology alkyl alcohol An aliphatic alcohol in which the aliphatic alkane chain is substituted by a hydroxy group at unspecified position. CHEBI:22937 CHEBI:50581 CHEBI:50584 alkyl alcohols chebi_ontology hydroxyalkane hydroxyalkanes bone density conservation agent An agent that inhibits bone resorption and/or favor bone mineralization and bone regeneration. Used to heal bone fractures and to treat bone diseases such as osteopenia and osteoporosis. CHEBI:50646 CHEBI:72497 Wikipedia:Osteoporosis anti-osteopenia agent anti-osteopenia agents anti-osteopenia drug anti-osteopenia drugs anti-osteoporosis agent anti-osteoporosis agents anti-osteoporosis drug anti-osteoporosis drugs anti-osteoporotic anti-osteoporotic agent anti-osteoporotic agents anti-osteoporotic drug anti-osteoporotic drugs anti-osteoporotics antiosteoporotic antiosteoporotics bone density conservation agents bone density conservation drug bone density conservation drugs chebi_ontology reproductive control drug A substance used either in the prevention or facilitation of pregnancy. CHEBI:50689 chebi_ontology reproductive control agent reproductive control drugs oligosaccharide A compound in which monosaccharide units are joined by glycosidic linkages. The term is commonly used to refer to a defined structure as opposed to a polymer of unspecified length or a homologous mixture. When the linkages are of other types the compounds are regarded as oligosaccharide analogues. CHEBI:25679 CHEBI:35319 CHEBI:50699 CHEBI:7758 KEGG:C00930 O-glycosylglycoside O-glycosylglycosides Oligosaccharide an oligosaccharide chebi_ontology oligosacarido oligosacaridos oligosaccharides nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance. CHEBI:50733 Dietary Supplement Food Supplementation Nutritional supplement chebi_ontology taurine zwitterion 0 125.015 125.14700 2-ammonioethanesulfonate 2-azaniumylethane-1-sulfonate C2H7NO3S CHEBI:507393 InChI=1S/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6) PMID:17765547 The zwitterion formed from taurine by transfer of a proton from the sulfonyl to the amino group. It is the major species existing at physiological pH. XOAAWQZATWQOTB-UHFFFAOYSA-N [NH3+]CCS([O-])(=O)=O chebi_ontology taurine progestogen A compound that interacts with progesterone receptors in target tissues to bring about effects similar to those of progesterone. CHEBI:50745 chebi_ontology gestagen gestagens progestagen progestagens progestogens antipsoriatic A drug used to treat psoriasis. CHEBI:50748 antipsoriatic agent antipsoriatic drug chebi_ontology appetite enhancer A drug which increases appetite. CHEBI:50779 Wikipedia:Appetite_stimulants appetite enhancing drug appetite stimulant chebi_ontology orexigenic appetite regulator An agent which regulates the physiologic mechanisms that control the appetite and food intake. CHEBI:50780 appetite regulators chebi_ontology immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system. Biomodulator CHEBI:50846 Immune factor Immunologic factor Immunological factor Wikipedia:Immunotherapy chebi_ontology immunomodulators antiatherogenic agent A cardiovascular drug that prevents atherogenesis, the accumulation of lipid containing plaques on the innermost layers of the arteries. CHEBI:50855 chebi_ontology anti-allergic agent A drug used to treat allergic reactions. CHEBI:50857 anti-allergic agents anti-allergic drug anti-allergic drugs chebi_ontology corticosteroid A natural or synthetic analogue of the hormones secreted by the adrenal gland. CHEBI:50858 chebi_ontology corticoides corticosteroides corticosteroids organic molecular entity Any molecular entity that contains carbon. CHEBI:25700 CHEBI:33244 CHEBI:50860 chebi_ontology organic compounds organic entity organic molecular entities azaarene CHEBI:50893 azaarenes chebi_ontology genotoxin A role played by a chemical compound to induce direct or indirect DNA damage. Such damage can potentially lead to the formation of a malignant tumour, but DNA damage does not lead inevitably to the creation of cancerous cells. CHEBI:50902 Wikipedia:Genotoxicity chebi_ontology genotoxic agent genotoxic agents genotoxins carcinogenic agent A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities. CHEBI:50903 agente carcinogeno cancerigene cancerogene carcinogen carcinogene carcinogenic agents carcinogeno carcinogens chebi_ontology allergen A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. CHEBI:50904 Wikipedia:Allergen alergeno allergene allergenic agent chebi_ontology teratogenic agent A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect. CHEBI:50905 agent teratogene chebi_ontology teratogen teratogeno role A role is particular behaviour which a material entity may exhibit. CHEBI:50906 chebi_ontology neurotoxin A poison that interferes with the functions of the nervous system. CHEBI:50910 CHEBI:50911 Wikipedia:Neurotoxin agente neurotoxico chebi_ontology nerve poison nerve poisons neurotoxic agent neurotoxic agents neurotoxicant neurotoxins EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor A-kinase inhibitor A-kinase inhibitors AP50 kinase inhibitor AP50 kinase inhibitors ATP-protein transphosphorylase inhibitor ATP-protein transphosphorylase inhibitors ATP:protein phosphotransferase (non-specific) inhibitor ATP:protein phosphotransferase (non-specific) inhibitors An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of non-specific serine/threonine protein kinase (EC 2.7.11.1), a kinase enzyme involved in phosphorylation of hydroxy group of serine or threonine. CHEBI:50925 CHEBI:75764 CK-2 inhibitor CK-2 inhibitors CKI inhibitor CKI inhibitors CKII inhibitor CKII inhibitors EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitors EC 2.7.11.1 inhibitor EC 2.7.11.1 inhibitors HIPK2 inhibitor HIPK2 inhibitors Hpr kinase inhibitor Hpr kinase inhibitors M phase-specific cdc2 kinase inhibitor M phase-specific cdc2 kinase inhibitors PAK-1 inhibitor PAK-1 inhibitors PAK1 inhibitor PAK1 inhibitors PKA inhibitor PKA inhibitors Prp4 protein kinase inhibitor Prp4 protein kinase inhibitors Raf kinase inhibitor Raf kinase inhibitors Raf-1 inhibitor Raf-1 inhibitors STK32 inhibitor STK32 inhibitors T-antigen kinase inhibitor T-antigen kinase inhibitors WEE1Hu inhibitor WEE1Hu inhibitors Wee 1-like kinase inhibitor Wee 1-like kinase inhibitors Wee-kinase inhibitor Wee-kinase inhibitors betaIIPKC inhibitor betaIIPKC inhibitors cAMP-dependent protein kinase A inhibitor cAMP-dependent protein kinase A inhibitors cAMP-dependent protein kinase inhibitor cAMP-dependent protein kinase inhibitors cGMP-dependent protein kinase inhibitor cGMP-dependent protein kinase inhibitors calcium-dependent protein kinase C inhibitor calcium-dependent protein kinase C inhibitors calcium/phospholipid-dependent protein kinase inhibitor calcium/phospholipid-dependent protein kinase inhibitors casein kinase (phosphorylating) inhibitor casein kinase (phosphorylating) inhibitors casein kinase 2 inhibitor casein kinase 2 inhibitors casein kinase I inhibitor casein kinase I inhibitors casein kinase II inhibitor casein kinase II inhibitors casein kinase inhibitor casein kinase inhibitors chebi_ontology cyclic AMP-dependent protein kinase A inhibitor cyclic AMP-dependent protein kinase A inhibitors cyclic AMP-dependent protein kinase inhibitor cyclic AMP-dependent protein kinase inhibitors cyclic monophosphate-dependent protein kinase inhibitor cyclic monophosphate-dependent protein kinase inhibitors cyclic nucleotide-dependent protein kinase inhibitor cyclic nucleotide-dependent protein kinase inhibitors cyclin-dependent kinase inhibitor cyclin-dependent kinase inhibitors dsk1 inhibitor dsk1 inhibitors epsilon PKC inhibitor epsilon PKC inhibitors glycogen synthase a kinase inhibitor glycogen synthase a kinase inhibitors glycogen synthase kinase inhibitor glycogen synthase kinase inhibitors hydroxyalkyl-protein kinase inhibitor hydroxyalkyl-protein kinase inhibitors mitogen-activated S6 kinase inhibitor mitogen-activated S6 kinase inhibitors non-specific serine/threonine protein kinase (EC 2.7.11.1) inhibitor non-specific serine/threonine protein kinase (EC 2.7.11.1) inhibitors non-specific serine/threonine protein kinase inhibitor non-specific serine/threonine protein kinase inhibitors p21 activated kinase-1 inhibitor p21 activated kinase-1 inhibitors p82 kinase inhibitor p82 kinase inhibitors phosphorylase b kinase kinase inhibitor phosphorylase b kinase kinase inhibitors protein glutamyl kinase inhibitor protein glutamyl kinase inhibitors protein kinase (phosphorylating) inhibitor protein kinase (phosphorylating) inhibitors protein kinase A inhibitor protein kinase A inhibitors protein kinase CK2 inhibitor protein kinase CK2 inhibitors protein kinase p58 inhibitor protein kinase p58 inhibitors protein phosphokinase inhibitor protein phosphokinase inhibitors protein serine kinase inhibitor protein serine kinase inhibitors protein serine-threonine kinase inhibitor protein serine-threonine kinase inhibitors protein-aspartyl kinase inhibitor protein-aspartyl kinase inhibitors protein-cysteine kinase inhibitor protein-cysteine kinase inhibitors protein-serine kinase inhibitor protein-serine kinase inhibitors protein-serine/threonine kinase inhibitors ribosomal S6 protein kinase inhibitor ribosomal S6 protein kinase inhibitors ribosomal protein S6 kinase II inhibitor ribosomal protein S6 kinase II inhibitors serine kinase inhibitor serine kinase inhibitors serine protein kinase inhibitor serine protein kinase inhibitors serine(threonine) protein kinase inhibitor serine(threonine) protein kinase inhibitors serine-specific protein kinase inhibitor serine-specific protein kinase inhibitors serine/threonine protein kinase inhibitor serine/threonine protein kinase inhibitors threonine-specific protein kinase inhibitor threonine-specific protein kinase inhibitors twitchin kinase inhibitor twitchin kinase inhibitors type-2 casein kinase inhibitor type-2 casein kinase inhibitors serotonin uptake inhibitor A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent. CHEBI:50949 SSRI Wikipedia:Selective_serotonin_reuptake_inhibitor chebi_ontology serotonin reuptake inhibitor non-covalently-bound molecular entity CHEBI:50967 Systems consisting of two or more molecular entities held together by non-covalent interactions. chebi_ontology non-covalently-bound molecular entities primary amino compound A compound formally derived from ammonia by replacing one hydrogen atom by an organyl group. CHEBI:50994 chebi_ontology primary amino compounds secondary amino compound A compound formally derived from ammonia by replacing two hydrogen atoms by organyl groups. CHEBI:50995 chebi_ontology secondary amino compounds tertiary amino compound A compound formally derived from ammonia by replacing three hydrogen atoms by organyl groups. CHEBI:50996 chebi_ontology tertiary amino compounds hormone agonist A chemical substance which binds to specific hormone receptors activating the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites. CHEBI:51060 chebi_ontology hormone receptor modulator A drug that modulates the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites. CHEBI:51061 chebi_ontology hormone receptor modulators organic halide salt CHEBI:51069 chebi_ontology organic halide salts (R)-colchicine 0 399.168 399.43704 Beilstein:3226657 C22H25NO6 CHEBI:51074 COc1cc2CC[C@@H](NC(C)=O)c3cc(=O)c(OC)ccc3-c2c(OC)c1OC IAKHMKGGTNLKSZ-MRXNPFEDSA-N InChI=1S/C22H25NO6/c1-12(24)23-16-8-6-13-10-19(27-3)21(28-4)22(29-5)20(13)14-7-9-18(26-2)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m1/s1 N-[(7R)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide chebi_ontology chemical role A role played by the molecular entity or part thereof within a chemical context. CHEBI:51086 chebi_ontology mianserin 0 1,2,3,4,10,14b-Hexahydro-2-methyldibenzo(c,f)pyrazino(1,2-a)azepine 2-methyl-1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine 264.163 264.36480 A dibenzoazepine (specifically 1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine) methyl-substituted on N-2. Closely related to (and now mostly superseded by) the tetracyclic antidepressant mirtazapinean, it is an atypical antidepressant used in the treatment of depression throughout Europe and elsewhere. Beilstein:755346 C18H20N2 CAS:24219-97-4 CHEBI:51137 CN1CCN2C(C1)c1ccccc1Cc1ccccc21 DrugBank:DB06148 Drug_Central:1796 InChI=1S/C18H20N2/c1-19-10-11-20-17-9-5-3-7-15(17)12-14-6-2-4-8-16(14)18(20)13-19/h2-9,18H,10-13H2,1H3 LINCS:LSM-1374 PMID:20825390 Patent:NL6603256 Patent:US3534041 UEQUQVLFIPOEMF-UHFFFAOYSA-N Wikipedia:Mianserin chebi_ontology mianserin mianserina mianserine mianserinum nitrogen molecular entity CHEBI:25556 CHEBI:51143 CHEBI:7594 KEGG:C06061 Nitrogenous compounds chebi_ontology nitrogen compounds nitrogen molecular entities dipolar compound An organic molecule that is electrically neutral carrying a positive and a negative charge in one of its major canonical descriptions. In most dipolar compounds the charges are delocalized; however the term is also applied to species where this is not the case. CHEBI:51151 chebi_ontology dipolar compounds fluoxetine (+-)-N-methyl-3-phenyl-3-((alpha,alpha,alpha-trifluoro-p-tolyl)oxy)propylamine (+-)-N-methyl-gamma-(4-(trifluoromethyl)phenoxy)benzenepropanamine 0 309.32610 A racemate comprising equimolar amounts of (R)- and (S)-fluoxetine. A selective serotonin reuptake inhibitor (SSRI), it is used (generally as the hydrochloride salt) for the treatment of depression (and the depressive phase of bipolar disorder), bullimia nervosa, and obsessive-compulsive disorder. Beilstein:39914106 C17H18F3NO CAS:54910-89-3 CHEBI:5118 DrugBank:DB00472 HMDB:HMDB0014615 KEGG:D00326 PMID:19144769 PMID:22903652 PMID:22923967 PMID:23885544 PMID:24184049 PMID:24399719 PMID:24464553 PMID:24997906 PMID:25448156 PMID:25639887 PMID:25671301 PMID:8694321 Patent:DE2500110 Patent:US4314081 Prozac Reaxys:3991406 Wikipedia:Fluoxetine chebi_ontology fluoxetina fluoxetine fluoxetinum rac-N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine thioester 0 59.967 60.07500 A compound of general formula RC(=O)SR'. Compare with thionoester, RC(=S)OR'. CHEBI:51277 COSR2 [*]C(=O)S[*] chebi_ontology thio ester thioesters thiol ester S-methyl thioacetate 0 90.014 90.14514 Beilstein:1736664 C3H6OS CAS:1534-08-3 CH3C(O)SCH3 CHEBI:38533 CHEBI:51279 CHEBI:51280 CSC(C)=O Gmelin:1316927 InChI=1S/C3H6OS/c1-3(4)5-2/h1-2H3 OATSQCXMYKYFQO-UHFFFAOYSA-N S-methyl ethanethioate chebi_ontology ethanethioic acid, S-methyl ester methanethiol acetate methyl ethanethioate methyl thioacetate methylthioacetate thioacetic acid S-methyl ester cinchona alkaloid An alkaloid based on a cinchonan skeleton. CHEBI:51323 chebi_ontology cinchona alkaloids muscle relaxant A drug used to produce muscle relaxation (excepting neuromuscular blocking agents). Its primary clinical and therapeutic use is the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. Also used for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in multiple sclerosis. CHEBI:51371 chebi_ontology muscle relaxants neuromuscular agent A drug used for its actions on skeletal muscle. CHEBI:51372 chebi_ontology GABA agent A substance, such as agonists, antagonists, degradation or uptake inhibitors, depleters, precursors, and modulators of receptor function, used for its pharmacological actions on GABAergic systems. CHEBI:51374 chebi_ontology D-ascorbic acid (5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one 0 176.032 176.12412 Beilstein:84273 C6H8O6 CAS:10504-35-5 CHEBI:51384 CIWBSHSKHKDKBQ-MVHIGOERSA-N D-lyxoascorbic acid D-threo-hex-2-enoic acid gamma-lactone D-threo-hex-2-enono-1,4-lactone D-xyloascorbic acid InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m1/s1 [H][C@]1(OC(=O)C(O)=C1O)[C@H](O)CO chebi_ontology organodiyl group Any organic substituent group, regardless of functional type, having two free valences at carbon atom(s). CHEBI:51422 chebi_ontology organodiyl groups organic divalent group CHEBI:51446 chebi_ontology organic univalent group CHEBI:51447 chebi_ontology N-acyl-amino acid A carboxamide resulting from the formal condensation of a carboxylic acid with the amino group of an amino acid. CHEBI:21653 CHEBI:22226 CHEBI:51569 N-acyl amino acid N-acyl amino acids N-acyl-amino-acid N-acyl-amino-acids N-acylamino acid N-acylamino acids acyl-amino-acid acyl-amino-acids acylamino acids chebi_ontology methoxybenzenes Any aromatic ether that consists of a benzene skeleton substituted with one or more methoxy groups. CHEBI:51683 chebi_ontology methoxybenzene enal 0 53.003 53.03940 An alpha,beta-unsaturated aldehyde of general formula R(1)R(2)C=CR(3)-CH=O in which the aldehydic C=O function is conjugated to a C=C double bond at the alpha,beta position. C3HOR3 CHEBI:51688 [H]C(=O)C(\[*])=C(/[*])[*] chebi_ontology enals enone 0 51.995 52.03150 An alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position. C3OR4 CHEBI:51689 Wikipedia:Enone [*]\C([*])=C(\[*])C([*])=O chebi_ontology enones alpha,beta-unsaturated aldehyde An aldehyde of general formula R(1)R(2)C=CR(3)-CH=O or RC#C-CH=O in which the aldehydic C=O function is conjugated to an unsaturated C-C bond at the alpha,beta position. CHEBI:51718 alpha,beta-unsaturated aldehydes chebi_ontology alpha,beta-unsaturated ketone A ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) or R(1)C#C-C(=O)R(2) (R(2) =/= H) in which the ketonic C=O function is conjugated to an unsaturated C-C bond at the alpha,beta position. CHEBI:51721 alpha,beta-unsaturated ketones chebi_ontology methyl ketone A ketone of formula RC(=O)CH3 (R =/= H). CHEBI:51867 chebi_ontology methyl ketones alpha-diketone A diketone that has its two ketone functionalities on adjacent atoms. CHEBI:51869 alpha-diketones chebi_ontology organic polycyclic compound CHEBI:51958 chebi_ontology organic polycyclic compounds organic tricyclic compound CHEBI:51959 chebi_ontology organic tricyclic compounds methoxide -1 31.018 31.03390 An organic anion that is the conjugate base of methanol. CH3O CHEBI:52090 C[O-] InChI=1S/CH3O/c1-2/h1H3/q-1 NBTOZLQBSIZIKS-UHFFFAOYSA-N Reaxys:1839368 chebi_ontology methoxide ion ethoxide -1 45.034 45.06050 An organic anion that is the conjugate base of ethanol. Beilstein:1839415 C2H5O CC[O-] CHEBI:52092 HHFAWKCIHAUFRX-UHFFFAOYSA-N InChI=1S/C2H5O/c1-2-3/h2H2,1H3/q-1 Reaxys:1839415 chebi_ontology ethoxy anion biochemical role A biological role played by the molecular entity or part thereof within a biochemical context. CHEBI:52206 chebi_ontology biophysical role CHEBI:52208 chebi_ontology aetiopathogenetic role A role played by the molecular entity or part thereof which causes the development of a pathological process. CHEBI:52209 chebi_ontology etiopathogenetic agent etiopathogenetic role pharmacological role A biological role which describes how a drug interacts within a biological system and how the interactions affect its medicinal properties. CHEBI:52210 chebi_ontology physiological role CHEBI:52211 chebi_ontology ligand Any molecule or ion capable of binding to a central metal atom to form coordination complexes. CHEBI:52214 Wikipedia:Ligand chebi_ontology ligands photochemical role A chemical role played by the molecular entity or part thereof in a photochemical process. CHEBI:52215 chebi_ontology photochemical roles pharmaceutical Any substance introduced into a living organism with therapeutic or diagnostic purpose. CHEBI:33293 CHEBI:33294 CHEBI:52217 chebi_ontology farmaco medicament pharmaceuticals apatite A phosphate mineral with the general formula Ca5(PO4)3X where X = OH, F or Cl. CHEBI:52254 HMDB:HMDB0033610 chebi_ontology hydroxyapatite hydroxylapatite A phosphate mineral with the formula Ca5(PO4)3(OH). CHEBI:52255 Ca5HO13P3 chebi_ontology mitogen A chemical substance that encourages a cell to commence cell division, triggering mitosis. CHEBI:52290 chebi_ontology mitogens oxyketone A compound with the general formula R2C=O (R=/=H) where one or more of the R groups contains an oxy (-O-) group. CHEBI:52395 chebi_ontology oxyketones alpha-oxyketone An oxyketone with the general formula R2C(=O) (R=/=H) where one or more of the R groups contains an oxy (-O-) group and the oxy and carbonyl groups are bonded to the same carbon atom. CHEBI:52396 alpha-oxyketones chebi_ontology EC 3.2.1.* (glycosidase) inhibitor An EC 3.2.* (glycosylase) inhibitor that interferes with the action of any glycosidase (i.e. enzymes hydrolysing O- and S-glycosyl compounds, EC 3.2.1.*). CHEBI:52424 CHEBI:76776 EC 3.2.1.* (glycosidase) inhibitors EC 3.2.1.* inhibitor EC 3.2.1.* inhibitors chebi_ontology glycosidase (EC 3.2.1.*) inhibitor glycosidase (EC 3.2.1.*) inhibitors glycosidase inhibitor glycosidase inhibitors glycoside hydrolase inhibitors EC 3.2.1.18 (exo-alpha-sialidase) inhibitor An antiviral drug targeted at influenza viruses. Its mode of action consists of blocking the function of the viral neuraminidase protein (EC 3.2.1.18), thus preventing the virus from budding from the host cell. CHEBI:52425 EC 3.2.1.18 (exo-alpha-sialidase) inhibitors EC 3.2.1.18 inhibitor EC 3.2.1.18 inhibitors N-acylneuraminate glycohydrolase inhibitor N-acylneuraminate glycohydrolase inhibitors acetylneuraminidase inhibitor acetylneuraminidase inhibitors acetylneuraminyl hydrolase inhibitor acetylneuraminyl hydrolase inhibitors alpha-neuraminidase inhibitor alpha-neuraminidase inhibitors chebi_ontology exo-alpha-sialidase (EC 3.2.1.18) inhibitor exo-alpha-sialidase (EC 3.2.1.18) inhibitors exo-alpha-sialidase inhibitor exo-alpha-sialidase inhibitors neuraminidase inhibitor neuraminidase inhibitors sialidase inhibitor sialidase inhibitors galactolipid A glycolipid and which the glyco component is specified as galactosyl. CHEBI:5254 a galactolipid chebi_ontology alkylglycerol A glycerol ether having at least one alkyl substituent on oxygen. CHEBI:52575 O-alkylglycerol O-alkylglycerols alkylglycerols chebi_ontology inorganic hydroxy compound CHEBI:52625 chebi_ontology inorganic hydroxides cyclic organic group An organic group that consists of a closed ring. It may be a substituent or a skeleton. CHEBI:52845 chebi_ontology cyclic organic groups sphingosylphosphocholine acid +1 2-{[{[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}(hydroxy)phosphoryl]oxy}-N,N,N-trimethylethanaminium 465.346 465.62730 A cationic phosphosphingolipid consisting of sphingosine having a phosphocholine moiety attached to its primary hydroxyl group. C23H50N2O5P CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(=O)OCC[N+](C)(C)C CHEBI:52897 InChI=1S/C23H49N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3/p+1/b18-17+/t22-,23+/m0/s1 JLVSPVFPBBFMBE-HXSWCURESA-O KEGG:C03640 Sphing-4-enine-1-phosphocholine Sphingosyl-phosphocholine chebi_ontology sphingosylphosphocholine sphingosylphosphocholine acid epitope CHEBI:53000 The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds. antigenic determinant chebi_ontology epitope function epitope role adenosine A2A receptor antagonist An antagonist at the A2A receptor. CHEBI:53121 Wikipedia:Adenosine_A2A_receptor adenosine A2A receptor antagonists chebi_ontology isocyanates CHEBI:53212 Organonitrogen compounds that are derivatives of isocyanic acid; compounds containing the isocyanate functional group -N=C=O (as opposed to the cyanate group, -O-C#N). chebi_ontology iso-cyanates 2-halophenol 0 2-halophenols 93.034 93.10330 A halophenol in which the halogen atom is bonded to the carbon atom adjacent to the C-OH group. C6H5O CHEBI:53291 Oc1ccccc1* chebi_ontology 3,3',5-triiodo-L-thyronine zwitterion (2S)-2-azaniumyl-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoate (S)-2-Amino-3-[4-(4-hydroxy-3-iodo-phenoxy)-3,5-diiodo-phenyl]-propionic acid 0 3,3',5-triiodo-L-thyronine 650.790 650.97350 AUYYCJSJGJYCDS-LBPRGKRZSA-N C15H12I3NO4 CHEBI:533015 InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1 MetaCyc:CPD-10813 The amino acid zwitterion formed from 3,3',5-triiodo-L-thyronine by tranfer of a proton from the carboxy group to the amino group. It is the major species at pH 7.3. [NH3+][C@@H](Cc1cc(I)c(Oc2ccc(O)c(I)c2)c(I)c1)C([O-])=O chebi_ontology polyanionic macromolecule A polymer carrying multiple negative charges. CHEBI:53309 chebi_ontology polyanion polyanions ionic macromolecule A macromolecule containing ionic groups. CHEBI:53368 chebi_ontology ionic polymer polyionic macromolecule globin CHEBI:5386 COMe:PRX000257 Globin KEGG:C06258 chebi_ontology globins pentacoordinate globin homovanillic acid (4-hydroxy-3-methoxyphenyl)acetic acid 0 182.058 182.17330 2-(4-hydroxy-3-methoxyphenyl)acetic acid 3-Methoxy-4-hydroxyphenylacetate 3-Methoxy-4-hydroxyphenylacetic acid 4-Hydroxy-3-methoxybenzeneacetic acid A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite. C9H10O4 CAS:306-08-1 CHEBI:545959 CHEBI:5758 COc1cc(CC(O)=O)ccc1O HMDB:HMDB0000118 HVA Homovanillic acid InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12) KEGG:C05582 KNApSAcK:C00029504 MetaCyc:CPD-7651 PMID:14688447 PMID:24007816 PMID:24416192 PMID:24423636 PMID:8353435 QRMZSPFSDQBLIX-UHFFFAOYSA-N Reaxys:2213447 Vanillacetic acid Wikipedia:Homovanillic_acid chebi_ontology gonadorelin 0 1181.573 1182.29010 5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosylglycyl-L-leucyl-L-arginyl-L-prolylglycinamide 5-oxo-PHWSYGLRPGNH2 A ten-membered synthetic oligopeptide comprising pyroglutamyl, histidyl, tryptophyl, seryl, tyrosyl, glycyl, leucyl, arginyl, prolyl and glycinamide residues joined in sequence. C55H75N17O13 CAS:33515-09-2 CC(C)C[C@H](NC(=O)CNC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@@H]1CCC(=O)N1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1CCC[C@H]1C(=O)NCC(N)=O CHEBI:5520 DrugBank:DB00644 Drug_Central:2958 Follicle-stimulating hormone-releasing factor GnRH-I Gonadoliberin I Gonadorelin Gonadotropin-releasing factor Gonadotropin-releasing hormone I InChI=1S/C55H75N17O13/c1-29(2)19-38(49(80)67-37(9-5-17-60-55(57)58)54(85)72-18-6-10-43(72)53(84)62-25-44(56)75)66-46(77)26-63-47(78)39(20-30-11-13-33(74)14-12-30)68-52(83)42(27-73)71-50(81)40(21-31-23-61-35-8-4-3-7-34(31)35)69-51(82)41(22-32-24-59-28-64-32)70-48(79)36-15-16-45(76)65-36/h3-4,7-8,11-14,23-24,28-29,36-43,61,73-74H,5-6,9-10,15-22,25-27H2,1-2H3,(H2,56,75)(H,59,64)(H,62,84)(H,63,78)(H,65,76)(H,66,77)(H,67,80)(H,68,83)(H,69,82)(H,70,79)(H,71,81)(H4,57,58,60)/t36-,37-,38-,39-,40-,41-,42-,43-/m0/s1 KEGG:C07607 KEGG:D08027 LH-Releasing factor LH-Releasing hormone Luteinizing hormone-releasing factor PMID:21872303 PMID:22112812 PMID:22214466 PMID:22289217 PMID:22504307 PMID:22761896 Reaxys:741807 Wikipedia:Gonadorelin XLXSAKCOAKORKW-AQJXLSMYSA-N chebi_ontology gonadorelin gonadorelina gonadorelinum luliberin p-Glu-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2 imidazolidinone An imidazolidine containing one or more oxo groups. CHEBI:55370 chebi_ontology imidazolidinones halothane 0 1,1,1-trifluoro-2-bromo-2-chloroethane 1,1,1-trifluoro-2-chloro-2-bromoethane 1-bromo-1-chloro-2,2,2-trifluoroethane 195.890 197.38125 2,2,2-trifluoro-1-chloro-1-bromoethane 2-bromo-2-chloro-1,1,1-trifluoroethane 2-bromo-2-chloro-1,1,1-trifluoroethane A haloalkane comprising ethane having three flouro substituents at the 1-position as well as bromo- and chloro substituents at the 2-position. BCQZXOMGPXTTIC-UHFFFAOYSA-N Beilstein:1736947 C2HBrClF3 CAS:151-67-7 CHEBI:5615 DrugBank:DB01159 Drug_Central:1356 Fluothane Gmelin:793752 Halothane InChI=1S/C2HBrClF3/c3-1(4)2(5,6)7/h1H KEGG:C07515 KEGG:D00542 Narcotane PMID:7519986 Phthorothanum Rhodialothan VSDB:1806 Wikipedia:Halothane [H]C(Cl)(Br)C(F)(F)F bromochlorotrifluoroethane chebi_ontology heptan-2-one 0 114.104 114.18546 2-Heptanone A dialkyl ketone with methyl and pentyl as the alkyl groups. Beilstein:1699063 C7H14O CAS:110-43-0 CATSNJVOTSVZJV-UHFFFAOYSA-N CCCCCC(C)=O CHEBI:5672 Gmelin:305860 Heptan-2-one InChI=1S/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3 KEGG:C08380 KNApSAcK:C00001254 LIPID_MAPS_instance:LMFA12000004 Methyl n-amyl ketone PMID:12769891 PMID:14759148 PMID:16025460 PMID:20416794 PMID:2270874 Reaxys:1699063 Wikipedia:2-Heptanone butylacetone chebi_ontology heptan-2-one methyl pentyl ketone n-amyl methyl ketone n-pentyl methyl ketone heterocyclic compound A cyclic compound having as ring members atoms of at least two different elements. CHEBI:5686 Heterocyclic compound chebi_ontology compuesto heterociclico compuestos heterociclicos heterocycle heterocyclic compounds ATP(3-) -3 503.972 504.15720 A ribonucleoside triphosphate oxoanion that is the trianion of adenosine 5'-triphosphate arising from deprotonation of three of the four free triphosphate OH groups. ATP(3-) Beilstein:9535056 C10H13N5O13P3 CHEBI:57299 InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/p-3/t4-,6-,7-,10-/m1/s1 Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP(O)([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-K chebi_ontology glycine zwitterion 0 2-azaniumylacetate 75.032 75.06660 An amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of glycine. C2H5NO2 CHEBI:57305 DHMQDGOQFOQNFH-UHFFFAOYSA-N Gmelin:1807 InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5) MetaCyc:GLY [NH3+]CC([O-])=O chebi_ontology glycine sarcosine zwitterion (methylammonio)acetate (methylazaniumyl)acetate 0 2-(methylazaniumyl)acetate 89.048 89.09320 An amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of sarcosine; major species at pH 7.3. C3H7NO2 CHEBI:57433 C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N Gmelin:323777 InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6) MetaCyc:SARCOSINE chebi_ontology sarcosine carnosine zwitterion (2S)-2-[(3-azaniumylpropanoyl)amino]-3-(1H-imidazol-4-yl)propanoate 0 226.107 226.23250 C9H14N4O3 CHEBI:57485 CQOVPNPJLQNMDC-ZETCQYMHSA-N Gmelin:397437 InChI=1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1 N(alpha)-(beta-alaniniumyl)-L-histidinate Zwitterionic form of carnosine. [NH3+]CCC(=O)N[C@@H](Cc1c[nH]cn1)C([O-])=O carnosine chebi_ontology long-chain fatty acid anion -1 43.990 A fatty acid anion with a chain length of C13 or greater. CHEBI:13652 CHEBI:57560 CO2R [O-]C([*])=O a long-chain carboxylate a long-chain fatty acid chebi_ontology long-chain fatty acid anions 5-oxoprolinate -1 128.035 128.10600 5-oxoprolinate anion 5-oxoproline 5-oxopyrrolidine-2-carboxylate 5-oxopyrrolidine-2-carboxylate Beilstein:4135383 C5H6NO3 CHEBI:57606 Gmelin:327019 InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/p-1 ODHCTXKNWHHXJC-UHFFFAOYSA-M Pyroglutamate The conjugate base of 5-oxoproline. [O-]C(=O)C1CCC(=O)N1 chebi_ontology gamma-amino-beta-hydroxybutyric acid zwitterion 0 119.058 119.11920 4-amino-3-hydroxybutanoate 4-ammonio-3-hydroxybutanoate 4-azaniumyl-3-hydroxybutanoate C4H9NO3 CHEBI:57630 InChI=1S/C4H9NO3/c5-2-3(6)1-4(7)8/h3,6H,1-2,5H2,(H,7,8) YQGDEPYYFWUPGO-UHFFFAOYSA-N Zwitterionic form of gamma-amino-beta-hydroxybutyric acid having an anionic carboxy group and a protonated amino group. [NH3+]CC(O)CC([O-])=O chebi_ontology chondroitin D-glucuronate anion Anionic form of chondroitin D-glucuronate arising from deprotonation of the carboxylic acid groups of the repeating units; major species at pH 7.3. CHEBI:57652 H2O(C14H20NO11)n chebi_ontology chondroitin D-glucuronate chondroitin D-glucuronate polyanion N-acylglycinate -1 101.011 101.06080 A carboxylic acid anion obtained by deprotonation of the carboxy group of any N-acylglycine. C3H3NO3R CHEBI:57670 [O-]C(=O)CNC([*])=O an N-acylglycine chebi_ontology D-proline zwitterion (2R)-pyrrolidinium-2-carboxylate 0 115.063 115.13050 A D-alpha-amino acid zwitterion that is D-proline in which a proton has been transferred from the carboxy group to the amino group. It is the major species at pH 7.3. C5H9NO2 CHEBI:57726 D-proline InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m1/s1 MetaCyc:D-PROLINE ONIBWKKTOPOVIA-SCSAIBSYSA-N [O-]C(=O)[C@H]1CCC[NH2+]1 chebi_ontology sphingosine(1+) (2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-aminium +1 300.290 300.49980 C18H38NO2 CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H]([NH3+])CO CHEBI:57756 InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/p+1/b15-14+/t17-,18+/m0/s1 The cationic sphingoid resulting from the protonation of the amino group of sphingosine. WWUZIQQURGPMPG-KRWOKUGFSA-O chebi_ontology sphing-4-enine nucleoside 5'-phosphate dianion -2 193.998 194.07920 C5H7O6PR2 CHEBI:57867 O[C@H]1[C@@H]([*])[C@H]([*])O[C@@H]1COP([O-])([O-])=O The conjugate base of a nucleoside 5'-phosphate. a nucleoside 5'-phosphate chebi_ontology nucleoside 5'-phosphate dianions tryptaminium +1 161.108 161.22310 2-(1H-indol-3-yl)ethanaminium APJYDQYYACXCRM-UHFFFAOYSA-O An ammonium ion that is the conjugate acid of tryptamine arising from protonation of the primary amino group; major species at pH 7.3. C10H13N2 CHEBI:57887 Gmelin:533978 InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2/p+1 [NH3+]CCc1c[nH]c2ccccc12 chebi_ontology tryptamine tryptaminium cation tryptaminium(1+) glutathionate(1-) -1 306.076 306.317 A peptide anion obtained by deprotonation of both carboxy groups and protonation of the glutamyl amino group of glutathione; major species at pH 7.3. C10H16N3O6S CHEBI:57925 InChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/p-1/t5-,6-/m0/s1 PMID:4200890 PMID:4745654 RWSXRVCMGQZWBV-WDSKDSINSA-M [NH3+][C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(=O)[O-])C(=O)[O-] chebi_ontology glutathionate glutathionate anion glutathionate ion glutathione nucleoside 5'-diphosphate(3-) -3 289.959 305.09310 C5H8O10P2R CHEBI:57930 C[C@@H]1O[C@H](COP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O NDP trianion NDP(3-) Trianion of nucleoside diiphosphate arising from deprotonation of all three free OH groups of the diphosphate; major species at pH 7.3. a ribonucleoside 5'-diphosphate chebi_ontology nucleoside diphosphate trianion ribonucleoside diphosphate trianion ribonucleoside diphosphate(3-) creatine zwitterion 0 131.069 131.13320 C4H9N3O2 CHEBI:57947 CN(CC([O-])=O)C(N)=[NH2+] CVSVTCORWBXHQV-UHFFFAOYSA-N InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9) MetaCyc:CREATINE Zwitterionic form of creatine arising from transfer of a proton from the carboxy to the guanidino group; major species at pH 7.3. chebi_ontology creatine {[amino(iminio)methyl](methyl)amino}acetate 5-oxo-D-prolinate (2R)-5-oxopyrrolidine-2-carboxylate -1 128.035 128.10600 5-oxo-D-prolinate 5-oxo-D-prolinate anion 5-oxo-D-prolinate(1-) 5-oxo-D-proline C5H6NO3 CHEBI:57948 InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/p-1/t3-/m1/s1 ODHCTXKNWHHXJC-GSVOUGTGSA-M The conjugate base of 5-oxo-D-proline; major species at pH 7.3. [O-]C(=O)[C@H]1CCC(=O)N1 chebi_ontology beta-alanine zwitterion 0 3-ammoniopropanoate 3-azaniumylpropanoate 89.048 89.09320 C3H7NO2 CHEBI:57966 Gmelin:454332 InChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6) UCMIRNVEIXFBKS-UHFFFAOYSA-N Zwitterionic form of beta-alanine arising from transfer of a proton from the carboxy to the amino group; major species at pH 7.3. [NH3+]CCC([O-])=O beta-alanine chebi_ontology bilirubin(2-) -2 2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoate 582.248 582.64630 A dicarboxylic acid dianion obtained by deprotonation of the two carboxy groups of bilirubin; major species at pH 7.3. BPYKTIZUTYGOLE-IFADSCNNSA-L Beilstein:4083310 C33H34N4O6 CC1=C(C=C)\C(NC1=O)=C\c1[nH]c(Cc2[nH]c(\C=C3NC(=O)C(C=C)=C/3C)c(C)c2CCC([O-])=O)c(CCC([O-])=O)c1C CHEBI:57977 InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/p-2/b26-13-,27-14- bilirubin IXalpha bilirubin dianion chebi_ontology primary aliphatic ammonium ion +1 31.042 31.05710 CH5NR CHEBI:58001 The conjugate acid of a primary aliphatic amine. [NH3+]C[*] an aliphatic amine chebi_ontology primary aliphatic ammonium cation primary aliphatic ammonium cations primary aliphatic ammonium ions octopaminium +1 1-(4-hydroxyphenyl)-2-aminoethanol 154.087 154.18640 2-hydroxy-2-(4-hydroxyphenyl)ethan-1-aminium 2-hydroxy-2-(4-hydroxyphenyl)ethanaminium 4-(2-ammonio-1-hydroxyethyl)phenol 4-(2-azaniumyl-1-hydroxyethyl)phenol C8H12NO2 CHEBI:58025 InChI=1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2/p+1 QHGUCRYDKWKLMG-UHFFFAOYSA-O The conjugate acid of octopamine; major species at pH 7.3. [NH3+]CC(O)c1ccc(O)cc1 chebi_ontology octopaminium cation octopaminium(1+) nucleoside 5'-monophosphate(2-) -2 211.001 211.08660 5'-ribonucleotide(2-) C5H8O7PR CHEBI:58043 CHEBI:85513 O[C@@H]1[C@H](O)[C@@H](COP([O-])([O-])=O)O[C@H]1[*] The dianion of a nucleoside monophosphate: major species at pH 7.3. a ribonucleoside 5'-phosphate chebi_ontology nucleoside monophosphate anion nucleoside monophosphate anions nucleoside monophosphate dianion nucleoside monophosphate dianions homocysteine zwitterion 0 135.035 135.18500 2-ammonio-4-sulfanylbutanoate 2-azaniumyl-4-sulfanylbutanoate An amino acid zwitterion of homocysteine arising from transfer of a proton from the carboxy to the amino group; major species at pH 7.3. C4H9NO2S CHEBI:58065 FFFHZYDWPBMWHY-UHFFFAOYSA-N InChI=1S/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7) [NH3+]C(CCS)C([O-])=O chebi_ontology nucleoside triphosphate(3-) -3 369.926 385.07300 C5H9O13P3R CHEBI:58104 C[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP(O)([O-])=O)[C@@H](O)[C@H]1O NTP trianion NTP(3-) Trianion of nucleoside triphosphate arising from deprotonation of three of the four free triphosphate OH groups; major species at pH 7.3. chebi_ontology nucleoside triphosphate trianion ribonucleoside triphosphate trianion ribonucleoside triphosphate(3-) (2S)-2-hydroxy monocarboxylic acid anion (2S)-2-hydroxy monocarboxylate (2S)-2-hydroxy monocarboxylates (2S)-2-hydroxy monocarboxylic acid anions (2S)-2-hydroxycarboxylate (2S)-alpha-hydroxy monocarboxylic acid anion (2S)-alpha-hydroxy monocarboxylic acid anions (S)-2-hydroxyacid anion (S)-2-hydroxyacid anions -1 74.000 74.03550 A hydroxy monocarboxylic acid anion where the hydroxy group is placed at position 2 (alpha to the carboxy group) and has (S)-stereochemistry; major species at pH 7.3. C2H2O3R CHEBI:58123 CHEBI:61394 CHEBI:70794 O[C@@H]([*])C([O-])=O PMID:10850983 a (2S)-2-hydroxycarboxylate chebi_ontology porphobilinogen(1-) -1 225.088 225.22120 3-[5-(azaniumylmethyl)-4-(carboxylatomethyl)-1H-pyrrol-3-yl]propanoate C10H13N2O4 CHEBI:58126 Conjugate base of porphobilinogen arising from deprotonation of the two carboxy groups and protonation of the amino group; major species at pH 7.3. InChI=1S/C10H14N2O4/c11-4-8-7(3-10(15)16)6(5-12-8)1-2-9(13)14/h5,12H,1-4,11H2,(H,13,14)(H,15,16)/p-1 QSHWIQZFGQKFMA-UHFFFAOYSA-M [NH3+]Cc1[nH]cc(CCC([O-])=O)c1CC([O-])=O chebi_ontology porphobilinogen porphobilinogen anion homocystine zwitterion 0 268.055 268.356 4,4'-disulfanediylbis(2-ammoniobutanoate) 4,4'-disulfanediylbis(2-azaniumylbutanoate) C(C(CCSSCCC(C(=O)[O-])[NH3+])[NH3+])([O-])=O C8H16N2O4S2 CHEBI:58163 Dizwitterionic form of homocystine arising from transfer of two protons from the carboxy to the amino groups; major species at pH 7.3. InChI=1S/C8H16N2O4S2/c9-5(7(11)12)1-3-15-16-4-2-6(10)8(13)14/h5-6H,1-4,9-10H2,(H,11,12)(H,13,14) ZTVZLYBCZNMWCF-UHFFFAOYSA-N chebi_ontology homocystine dizwitterion 3',5'-cyclic AMP(1-) -1 3',5'-cyclic AMP 3',5'-cyclic AMP anion 328.045 328.19800 An organophosphate oxoanion that is the conjugate base of 3',5'-cyclic AMP arising from deprotonation of the free phosphate OH group; major species at pH 7.3. C10H11N5O6P CHEBI:58165 IVOMOUWHDPKRLL-KQYNXXCUSA-M InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/p-1/t4-,6-,7-,10-/m1/s1 Nc1ncnc2n(cnc12)[C@@H]1O[C@@H]2COP([O-])(=O)O[C@H]2[C@H]1O PMID:7870041 PMID:7870042 Reaxys:3720459 adenosine 3',5'-cyclic monophosphate adenosine 3',5'-cyclic monophosphate anion adenosine 3',5'-cyclic monophosphate(1-) adenosine 3',5'-phosphate chebi_ontology O-phosphonatoethanaminium(1-) -1 140.011 140.05500 2-ammonioethyl phosphate 2-azaniumylethyl phosphate An organophosphate oxoanion that is the conjugate base of O-phosphoethanolamine arising from deprotonation of the phosphate OH groups and protonation of the amino group; major species at pH 7.3. C2H7NO4P CHEBI:58190 InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)/p-1 O-phosphonatoethanaminium SUHOOTKUPISOBE-UHFFFAOYSA-M [NH3+]CCOP([O-])([O-])=O chebi_ontology phosphoethanolamine (2R)-2-hydroxy monocarboxylic acid anion (2R)-2-hydroxy monocarboxylic acid anions (2R)-2-hydroxycarboxylate (2R)-alpha-hydroxy monocarboxylic acid anion (2R)-alpha-hydroxy monocarboxylic acid anions (R)-2-hydroxyacid anion (R)-2-hydroxyacid anions -1 74.000 A hydroxy monocarboxylic acid anion where the hydroxy group is placed at position 2 (alpha to the carboxy group) and has (R)-stereochemistry; major species at pH 7.3. C2H2O3R CHEBI:58314 MetaCyc:2R-hydroxy-carboxylates O[C@H]([*])C([O-])=O a (2R)-2-hydroxycarboxylate chebi_ontology trans-4-hydroxy-L-proline zwitterion (2S,4R)-4-hydroxypyrrolidinium-2-carboxylate 0 131.058 131.12990 An L-alpha-amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of trans-4-hydroxy-L-proline; major species at pH 7.3. C5H9NO3 CHEBI:58375 InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1 O[C@H]1C[NH2+][C@@H](C1)C([O-])=O PMMYEEVYMWASQN-DMTCNVIQSA-N chebi_ontology hydroxyproline zwitterion trans-4-hydroxy-L-proline trimethylammonium +1 60.081 60.11820 An ammonium ion that is the conjugate acid of trimethylamine, obtained via protonation of the nitrogen; major species at pH 7.3. C3H10N CHEBI:58389 C[NH+](C)C GETQZCLCWQTVFV-UHFFFAOYSA-O InChI=1S/C3H9N/c1-4(2)3/h1-3H3/p+1 MetaCyc:TRIMETHYLAMINE N,N-dimethylmethanaminium Reaxys:16709444 chebi_ontology trimethylamine trimethylammonium cation trimethylazanium trimethylazanium cation 5-oxo-L-prolinate (2S)-5-oxopyrrolidine-2-carboxylate -1 128.035 128.10600 5-oxo-L-prolate 5-oxo-L-proline Beilstein:4783230 C5H6NO3 CHEBI:58402 Conjugate base of 5-oxo-L-proline. Gmelin:675391 InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/p-1/t3-/m0/s1 MetaCyc:5-OXOPROLINE ODHCTXKNWHHXJC-VKHMYHEASA-M [O-]C(=O)[C@@H]1CCC(=O)N1 chebi_ontology 4-hydroxy-L-proline zwitterion (2S)-4-hydroxypyrrolidinium-2-carboxylate 0 131.058 131.12990 4-hydroxy-L-proline C5H9NO3 CHEBI:58419 InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3?,4-/m0/s1 OC1C[NH2+][C@@H](C1)C([O-])=O PMMYEEVYMWASQN-BKLSDQPFSA-N The amino acid zwitterion formed from 4-hydroxy-L-proline. It is the major microspecies present at pH 7.3. chebi_ontology histaminium +1 112.087 112.15300 2-(1H-imidazol-4-yl)ethanaminium An ammonium ion that is the conjugate acid of histamine protonated on the side-chain nitrogen. C5H10N3 CHEBI:58432 InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)/p+1 NTYJJOPFIAHURM-UHFFFAOYSA-O [NH3+]CCc1c[nH]cn1 chebi_ontology histamine histaminium cation nucleoside 3',5'-cyclic phosphate anion -1 176.995 177.07190 C5H6O5PR2 CHEBI:58464 The conjugate base of a nucleoside 3',5'-cyclic phosphate. [O-]P1(=O)OC[C@H]2O[C@@H]([*])[C@H]([*])[C@@H]2O1 a nucleoside 3',5'-cyclic phosphate chebi_ontology nucleoside 3',5'-cyclic phosphate anions dermatan sulfate polyanion CHEBI:58465 H2O.(C14H219NO14S)n The conjugate base of dermatan sulfate, obtained by deprotonation of carboxy and sulfate groups. chebi_ontology dermatan 4'-sulfate sphingosine-1-phosphocholine(1+) (2S,3R,4E)-2-azaniumyl-3-hydroxyoctadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphate +1 465.346 465.62730 An ammonium ion that is the conjugate acid of sphingosylphosphocholine, obtained by protonation of the amino group. Major species at pH 7.3. C23H50N2O5P CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H]([NH3+])COP([O-])(=O)OCC[N+](C)(C)C CHEBI:58906 InChI=1S/C23H49N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3/p+1/b18-17+/t22-,23+/m0/s1 JLVSPVFPBBFMBE-HXSWCURESA-O chebi_ontology sphing-4-enine-phosphocholine sphingosylphosphorylcholine(1+) organophosphate oxoanion An organic phosphoric acid derivative in which one or more oxygen atoms of the phosphate group(s) has been deprotonated. CHEBI:58945 chebi_ontology organophosphate oxoanions short-chain fatty acid anion -1 43.990 Any fatty acid anion obtained by removal of a proton from the carboxy group of a short-chain fatty acid (chain length of less than C6). CHEBI:58951 CO2R [O-]C([*])=O a short-chain fatty acid chebi_ontology short-chain fatty acid anions saturated fatty acid anion Any fatty acid anion in which there is no C-C unsaturation. CHEBI:58953 a saturated fatty acid chebi_ontology saturated fatty acid anions straight-chain saturated fatty acid anion Any saturated fatty acid anion lacking a carbon side-chain. CHEBI:58954 chebi_ontology straight-chain saturated fatty acid anions branched-chain fatty acid anion Any fatty acid anion with a carbon side-chain or isopropyl termination. CHEBI:58955 a branched-chain fatty acid branched-chain fatty acid anions chebi_ontology branched-chain saturated fatty acid anion Any saturated fatty acid anion with a carbon side-chain or isopropyl termination. CHEBI:58956 branched-chain saturated fatty acid anions chebi_ontology organosulfate oxoanion -1 95.952 96.06300 An organic anion of general formula RS(=O)2O(-) where R is an organyl group. CHEBI:58958 O4SR [O-]S(=O)(=O)O[*] chebi_ontology organosulfate oxoanions methyl isocyanate 0 57.021 57.05130 Beilstein:605318 C2H3NO CAS:624-83-9 CHEBI:59059 CN=C=O DrugBank:DB04337 Gmelin:100500 HAMGRBXTJNITHG-UHFFFAOYSA-N InChI=1S/C2H3NO/c1-3-2-4/h1H3 Iso-cyanatomethane Isocyanate de methyle MIC Methyl carbonimide Methyl isocyanide Methylcarbylamine PMID:16091349 PMID:19494520 PMID:24081639 PMID:3622432 PMID:6821040 Reaxys:605318 The isocyanate that is methane modified by a single isocyanato substituent. chebi_ontology isocyanatomethane isocyanatomethane (8xi)-cinchonan (8xi)-cinchonan 0 278.178 278.39140 C19H22N2 C=C[C@H]1C[N@@]2CC[C@H]1CC2Cc1ccnc2ccccc12 CHEBI:59137 Cinchonan or its (8S)-epimer. InChI=1S/C19H22N2/c1-2-14-13-21-10-8-15(14)11-17(21)12-16-7-9-20-19-6-4-3-5-18(16)19/h2-7,9,14-15,17H,1,8,10-13H2/t14-,15-,17?/m0/s1 UFJOYVQIDSNLHC-GIIGEWEBSA-N chebi_ontology (8S)-cinchonan (8S)-cinchonan (8alpha)-cinchonan 0 278.178 278.39140 4-((1S,2S,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]oct-2-ylmethyl)quinoline Beilstein:88419 C19H22N2 CHEBI:59138 InChI=1S/C19H22N2/c1-2-14-13-21-10-8-15(14)11-17(21)12-16-7-9-20-19-6-4-3-5-18(16)19/h2-7,9,14-15,17H,1,8,10-13H2/t14-,15-,17-/m0/s1 The (8S)-epimer of cinchonan. UFJOYVQIDSNLHC-ZOBUZTSGSA-N [H][C@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)Cc1ccnc2ccccc12 chebi_ontology biomarker A substance used as an indicator of a biological state. CHEBI:59163 biological marker chebi_ontology hapten Any substance capable of eliciting an immune response only when attached to a large carrier such as a protein. Examples include dinitrophenols; oligosaccharides; peptides; and heavy metals. CHEBI:59174 PMID:17875790 PMID:17986299 PMID:19101624 PMID:291959 PMID:3782019 chebi_ontology haptens straight-chain fatty acid Any fatty acid whose skeletal carbon atoms form an unbranched open chain. CHEBI:59202 chebi_ontology straight-chain fatty acids straight-chain fatty acid anion A fatty acid anion formed by deprotonation of the carboxylic acid functional group of a straight-chain fatty acid. CHEBI:59203 chebi_ontology straight-chain FA anion straight-chain FA anions straight-chain fatty acid anions cyclic fatty acid Any fatty acid containing anywhere in its structure a ring of atoms. CHEBI:59238 PMID:17113094 PMID:9300789 acides gras cycliques acidos grasos ciclicos chebi_ontology cyclic fatty acids zyklische Fettsaeuren EC 3.4.21.* (serine endopeptidase) inhibitor Any EC 3.4.* (hydrolases acting on peptide bond) inhibitor that inhibits the activity of a serine endopeptidase (EC 3.4.21.*). CHEBI:5924 EC 3.4.21.* (serine endopeptidase) inhibitors EC 3.4.21.* inhibitor EC 3.4.21.* inhibitors chebi_ontology inhibitor of serine endopeptidase (EC 3.4.21.*) inhibitor of serine endopeptidase (EC 3.4.21.*)s serine endopeptidase inhibitor serine endopeptidase inhibitors linear tetrapyrrole anion An organic anion arising from deprotonation of a acyclic tetrapyrrole compound. CHEBI:59252 acyclic tetrapyrrole anion acyclic tetrapyrrole anions chebi_ontology linear tetrapyrrole anions insulin (human) 0 5789.622 5793.54400 A peptide hormone produced in the pancreas and involved in regulating the metabolism of carbohydrates (particularly glucose) and fats. Commonly thought of as a protein, it consists of two petide chains, one containing 21 amino acid residues and the other containing 30; the chains are joined together by 2 disulfide bonds. Recombinant insulin is identical to human insulin, but is synthesised by inserting the human insulin gene into E. coli, which then produces insulin for human use. It is used in the treatment of type I and type II diabetes. C256H381N65O77S6 CAS:9004-10-8 CC[C@@H](C)[C@H](NC(=O)CN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H]1CSSC[C@H]2NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CSSC[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc3c[nH]cn3)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)Cc3ccccc3)C(C)C)C(N)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](Cc3c[nH]cn3)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc3ccc(O)cc3)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](Cc3ccc(O)cc3)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](Cc3ccc(O)cc3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC2=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](Cc2ccc(O)cc2)C(=O)N[C@@H]([C@H](C)O)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@H](C)O)C(O)=O)NC1=O)[C@H](C)O)[C@H](C)CC CHEBI:5931 DrugBank:DB00030 InChI=1S/C256H381N65O77S6/c1-29-130(23)202(311-190(337)103-258)250(391)315-200(128(19)20)246(387)286-158(75-82-197(347)348)216(357)281-154(70-77-186(261)333)220(361)306-181-115-402-403-116-182-241(382)303-176(110-323)238(379)293-161(88-122(7)8)224(365)294-167(95-139-53-61-145(328)62-54-139)227(368)282-153(69-76-185(260)332)217(358)289-160(87-121(5)6)222(363)283-157(74-81-196(345)346)219(360)301-173(101-188(263)335)233(374)297-169(97-141-57-65-147(330)66-58-141)230(371)307-180(240(381)302-174(254(395)396)102-189(264)336)114-401-400-113-179(213(354)272-106-191(338)277-152(72-79-194(341)342)215(356)280-150(51-42-84-270-256(266)267)211(352)271-107-192(339)278-165(93-137-46-36-32-37-47-137)226(367)296-166(94-138-48-38-33-39-49-138)229(370)298-170(98-142-59-67-148(331)68-60-142)236(377)318-205(134(27)326)253(394)321-85-43-52-184(321)244(385)284-151(50-40-41-83-257)221(362)319-206(135(28)327)255(397)398)309-247(388)199(127(17)18)314-234(375)163(90-124(11)12)291-228(369)168(96-140-55-63-146(329)64-56-140)295-223(364)159(86-120(3)4)288-209(350)132(25)276-214(355)156(73-80-195(343)344)285-245(386)198(126(15)16)313-235(376)164(91-125(13)14)292-232(373)172(100-144-105-269-119-275-144)300-237(378)175(109-322)279-193(340)108-273-212(353)178(112-399-404-117-183(308-242(181)383)243(384)317-204(133(26)325)251(392)304-177(111-324)239(380)316-203(131(24)30-2)249(390)310-182)305-225(366)162(89-123(9)10)290-231(372)171(99-143-104-268-118-274-143)299-218(359)155(71-78-187(262)334)287-252(393)207(208(265)349)320-248(389)201(129(21)22)312-210(351)149(259)92-136-44-34-31-35-45-136/h31-39,44-49,53-68,104-105,118-135,149-184,198-207,322-331H,29-30,40-43,50-52,69-103,106-117,257-259H2,1-28H3,(H2,260,332)(H2,261,333)(H2,262,334)(H2,263,335)(H2,264,336)(H2,265,349)(H,268,274)(H,269,275)(H,271,352)(H,272,354)(H,273,353)(H,276,355)(H,277,338)(H,278,339)(H,279,340)(H,280,356)(H,281,357)(H,282,368)(H,283,363)(H,284,385)(H,285,386)(H,286,387)(H,287,393)(H,288,350)(H,289,358)(H,290,372)(H,291,369)(H,292,373)(H,293,379)(H,294,365)(H,295,364)(H,296,367)(H,297,374)(H,298,370)(H,299,359)(H,300,378)(H,301,360)(H,302,381)(H,303,382)(H,304,392)(H,305,366)(H,306,361)(H,307,371)(H,308,383)(H,309,388)(H,310,390)(H,311,337)(H,312,351)(H,313,376)(H,314,375)(H,315,391)(H,316,380)(H,317,384)(H,318,377)(H,319,362)(H,320,389)(H,341,342)(H,343,344)(H,345,346)(H,347,348)(H,395,396)(H,397,398)(H4,266,267,270)/t130-,131-,132+,133+,134+,135+,149+,150+,151+,152+,153+,154+,155+,156+,157+,158+,159+,160+,161+,162+,163+,164+,165+,166+,167+,168+,169+,170+,171+,172+,173+,174+,175+,176+,177+,178+,179+,180+,181+,182-,183+,184+,198+,199+,200+,201+,202+,203+,204+,205+,206+,207+/m1/s1 Insulin Insulin recombinant KEGG:C00723 KEGG:D00085 PMID:22249812 PMID:22617471 PMID:22715632 PMID:22843207 PMID:8019699 Wikipedia:Insulin YAJCHEVQCOHZDC-QMMNLEPNSA-N chebi_ontology insulin (recombinant) prostaglandin carboxylic acid anion A prostanoid anion obtained by deprotonation of the carboxy group of any prostaglandin. CHEBI:59326 chebi_ontology prostaglandin carboxylic acid anions medium-chain fatty acid 0 44.998 45.01740 Any fatty acid with a chain length of between C6 and C12. CHEBI:59554 CHO2R MCFA MCFAs OC([*])=O chebi_ontology medium-chain fatty acids medium-chain fatty acid anion -1 43.990 A fatty acid anion resulting from the deprotonation of the carboxylic acid moiety of a medium-chain fatty acid. CHEBI:59558 CO2R MCFA anion MCFA anions [O-]C([*])=O a medium chain fatty acid chebi_ontology medium-chain FA anion medium-chain FA anions medium-chain fatty acid anions diamino acid anion An organic anion that is the conjugate base of diamino acid. CHEBI:59561 chebi_ontology diamino acid anions oxo fatty acid Any fatty acid containing at least one aldehydic or ketonic group in addition to the carboxylic acid group. CHEBI:59644 PMID:6434570 PMID:8454196 PMID:8638935 chebi_ontology oxo fatty acids phosphoric acids CHEBI:59698 Compounds containing one or more phosphoric acid units. chebi_ontology ribonucleoside triphosphate oxoanion An organophosphate anion resulting from deprotonation of at least one of the acidic hydroxy groups from the triphosphate moiety of a nucleoside triphosphate. CHEBI:59724 chebi_ontology ribonucleoside triphosphate anion ribonucleoside triphosphate anions ribonucleoside triphosphate oxoanions nucleophilic reagent A reagent that forms a bond to its reaction partner (the electrophile) by donating both bonding electrons. CHEBI:59740 chebi_ontology nucleophile nucleophiles nucleophilic reagents (S)-nicotinium(1+) (2S)-1-methyl-2-(pyridin-3-yl)pyrrolidinium (S)-nicotine (S)-nicotinium cation +1 163.124 163.23900 C10H15N2 CHEBI:59806 C[NH+]1CCC[C@H]1c1cccnc1 Gmelin:329042 InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/p+1/t10-/m0/s1 MetaCyc:NICOTINE SNICXCGAKADSCV-JTQLQIEISA-O The conjugate acid of (S)-nicotine arising from selective protonation of the tertiary amino group; major species at pH 7.3. chebi_ontology L-alpha-amino acid anion -1 73.016 88.08520 C2H3NO2R CHEBI:59814 C[C@H](N)C([O-])=O Conjugate base of an L-alpha-amino acid arising from deprotonation of the C-1 carboxy group. L-alpha-amino carboxylate chebi_ontology progestin A synthetic progestogen. CHEBI:59826 Wikipedia:Progestin chebi_ontology progestins hydroxy fatty acid anion CHEBI:59835 OH-FA anion OH-FA-anions OH-fatty acid anion OH-fatty acid anions The conjugate base of any hydroxy fatty acid, formed by deprotonation of the carboxylic acid moiety. chebi_ontology hydroxy fatty acid anions oxo fatty acid anion A fatty acid anion carrying one or more oxo substituents CHEBI:59836 chebi_ontology oxo fatty acid anions oxo-FA anion oxo-FA anions 3-hydroxy fatty acid 0 3-OH fatty acid 3-OH fatty acids 3-hydroxy fatty acids 89.024 89.07000 Any fatty acid with a hydroxy functional group in the beta- or 3-position. beta-Hydroxy fatty acids accumulate during cardiac hypoxia, and can also be used as chemical markers of bacterial endotoxins. C3H5O3R CHEBI:59845 OC([*])CC(O)=O PMID:1226425 PMID:17392575 PMID:3094448 PMID:7406063 beta-OH fatty acid beta-OH fatty acids beta-hydroxy fatty acid beta-hydroxy fatty acids chebi_ontology L-alpha-amino acid zwitterion 0 74.024 C2H4NO2R CHEBI:59869 L-alpha-amino acid zwitterions Zwitterionic form of an L-alpha-amino acid having an anionic carboxy group and a protonated amino group. [NH3+][C@@H]([*])C([O-])=O an L-alpha-amino acid chebi_ontology D-alpha-amino acid zwitterion 0 74.024 C2H4NO2R CHEBI:59871 D-alpha-amino acid zwitterions Zwitterionic form of a D-alpha-amino acid having an anionic carboxy group and a protonated amino group. [NH3+][C@H]([*])C([O-])=O a D-amino acid chebi_ontology N-acyl-L-alpha-amino acid anion -1 100.003 100.05290 A carboxylic acid anion that is the conjugate base of an N-acyl-L-alpha-amino acid arising from deprotonation of the C-1 carboxy group. C3H2NO3R2 CHEBI:59874 N-acyl-L-alpha-amino acid(1-) [O-]C(=O)[C@H]([*])NC([*])=O an N-acyl-L-amino acid chebi_ontology N-acyl-D-alpha-amino acid anion -1 100.003 100.05290 C3H2NO3R2 CHEBI:59876 N-acyl-D-alpha-amino acid(1-) The conjugate base of an N-acyl-D-alpha-amino acid arising from deprotonation of the C-1 carboxy group. [O-]C(=O)[C@@H]([*])NC([*])=O a N-acyl-D-amino acid chebi_ontology gamma-aminobutyric acid zwitterion 0 103.063 103.11980 4-aminobutanoate 4-ammoniobutanoate 4-azaniumylbutanoate BTCSSZJGUNDROE-UHFFFAOYSA-N C4H9NO2 CHEBI:59888 Gmelin:1041559 InChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7) Zwitterionic form of gamma-aminobutyric acid having an anionic carboxy group and a protonated amino group. [NH3+]CCCC([O-])=O chebi_ontology dopaminium(1+) +1 154.087 154.18640 2-(3,4-dihydroxyphenyl)ethan-1-aminium 2-(3,4-dihydroxyphenyl)ethanaminium An ammonium ion that is the conjugate acid of dopamine; major species at pH 7.3. C8H12NO2 CHEBI:59905 Gmelin:328863 InChI=1S/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2/p+1 VYFYYTLLBUKUHU-UHFFFAOYSA-O [NH3+]CCc1ccc(O)c(O)c1 chebi_ontology dopamine dopaminium cation chemical substance A chemical substance is a portion of matter of constant composition, composed of molecular entities of the same type or of different types. CHEBI:59999 Chemische Substanz chebi_ontology mixture A mixture is a chemical substance composed of multiple molecules, at least two of which are of a different kind. CHEBI:60004 Mischung chebi_ontology polymer A polymer is a mixture, which is composed of macromolecules of different kinds and which may be differentiated by composition, length, degree of branching etc.. CHEBI:60027 Kunststoff Polymer Wikipedia:Polymer chebi_ontology L-proline zwitterion (2S)-pyrrolidinium-2-carboxylate 0 115.063 115.13050 C5H9NO2 CHEBI:58054 CHEBI:60039 InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1 L-proline MetaCyc:PRO ONIBWKKTOPOVIA-BYPYZUCNSA-N The zwitterion formed from L-proline by proton transfer from the carboxy group to the ring nitrogen. It is the predominant species at physiological pH. [O-]C(=O)[C@@H]1CCC[NH2+]1 chebi_ontology dermatan anion A carbohydrate acid derivative anion obtained from dermatan by deprotonation of the carboxylic acid groups of the repeating units; the major species at pH 7.3. CHEBI:58701 CHEBI:60059 H2O(C14H20NO11)n chebi_ontology dermatan dermatan polyanion N-acylneuraminate -1 293.075 293.22740 5-alkanamido-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonate A sialic acid anion arising from deprotonation of the carboxy group of an N-acylneuraminic acid; major species at pH 7.3. C10H15NO9R CHEBI:60073 N-acylneuraminate cation [H][C@]1(OC(O)(C[C@H](O)[C@H]1NC([*])=O)C([O-])=O)[C@H](O)[C@H](O)CO an N-acylneuraminate chebi_ontology isoflurane 0 1-chloro-2,2,2-trifluoroethyl difluoromethyl ether 183.971 184.49210 2-chloro-2-difluoromethoxy-1,1,1-trifluoroethane Aerrane C3H2ClF5O CAS:26675-46-7 CHEBI:6015 DrugBank:DB00753 Drug_Central:1493 Ethane FC(F)OC(Cl)C(F)(F)F Forane Forene InChI=1S/C3H2ClF5O/c4-1(3(7,8)9)10-2(5)6/h1-2H Isoflurane KEGG:C07518 KEGG:D00545 PIWKPBJCKXDKJR-UHFFFAOYSA-N VSDB:1804 Wikipedia:Isoflurane chebi_ontology isoflurane isoflurano isofluranum ionic polymer An ionic polymer is a polymer, composed of ionic macromolecules. CHEBI:60164 chebi_ontology polyionic polymer divalent metal cation A metal cation with a valence of two. CHEBI:60240 a divalent metal cation chebi_ontology monovalent inorganic cation An atom or small molecule with a positive charge that does not contain carbon in covalent linkage, with a valency of one. CHEBI:60242 a monovalent cation chebi_ontology EC 3.4.* (hydrolases acting on peptide bond) inhibitor A hydrolase inhibitor that interferes with the action of any hydrolase acting on peptide bonds (peptidase), EC 3.4.*.*). CHEBI:60258 CHEBI:76763 EC 3.4.* (hydrolase acting on peptide bond) inhibitor EC 3.4.* (hydrolase acting on peptide bonds) inhibitors EC 3.4.* (hydrolases acting on peptide bond) inhibitors EC 3.4.* (peptidase) inhibitor EC 3.4.* (peptidase) inhibitors EC 3.4.* inhibitor EC 3.4.* inhibitors chebi_ontology inhibitor of hydrolases acting on peptide bond (EC 3.4.*) inhibitors of hydrolases acting on peptide bond (EC 3.4.*) peptidase inhibitors protease inhibitor protease inhibitors 3,3',5-triiodo-L-thyroninate (2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoate (2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propionate -1 3,3',5-triiodo-L-thyronine anion 3,3',5-triiodo-L-thyronine(1-) 649.782 649.96560 AUYYCJSJGJYCDS-LBPRGKRZSA-M C15H11I3NO4 CHEBI:60308 InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/p-1/t12-/m0/s1 N[C@@H](Cc1cc(I)c(Oc2ccc(O)c(I)c2)c(I)c1)C([O-])=O The anion resulting from the removal of the proton from the carboxylic acid group of 3,3',5-triiodo-L-thyronine. chebi_ontology liothyronine anion liothyronine(1-) thyroid hormone Any hormone produced by the thyroid gland CHEBI:60311 chebi_ontology thyroid hormones 2-methyl-2-(methylsulfanyl)propanal oxime 0 133.056 133.21200 2-(methylthio)-2-methylpropionaldehyde oxime 2-(methylthio)isobutyraldehyde oxime 2-methyl-2-(methylsulfanyl)propanaldoxime 2-methyl-2-(methylthio)propanal oxime 2-methyl-2-(methylthio)propionaldehyde oxime 2-methyl-2-(methylthio)propionaldoxime ADO Beilstein:2038299 C5H11NOS CAS:1646-75-9 CHEBI:60330 InChI=1S/C5H11NOS/c1-5(2,8-3)4-6-7/h4,7H,1-3H3 N-hydroxy-2-methyl-2-(methylsulfanyl)propan-1-imine Patent:US3217037 Reaxys:2038299 Temik oxime The oxime resulting from the formal condensation of 2-methyl-2-(methylsulfanyl)propanal with hydroxylamine. Addition of the oxime group to methyl isocyanate forms the final step in the synthesis of the systemic insecticide aldicarb. ZFGMCJAXIZTVJA-UHFFFAOYSA-N [H]C(=NO)C(C)(C)SC aldicarb oxime chebi_ontology peptide anion An anion formed by deprotonation of at least one peptide carboxy group. CHEBI:60334 chebi_ontology peptide anions peptide zwitterion 0 C2H4NO2R(C2H2NOR)n CHEBI:60466 Zwitterionic form of any peptide where the amino terminus is positively charged and the carboxy terminus is negatively charged. chebi_ontology peptide zwitterions molybdenum cofactor(2-) -2 552.33000 553.856 C10H11MoN5O8PS3 CHEBI:60525 MoCo Molybdenum cofactor MoCo protonated to pH 7.3. PDB:3HBG PDB:3HBP PDB:3HBQ PDBeChem:MSS PMID:20356030 chebi_ontology NMDA receptor antagonist Any substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs. CHEBI:60643 CHEBI:60797 N-methyl-D-aspartate receptor antagonist N-methyl-D-aspartate receptor antagonists NMDA receptor antagonists NMDAR antagonist NMDAR antagonists chebi_ontology prostaglandin E2(1-) (5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dien-1-oate -1 351.217 351.45710 Beilstein:8364130 C20H31O5 CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC([O-])=O CHEBI:606564 InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/p-1/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1 The conjugate base of prostaglandin E2; major species at pH 7.3. XEYBRNLFEZDVAW-ARSRFYASSA-M chebi_ontology prostaglandin E2 prostaglandin E2 anion N-benzoylglycinate (benzoylamino)acetate -1 178.050 178.16470 2-benzamidoacetate An alpha-amino-acid anion that is the conjugate base of N-benzoylglycine; major species at pH 7.3. Beilstein:3610359 C9H8NO3 CHEBI:24594 CHEBI:606565 Gmelin:329632 InChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)/p-1 MetaCyc:CPD-425 N-benzoylglycinate anion N-benzoylglycinate(1-) N-benzoylglycine PMID:22153801 QIAFMBKCNZACKA-UHFFFAOYSA-M Reaxys:3610359 [O-]C(=O)CNC(=O)c1ccccc1 chebi_ontology hippurate excitatory amino acid antagonist Any substance which inhibits the action of receptors for excitatory amino acids. CHEBI:60798 EAA receptor antagonist EAA receptor antagonists chebi_ontology excitatory amino acid antagonists excitatory amino acid receptor antagonist excitatory amino acid receptor antagonists adjuvant Any pharmacological or immunological agent that modifies the effect of other agents such as drugs or vaccines while having few if any direct effects when given by itself. CHEBI:60809 adjuvants chebi_ontology tubulin modulator Any substance that interacts with tubulin to inhibit or promote polymerisation of microtubules. CHEBI:60832 chebi_ontology tubulin modulators D-alpha-amino acid anion -1 73.016 88.08520 Any alpha-amino acid anion in which the parent amino acid has D-configuration. C2H3NO2R CHEBI:60895 C[C@@H](N)C([O-])=O D-alpha-amino acid anions D-alpha-amino carboxylate chebi_ontology racemate A racemate is an equimolar mixture of a pair of enantiomers. CHEBI:60911 chebi_ontology melange racemique racemates racemic mixture keratan sulfate A sulfated glycosaminoglycan, a linear polymer that consists of the repeating disaccharide [3)-beta-Gal-(1->4)-beta-GlcNAc-(1->] and containing sulfo groups located at random positions. CHEBI:60924 chebi_ontology keratan sulfates keratosulfate amino monosaccharide Any amino sugar that is a monosaccharide in which one alcoholic hydroxy group is replaced by an amino group. CHEBI:60926 amino monosaccharides chebi_ontology EC 3.5.1.98 (histone deacetylase) inhibitor An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the function of histone deacetylase (EC 3.5.1.98). CHEBI:61115 EC 3.5.1.98 (histone deacetylase) inhibitors EC 3.5.1.98 inhibitor EC 3.5.1.98 inhibitors HDAC inhibitor HDAC inhibitors HDACi HDACis HDI HDIs Wikipedia:Histone_deacetylase_inhibitor chebi_ontology histone amidohydrolase inhibitor histone amidohydrolase inhibitors histone deacetylase (EC 3.5.1.98) inhibitor histone deacetylase (EC 3.5.1.98) inhibitors histone deacetylase inhibitor histone deacetylase inhibitors nucleobase-containing molecular entity Any compound that has a nucleobase as a part. CHEBI:61120 chebi_ontology nucleobase-containing compound nucleobase-containing compounds nucleobase-containing molecular entities adenyl nucleotide A nucleotide having adenine as the base. CHEBI:61293 adenine nucleotide chebi_ontology adenyl ribonucleotide A purine riboncleotide where adenine is the purine. CHEBI:61296 adenine ribonucleotide chebi_ontology C21-steroid 0 288.282 288.511 A steroid that has a structure based on a 21-carbon (pregnane) skeleton. Note that individual examples may have ring substituents at other positions and/or contain double bonds, aromatic A-rings, expanded/contracted rings etc., so the formula and mass may vary from that given for the generic structure. C1CCCC2C1(C3C(CC2)C4C(CC3)(C(CC4)CC)C)C C21H36 CHEBI:61313 InChI=1S/C21H36/c1-4-15-9-11-18-17-10-8-16-7-5-6-13-20(16,2)19(17)12-14-21(15,18)3/h15-19H,4-14H2,1-3H3 JWMFYGXQPXQEEM-UHFFFAOYSA-N a C21-steroid chebi_ontology C4-dicarboxylate A dicarboxylate that contains four carbon atoms. CHEBI:61336 chebi_ontology 3-hydroxy carboxylic acid 3-hydroxy carboxylic acids 3-hydroxycarboxylic acid 3-hydroxycarboxylic acids Any hydroxy carboxylic acid which contains a hydroxy group located beta- to the carboxylic acid group. CHEBI:61355 beta-hydroxy carboxylic acid beta-hydroxy carboxylic acids beta-hydroxycarboxylic acid beta-hydroxycarboxylic acids chebi_ontology sulfolipid A compound containing a sulfonic acid residue joined by a carbon-sulfur bond to a lipid. CHEBI:61384 chebi_ontology sulfolipids dihydroxyphenylacetic acid A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents. CHEBI:23787 CHEBI:61409 chebi_ontology dihydroxyphenylacetic acids polyanionic polymer A polymer, composed of polyanion macromolecules. CHEBI:61469 chebi_ontology polyanion polyanions nucleoside triphosphate(4-) -4 368.918 384.06500 A ribonucleoside triphosphate oxoanion arising from global deprotonation of the triphosphate group of any nucleoside triphosphate. C5H8O13P3R CHEBI:61557 C[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O NTP tetraanion NTP(4-) a ribonucleoside 5'-triphosphate chebi_ontology nucleoside 5'-triphosphate tetraanion nucleoside triphosphate(4-) pyridoisoquinoline An organic heterotricyclic compound with a skeleton derived from a pyridine ring fused to an isoquinoline. CHEBI:61692 chebi_ontology pyridoisoquinolines fatty acid derivative Any organic molecular entity derived from a fatty acid. CHEBI:61697 FA derivative FA derivatives chebi_ontology fatty acid derivatives microtubule-destabilising agent Any substance that interacts with tubulin to inhibit polymerisation of microtubules. CHEBI:61951 PMID:17099073 chebi_ontology microtubule destabilising agent microtubule destabilising agents microtubule destabilising role microtubule destabilizing role microtubule-destabilising agents microtubule-destabilizing agent microtubule-destabilizing agents polar amino acid zwitterion 0 74.024 74.05870 C2H4NO2R CHEBI:62031 MetaCyc:Polar-amino-acids Zwitterionic form of a polar amino acid having an anionic carboxy group and a protonated amino group. [NH3+]C([*])C([O-])=O a polar amino acid chebi_ontology 1,1-diunsubstituted alkanesulfonate -1 1,1-di-unsubstituted alkanesulfonate 1,1-di-unsubstituted alkanesulfonates 1,1-diunsubstituted alkanesulfonates 93.972 94.09000 An alkanesulfonate in which the carbon at position 1 is attached to at least two hydrogens. CH2O3SR CHEBI:62081 KEGG:C15521 MetaCyc:Alkanesulfonates [H]C([H])([*])S([O-])(=O)=O chebi_ontology signalling molecule A molecular messenger in which the molecule is specifically involved in transmitting information between cells. Such molecules are released from the cell sending the signal, cross over the gap between cells by diffusion, and interact with specific receptors in another cell, triggering a response in that cell by activating a series of enzyme controlled reactions which lead to changes inside the cell. CHEBI:62488 chebi_ontology signal molecule signal molecules signaling molecule signaling molecules signalling molecules sphingomyelin d18:1(1+) +1 492.333 A quaternary ammonium ion that is the conjugate acid of sphingomyelin d18:1, obtined by protonation of the anionic phosphate function. C24H49N2O6PR CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP(O)(=O)OCC[N+](C)(C)C)NC([*])=O CHEBI:58216 CHEBI:62490 KEGG:C00550 LIPID_MAPS_instance:LMSP03010000 MetaCyc:Sphingomyelins N-acyl-sphing-4-enine-1-phosphocholine N-acyl-sphingosylphosphocholine N-acyl-sphingosylphosphocholines N-acyl-sphingosylphosphorylcholine N-acyl-sphingosylphosphorylcholines N-acylsphingosylphosphocholine PMID:10951276 PMID:10970788 PMID:12649340 PMID:16341241 PMID:19443184 PMID:2187537 PMID:8086039 Sphingomyelin chebi_ontology sphingomyelins methyl-branched fatty acid Any branched-chain fatty acid containing methyl branches only. CHEBI:62499 PMID:17030019 PMID:19747846 PMID:19933331 chebi_ontology methyl-branched fatty acids folate(2-) -2 439.124 439.38160 C19H17N7O6 CHEBI:62501 InChI=1S/C19H19N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/p-2/t12-/m0/s1 MetaCyc:CPD-12826 N-(4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamate(2-) Nc1nc2ncc(CNc3ccc(cc3)C(=O)N[C@@H](CCC([O-])=O)C([O-])=O)nc2c(=O)[nH]1 OVBPIULPVIDEAO-LBPRGKRZSA-L The dicarboxylic acid dianion formed from folic acid by loss of a proton from each of the two carboxy groups in the glutamic acid moiety. chebi_ontology folate anionic phospholipid Any organophosphate oxoanion that is a negatively charged phospholipid, e.g. phosphatidylserine(1-), phosphatidate(2-), phosphatidylglycerol(1-). CHEBI:62643 anionic phospholipids chebi_ontology phospholipid anion phospholipid anions tyrosine derivative An amino acid derivative resulting from reaction of tyrosine at the amino group or the carboxy group, any substitution of phenyl hydrogens, or from the replacement of any hydrogen of tyrosine by a heteroatom. The definition normally excludes peptides containing tyrosine residues. CHEBI:62761 chebi_ontology tyrosine derivatives reactive nitrogen species A family of nitrogen molecular entities which are highly reactive and derived from nitric oxide (.NO) and superoxide (O2.(-)) produced via the enzymatic activity of inducible nitric oxide synthase 2 (NOS2) and NADPH oxidase respectively. CHEBI:62764 PMID:12076975 PMID:17667957 PMID:9741578 RNI RNS Wikipedia:Reactive_nitrogen_species chebi_ontology fuel additive Any additive that enhances the efficiency of fuel. CHEBI:62803 chebi_ontology fuel additives fuel enhancer hepatoprotective agent Any compound that is able to prevent damage to the liver. CHEBI:62868 antihepatotoxic agent chebi_ontology hepatoprotective agents icosanoid anion CHEBI:62937 The carboxylic acid anion that is the conjugate base of an icosanoid, formed when the carboxy group is deprotonated. chebi_ontology eicosanoid anion eicosanoid anions icosanoid anion icosanoid anions glycosylceramide A ceramide compound formed by the replacement of the glycosidic hydroxy group of a cyclic form of a monosaccharide (or derivative) by a ceramide group. CHEBI:62941 chebi_ontology glycosylceramides leukotriene anion A eicosanoid anion that is the conjugate base of a leukotriene. CHEBI:62942 chebi_ontology leukotriene anions prostanoid anion An icosanoid anion that is the conjugate base of a prostanoid. CHEBI:62943 chebi_ontology prostanoid anions sialic acid anion A carboxylic acid anion that is the conjugate base of a sialic acid, formed by deprotonation of the carboxy group. CHEBI:62944 chebi_ontology sialic acid anions thromboxane anion A prostanoid anion that is the conjugate base of a thromboxane. CHEBI:62945 chebi_ontology thromboxane anions 4-hydroxyprolinate -1 130.050 130.12190 4-hydroxyproline anion 4-hydroxypyrrolidine-2-carboxylate C5H8NO3 CHEBI:62978 InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/p-1 OC1CNC(C1)C([O-])=O PMMYEEVYMWASQN-UHFFFAOYSA-M The alpha-amino-acid anion formed by loss of a proton from the carboxy group of 4-hydroxyproline. chebi_ontology hydroxyprolinate hydroxyproline anion 4-hydroxy-L-prolinate (2S)-4-hydroxypyrrolidine-2-carboxylate -1 130.050 130.12190 4-hydroxy-L-proline anion C5H8NO3 CHEBI:62981 InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/p-1/t3?,4-/m0/s1 OC1CN[C@@H](C1)C([O-])=O PMMYEEVYMWASQN-BKLSDQPFSA-M Reaxys:4742919 The L-alpha-amino acid anion that is the conjugate base of 4-hydroxy-L-proline, formed by proton loss from the carboxy group. It is the major microspecies present at pH > 10.6. chebi_ontology emulsifier CHEBI:63046 The chemical role played by a substance that stabilizes an emulsion by increasing its kinetic stability. chebi_ontology emulgent emulgents emulsifiers beta-alaninate -1 3-aminopropanoate 88.040 88.08520 A beta-amino-acid anion that is the conjugate base of beta-alanine. C3H6NO2 CHEBI:63070 InChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6)/p-1 NCCC([O-])=O Reaxys:3536336 UCMIRNVEIXFBKS-UHFFFAOYSA-M beta-alaninate anion beta-alaninate(1-) chebi_ontology 4-hydroxyproline zwitterion 0 131.058 131.12990 4-hydroxypyrrolidinium-2-carboxylate C5H9NO3 CHEBI:63137 InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9) OC1C[NH2+]C(C1)C([O-])=O PMMYEEVYMWASQN-UHFFFAOYSA-N The amino acid zwitterion formed from 4-hydroxyproline. chebi_ontology glycosyl compound A carbohydrate derivative arising formally from the elimination of water from a glycosidic hydroxy group and an H atom bound to an oxygen, carbon, nitrogen or sulfur atom of a separate entity. CHEBI:63161 chebi_ontology glycosyl compounds ribonucleoside monophosphate oxoanion An organophosphate oxoanion resulting from deprotonation of at least one of the acidic hydroxy groups from the phosphate moiety of a ribonucleoside monophosphate. CHEBI:63165 chebi_ontology ribonucleoside monophosphate oxoanions pyranopterin An organic heterotricyclic compound that consists of a pterin ring system having a pyran ring ortho-fused at any position. CHEBI:63169 chebi_ontology pyranopterins oxidising agent A substance that removes electrons from another reactant in a redox reaction. CHEBI:63248 chebi_ontology oxidant oxidants oxidiser oxidisers oxidising agents oxidizer oxidizers oxidizing agent oxidizing agents carbohydrate derivative Any organooxygen compound derived from a carbohydrate by replacement of one or more hydroxy group(s) by an amino group, a thiol group or similar heteroatomic groups. The term also includes derivatives of these compounds. CHEBI:63299 carbohydrate derivatives chebi_ontology derivatised carbohydrate derivatised carbohydrates derivatized carbohydrate derivatized carbohydrates monosaccharide derivative A carbohydrate derivative that is formally obtained from a monosaccharide. CHEBI:63367 chebi_ontology monosaccharide derivatives ketoaldonic acid derivative A monosaccharide derivative that is formally obtained from a ketoaldonic acid. CHEBI:63394 chebi_ontology ketoaldonic acid derivatives pentose derivative A monosaccharide derivative that is formally obtained from a pentose. CHEBI:63409 chebi_ontology pentose derivatives all-trans-retinyl ester 0 313.217 313.45380 A retintinyl ester in which all double bonds of the retinyl side-chain have trans-configuration. C21H29O2R CC(\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C)=C/COC([*])=O CHEBI:63410 HMDB:HMDB0003598 KEGG:C02075 MetaCyc:All-trans-Retinyl-Esters PMID:12741839 PMID:16116091 PMID:19490105 an all-trans-retinyl ester chebi_ontology carbohydrate acid derivative A carbohydrate derivative that is formally obtained from a carbohydrate acid. CHEBI:63436 carbohydrate acid derivatives chebi_ontology sulfur-containing amino-acid anion A sulfur-containing amino acid whose alpha-carboxylic acid group is ionized (not protonated). CHEBI:63470 chebi_ontology sulfur-containing amino-acid anions branched-chain amino-acid anion A branched-chain amino acid whose alpha-carboxylic acid group is ionized (not protonated). CHEBI:63471 branched-chain amino-acid anions chebi_ontology aromatic amino-acid anion An aromatic amino acid whose alpha-carboxylic acid group is ionized (non-protonated). CHEBI:63473 aromatic amino-acid anions chebi_ontology iodothyroninate An iodothyronine whose alpha carboxylic acid group of the tyrosine is ionized (not protonated). CHEBI:63477 chebi_ontology iodothyroninates explosive A substance capable of undergoing rapid and highly exothermic decomposition. CHEBI:63490 Wikipedia:Explosive_material chebi_ontology explosive compound explosive compounds explosive material explosives explosives chemical explosives chemicals gonadotropin releasing hormone agonist Any drug which binds to gonadotropin-releasing hormone receptors and triggers a response. CHEBI:63533 GnRH agonist GnRH agonists GnRH-A Wikipedia:Gonadotropin-releasing_hormone_agonist chebi_ontology gonadotrophin releasing hormone agonist gonadotrophin releasing hormone agonists gonadotropin releasing hormone agonists monoamine An aralylamino compound which contains one amino group connected to an aromatic ring by a two-carbon chain. Monoamines are derived from aromatic amino acids like phenylalanine, tyrosine, tryptophan, and the thyroid hormones by the action of aromatic amino acid decarboxylase enzymes. CHEBI:63534 PMID:21822758 PMID:21993877 PMID:22005599 PMID:22082101 PMID:22153577 PMID:22213370 PMID:22218931 PMID:22342987 PMID:22371656 chebi_ontology monoamines naturally occurring monoamine naturally occurring monoamines carbohydrate acid derivative anion A carboxylic acid anion resulting from the deprotonation of the carboxy group of a carbohydrate acid derivative. CHEBI:63551 carbohydrate acid anion derivative carbohydrate acid anion derivatives carbohydrate acid derivative anions chebi_ontology ketoaldonate derivative A carbohydrate acid derivative anion that is formally obtained from a ketoaldonate. CHEBI:63561 chebi_ontology ketoaldonate derivatives neuroprotective agent Any compound that can be used for the treatment of neurodegenerative disorders. CHEBI:63726 chebi_ontology neuroprotectant neuroprotectants neuroprotective agents retinoid X receptor agonist An agonist that selectively binds to and activates a retinoid X receptor. CHEBI:63794 Wikipedia:Retinoid_X_receptor chebi_ontology retinoid X receptor agonists protein kinase C agonist An agonist that selectively binds to and activates a protein kinase C receptor CHEBI:64018 chebi_ontology protein kinase C agonists food additive Any substance which is added to food to preserve or enhance its flavour and/or appearance. CHEBI:64047 Wikipedia:Food_additive chebi_ontology food additives food acidity regulator A food additive that is used to change or otherwise control the acidity or alkalinity of foods. They may be acids, bases, neutralising agents or buffering agents. CHEBI:64049 Wikipedia:Acidity_regulator acidity regulator acidity regulators chebi_ontology food acidity regulators pH control agent pH control agents protein kinase agonist An agonist that selectively binds to and activates a protein kinase receptor. CHEBI:64106 chebi_ontology protein kinase agonists aralkylamino compound An organic amino compound in which an aminoalkyl group is linked to an arene. CHEBI:64365 aralkylamino compounds chebi_ontology biaryl An organic aromatic compound whose structure contains two aromatic rings or ring systems, joined to each other by a single bond. CHEBI:64459 biaryls chebi_ontology tryptophan zwitterion 0 2-ammonio-3-(1H-indol-3-yl)propanoate 2-azaniumyl-3-(1H-indol-3-yl)propanoate 204.090 204.22520 An amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of tryptophan; major species at pH 7.3. C11H12N2O2 CHEBI:64554 InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15) QIVBCDIJIAJPQS-UHFFFAOYSA-N [NH3+]C(Cc1c[nH]c2ccccc12)C([O-])=O chebi_ontology methionine zwitterion 0 149.051 149.21100 2-ammonio-4-(methylsulfanyl)butanoate 2-azaniumyl-4-(methylsulfanyl)butanoate An amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of methionine; major species at pH 7.3. C5H11NO2S CHEBI:64558 CSCCC([NH3+])C([O-])=O FFEARJCKVFRZRR-UHFFFAOYSA-N InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8) chebi_ontology methionine EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor 5,10-methylenetetrahydrofolate:glycine hydroxymethyltransferase inhibitor 5,10-methylenetetrahydrofolate:glycine hydroxymethyltransferase inhibitors An EC 2.1.2.* (hydroxymethyl-, formyl- and related transferases) inhibitor that interferes with the action of glycine hydroxymethyltransferase (EC 2.1.2.1). CHEBI:64570 EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitors EC 2.1.2.1 inhibitor EC 2.1.2.1 inhibitors L-serine hydroxymethyltransferase inhibitor L-serine hydroxymethyltransferase inhibitors L-threonine aldolase inhibitor L-threonine aldolase inhibitors Wikipedia:Glycine_hydroxymethyltransferase allothreonine aldolase inhibitor allothreonine aldolase inhibitors chebi_ontology glycine hydroxymethyltransferase (EC 2.1.2.1) inhibitor glycine hydroxymethyltransferase (EC 2.1.2.1) inhibitors glycine hydroxymethyltransferase inhibitor glycine hydroxymethyltransferase inhibitors serine aldolase inhibitor serine aldolase inhibitors serine hydroxymethylase inhibitor serine hydroxymethylase inhibitors serine hydroxymethyltransferase inhibitor serine hydroxymethyltransferase inhibitors serine transhydroxymethylase inhibitor serine transhydroxymethylase inhibitors threonine aldolase inhibitor threonine aldolase inhibitors NMDA receptor agonist An excitatory amino acid agonist which binds to NMDA receptors and triggers a response. CHEBI:64571 N-methyl-D-aspartate receptor agonist N-methyl-D-aspartate receptor agonists NMDA receptor agonists NMDAR agonist NMDAR agonists chebi_ontology flour treatment agent A food additive which is added to flour or dough to improve baking quality and/or colour. CHEBI:64577 Wikipedia:Flour_treatment_agent chebi_ontology dough improver dough improvers flour treatment agent improving agent improving agents sphingomyelin 0 282.098 282.23070 Any of a class of phospholipids in which the amino group of a sphingoid base is in amide linkage with one of several fatty acids, while the terminal hydroxy group of the sphingoid base is esterified to phosphorylcholine. C9H19N2O6PR2 CHEBI:64583 C[N+](C)(C)CCOP([O-])(=O)OC[C@H](NC([*])=O)[C@H](O)[*] Ceramide phosphocholine LIPID_MAPS_class:LMSP0301 N-(acyl)-sphingosylphosphocholine PMID:27242221 chebi_ontology uremic toxin A toxin that accumulates in patients with chronic kidney disease. CHEBI:64584 Wikipedia:Uremic_toxin chebi_ontology uremic toxins glycine transporter 1 inhibitor Any glycine transporter inhibitor that interferes with the action of glycine 1 transporters. CHEBI:64588 GlyT1 inhibitor GlyT1 inhibitors PMID:17504107 PMID:18758757 PMID:20678516 PMID:21141920 PMID:21531289 PMID:22177408 Wikipedia:Glycine_transporter_1 chebi_ontology glycine transporter 1 inhibitors glycine receptor agonist An agonist that binds to and activates glycine receptors CHEBI:64589 chebi_ontology glycine receptor agonists C21-steroid hormone A steroid compound with a structure based on a 21-carbon (pregnane) skeleton that acts as a hormone. C21-steroid hormones CHEBI:64600 chebi_ontology ether lipid A lipid similar in structure to a glycerolipid but in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. CHEBI:64611 PMID:21309516 PMID:22114698 PMID:22148427 PMID:22306069 PMID:22348073 PMID:22366205 PMID:22506086 PMID:22609598 Wikipedia:Ether_lipid chebi_ontology ether glycerolipid ether glycerolipids ether lipids divalent inorganic cation An inorganic cation with a valency of two. CHEBI:64641 chebi_ontology one-carbon compound An organic molecular entity containing a single carbon atom (C1). CHEBI:64708 chebi_ontology one-carbon compounds organic acid Any organic molecular entity that is acidic and contains carbon in covalent linkage. CHEBI:64709 chebi_ontology organic acids anionic group A group that carries an overall negative charge. CHEBI:64767 anionic groups chebi_ontology organic anionic group An anionic group that contains carbon. CHEBI:64775 chebi_ontology organic anionic groups cosmetic CHEBI:64857 The role played by a substance in enhancing the appearance or odour of the human body; a name given to the substance itself or to a component of it. Wikipedia:Cosmetics chebi_ontology cosmetic component cosmetics poison Any substance that causes disturbance to organisms by chemical reaction or other activity on the molecular scale, when a sufficient quantity is absorbed by the organism. CHEBI:64909 Wikipedia:Poison chebi_ontology poisonous agent poisonous agents poisonous substance poisonous substances poisons toxic agent toxic agents toxic substance toxic substances antimitotic Any compound that inhibits cell division (mitosis). CHEBI:64911 Wikipedia:Mitotic_inhibitor antimitotics chebi_ontology mitosis inhibitor mitosis inhibitors mitotic inhibitor mitotic inhibitors antiplasmodial drug An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria. CHEBI:64915 antiplasmodial agent antiplasmodial agents antiplasmodial drugs antiplasmodium agent antiplasmodium agents antiplasmodium drug antiplasmodium drugs chebi_ontology lipoprotein A clathrate complex consisting of a lipid enwrapped in a protein host without covalent binding in such a way that the complex has a hydrophilic outer surface consisting of all the protein and the polar ends of any phospholipids. CHEBI:6495 KEGG:C01834 Lipoprotein chebi_ontology lipoprotein particle lipoproteins anti-asthmatic agent Any compound that has anti-asthmatic effects. CHEBI:65023 anti-asthmatic agents antiasthmatic agent antiasthmatic agents chebi_ontology polysaccharide derivative A carbohydrate derivative that is any derivative of a polysaccharide. CHEBI:65212 chebi_ontology polysaccharide derivatives food preservative CHEBI:65255 Substances which are added to food in order to prevent decomposition caused by microbial growth or by undesirable chemical changes. chebi_ontology food preservatives antimicrobial food preservative A food preservative which prevents decomposition of food by preventing the growth of fungi or bacteria. In European countries, E-numbers for permitted food preservatives are from E200 to E299, divided into sorbates (E200-209), benzoates (E210-219), sulfites (E220-229), phenols and formates (E230-239), nitrates (E240-259), acetates (E260-269), lactates (E270-279), propionates (E280-289) and others (E290-299). CHEBI:65256 antimicrobial food preservatives antimicrobial preservative antimicrobial preservatives chebi_ontology GABA antagonist A compound that inhibits the action of gamma-aminobutyric acid. CHEBI:65259 GABA antagonists Wikipedia:GABA_antagonist chebi_ontology gamma-aminobutyric acid receptor antagonist gamma-aminobutyric acid receptor antagonists antacid Any substance which is used to neutralise stomach acidity. CHEBI:65265 Wikipedia:Antacid antacids chebi_ontology primary ammonium ion +1 17.027 An ammonium ion resulting from the protonation of the nitrogen atom of a primary amine. Major species at pH 7.3. CHEBI:65296 H3NR [NH3+][*] a primary amine chebi_ontology substituted ammonium C4-dicarboxylic acid Any dicarboxylic acid that contains four carbon atoms. C4-dicarboxylic acids CHEBI:66873 chebi_ontology carnosinate (2S)-2-(beta-alanylamino)-3-(1H-imidazol-4-yl)propanoate -1 225.099 225.22450 An N-acyl-L-alpha-amino acid anion that is the conjugate base of carnosine, obtained by deprotonation of the carboxy group. C9H13N4O3 CHEBI:66874 CQOVPNPJLQNMDC-ZETCQYMHSA-M InChI=1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)/p-1/t7-/m0/s1 N(alpha)-(beta-alanyl)-L-histidinate NCCC(=O)N[C@@H](Cc1c[nH]cn1)C([O-])=O Reaxys:6337985 carnosinate anion carnosinate(1-) chebi_ontology N-alkylglycine zwitterion 0 74.024 An amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of any N-alkylglycine; major species at pH 7.3. C2H4NO2R CHEBI:66884 MetaCyc:N-Alkylglycine PMID:9989229 [O-]C(=O)C[NH2+][*] an N-alkylglycine chebi_ontology alanine zwitterion 0 2-ammoniopropanoate 2-azaniumylpropanoate 89.048 89.09320 An amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of alanine; major species at pH 7.3. C3H7NO2 CC([NH3+])C([O-])=O CHEBI:66916 InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6) QNAYBMKLOCPYGJ-UHFFFAOYSA-N chebi_ontology citrullinate -1 174.088 174.17780 2-amino-5-(carbamoylamino)pentanoate An alpha-amino acid anion that is the conjugate base of citrulline, obtained by deprotonation of the carboxy group. C6H12N3O3 CHEBI:66922 InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/p-1 NC(CCCNC(N)=O)C([O-])=O RHGKLRLOHDJJDR-UHFFFAOYSA-M chebi_ontology creatinate (N-methylcarbamimidamido)acetate -1 130.062 130.12520 An alpha-amino acid anion that is the conjugate base of creatine, obtained by deprotonation of the carboxy group. C4H8N3O2 CHEBI:66924 CN(CC([O-])=O)C(N)=N CVSVTCORWBXHQV-UHFFFAOYSA-M InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9)/p-1 N-[amino(imino)methyl]-N-methylglycinate chebi_ontology {[imino(amino)methyl](methyl)amino}acetate N-alkylglycine 0 74.024 Any glycine derivative in which glycine is substituted at position 2 by an alkyl group. C2H4NO2R CHEBI:66933 MetaCyc:N-Alkylglycine N-alkylglycines OC(=O)CN[*] PMID:9989229 chebi_ontology homocysteinate -1 134.028 134.17700 2-amino-4-sulfanylbutanoate An alpha-amino acid anion that is the conjugate base of homocysteine, obtained by deprotonation of the carboxy group. C4H8NO2S CHEBI:66952 FFFHZYDWPBMWHY-UHFFFAOYSA-M InChI=1S/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)/p-1 NC(CCS)C([O-])=O chebi_ontology folates An N-acyl-L-alpha-amino acid anion obtained by deprotonation of any folic acid. CHEBI:67011 chebi_ontology folate folate anion folate anions methyl-branched fatty acid anion Any branched-chain fatty acid anion containing methyl branches only. CHEBI:67013 chebi_ontology methyl-branched fatty acid anions tetrahydrofolate A folate obtained by deprotonation of any tetrahydrofolic acid. CHEBI:67016 chebi_ontology tetrahydrofolate anion tetrahydrofolate anions tetrahydrofolates anti-inflammatory agent Any compound that has anti-inflammatory effects. CHEBI:67079 anti-inflammatory agents antiinflammatory agent antiinflammatory agents chebi_ontology ryanodine receptor agonist A ryanodine receptor modulator which activates the receptor. Ryanodine receptors (RyRs) act as selective ion channels, modulating the release of calcium. Activating the receptors causes the release of calcium, so depleting internal calcium and ultimately preventing further muscle contraction. CHEBI:67114 PMID:8597061 RyR activator RyR activators RyR agonist RyR agonists RyRs activator RyRs agonist Wikipedia:Ryanodine_receptor chebi_ontology ryanodine receptor activator ryanodine receptor activators nucleobase analogue A molecule that can substitute for a normal nucleobase in nucleic acids. CHEBI:67142 Wikipedia:Base_analog base analog base analogs base analogue base analogues chebi_ontology nucleobase analog nucleobase analogs nucleobase analogues gap junctional intercellular communication inhibitor An inhibitor that interferes with the process of gap junctional intercellular communication. CHEBI:67195 Wikipedia:Gap_junction chebi_ontology gap junctional intercellular communication inhibitors retinoic acid receptor agonist An agonist that selectively binds to and activates a retinoic acid receptor. CHEBI:67198 Wikipedia:Retinoic_acid_receptor chebi_ontology retinoic acid receptor agonists AP-1 antagonist AP-1 antagonists An antogonist that interferes with the action of activator protein 1 (AP-1). CHEBI:67199 Wikipedia:Activator_protein_1 activator protein-1 antagonist activator protein-1 antagonists chebi_ontology provitamin A A provitamin that can be converted into vitamin A by enzymes from animal tissues. CHEBI:67200 chebi_ontology provitamin As methomyl 0 1-(Methylthio)acetaldehyde O-methylcarbamoyloxime 1-(Methylthio)ethylideneamino methylcarbamate 162.046 162.21118 A carbamate ester obtained by the formal condensation of methylcarbamic acid with the hydroxy group of 1-(methylsulfanyl)acetaldoxime. Beilstein:2042050 C5H10N2O2S CAS:16752-77-5 CHEBI:6835 CNC(=O)ON=C(C)SC HMDB:HMDB0031804 InChI=1S/C5H10N2O2S/c1-4(10-3)7-9-5(8)6-2/h1-3H3,(H,6,8) KEGG:C11196 LINCS:LSM-24991 Lannate Methomyl Methomyl lannate N-(((methylamino)carbonyl)oxy)ethanimidothioic acid methyl ester PMID:11327381 PMID:11758270 PPDB:458 Pesticides:methomyl Reaxys:2042050 S-Methyl N-(methylcarbamoyloxy)thioacetimidate UHXUZOCRWCRNSJ-UHFFFAOYSA-N Wikipedia:Methomyl chebi_ontology methyl N-(methylcarbamoyloxy)ethanimidothioate azole Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen. CHEBI:68452 Wikipedia:Azole azoles chebi_ontology apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. CHEBI:68495 Type I cell-death inducer Type I cell-death inducers Type I programmed cell-death inducer Type I programmed cell-death inducers apoptosis inducers chebi_ontology 3-methylglutaric acid 0 146.058 146.14120 3-methylpentanedioic acid An alpha,omega-dicarboxylic acid that is glutaric acid substituted at position 3 by a methyl group. C6H10O4 CAS:626-51-7 CC(CC(O)=O)CC(O)=O CHEBI:68566 HMDB:HMDB0000752 InChI=1S/C6H10O4/c1-4(2-5(7)8)3-6(9)10/h4H,2-3H2,1H3,(H,7,8)(H,9,10) LIPID_MAPS_instance:LMFA01170117 PMID:22770225 Reaxys:1759502 XJMMNTGIMDZPMU-UHFFFAOYSA-N beta-methylglutaric acid chebi_ontology (-)-cotinine (5S)-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one (S)-(-)-Cotinine (S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone (S)-Cotinine 0 176.095 176.21510 An N-alkylpyrrolidine that consists of N-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5S-enantiomer). It is an alkaloid commonly found in Nicotiana tabacum. C10H12N2O CAS:486-56-6 CHEBI:68641 Drug_Central:737 HMDB:HMDB0001046 InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1 KNApSAcK:C00034470 LINCS:LSM-5986 MetaCyc:CPD-2742 PMID:14700346 PMID:21655912 PMID:21953524 PMID:22027507 PMID:22137886 PMID:22169225 PMID:22180597 PMID:22200307 PMID:22244928 PMID:22253001 PMID:22434216 PMID:22460317 PMID:22487419 PMID:22489581 PMID:22574797 PMID:22608097 PMID:22678157 PMID:22687995 PMID:22770225 PMID:22809871 PMID:22871902 PMID:22878732 PMID:22899265 PMID:22919158 PMID:23000417 PMID:23011941 PMID:23087643 Reaxys:5736575 Reaxys:83099 UIKROCXWUNQSPJ-VIFPVBQESA-N Wikipedia:Cotinine [H][C@]1(CCC(=O)N1C)c1cccnc1 chebi_ontology cotinina cotinine cotininum myoglobin CHEBI:7044 COMe:PRX000322 KEGG:C05782 Myoglobin chebi_ontology vertebrate myoglobin progesterone receptor agonist A hormone agonist that binds to and activates progesterone receptors. CHEBI:70709 PR agonist PR agonists chebi_ontology progesterone receptor agonists adenosine receptor antagonist An antagonist at any adenosine receptor. CHEBI:71232 Wikipedia:Adenosine_receptor adenosine receptor antagonists chebi_ontology EC 2.* (transferase) inhibitor An enzyme inhibitor that inhibits the action of a transferase (EC 2.*) CHEBI:71300 EC 2 inhibitor EC 2 inhibitors EC 2.* (transferase) inhibitors EC 2.* inhibitor EC 2.* inhibitors Wikipedia:Transferase chebi_ontology transferase inhibitor transferase inhibitors gamma-amino acid anion An amino-acid anion in which the amino group is situated gamma- to the carboxylate group. CHEBI:71666 chebi_ontology gamma-amino acid anions aldonate(1-) -1 105.019 105.06940 A carbohydrate acid anion obtained by deprotonation of any aldonic acid. Major structure at pH 7.3 of aldonate compounds. C3H5O4 CHEBI:71671 aldonates an aldonate chebi_ontology organic molecule Any molecule that consists of at least one carbon atom as part of the electrically neutral entity. CHEBI:72695 chebi_ontology organic compound organic compounds organic molecules exopolysaccharide A biomacromolecule composed of carbohydrate residues which is secreted by a microorganism into the surrounding environment. CHEBI:72813 MetaCyc:Exopolysaccharides PMID:11160795 PMID:11785425 PMID:1444258 PMID:15738217 PMID:16075348 PMID:17440912 PMID:18097339 PMID:19453747 PMID:20172021 PMID:20631870 PMID:20718297 PMID:2688547 PMID:6354590 Wikipedia:Exopolysaccharide Wikipedia:Extracellular_polymeric_substance chebi_ontology exopolysaccharides extracellular polymeric substance extracellular polymeric substances vulnerary A drug used in treating and healing of wounds. CHEBI:73336 Wikipedia:Wound_healing chebi_ontology vulneraries wound-healing agent wound-healing agents wound-healing drug wound-healing drugs indole skeleton 0 110.003 110.09230 A mancude heterobicyclic organic group consisting of a benzene ring fused to a pyrrole ring. C8N CHEBI:73398 chebi_ontology organic heterobicyclic ring A bicyclic organic group that contains both carbon and hetero atoms. CHEBI:73541 chebi_ontology organic heterobicyclic rings D3 vitamins A vitamin D that is calciol or its hydroxylated metabolites calcidiol and calcitriol. Calciol (also known as vitamin D3) acts as a hormone precursor, being hydroxylated in the liver to calcidiol (25-hydroxyvitamin D3), which is then further hydroxylated in the kidney to give calcitriol (1,25-dihydroxyvitamin D3), the active hormone. CHEBI:73558 D3 vitamin chebi_ontology vitamin D3s ketone body A carbonyl compound produced as a water-soluble byproduct when fatty acids are broken down for energy in the liver. There are three endogenous ketone bodies: acetone, acetoacetic acid, and (R)-3-hydroxybutyric acid; others may be produced as a result of the metabolism of synthetic triglycerides. CHEBI:73693 PMID:10634967 PMID:19159745 PMID:22259088 PMID:22268909 PMID:22524563 PMID:22879057 PMID:23082721 PMID:23148246 PMID:23396451 PMID:23466063 PMID:23557707 Wikipedia:Ketone_body chebi_ontology ketone bodies ethylmalonic acid 0 1,1-propanedicarboxylic acid 132.042 132.11460 2-ethylmalonic acid A dicarboxylic acid obtained by substitution of one of the methylene hydrogens of malonic acid by an ethyl group. C5H8O4 CAS:516-05-2 CAS:601-75-2 CCC(C(O)=O)C(O)=O CHEBI:741548 HMDB:HMDB0000622 InChI=1S/C5H8O4/c1-2-3(4(6)7)5(8)9/h3H,2H2,1H3,(H,6,7)(H,8,9) PMID:20187168 PMID:22133302 PMID:23161776 PMID:6860317 Reaxys:774334 UKFXDFUAPNAMPJ-UHFFFAOYSA-N alpha-carboxybutyric acid chebi_ontology ethylpropanedioic acid gamma-lactam A lactam in which the amide bond is contained within a five-membered ring, which includes the amide nitrogen and the carbonyl carbon. CHEBI:74222 chebi_ontology gamma-lactams pyrrolidin-2-ones 0 2-pyrrolidinones 2-pyrrolidones 77.998 78.04890 A pyrrolidinone in which the oxo group is at position 2 of the pyrrolidine ring. C4NOR7 CHEBI:74223 [*]N1C(=O)C([*])([*])C([*])([*])C1([*])[*] chebi_ontology pyrrolidine-2-ones 1-(5-hydroxy-2-oxo-2,3-dihydroimidazol-4-yl)urea 0 1-(5-hydroxy-2-oxo-2,3-dihydro-1H-imidazol-4-yl)urea 158.044 158.11540 2-oxo-4-hydroxy-5-ureidoimidazoline An imidazolidinone that is imidazolin-2-one substituted at positions 4 and 5 by hydroxy and ureido groups respectively. C4H6N4O3 CHEBI:74345 InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h9H,(H3,5,6,10)(H2,7,8,11) MLVVTNIFHMERMU-UHFFFAOYSA-N NC(=O)Nc1[nH]c(=O)[nH]c1O PMID:20826786 allantoin, enol-form chebi_ontology astringent A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions. CHEBI:74783 Wikipedia:Astringent adstringent adstringents astringents chebi_ontology cathartic Any substance that accelerates defecation. Compare with laxatives, which are substances that ease defecation (usually by softening faeces). A substance can be both a laxative and a cathartic. CHEBI:75325 Wikipedia:Cathartic cathartics chebi_ontology ghrelin 0 3368.879 3370.867 A 28-membered appetite-stimulating polypeptide consisting of Gly, Ser, Ser(octanoyl), Phe, Leu, Ser, Pro, Glu, His, Gln, Arg, Val, Gln, Gln, Arg, Lys, Glu, Ser, Lys, Lys, Pro, Pro, Ala, Lys, Leu, Gln, Pro and Arg residues joined in sequence. The O-n-octanoylation of the side-chain hydroxy group of serine-3 (Ser3) is essential for ghrelin's activity. C(C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(N1[C@@H](CCC1)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(N2[C@@H](CCC2)C(N3[C@@H](CCC3)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(N4[C@@H](CCC4)C(=O)N[C@H](C(=O)O)CCCNC(=N)N)=O)CCC(=O)N)CC(C)C)CCCCN)C)=O)=O)CCCCN)CCCCN)CO)CCC(=O)O)CCCCN)CCCNC(N)=N)CCC(=O)N)CCC(=O)N)C(C)C)CCCNC(N)=N)CCC(=O)N)CC=5N=CNC5)CCC(=O)O)=O)CO)CC(C)C)CC=6C=CC=CC6)COC(=O)CCCCCCC)CO)N C149H249N47O42 CAS:258279-04-8 CAS:304853-26-7 CHEBI:75431 GNKDKYIHGQKHHM-RJKLHVOGSA-N GS-S(n-octanoyl)-FLSPEHQRVQQRKESKKPPAKLQPR GSS(octanoyl)FLSPEHQRVQQRKESKKPPAKLQPR Gastric MLTRP Ghrelin (human) Gly-Ser-Ser(octanoyl)-Phe-Leu-Ser-Pro-Glu-His-Gln-Arg-Val-Gln-Gln-Arg-Lys-Glu-Ser-Lys-Lys-Pro-Pro-Ala-Lys-Leu-Gln-Pro-Arg H-Gly-Ser-Ser(n-octanoyl)-Phe-Leu-Ser-Pro-Glu-His-Gln-Arg-Val-Gln-Gln-Arg-Lys-Glu-Ser-Lys-Lys-Pro-Pro-Ala-Lys-Leu-Gln-Pro-Arg-OH Human ghrelin InChI=1S/C149H249N47O42/c1-9-10-11-12-16-45-118(209)238-78-106(191-135(225)103(75-197)171-115(204)73-154)137(227)187-101(71-84-32-14-13-15-33-84)133(223)186-100(70-81(4)5)132(222)190-105(77-199)144(234)194-66-29-42-108(194)139(229)180-95(51-57-117(207)208)128(218)188-102(72-85-74-165-79-169-85)134(224)179-92(47-53-112(156)201)126(216)175-90(39-26-63-167-148(161)162)130(220)192-119(82(6)7)141(231)181-93(48-54-113(157)202)127(217)177-91(46-52-111(155)200)125(215)174-89(38-25-62-166-147(159)160)122(212)173-87(35-18-22-59-151)121(211)178-94(50-56-116(205)206)129(219)189-104(76-198)136(226)176-88(36-19-23-60-152)123(213)182-96(37-20-24-61-153)142(232)196-68-31-44-110(196)145(235)195-67-30-41-107(195)138(228)170-83(8)120(210)172-86(34-17-21-58-150)124(214)185-99(69-80(2)3)131(221)183-97(49-55-114(158)203)143(233)193-65-28-43-109(193)140(230)184-98(146(236)237)40-27-64-168-149(163)164/h13-15,32-33,74,79-83,86-110,119,197-199H,9-12,16-31,34-73,75-78,150-154H2,1-8H3,(H2,155,200)(H2,156,201)(H2,157,202)(H2,158,203)(H,165,169)(H,170,228)(H,171,204)(H,172,210)(H,173,212)(H,174,215)(H,175,216)(H,176,226)(H,177,217)(H,178,211)(H,179,224)(H,180,229)(H,181,231)(H,182,213)(H,183,221)(H,184,230)(H,185,214)(H,186,223)(H,187,227)(H,188,218)(H,189,219)(H,190,222)(H,191,225)(H,192,220)(H,205,206)(H,207,208)(H,236,237)(H4,159,160,166)(H4,161,162,167)(H4,163,164,168)/t83-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,119-/m0/s1 KEGG:C16025 Motilin-related peptide PMID:15788704 PMID:23159561 PMID:23178701 PMID:23278489 PMID:23307791 PMID:23316086 PMID:23317782 PMID:23359315 PMID:23428971 PMID:23481295 PMID:23524619 PMID:23624808 PMID:23631903 PMID:23652386 PMID:23652399 PMID:23652420 PMID:23698230 PMID:23704134 PMID:23778458 PMID:23804489 PMID:23808302 PMID:23843943 PMID:23847595 PMID:23965296 PMID:23982275 PMID:23989358 PMID:28538835 PMID:28542403 PMID:28547758 PMID:28590260 PMID:28621678 PMID:28704966 Reaxys:24715767 Wikipedia:Ghrelin chebi_ontology glycyl-L-seryl-O-octanoyl-L-seryl-L-phenylalanyl-L-leucyl-L-seryl-L-prolyl-L-alpha-glutamyl-L-histidyl-L-glutaminyl-L-arginyl-L-valyl-L-glutaminyl-L-glutaminyl-L-arginyl-L-lysyl-L-alpha-glutamyl-L-seryl-L-lysyl-L-lysyl-L-prolyl-L-prolyl-L-alanyl-L-lysyl-L-leucyl-L-glutaminyl-L-prolyl-L-arginine lenomorelin lenomorelina lenomoreline lenomorelinum EC 6.3.* (C-N bond-forming ligase) inhibitor A ligase inhibitor that interferes with the action of a C-N bond-forming ligase (EC 6.3.*.*). C--N bond-forming ligase inhibitor C--N bond-forming ligase inhibitors C-N bond-forming ligase (EC 6.3.*) inhibitor C-N bond-forming ligase (EC 6.3.*) inhibitors C-N bond-forming ligase inhibitor C-N bond-forming ligase inhibitors CHEBI:75600 EC 6.3.* (C-N bond-forming ligase) inhibitorS EC 6.3.* inhibitor EC 6.3.* inhibitors EC 6.3.*.* inhibitor EC 6.3.*.* inhibitors chebi_ontology EC 6.* (ligase) inhibitor Any enzyme inhibitor that interferes with the action of a ligase (EC 6.*.*.*). Ligases are enzymes that catalyse the joining of two molecules with concomitant hydrolysis of the diphosphate bond in ATP or a similar triphosphate. CHEBI:75603 EC 6.* (ligase) inhibitors EC 6.* inhibitor EC 6.* inhibitors EC 6.*.*.* inhibitor EC 6.*.*.* inhibitors Wikipedia:Ligase chebi_ontology ligase inhibitor ligase inhibitors EC 6.4.* (C-C bond-forming ligase) inhibitor A ligase inhibitor that interferes with the action of a C-C bond-forming ligase (EC 6.4.*.*). C--C bond-forming ligase inhibitor C--C bond-forming ligase inhibitors C-C bond-forming ligase (EC 6.4.*) inhibitor C-C bond-forming ligase (EC 6.4.*) inhibitorS C-C bond-forming ligase inhibitor C-C bond-forming ligase inhibitors CHEBI:75604 EC 6.4.* (C-C bond-forming ligase) inhibitorS EC 6.4.* inhibitor EC 6.4.* inhibitors EC 6.4.*.* inhibitor EC 6.4.*.* inhibitors chebi_ontology N-nicotinoylglycine 0 180.053 180.16070 An N-acylglycine having nicotinoyl as the acyl substituent. Beilstein:8859 C8H8N2O3 CAS:583-08-4 CHEBI:7563 HMDB:HMDB0003269 InChI=1S/C8H8N2O3/c11-7(12)5-10-8(13)6-2-1-3-9-4-6/h1-4H,5H2,(H,10,13)(H,11,12) KEGG:C05380 N-(Pyridin-3-ylcarbonyl)glycine N-Nicotinylglycine Nicotinoylglycine Nicotinurate Nicotinuric acid Nicotinylglycine OC(=O)CNC(=O)c1cccnc1 PMID:14745162 PMID:15620531 PMID:16193536 PMID:20853461 PMID:22770225 PMID:3243933 PMID:699281 PMID:7866544 Reaxys:8859 ZBSGKPYXQINNGF-UHFFFAOYSA-N chebi_ontology eukaryotic metabolite Any metabolite produced during a metabolic reaction in eukaryotes, the taxon that include members of the fungi, plantae and animalia kingdoms. CHEBI:75763 chebi_ontology eukaryotic metabolites animal metabolite Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals. CHEBI:75767 CHEBI:77721 CHEBI:77743 animal metabolites chebi_ontology mammalian metabolite Any animal metabolite produced during a metabolic reaction in mammals. CHEBI:75768 CHEBI:77464 CHEBI:77744 chebi_ontology mammalian metabolites B vitamin Any of the group of eight water-soluble vitamins originally thought to be a single compound (vitamin B) that play important roles in cell metabolism. The group comprises vitamin B1, B2, B3, B5, B6, B7, B9, and B12. (Around 20 other compounds were once thought to be B vitamins but are no longer classified as such.) B vitamins B-group vitamin B-group vitamins CHEBI:75769 PMID:22743781 PMID:23093174 PMID:23238962 PMID:23449527 PMID:23462586 PMID:23690582 Wikipedia:B_vitamin chebi_ontology vitamin B mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). CHEBI:75771 Mus musculus metabolite Mus musculus metabolites chebi_ontology mouse metabolites Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae). CHEBI:75772 CHEBI:76949 CHEBI:76951 S. cerevisiae metabolite S. cerevisiae metabolites S. cerevisiae secondary metabolite S. cerevisiae secondary metabolites Saccharomyces cerevisiae metabolites Saccharomyces cerevisiae secondary metabolites baker's yeast metabolite baker's yeast metabolites baker's yeast secondary metabolite baker's yeast secondary metabolites chebi_ontology prokaryotic metabolite Any metabolite produced during a metabolic reaction in prokaryotes, the taxon that include members of domains such as the bacteria and archaea. CHEBI:75787 chebi_ontology prokaryotic metabolites aromatic amino-acid zwitterion 0 74.024 An amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of any aromatic amino-acid. C2H4NO2R CHEBI:76042 MetaCyc:Aromatic-Amino-Acids [NH3+]C([*])C([O-])=O an aromatic amino-acid aromatic amino-acid zwitterions chebi_ontology xenobiotic metabolite Any metabolite produced by metabolism of a xenobiotic compound. CHEBI:76206 chebi_ontology xenobiotic metabolites greenhouse gas A gas in an atmosphere that absorbs and emits radiation within the thermal infrared range, so contributing to the 'greenhouse effect'. CHEBI:76413 Wikipedia:Greenhouse_gas chebi_ontology greenhouse gases propellant A compressed gas or liquid with a boiling point lower than room temperature which to used to propel and dispense liquids such as deodorants, insecticides, paints, etc. from aerosol cans. CHEBI:76414 PMID:22519407 PMID:24001847 chebi_ontology propellants marine metabolite Any metabolite produced during a metabolic reaction in marine macro- and microorganisms. CHEBI:76507 CHEBI:77078 chebi_ontology marine metabolites omega-methyl fatty acid anion -1 59.013 A fatty acid anion obtained by deprotonation of the carboxy group of any omega-methyl fatty acid; major species at pH 7.3. C2H3O2R CHEBI:76619 C[*]C([O-])=O an omega-methyl fatty acid chebi_ontology EC 2.1.* (C1-transferase) inhibitor A transferase inhibitor inhibiting the action of transferase of a one-carbon-containing group (EC 2.1.*.*). C1-transferase (EC 2.1.*) inhibitor C1-transferase (EC 2.1.*) inhibitors C1-transferase inhibitor C1-transferase inhibitors CHEBI:76655 EC 2.1.* (C1-transferase) inhibitors EC 2.1.* inhibitor EC 2.1.* inhibitors chebi_ontology one-carbon-containing group transferase inhibitor one-carbon-containing group transferase inhibitors EC 2.7.* (P-containing group transferase) inhibitor A transferase inhibitor that inhibits the action of a phosphorus-containing group transferase (EC 2.7.*.*). CHEBI:76668 EC 2.7.* (P-containing group transferase) inhibitors EC 2.7.* (phosphorus-containing group transferase) inhibitor EC 2.7.* (phosphorus-containing group transferase) inhibitors EC 2.7.* inhibitor EC 2.7.* inhibitors chebi_ontology phosphorus-containing group transferase (EC 2.7.*) inhibitor phosphorus-containing group transferase (EC 2.7.*) inhibitors phosphorus-containing group transferase inhibitor phosphorus-containing group transferase inhibitors EC 4.* (lyase) inhibitor An enzyme inhibitor which interferes with the action of a lyase (EC 4.*.*.*). Lyases are enzymes cleaving C-C, C-O, C-N and other bonds by other means than by hydrolysis or oxidation. CHEBI:76710 EC 4.* (lyase) inhibitors EC 4.* inhibitor EC 4.* inhibitors EC 4.*.*.* inhibitor EC 4.*.*.* inhibitors Wikipedia:Lyase chebi_ontology lyase (EC 4.*) inhibitor lyase (EC 4.*) inhibitorS lyase inhibitor lyase inhibitors EC 4.3.* (C-N lyase) inhibitor A lyase inhibitor which inhibits the action of a C-N lyase (EC 4.3.*.*). C-N lyase (EC 4.3.*) inhibitor C-N lyase (EC 4.3.*) inhibitors C-N lyase inhibitor C-N lyase inhibitors CHEBI:76713 EC 4.3.* (C-N lyase) inhibitors EC 4.3.* inhibitor EC 4.3.* inhibitors chebi_ontology EC 1.* (oxidoreductase) inhibitor An enzyme inhibitor which interferes with the action of an oxidoreductase (EC 1.*.*.*). CHEBI:76725 EC 1.* (oxidoreductase) inhibitors EC 1.* inhibitor EC 1.* inhibitors Wikipedia:Oxidoreductase chebi_ontology oxidoreductase (EC 1.*) inhibitor oxidoreductase (EC 1.*) inhibitors oxidoreductase inhibitor oxidoreductase inhibitors EC 1.1.* (oxidoreductase acting on donor CH-OH group) inhibitor An oxidoreductase inhibitor which interferes with the action of an oxidoreductase acting on the CH-OH group of donors (EC 1.1.*.*). CHEBI:76726 EC 1.1.* (oxidoreductase acting on donor CH-OH group) inhibitors EC 1.1.* inhibitor EC 1.1.* inhibitors chebi_ontology inhibitor of oxidoreductase acting on CH-OH group of donor inhibitor of oxidoreductase acting on CH-OH group of donors inhibitors of oxidoreductase acting on CH-OH group of donor inhibitors of oxidoreductase acting on CH-OH group of donors oxidoreductase acting on donor CH-OH group (EC 1.1.*) inhibitor oxidoreductase acting on donor CH-OH group (EC 1.1.*) inhibitors oxidoreductase acting on donor CH-OH group inhibitor oxidoreductase acting on donor CH-OH group inhibitors EC 3.* (hydrolase) inhibitor Any enzyme inhibitor that interferes with the action of a hydrolase (EC 3.*.*.*). CHEBI:76759 EC 3.* (hydrolase) inhibitors EC 3.* inhibitor EC 3.* inhibitors EC 3.*.*.* inhibitor EC 3.*.*.* inhibitors Wikipedia:Hydrolase chebi_ontology hydrolase (EC 3.*) inhibitor hydrolase (EC 3.*) inhibitors hydrolase inhibitor hydrolase inhibitors EC 3.1.* (ester hydrolase) inhibitor A hydrolase inhibitor that interferes with the action of any ester hydrolase (EC 3.1.*.*). CHEBI:76760 EC 3.1.* (ester hydrolase) inhibitors EC 3.1.* inhibitor EC 3.1.* inhibitors chebi_ontology ester hydrolase (EC 3.1.*) inhibitor ester hydrolase (EC 3.1.*) inhibitors ester hydrolase inhibitor ester hydrolase inhibitors EC 3.2.* (glycosylase) inhibitor A hydrolase inhibitor that interferes with the action of any glycosylase (EC 3.2.*.*). CHEBI:76761 EC 3.2.* (glycosylase) inhibitors EC 3.2.* inhibitor EC 3.2.* inhibitors chebi_ontology glycosylase (EC 3.2.*) inhibitor glycosylase (EC 3.2.*) inhibitors glycosylase inhibitor glycosylase inhibitors EC 3.5.* (hydrolases acting on non-peptide C-N bonds) inhibitor Any hydrolase inhibitor that interferes with the action of a hydrolase acting on C-N bonds, other than peptide bonds (EC 3.5.*.*). CHEBI:76764 EC 3.5.* (hydrolase acting on non-peptide C-N bond) inhibitor EC 3.5.* (hydrolase acting on non-peptide C-N bond) inhibitors EC 3.5.* (hydrolases acting on C-N bonds, other than peptide bonds) inhibitor EC 3.5.* (hydrolases acting on C-N bonds, other than peptide bonds) inhibitors EC 3.5.* (hydrolases acting on non-peptide C-N bonds) inhibitors EC 3.5.* inhibitor EC 3.5.* inhibitors chebi_ontology EC 3.1.1.* (carboxylic ester hydrolase) inhibitor An EC 3.1.* (ester hydrolase) inhibitor that interferes with the action of a carboxylic ester hydrolase (EC 3.1.1.*). CHEBI:76773 EC 3.1.1.* (carboxylic ester hydrolase) inhibitors EC 3.1.1.* inhibitor EC 3.1.1.* inhibitors carboxylic ester hydrolase (EC 3.1.1.*) inhibitor carboxylic ester hydrolase (EC 3.1.1.*) inhibitors chebi_ontology EC 3.4.21.26 (prolyl oligopeptidase) inhibitor Any EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of prolyl oligopeptidase (EC 3.4.21.26). CHEBI:76779 EC 3.4.21.26 (prolyl oligopeptidase) inhibitors EC 3.4.21.26 inhibitor EC 3.4.21.26 inhibitors chebi_ontology endoprolylpeptidase inhibitor endoprolylpeptidase inhibitors post-proline cleaving enzyme inhibitor post-proline cleaving enzyme inhibitors post-proline endopeptidase inhibitor post-proline endopeptidase inhibitors proline endopeptidase inhibitor proline endopeptidase inhibitors proline-specific endopeptidase inhibitor proline-specific endopeptidase inhibitors prolyl endopeptidase inhibitor prolyl endopeptidase inhibitors prolyl oligopeptidase (EC 3.4.21.26) inhibitor prolyl oligopeptidase (EC 3.4.21.26) inhibitors prolyl oligopeptidase inhibitor EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor An EC 3.5.* (hydrolases acting on non-peptide C-N bonds) inhibitor that interferes with the action of any non-peptide linear amide C-N hydrolase (EC 3.5.1.*). CHEBI:76807 EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitors EC 3.5.1.* inhibitor EC 3.5.1.* inhibitors chebi_ontology non-peptide linear amide C-N hydrolase (EC 3.5.1.*) inhibitor non-peptide linear amide C-N hydrolase (EC 3.5.1.*) inhibitors EC 2.7.11.* (protein-serine/threonine kinase) inhibitor An EC 2.7.* (P-containing group transferase) inhibitor that interferes with the action of any protein-serine/threonine kinase (EC 2.7.11.*). CHEBI:76812 EC 2.7.11.* (protein-serine/threonine kinase) inhibitors EC 2.7.11.* inhibitor EC 2.7.11.* inhibitors chebi_ontology protein-serine/threonine kinase (EC 2.7.11.*) inhibitor protein-serine/threonine kinase (EC 2.7.11.*) inhibitors protein-serine/threonine kinase inhibitor protein-serine/threonine kinase inhibitors EC 2.7.7.* (nucleotidyltransferase) inhibitor An EC 2.7.* (P-containing group transferase) inhibitor that interferes with the action of any nucleotidyltransferase (EC 2.7.7.*). CHEBI:76815 EC 2.7.7.* (nucleotidyltransferase) inhibitors chebi_ontology inhibitor of nucleotidyltransferases inhibitor of nucleotidyltransferases (EC 2.7.7.*) inhibitors of nucleotidyltransferases inhibitors of nucleotidyltransferases (EC 2.7.7.*) nucleotidyltransferase (EC 2.7.7.*) inhibitor nucleotidyltransferase (EC 2.7.7.*) inhibitors nucleotidyltransferase inhibitor nucleotidyltransferase inhibitors EC 6.3.1.* (acid-ammonia/amine ligase) inhibitor An EC 6.3.* (C-N bond-forming ligase) inhibitor that interferes with the action of any acid-ammonia (or amine) ligase (EC 6.3.1.*). CHEBI:76823 EC 6.3.1.* (acid-ammonia/amine ligase) inhibitors EC 6.3.1.* inhibitor EC 6.3.1.* inhibitors acid-ammonia (or amine) ligase inhibitor acid-ammonia (or amine) ligase inhibitors chebi_ontology EC 6.4.1.* (carboxylase) inhibitor An EC 6.4.* (C-C bond-forming ligase) inhibitor that interferes with the action of a carboxylating enzyme (EC 6.4.1.*). CHEBI:76824 EC 6.4.1.* (C-C bond forming ligase) inhibitor EC 6.4.1.* (C-C bond forming ligase) inhibitors EC 6.4.1.* (C-C bond-forming ligase) inhibitors EC 6.4.1.* (carboxylase) inhibitors EC 6.4.1.* inhibitor EC 6.4.1.* inhibitors chebi_ontology inhibitor of ligases forming C-C bonds inhibitor of ligases forming C-C bonds (EC 6.4.1.*) inhibitors of ligases forming C-C bonds inhibitors of ligases forming C-C bonds (EC 6.4.1.*) EC 4.3.1.* (ammonia-lyase) inhibitor An EC 4.3.* (C-N lyase) inhibitor that interferes with the action of any ammonia-lyase (EC 4.3.1.*). CHEBI:76832 EC 4.3.1.* (ammonia-lyase) inhibitors EC 4.3.1.* (ammonia-lyases) inhibitor EC 4.3.1.* (ammonia-lyases) inhibitors EC 4.3.1.* inhibitor EC 4.3.1.* inhibitors ammonia-lyase (EC 4.3.1.*) inhibitor ammonia-lyase (EC 4.3.1.*) inhibitors ammonia-lyase inhibitor ammonia-lyase inhibitors chebi_ontology EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor An EC 1.1.* (oxidoreductase acting on donor CH-OH group) inhibitor that uses NAD(+) or NADP(+) as acceptor (EC 1.1.1.*). CHEBI:76835 EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+)acceptor) inhibitors EC 1.1.1.* inhibitor EC 1.1.1.* inhibitors chebi_ontology oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor (EC 1.1.1.*) inhibitor oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor (EC 1.1.1.*) inhibitors EC 2.1.2.* (hydroxymethyl-, formyl- and related transferases) inhibitor An EC 2.1.* (C1-transferase) inhibitor that interferes with the action of any hydroxymethyl-, formyl- and related transferase (EC 2.1.2.*). CHEBI:76874 EC 2.1.2.* (hydroxymethyl-, formyl- and related transferases) inhibitors EC 2.1.2.* inhibitor EC 2.1.2.* inhibitors chebi_ontology hydroxymethyl-, formyl- and related transferases (EC 2.1.2.*) inhibitor hydroxymethyl-, formyl- and related transferases (EC 2.1.2.*) inhibitors plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. CHEBI:75766 CHEBI:76924 CHEBI:76925 chebi_ontology plant metabolites plant secondary metabolites 2,3-saturated fatty acid(1-) -1 2,3-saturated fatty acid 72.021 A fatty acid anion obtained by deprotonation of the carboxy group of any 2,3-saturated fatty acid. C3H4O2R CHEBI:76928 [O-]C(=O)CC[*] chebi_ontology 2,3-saturated fatty acid 0 73.029 Any fatty acid in which the first two carbons of the chain attached to the carboxy group are saturated and unbranched. C3H5O2R CHEBI:76929 OC(=O)CC[*] chebi_ontology pathway inhibitor An enzyme inhibitor that interferes with one or more steps in a metabolic pathway. CHEBI:76932 chebi_ontology metabolic pathway inhibitor metabolic pathway inhibitors pathway inhibitors fungal metabolite Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds. CHEBI:75765 CHEBI:76946 CHEBI:76947 chebi_ontology fungal metabolites Aspergillus metabolite Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus. Aspergillus metabolites CHEBI:75864 CHEBI:76956 CHEBI:76958 chebi_ontology human xenobiotic metabolite Any human metabolite produced by metabolism of a xenobiotic compound in humans. CHEBI:76967 chebi_ontology human xenobiotic metabolites bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. CHEBI:75760 CHEBI:76969 CHEBI:76970 chebi_ontology Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. CHEBI:76971 E.coli metabolite E.coli metabolites Escherichia coli metabolites chebi_ontology xenoestrogen A synthetic or semi-synthetic compound that has oestrogenic activity. CHEBI:76988 Wikipedia:Xenoestrogen chebi_ontology xenoestrogens EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor (5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate:NADP(+) 9-oxidoreductase inhibitor (5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate:NADP(+) 9-oxidoreductase inhibitors 9-keto-prostaglandin E2 reductase inhibitor 9-keto-prostaglandin E2 reductase inhibitors 9-ketoprostaglandin reductase inhibitor 9-ketoprostaglandin reductase inhibitors An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of prostaglandin-E2 9-reductase (EC 1.1.1.189). CHEBI:77119 EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitors EC 1.1.1.189 inhibitor EC 1.1.1.189 inhibitors PGE-9-ketoreductase inhibitor PGE-9-ketoreductase inhibitors PGE2 9-oxoreductase inhibitor PGE2 9-oxoreductase inhibitors PGE2-9-OR inhibitor PGE2-9-OR inhibitors PGE2-9-ketoreductase inhibitor PGE2-9-ketoreductase inhibitors Wikipedia:Prostaglandin-E2_9-reductase chebi_ontology prostaglandin 9-ketoreductase inhibitor prostaglandin 9-ketoreductase inhibitors prostaglandin E 9-ketoreductase inhibitor prostaglandin E 9-ketoreductase inhibitors prostaglandin E2-9-oxoreductase inhibitor prostaglandin E2-9-oxoreductase inhibitors prostaglandin-E2 9-reductase (EC 1.1.1.189) inhibitor prostaglandin-E2 9-reductase (EC 1.1.1.189) inhibitors reductase, 15-hydroxy-9-oxoprostaglandin inhibitor reductase, 15-hydroxy-9-oxoprostaglandin inhibitors food colouring A food additive that imparts colour to food. In European countries, E-numbers for permitted food colours are from E 100 to E 199, divided into yellows (E 100-109), oranges (E 110-119), reds (E 120-129), blues and violets (E 130-139), greens (E 140-149), browns and blacks (E 150-159), and others (E 160-199). CHEBI:77182 Wikipedia:Food_coloring chebi_ontology food coloring food colorings food colourings dicarboxylic acid monoamide(1-) -1 88.003 A monocarboxylic acid anion obtained by deprotonation of the carboxy group of any dicarboxylic acid monoamide; major species at pH 7.3. C2H2NO3R CHEBI:77450 MetaCyc:dicarboxylic acid monoamide NC(=O)[*]C([O-])=O a monoamide of a dicarboxylate chebi_ontology EC 4.3.1.3 (histidine ammonia-lyase) inhibitor An EC 4.3.1.* (ammonia-lyase) inhibitor that interferes with the action of histidine ammonia-lyase (EC 4.3.1.3). CHEBI:77703 EC 4.3.1.3 (histidine ammonia-lyase) inhibitors EC 4.3.1.3 inhibitor EC 4.3.1.3 inhibitors L-histidine ammonia-lyase (urocanate-forming) inhibitor L-histidine ammonia-lyase (urocanate-forming) inhibitors L-histidine ammonia-lyase inhibitor L-histidine ammonia-lyase inhibitors Wikipedia:Histidine_ammonia-lyase chebi_ontology histidase inhibitor histidase inhibitors histidinase inhibitor histidinase inhibitors histidine alpha-deaminase inhibitor histidine alpha-deaminase inhibitors histidine ammonia-lyase (EC 4.3.1.3) inhibitor histidine ammonia-lyase (EC 4.3.1.3) inhibitors histidine ammonia-lyase inhibitor histidine ammonia-lyase inhibitors human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). CHEBI:75770 CHEBI:77123 CHEBI:77746 H. sapiens metabolite H. sapiens metabolites Homo sapiens metabolite Homo sapiens metabolites chebi_ontology EC 3.5.1.4 (amidase) inhibitor An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the action of amidase (EC 3.5.1.4). CHEBI:77941 EC 3.5.1.4 (amidase) inhibitors EC 3.5.1.4 inhibitor EC 3.5.1.4 inhibitors N-acetylaminohydrolase inhibitor N-acetylaminohydrolase inhibitors Wikipedia:Amidase acylamidase inhibitor acylamidase inhibitors acylamide amidohydrolase inhibitor acylamide amidohydrolase inhibitors amidase (EC 3.5.1.4) inhibitor amidase (EC 3.5.1.4) inhibitors amidase inhibitor amidase inhibitors amidohydrolase inhibitor amidohydrolase inhibitors chebi_ontology deaminase inhibitor deaminase inhibitors fatty acylamidase inhibitor fatty acylamidase inhibitors L-erythro-sphingosine(1+) (2R,3S,4E)-1,3-dihydroxyoctadec-4-en-2-aminium +1 300.290 300.49930 A cationic sphingoid resulting from the protonation of the amino group of L-erythro-sphingosine; major species at pH 7.3. C18H38NO2 CCCCCCCCCCCCC\C=C\[C@H](O)[C@H]([NH3+])CO CHEBI:77956 D-erythro-sphing-4-enine InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/p+1/b15-14+/t17-,18+/m1/s1 L-erythro-sphing-4-enine(1+) PMID:12783875 PMID:632688 WWUZIQQURGPMPG-MCXRAWCPSA-O chebi_ontology food firming agent A food additive that is used to make or keep fruit or vegetable tissues firm and crisp. or which interacts with gelling agents such as pectin to produce or strengthen a gel. CHEBI:77960 Wikipedia:Firming_agent chebi_ontology firming agent firming agents food firming agents food antioxidant An antioxidant that used as a food additives to help guard against food deterioration. CHEBI:77962 chebi_ontology food antioxidants humectant A compound that is used to keep a substance moist. CHEBI:77968 Wikipedia:humectant chebi_ontology humectants food humectant A humectant that is used as a food additive to prevent foodstuffs from drying out. CHEBI:77969 chebi_ontology food humectants food packaging gas A food additive that is a (generally inert) gas which is used to envelop foodstuffs during packing and so protect them from unwanted chemical reactions such as food spoilage or oxidation during subsequent transport and storage. The term includes propellant gases, used to expel foods from a container. CHEBI:77974 Wikipedia:Packaging_gas chebi_ontology food packaging gases food propellant A propellant that is used to expel foods from an aerosol container. CHEBI:78017 chebi_ontology food propellants true fatty acid anion 3:0 -1 73.029 73.07060 Any saturated fatty acid anion containing 3 carbons. Formed by deprotonation of the carboxylic acid moiety. Major species at pH 7.3. C3H5O2 CHEBI:78113 [O-]C([*])=O chebi_ontology fatty acid 3:0 fatty acid anion 4:0 -1 87.045 87.09718 Any saturated fatty acid anion containing 4 carbons. Formed by deprotonation of the carboxylic acid moiety. Major species at pH 7.3. C4H7O2 CHEBI:78115 [O-]C([*])=O chebi_ontology fatty acid 4:0 fatty acid anion 6:0 -1 115.076 115.15034 Any saturated fatty acid anion containing 6 carbons. Formed by deprotonation of the carboxylic acid moiety. Major species at pH 7.3. C6H11O2 CHEBI:78116 [O-]C([*])=O chebi_ontology fatty acid 6:0 fatty acid anion 14:0 -1 227.201 227.36298 Any saturated fatty acid anion containing 14 carbons. Formed by deprotonation of the carboxylic acid moiety. Major species at pH 7.3. C14H27O2 CHEBI:78121 [O-]C([*])=O chebi_ontology fatty acid 14:0 fatty acid anion 16:0 -1 255.232 255.41610 Any saturated fatty acid anion containing 16 carbons. Formed by deprotonation of the carboxylic acid moiety. Major species at pH 7.3. C16H31O2 CHEBI:78123 [O-]C([*])=O chebi_ontology fatty acid 16:0 food component Any substance that is distributed in foodstuffs. It includes materials derived from plants or animals, such as vitamins or minerals, as well as environmental contaminants. CHEBI:78295 chebi_ontology dietary component dietary components food components environmental contaminant Any minor or unwanted substance introduced into the environment that can have undesired effects. CHEBI:78298 chebi_ontology environmental contaminants 2-hydroxypropanoic acid 0 2-Hydroxypropanoic acid 2-Hydroxypropionic acid 2-hydroxypropanoic acid 90.032 90.07790 A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group. C3H6O3 CAS:50-21-5 CC(O)C(O)=O CHEBI:78320 InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6) JVTAAEKCZFNVCJ-UHFFFAOYSA-N KEGG:C01432 KEGG:D00111 Lactic acid chebi_ontology refrigerant A substance used in a thermodynamic heat pump cycle or refrigeration cycle that undergoes a phase change from a gas to a liquid and back. Refrigerants are used in air-conditioning systems and freezers or refrigerators and are assigned a "R" number (by ASHRAE - formerly the American Society of Heating, Refrigerating and Air Conditioning Engineers), which is determined systematically according to their molecular structure. CHEBI:78433 Wikipedia:Refrigerant chebi_ontology refrigerants EC 3.1.1.1 (carboxylesterase) inhibitor Alpha-carboxylesterase inhibitor Alpha-carboxylesterase inhibitors Any EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that inhibits the action of carboxylesterase (EC 3.1.1.1 ). Beta-esterase inhibitor Beta-esterase inhibitors CHEBI:78444 EC 3.1.1.1 (carboxylesterase) inhibitors ali-esterase inhibitor ali-esterase inhibitors butyrate esterase inhibitor butyrate esterase inhibitors butyryl esterase inhibitor butyryl esterase inhibitors carboxyl ester hydrolase inhibitor carboxyl ester hydrolase inhibitors carboxylate esterase inhibitor carboxylate esterase inhibitors carboxylesterase inhibitor carboxylesterase inhibitors carboxylic acid esterase inhibitor carboxylic acid esterase inhibitors carboxylic esterase inhibitor carboxylic esterase inhibitors carboxylic-ester hydrolase inhibitor carboxylic-ester hydrolase inhibitors chebi_ontology cocaine esterase inhibitor cocaine esterase inhibitors esterase A inhibitor esterase A inhibitors esterase B inhibitor esterase B inhibitors esterase D inhibitor esterase D inhibitors methylbutyrase inhibitor methylbutyrase inhibitors methylbutyrate esterase inhibitor methylbutyrate esterase inhibitors monobutyrase inhibitor monobutyrase inhibitors nonspecific carboxylesterase inhibitor nonspecific carboxylesterase inhibitors procaine esterase inhibitor procaine esterase inhibitors propionyl esterase inhibitor propionyl esterase inhibitors serine esterase inhibitor serine esterase inhibitors triacetin esterase inhibitor triacetin esterase inhibitors vitamin A esterase inhibitor vitamin A esterase inhibitors pyrimidinecarboxylic acid Any pyrimidine that bears one or more carboxylic acid substituents. CHEBI:78574 chebi_ontology pyrimidinecarboxylic acids alpha-amino acid zwitterion 0 74.024 An amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of any alpha-amino acid; major species at pH 7.3. C2H4NO2R CHEBI:78608 CHEBI:83409 MetaCyc:Alpha-Amino-Acids [NH3+]C([*])C([O-])=O an alpha-amino acid chebi_ontology carbohydrates and carbohydrate derivatives Any organooxygen compound that is a polyhydroxy-aldehyde or -ketone, or a compound derived from one. Carbohydrates contain only carbon, hydrogen and oxygen and usually have an empirical formula Cm(H2O)n; carbohydrate derivatives may contain other elements by substitution or condensation. CHEBI:78616 carbohydrates and derivatives carbohydrates and their derivatives chebi_ontology chroman-6-ol 0 150.068 150.17450 3,4-dihydro-2H-chromen-6-ol 3,4-dihydrobenzopyran-6-ol A chromanol that is chromane in which the hydrogen at position 6 is replaced by a hydroxy group. C9H10O2 CHEBI:78631 GZCJJOLJSBCUNR-UHFFFAOYSA-N InChI=1S/C9H10O2/c10-8-3-4-9-7(6-8)2-1-5-11-9/h3-4,6,10H,1-2,5H2 Oc1ccc2OCCCc2c1 Reaxys:1283166 chebi_ontology fundamental metabolite Any metabolite produced by all living cells. CHEBI:78675 chebi_ontology essential metabolite essential metabolites fundamental metabolites olefinic compound Any organic molecular entity that contains at least one C=C bond. CHEBI:78840 chebi_ontology olefinic compounds (omega-1)-hydroxy fatty acid (omega-1)-hydroxy fatty acids A hydroxy fatty acid that is a straight-chain fatty acid in which one of the hydrogens attached to the carbon adjacent to the terminal methyl group (i.e. at the (omega-1) position) is replaced by a hydroxy group. CHEBI:78954 chebi_ontology hexadecanoate (16:0) -1 1-hexyldecanoate 1-pentadecanecarboxylate 255.232 255.41610 A long-chain fatty acid anion that is the conjugate base of hexadecanoic acid (palmitic acid); major species at pH 7.3. Beilstein:3589907 C16H31O2 CAS:143-20-4 CCCCCCCCCCCCCCCC([O-])=O CH3-[CH2]14-COO(-) CHEBI:231736 CHEBI:7896 Gmelin:344266 HMDB:HMDB0000220 Hexadecanoic acid, ion(1-) IPCSVZSSVZVIGE-UHFFFAOYSA-M InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)/p-1 MetaCyc:PALMITATE Reaxys:3589907 chebi_ontology hexadecanoate n-hexadecanoate n-hexadecoate palmitate pentadecanecarboxylate (R)-nicotinium(1+) (2R)-1-methyl-2-(pyridin-3-yl)pyrrolidinium (R)-nicotine +1 163.124 163.23900 C10H15N2 CHEBI:79008 C[NH+]1CCC[C@@H]1c1cccnc1 InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/p+1/t10-/m1/s1 MetaCyc:R-NICOTINE SNICXCGAKADSCV-SNVBAGLBSA-O The conjugate acid of (R)-nicotine arising from selective protonation of the tertiary amino group; major species at pH 7.3. chebi_ontology alpha,beta-unsaturated monocarboxylic acid 2,3-unsaturated monocarboxylic acid 2,3-unsaturated monocarboxylic acids A monocarboxylic acid in which the carbon of the carboxy group is directly attached to a C=C or C#C bond. CHEBI:79020 alpha,beta-unsaturated monocarboxylic acids chebi_ontology molybdenum cofactor(3-) -3 551.33000 552.848 An organic anionic group derived from molybdenum cofactor(3-). It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.). C10H10MoN5O8PS3 CHEBI:79026 Nc1nc2N[C@@H]3O[C@H](COP([O-])([O-])=O)C4=C(S[Mo]([O-])(=O)(S-*)S4)[C@@H]3Nc2c(=O)[nH]1 chebi_ontology molybdenum cofactor trivalent inorganic anion Any inorganic anion with a valency of three. CHEBI:79387 chebi_ontology trivalent inorganic anions divalent inorganic anion Any inorganic anion with a valency of two. CHEBI:79388 chebi_ontology divalent inorganic anions monovalent inorganic anion Any inorganic anion with a valency of one. CHEBI:79389 chebi_ontology monovalent inorganic anions Gonadotropin-releasing hormone II CHEBI:80298 GnRH-II Gonadoliberin-II KEGG:C16084 chebi_ontology thyroid stimulating hormone CHEBI:138153 CHEBI:81567 chebi_ontology Luteinizing hormone CAS:9002-67-9 CHEBI:81568 ICSH Interstitial cell stimulating hormone KEGG:C18183 LH chebi_ontology Follicle stimulating hormone CAS:9002-68-0 CHEBI:81569 FSH Follitropin KEGG:C18184 chebi_ontology elemental iron An elemental molecular entity in which all of the atoms have atomic number 26. CHEBI:82663 chebi_ontology monounsaturated fatty acid anion -1 Any unsaturated fatty acid anion with one double or triple bond in the fatty acid chain. CHEBI:82680 [O-]C([*])=O chebi_ontology monounsaturated fatty acid anions aliphatic aldoxime 0 44.014 44.03270 Any aldoxime derived from an aliphatic aldehyde. CH2NOR CHEBI:82744 MetaCyc:Aliphatic-Aldoximes ON=C[*] an aliphatic aldoxime chebi_ontology sphingosine-based sphingolipid 0 325.262 A family of sphingolipids that share a common structural feature, a sphingosine base backbone. C19H35NO3R2 CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO[*])NC([*])=O CHEBI:82830 Sphing-4-enine-based sphingolipid chebi_ontology Daphnia galeata metabolite A Daphnia metabolite produced by the species Daphnia galeata. CHEBI:83038 Daphnia galeata metabolites chebi_ontology crustacean metabolite An animal metabolite produced by arthropods such as crabs, lobsters, crayfish, shrimps and krill. CHEBI:83039 chebi_ontology crustacean metabolites Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna. CHEBI:83056 Daphnia magna metabolites chebi_ontology Daphnia metabolite A crustacean metabolite produced by the genus of small planktonic arthropods, Daphnia CHEBI:83057 Daphnia metabolites Wikipedia:Daphnia chebi_ontology organosulfonic ester 0 79.957 80.06300 An ester resulting from the formal condensation of the hydroxy group of an alcohol, phenol, heteroarenol, or enol with an organosulfonic acid. CHEBI:83347 O3SR2 [*]S(=O)(=O)O[*] chebi_ontology organosulfonate ester organosulfonate esters organosulfonic esters porphyrin 0 21H,23H-Porphin 21H,23H-porphine 310.122 310.35200 Beilstein:1222991 Beilstein:36080 Beilstein:622855 C20H14N4 CAS:101-60-0 CHEBI:8337 Gmelin:205920 HMDB:HMDB0000839 InChI=1S/C20H14N4/c1-2-14-10-16-5-6-18(23-16)12-20-8-7-19(24-20)11-17-4-3-15(22-17)9-13(1)21-14/h1-12,21,24H/b13-9-,14-10-,15-9-,16-10-,17-11-,18-12-,19-11-,20-12- KEGG:C05113 PMID:22735334 Porphyrin RKCAIXNGYQCCAL-CEVVSZFKSA-N Reaxys:1160988 Wikipedia:Porphyrin c1cc2cc3ccc(cc4ccc(cc5ccc(cc1n2)[nH]5)n4)[nH]3 chebi_ontology porphine porphyrin marine xenobiotic metabolite Any metabolite produced by metabolism of a xenobiotic compound in marine macro- and microorganisms. CHEBI:83399 chebi_ontology marine xenobiotic metabolites (trifluoromethyl)benzenes An organofluorine compound that is (trifluoromethyl)benzene and derivatives arising from substitution of one or more of the phenyl hydrogens. CHEBI:83565 chebi_ontology proteinogenic amino acid derivative Any derivative of a proteinogenic amino acid resulting from reaction at an amino group, carboxy group, or a side-chain functional group, or from the replacement of any hydrogen by a heteroatom. CHEBI:83811 canonical amino acid derivative canonical amino acid derivatives canonical amino-acid derivative canonical amino-acid derivatives chebi_ontology proteinogenic amino acid derivatives proteinogenic amino-acid derivative proteinogenic amino-acid derivatives non-proteinogenic amino acid derivative Any derivative of a non-proteinogenic amino acid resulting from reaction at an amino group or carboxy group, or from the replacement of any hydrogen by a heteroatom. CHEBI:83812 chebi_ontology non-canonical amino acid derivative non-canonical amino-acid derivatives non-proteinogenic amino-acid derivatives proteinogenic amino acid Any of the 23 alpha-amino acids that are precursors to proteins, and are incorporated into proteins during translation. The group includes the 20 amino acids encoded by the nuclear genes of eukaryotes together with selenocysteine, pyrrolysine, and N-formylmethionine. Apart from glycine, which is non-chiral, all have L configuration. CHEBI:83813 Wikipedia:Proteinogenic_amino_acid canonical amino acid canonical amino acids chebi_ontology proteinogenic amino acids non-proteinogenic amino acid Any amino-acid that is not naturally encoded in the genetic code of any organism. CHEBI:83820 Wikipedia:Non-proteinogenic_amino_acids chebi_ontology non-canonical amino acid non-canonical amino acids non-canonical amino-acid non-canonical amino-acids non-coded amino acid non-coded amino acids non-coded amino-acid non-coded amino-acids non-proteinogenic amino acids non-proteinogenic amino-acid non-proteinogenic amino-acids amino acid derivative Any derivative of an amino acid resulting from reaction at an amino group, carboxy group, side-chain functional group, or from the replacement of any hydrogen by a heteroatom. The definition normally excludes peptides containing amino acid residues. CHEBI:25359 CHEBI:83821 amino acid derivatives chebi_ontology modified amino acids non-proteinogenic L-alpha-amino acid Any L-alpha-amino acid which is not a member of the group of 23 proteinogenic amino acids. CHEBI:83822 chebi_ontology non-proteinogenic L-alpha-amino acids L-cysteine derivative A proteinogenic amino acid derivative resulting from the formal reaction of L-cysteine at the amino group, carboxy group, or thiol group, or from the replacement of any hydrogen of L-cysteine by a heteroatom. CHEBI:83824 L-cysteine derivatives chebi_ontology pregnane 0 288.282 288.51054 C21H36 CAS:481-26-5 CHEBI:8386 InChI=1S/C21H36/c1-4-15-9-11-18-17-10-8-16-7-5-6-13-20(16,2)19(17)12-14-21(15,18)3/h15-19H,4-14H2,1-3H3/t15-,16?,17-,18-,19-,20-,21+/m0/s1 JWMFYGXQPXQEEM-WZBAXQLOSA-N KEGG:C01523 [H][C@]1(CC)CC[C@@]2([H])[C@]3([H])CCC4([H])CCCC[C@]4(C)[C@@]3([H])CC[C@]12C chebi_ontology pregnane cationic sphingoid An organic cation obtained by protonation of the amino function of any sphingoid CHEBI:83876 cationic sphingoids chebi_ontology sphingoid cation sphingoid cations non-proteinogenic alpha-amino acid Any alpha-amino acid which is not a member of the group of 23 proteinogenic amino acids. CHEBI:83925 chebi_ontology non-proteinogenic alpha-amino acids non-proteinogenic alpha-amino-acid non-proteinogenic alpha-amino-acids 2-saturated fatty acid anion -1 1,2-saturated fatty acid 1,2-saturated fatty acid anion 58.005 A fatty acid anion obtained by deprotonation of the carboxy group of any 2-saturated fatty acid. C2H2O2R CHEBI:83955 [O-]C(=O)C[*] chebi_ontology 3-methyl fatty acid anion -1 3-methyl fatty acid 3-methyl-branched fatty acid anion 3-methyl-branched fatty acid(1-) 86.037 A methyl-branched fatty acid anion obtained by deprotonation of the carboxy group of any 3-methyl fatty acid; major species at pH 7.3. C4H6O2R CC([*])CC([O-])=O CHEBI:83972 chebi_ontology L-glutamic acid derivative A proteinogenic amino acid derivative resulting from reaction of L-glutamic acid at the amino group or either of the carboxy groups, or from the replacement of any hydrogen of L-glutamic acid by a heteroatom. CHEBI:83982 L-glutamic acid derivatives chebi_ontology pentose phosphate Any phospho sugar that is the phosphate derivative of pentose. CHEBI:84055 chebi_ontology pentose phosphates human urinary metabolite Any metabolite (endogenous or exogenous) found in human urine samples. CHEBI:84087 chebi_ontology human urinary metabolites D-proline derivative A non-proteinogenic amino acid derivative resulting from reaction of D-proline at the amino group or the carboxy group, or from the replacement of any hydrogen of D-proline by a heteroatom. CHEBI:84185 D-proline derivatives chebi_ontology L-proline derivative A proteinogenic amino acid derivative resulting from reaction of L-proline at the amino group or the carboxy group, or from the replacement of any hydrogen of L-proline by a heteroatom. CHEBI:84186 L-proline derivatives chebi_ontology 3-hydroxy fatty acid anion -1 3-hydroxy fatty acid 88.016 A hydroxy fatty acid anion obtained by deprotonation of the carboxy group of any 3-hydroxy fatty acid. C3H4O3R CHEBI:84196 OC([*])CC([O-])=O chebi_ontology sphingoid base(1+) +1 2-amino-1,3-dihydroxysphingoid base(1+) 91.063 91.10850 A cationic sphingoid obtained by protonation of the amino group of any 2-amino-1,3-dihydroxysphingoid base. C3H9NO2R CHEBI:84410 [NH3+][C@@H](CO)[C@H](O)[*] a sphingoid base chebi_ontology (omega-1)-hydroxy fatty acid anion (omega-1)-hydroxy fatty acid (omega-1)-hydroxy fatty acid anion -1 89.024 A hydroxy fatty acid anion obtained by deprotonation of the carboxy group of any (omega-1)-hydroxy fatty acid; major species at pH 7.3. C3H5O3R CC(O)[*]C([O-])=O CHEBI:84497 chebi_ontology hydroxyindoles Any member of the class of indoles carrying at least one hydroxy group. CHEBI:84729 chebi_ontology algal metabolite Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae. CHEBI:84735 algal metabolites chebi_ontology prostanoic acid 0 310.287 310.51452 7-[(1S,2S)-2-octylcyclopentyl]heptanoic acid A carbocyclic fatty acid composed of heptanoic acid having a (1S,2S)-2-octylcyclopentyl substituent at position 7. Beilstein:5744307 C20H38O2 CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O CHEBI:8504 InChI=1S/C20H38O2/c1-2-3-4-5-6-9-13-18-15-12-16-19(18)14-10-7-8-11-17-20(21)22/h18-19H,2-17H2,1H3,(H,21,22)/t18-,19-/m0/s1 KEGG:C02064 LIPID_MAPS_instance:LMFA03010000 PMID:6234649 Prostanoic acid Reaxys:5744307 WGJJROVFWIXTPA-OALUTQOASA-N chebi_ontology prostan-1-oic acid skin lightening agent Any cosmetic used to lighten the colour of skin by reducing the concentration of melanin. CHEBI:85046 PMID:21265866 PMID:22132817 PMID:22314516 PMID:23891889 PMID:23974587 PMID:25535470 PMID:25574195 PMID:25643794 Wikipedia:Skin_whitening chebi_ontology melanogenesis inhibitor melanogenesis inhibitors skin bleaching agent skin bleaching agents skin depigmenting agent skin depigmenting agents skin lightening agents skin whitening agent skin whitening agents sphingoid-1-phosphocholine(1+) +1 256.119 A quaternary ammonium ion that is a deacylated sphingomyelin with undefined sphingoid base. C8H21N2O5PR CHEBI:85171 C[N+](C)(C)CCOP([O-])(=O)OC[C@H]([NH3+])[C@H](O)[*] chebi_ontology sphingosylphosphocholine sphingosylphosphocholine(1+) human blood serum metabolite Any metabolite (endogenous or exogenous) found in human blood serum samples. CHEBI:85234 chebi_ontology human blood serum metabolites 17beta-hydroxyandrostan-3-one (17beta)-17-hydroxyandrostan-3-one 0 17beta-hydroxyandrostanone 290.225 290.44030 A 17beta-hydroxy steroid that is testosterone in which the 4-5 double bond has been reduced to a single bond with unspecified configuration at position 5. C19H30O2 CAS:29873-50-5 CHEBI:85278 C[C@]12CC[C@H]3[C@@H](CCC4CC(=O)CC[C@]34C)[C@@H]1CC[C@@H]2O InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-17,21H,3-11H2,1-2H3/t12?,14-,15-,16-,17-,18-,19-/m0/s1 NVKAWKQGWWIWPM-QHDNXLQLSA-N chebi_ontology dihydrotestosterone glycine transporter inhibitor Any substance that inhibits the action of glycine transporters. CHEBI:85425 chebi_ontology glycine transporter inhibitors methyl sulfide 0 46.996 Any aliphatic sulfide in which at least one of the organyl groups attached to the sulfur is a methyl group. CH3SR CHEBI:25260 CHEBI:86315 CS[*] MetaCyc:Methyl-thioethers a methyl thioether chebi_ontology methyl sulfides methyl thioether methyl thioethers antifungal drug Any antifungal agent used to prevent or treat fungal infections in humans or animals. CHEBI:86327 Wikipedia:Antifungal anti-fungal drug anti-fungal drugs anti-fungal medication anti-fungal medications antifungal drugs antifungal medication antifungal medications chebi_ontology pharmaceutical fungicide pharmaceutical fungicides monohydroxyproline 131.12990 A hydroxy-amino acid in which the amino acid specified is proline. A "closed" class. C5H9NO3 CHEBI:86499 chebi_ontology N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine 0 309.134 309.32610 An aromatic ether consisting of 4-trifluoromethylphenol in which the hydrogen of the phenolic hydroxy group is replaced by a 3-(methylamino)-1-phenylpropyl group. C17H18F3NO CHEBI:86990 CNCCC(Oc1ccc(cc1)C(F)(F)F)c1ccccc1 InChI=1S/C17H18F3NO/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20/h2-10,16,21H,11-12H2,1H3 LINCS:LSM-1449 N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine RTHCYVBBDHJXIQ-UHFFFAOYSA-N VSDB:1851 chebi_ontology (R)-fluoxetine (+)-fluoxetine (3R)-N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine (R)-(+)-fluoxetine (R)-N-methyl-3-(4-trifluoromethylphenoxy)-3-phenylpropylamine (R)-N-methyl-3-(4-trifluoromethylphenyloxy)-3-(phenyl)propylamine (R)-N-methyl-3-phenyl-3-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]propylamine (R)-N-methyl-gamma-(4-trifluoromethylphenoxy)-3-phenylpropylamine (R)-Prozac 0 309.134 309.32610 An N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine that has R configuration. [The antidepressant drug fluoxetine is a racemate comprising equimolar amounts of (R)- and (S)-fluoxetine]. C17H18F3NO CAS:100568-03-4 CHEBI:86991 CNCC[C@@H](Oc1ccc(cc1)C(F)(F)F)c1ccccc1 InChI=1S/C17H18F3NO/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20/h2-10,16,21H,11-12H2,1H3/t16-/m1/s1 PMID:19144769 PMID:19788198 PMID:20663810 PMID:22903652 PMID:22923967 PMID:23885544 PMID:24464553 PMID:24997906 RTHCYVBBDHJXIQ-MRXNPFEDSA-N Reaxys:4356432 chebi_ontology (S)-fluoxetine (-)-fluoxetine (3S)-N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine (S)-(-)-fluoxetine (S)-N-methyl-3-(4-trifluoromethylphenoxy)-3-phenylpropylamine (S)-N-methyl-3-(4-trifluoromethylphenyloxy)-3-(phenyl)propylamine (S)-N-methyl-3-phenyl-3-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]propylamine (S)-N-methyl-gamma-(4-trifluoromethylphenoxy)-3-phenylpropylamine (S)-Prozac 0 309.134 309.32610 An N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine that has S configuration. [The antidepressant drug fluoxetine is a racemate comprising equimolar amounts of (R)- and (S)-fluoxetine]. C17H18F3NO CHEBI:86992 CNCC[C@H](Oc1ccc(cc1)C(F)(F)F)c1ccccc1 InChI=1S/C17H18F3NO/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20/h2-10,16,21H,11-12H2,1H3/t16-/m0/s1 PMID:19144769 PMID:19788198 PMID:20663810 PMID:22903652 PMID:22923967 PMID:23885544 PMID:24464553 PMID:24997906 RTHCYVBBDHJXIQ-INIZCTEOSA-N Reaxys:4356433 chebi_ontology (R)-fluoxetine(1+) (+)-fluoxetine(1+) (3R)-N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-aminium +1 310.142 310.33350 An organic cation resulting from the protonation of the amino group of (R)-fluoxetine. C17H19F3NO CHEBI:86993 C[NH2+]CC[C@@H](Oc1ccc(cc1)C(F)(F)F)c1ccccc1 InChI=1S/C17H18F3NO/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20/h2-10,16,21H,11-12H2,1H3/p+1/t16-/m1/s1 RTHCYVBBDHJXIQ-MRXNPFEDSA-O Reaxys:25263171 chebi_ontology (S)-fluoxetine(1+) (-)-fluoxetine(1+) (3S)-N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-aminium +1 310.142 310.33350 An organic cation resulting from the protonation of the amino group of (S)-fluoxetine. C17H19F3NO CHEBI:86995 C[NH2+]CC[C@H](Oc1ccc(cc1)C(F)(F)F)c1ccccc1 InChI=1S/C17H18F3NO/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20/h2-10,16,21H,11-12H2,1H3/p+1/t16-/m0/s1 RTHCYVBBDHJXIQ-INIZCTEOSA-O Reaxys:25263174 chebi_ontology ADP(2-) -2 425.014 425.18630 5'-O-{[(hydroxyphosphinato)oxy]phosphinato}adenosine An organophosphate oxoanion obtained by deprotonation of two of the three diphosphate OH groups of adenosine 5'-diphosphate. C10H13N5O10P2 CHEBI:87518 InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/p-2/t4-,6-,7-,10-/m1/s1 Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP([O-])(=O)OP(O)([O-])=O)[C@@H](O)[C@H]1O Reaxys:7558006 XTWYTFMLZFPYCI-KQYNXXCUSA-L chebi_ontology metal allergen Any metal which causes the onset of an allergic reaction. CHEBI:88184 allergenic metal allergenic metals chebi_ontology metal allergens drug allergen Any drug which causes the onset of an allergic reaction. CHEBI:88188 allergenic drug chebi_ontology methylsuccinic acid (+-)-methylsuccinic acid (RS)-2-methylbutanedioic acid (RS)-methylsuccinic acid 0 1,2-Propanedicarboxylic acid 132.115 2-methyl-butanedioic acid 2-methylbutanedioic acid A racemate comprising equimolar amounts of (R)- and (S)-methylsuccinic acid C5H8O4 CAS:498-21-5 CHEBI:89843 HMDB:HMDB0001844 LIPID_MAPS_instance:LMFA01170119 MetaCyc:CPD-2461 Methyl Succinic acid Methylbutanedioic acid Pyrotartaric acid Reaxys:1722946 chebi_ontology rac-2-methylbutanedioic acid EC 6.4.1.1 (pyruvate carboxylase) inhibitor An EC 6.4.1.* (carboxylase) inhibitor that interferes with the action of pyruvate carboxylase (EC 6.4.1.1). CHEBI:90318 EC 6.4.1.1 (pyruvate carboxylase) inhibitors EC 6.4.1.1 inhibitor EC 6.4.1.1 inhibitors Wikipedia:Pyruvate_carboxylase chebi_ontology pyruvate carboxylase (EC 6.4.1.1) inhibitor pyruvate carboxylase (EC 6.4.1.1) inhibitors pyruvate carboxylase inhibitor pyruvate carboxylase inhibitors pyruvate:carbon-dioxide ligase (ADP-forming) inhibitor pyruvate:carbon-dioxide ligase (ADP-forming) inhibitors pyruvic carboxylase inhibitor pyruvic carboxylase inhibitors retinoic acid receptor modulator A nuclear receptor modulator that affects the retinoic acid receptor CHEBI:90708 chebi_ontology retinoic acid receptor modulators nuclear receptor modulator Any receptor modulator acting on nuclear receptors CHEBI:90709 chebi_ontology nuclear receptor modulators receptor modulator A drug that acts as an antagonist, agonist, reverse agonist, or in some other fashion when interacting with cellular receptors. CHEBI:90710 chebi_ontology receptor modulators dipeptide zwitterion 0 130.038 130.102 Any peptide zwitterion comprising two amino acid residues. Major structure at pH 7.3. C4H6N2O3R2 CHEBI:90799 [NH3+]C(C(NC(C([O-])=O)*)=O)* a dipeptide chebi_ontology aromatic carboxylate *C([O-])=O -1 43.990 44.010 A carboxylic acic anion obtained by deprotonation of the carboxy group of any aromatic carboxylic acid. Major species at pH 7.3. CHEBI:91007 CO2R an aromatic carboxylate chebi_ontology 2-methylbutanedioic acid 0 132.042 132.115 2-methylbutanedioic acid A dicarboxylic acid that is butanedioic acid substituted at position 2 by a methyl group. C5H8O4 CHEBI:91315 InChI=1S/C5H8O4/c1-3(5(8)9)2-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9) OC(=O)C(CC(O)=O)C WXUAQHNMJWJLTG-UHFFFAOYSA-N chebi_ontology (S)-methylsuccinic acid (2S)-2-methylbutanedioic acid (S)-2-methylbutanedioic acid 0 132.042 132.115 A 2-methylbutanedioic acid in which the methyl group at position 2 has S-configuration. C5H8O4 CHEBI:91316 InChI=1S/C5H8O4/c1-3(5(8)9)2-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)/t3-/m0/s1 OC(=O)[C@H](CC(O)=O)C Reaxys:1722948 WXUAQHNMJWJLTG-VKHMYHEASA-N chebi_ontology (R)-methylsuccinic acid (2R)-2-methylbutanedioic acid (R)-2-methylbutanedioic acid 0 132.042 132.115 A 2-methylbutanedioic acid in which the methyl group at position 2 has R-configuration. C5H8O4 CAS:3641-51-8 CHEBI:91317 InChI=1S/C5H8O4/c1-3(5(8)9)2-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)/t3-/m1/s1 OC(=O)[C@@H](CC(O)=O)C Reaxys:1722947 WXUAQHNMJWJLTG-GSVOUGTGSA-N chebi_ontology d-Methylsuccinic acid vasopressin A family of cyclic nonapeptide hormones found in most mammals. Synthesised in the hypothalamus and stored in the post-pituitary, vasopressins play a key role in homeostasis, particularly in regulating the body's water content. Together with the similar neuropeptide oxytocin, they are believed to influence social cognition and behaviour. ADH AVP Antidiuretic hormone C46H65N15O12S2.C46H65N13O12S2 CAS:11000-17-2 CHEBI:9937 Inyectable de vasopresina KEGG:C00840 KEGG:D00101 PMID:18988842 PMID:20445498 Solute injectable de vasopressine VP Vasopressin Vasopressini injectio arginine vasopressin argipressin beta-Hypophamine chebi_ontology is conjugate acid of chebi_ontology false is_conjugate_acid_of true has parent hydride chebi_ontology false false has_parent_hydride is conjugate base of chebi_ontology false is_conjugate_base_of true is tautomer of chebi_ontology is_tautomer_of true is substituent group from chebi_ontology false false is_substituent_group_from has role RO:0000087 chebi_ontology false false has_role has_role has functional parent chebi_ontology false false has_functional_parent is enantiomer of chebi_ontology false is_enantiomer_of true