CHEBI:15843 - arachidonic acid

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ChEBI Name arachidonic acid
ChEBI ID CHEBI:15843
Definition A long-chain fatty acid that is a C20, polyunsaturated fatty acid having four (Z)-double bonds at positions 5, 8, 11 and 14.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40501, CHEBI:22608, CHEBI:2799
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Formula C20H32O2
Net Charge 0
Average Mass 304.46690
Monoisotopic Mass 304.24023
InChI InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
InChIKey YZXBAPSDXZZRGB-DOFZRALJSA-N
SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) See: MetaboLights Study
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Daphnia galeata (NCBI:txid27404) See: Is the fatty acid composition of Daphnia galeata determined by the fatty acid composition of the ingested diet?Weers P.M.M., Siewertsen K., and Gulati R.D.Freshwater Biology (1997), 38, 731-738
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): EC 3.1.1.1 (carboxylesterase) inhibitor
Any EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that inhibits the action of carboxylesterase (EC 3.1.1.1 ).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via icosatetraenoic acid )
Daphnia galeata metabolite
A Daphnia metabolite produced by the species Daphnia galeata.
Caenorhabditis elegans metabolite
A nematode metabolite produced by Caenorhabditis elegans.
(via icosatetraenoic acid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing arachidonic acid (CHEBI:15843) has parent hydride (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraene (CHEBI:37834)
arachidonic acid (CHEBI:15843) has role Daphnia galeata metabolite (CHEBI:83038)
arachidonic acid (CHEBI:15843) has role EC 3.1.1.1 (carboxylesterase) inhibitor (CHEBI:78444)
arachidonic acid (CHEBI:15843) has role human metabolite (CHEBI:77746)
arachidonic acid (CHEBI:15843) has role mouse metabolite (CHEBI:75771)
arachidonic acid (CHEBI:15843) is a ω−6 fatty acid (CHEBI:36009)
arachidonic acid (CHEBI:15843) is a icosa-5,8,11,14-tetraenoic acid (CHEBI:36306)
arachidonic acid (CHEBI:15843) is a long-chain fatty acid (CHEBI:15904)
arachidonic acid (CHEBI:15843) is conjugate acid of arachidonate (CHEBI:32395)
Incoming (5Z,8R,9R,11Z,14Z)-8,9-dihydroxyicosatrienoic acid (CHEBI:138586) has functional parent arachidonic acid (CHEBI:15843)
(5Z,8S,9S,11Z,14Z)-8,9-dihydroxyicosatrienoic acid (CHEBI:138585) has functional parent arachidonic acid (CHEBI:15843)
(5Z,8Z,11R,12R,14Z)-11,12-dihydroxyicosatrienoic acid (CHEBI:138593) has functional parent arachidonic acid (CHEBI:15843)
(5Z,8Z,11S,12S,14Z)-11,12-dihydroxyicosatrienoic acid (CHEBI:138594) has functional parent arachidonic acid (CHEBI:15843)
(5Z,8Z,11Z,14R,15R)-14,15-dihydroxyicosatrienoic acid (CHEBI:138591) has functional parent arachidonic acid (CHEBI:15843)
(5Z,8Z,11Z,14S,15S)-14,15-dihydroxyicosatrienoic acid (CHEBI:138592) has functional parent arachidonic acid (CHEBI:15843)
1,2-diarachidonoyl-sn-glycerol (CHEBI:77125) has functional parent arachidonic acid (CHEBI:15843)
1-(1Z)-hexadecenyl-2-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:77292) has functional parent arachidonic acid (CHEBI:15843)
1-(1Z-hexadecenyl)-2-arachidonoyl-sn-glycero-3-phosphoethanolamine (CHEBI:84527) has functional parent arachidonic acid (CHEBI:15843)
1-(1Z-octadecenyl)-2-arachidonoyl-sn-glycero-3-phosphoethanolamine (CHEBI:79207) has functional parent arachidonic acid (CHEBI:15843)
1-(1Z-octadecenyl)-2-arachidonoyl-sn-glycero-3-phosphoserine (CHEBI:79211) has functional parent arachidonic acid (CHEBI:15843)
1-(1Z-octadecenyl)-sn-glycero-3-phospho-(N-arachidonoyl)ethanolamine (CHEBI:138096) has functional parent arachidonic acid (CHEBI:15843)
1-(9Z-octadecenyl)-2-arachidonoyl-sn-glycero-3-phosphate (CHEBI:85672) has functional parent arachidonic acid (CHEBI:15843)
1-O-alkyl-2-O-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:28894) has functional parent arachidonic acid (CHEBI:15843)
1-O-alkyl-2-arachidonoyl-sn-glycero-3-phosphoethanolamine zwitterion (CHEBI:76251) has functional parent arachidonic acid (CHEBI:15843)
1-O-arachidonoyl-N-acetylsphingosine (CHEBI:76080) has functional parent arachidonic acid (CHEBI:15843)
1-[(1Z)-octadecenyl]-2-[(5Z,8Z,11Z,14Z)-icosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:84828) has functional parent arachidonic acid (CHEBI:15843)
1-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-2-[(9Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholine (CHEBI:86184) has functional parent arachidonic acid (CHEBI:15843)
1-[(7Z)-hexadecenoyl]-2-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:64505) has functional parent arachidonic acid (CHEBI:15843)
1-[(9Z)-hexadecenoyl]-2-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:84816) has functional parent arachidonic acid (CHEBI:15843)
1-[(9Z)-octadecenyl]-2-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:84827) has functional parent arachidonic acid (CHEBI:15843)
1-[(9Z)-tetradecenoyl]-2-[(5Z,8Z,11Z,14Z)-icosatetraenoyl]-sn-glycerol (CHEBI:86977) has functional parent arachidonic acid (CHEBI:15843)
1-[(9Z,12Z)-octadecadienoyl]-2-[(5Z,8Z,11Z,14Z)-icosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:84563) has functional parent arachidonic acid (CHEBI:15843)
1-acyl-2-arachidonoyl-sn-glycero-3-phosphate (CHEBI:75112) has functional parent arachidonic acid (CHEBI:15843)
1-acyl-2-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:75063) has functional parent arachidonic acid (CHEBI:15843)
1-acyl-2-arachidonoyl-sn-glycero-3-phosphoethanolamine zwitterion (CHEBI:75067) has functional parent arachidonic acid (CHEBI:15843)
1-arachidonoyl-2-oleoyl-sn-glycero-3-phosphate (CHEBI:75141) has functional parent arachidonic acid (CHEBI:15843)
1-arachidonoyl-2-oleoylglycerol (CHEBI:75611) has functional parent arachidonic acid (CHEBI:15843)
1-arachidonoyl-2-palmitoyl-sn-glycero-3-phosphocholine (CHEBI:77694) has functional parent arachidonic acid (CHEBI:15843)
1-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:83053) has functional parent arachidonic acid (CHEBI:15843)
1-arachidonoyl-sn-glycero-3-phospho-L-serine (CHEBI:85435) has functional parent arachidonic acid (CHEBI:15843)
1-arachidonoyl-sn-glycero-3-phospho-L-serine(1−) (CHEBI:84723) has functional parent arachidonic acid (CHEBI:15843)
1-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:74344) has functional parent arachidonic acid (CHEBI:15843)
1-arachidonoyl-sn-glycero-3-phosphoethanolamine (CHEBI:64395) has functional parent arachidonic acid (CHEBI:15843)
1-arachidonoyl-sn-glycerol 3-phosphate (CHEBI:73792) has functional parent arachidonic acid (CHEBI:15843)
1-arachidonoylglycerol (CHEBI:75612) has functional parent arachidonic acid (CHEBI:15843)
1-arachidonoylglycerone 3-phosphate (CHEBI:78175) has functional parent arachidonic acid (CHEBI:15843)
1-heptadecanoyl-2-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:84470) has functional parent arachidonic acid (CHEBI:15843)
1-heptadecanoyl-2-arachidonoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85408) has functional parent arachidonic acid (CHEBI:15843)
1-heptadecanoyl-2-arachidonoyl-sn-glycero-3-phosphoserine (CHEBI:85400) has functional parent arachidonic acid (CHEBI:15843)
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-icosatetraenoyl)-sn-glycero-3-phosphoethanolamine (CHEBI:73117) has functional parent arachidonic acid (CHEBI:15843)
1-icosanoyl-2-arachidonoyl-sn-glycerol (CHEBI:87223) has functional parent arachidonic acid (CHEBI:15843)
1-oleoyl-2-arachidonoyl-sn-glycero-3-phosphate (CHEBI:75118) has functional parent arachidonic acid (CHEBI:15843)
1-oleoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:82762) has functional parent arachidonic acid (CHEBI:15843)
1-oleoyl-2-arachidonoyl-sn-glycero-3-phospho-L-serine (CHEBI:75099) has functional parent arachidonic acid (CHEBI:15843)
1-oleoyl-2-arachidonoyl-sn-glycerol (CHEBI:75449) has functional parent arachidonic acid (CHEBI:15843)
1-oleoyl-2-arachidonoyl-sn-glycerol-3-phosphoethanolamine (CHEBI:75169) has functional parent arachidonic acid (CHEBI:15843)
1-palmitoyl-2-arachidonoyl-sn-glycero-3-phospho-(1'-sn-glycerol) (CHEBI:84526) has functional parent arachidonic acid (CHEBI:15843)
1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:73003) has functional parent arachidonic acid (CHEBI:15843)
1-palmitoyl-2-arachidonoyl-sn-glycerol (CHEBI:77096) has functional parent arachidonic acid (CHEBI:15843)
1-palmityl-2-arachidonoyl-sn-glycero-3-phosphate (CHEBI:77355) has functional parent arachidonic acid (CHEBI:15843)
1-palmityl-2-arachidonoyl-sn-glycerol (CHEBI:77184) has functional parent arachidonic acid (CHEBI:15843)
1-pentadecanoyl-2-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:86344) has functional parent arachidonic acid (CHEBI:15843)
1-stearoyl-2-arachidonoyl-3-oleoyl-sn-glycerol (CHEBI:75729) has functional parent arachidonic acid (CHEBI:15843)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol) (CHEBI:75646) has functional parent arachidonic acid (CHEBI:15843)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-(1D-myo-inositol 3,4,5-triphosphate) (CHEBI:83980) has functional parent arachidonic acid (CHEBI:15843)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:84153) has functional parent arachidonic acid (CHEBI:15843)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-biphosphate (CHEBI:77276) has functional parent arachidonic acid (CHEBI:15843)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol 4-phosphate (CHEBI:77271) has functional parent arachidonic acid (CHEBI:15843)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol 5-phosphate (CHEBI:77345) has functional parent arachidonic acid (CHEBI:15843)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphoethanolamine (CHEBI:79110) has functional parent arachidonic acid (CHEBI:15843)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphoserine (CHEBI:79113) has functional parent arachidonic acid (CHEBI:15843)
1-stearoyl-2-arachidonoyl-sn-glycerol (CHEBI:75728) has functional parent arachidonic acid (CHEBI:15843)
1-stearoyl-2-arachidonoylglycerol (CHEBI:83288) has functional parent arachidonic acid (CHEBI:15843)
1-stearoyl-2-arachidonoylphosphatidic acid (CHEBI:84165) has functional parent arachidonic acid (CHEBI:15843)
1-tetradecanoyl-2-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:86102) has functional parent arachidonic acid (CHEBI:15843)
10-HETE (CHEBI:134453) has functional parent arachidonic acid (CHEBI:15843)
11,12-epoxy-20-hydroxy-(5Z,8Z,14Z)-icosatrienoic acid (CHEBI:138273) has functional parent arachidonic acid (CHEBI:15843)
13-HETE (CHEBI:137345) has functional parent arachidonic acid (CHEBI:15843)
14,15-epoxy-20-hydroxy-(5Z,8Z,11Z)-icosatrienoic acid (CHEBI:138274) has functional parent arachidonic acid (CHEBI:15843)
17,18-DiHETE (CHEBI:88349) has functional parent arachidonic acid (CHEBI:15843)
18(R)-HETE (CHEBI:91132) has functional parent arachidonic acid (CHEBI:15843)
19(S)-HETE (CHEBI:34185) has functional parent arachidonic acid (CHEBI:15843)
19-HETE (CHEBI:63998) has functional parent arachidonic acid (CHEBI:15843)
2-arachidonoyl-sn-glycero-3-phosphate (CHEBI:79059) has functional parent arachidonic acid (CHEBI:15843)
2-arachidonoyl-sn-glycero-3-phospho-L-serine (CHEBI:78703) has functional parent arachidonic acid (CHEBI:15843)
2-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:76079) has functional parent arachidonic acid (CHEBI:15843)
2-arachidonoyl-sn-glycero-3-phosphoethanolamine zwitterion (CHEBI:76091) has functional parent arachidonic acid (CHEBI:15843)
2-arachidonoylglycerol (CHEBI:52392) has functional parent arachidonic acid (CHEBI:15843)
2-arachidonyl-sn-glycero-3-phosphoethanolamine (CHEBI:72741) has functional parent arachidonic acid (CHEBI:15843)
20-HETE (CHEBI:34306) has functional parent arachidonic acid (CHEBI:15843)
20-oxoarachidonic acid (CHEBI:76965) has functional parent arachidonic acid (CHEBI:15843)
5,6-epoxy-20-hydroxy-(8Z,11Z,14Z)-icosatrienoic acid (CHEBI:138271) has functional parent arachidonic acid (CHEBI:15843)
7-HETE (CHEBI:137344) has functional parent arachidonic acid (CHEBI:15843)
8(S),15(S)-DiHETE (CHEBI:136485) has functional parent arachidonic acid (CHEBI:15843)
8(S),15(S)-DiHPETE (CHEBI:136400) has functional parent arachidonic acid (CHEBI:15843)
8,9-epoxy-20-hydroxy-(5Z,11Z,14Z)-icosatrienoic acid (CHEBI:138272) has functional parent arachidonic acid (CHEBI:15843)
9-oxo-ETE (CHEBI:136365) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoyl-γ-aminobutyric acid (CHEBI:132722) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85784) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoyl-1-oleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85666) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoyl-2-oxoserotonin (CHEBI:132256) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85671) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoyl-L-alanine (CHEBI:132708) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoyl-L-leucine (CHEBI:136683) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoyl-L-phenylalanine (CHEBI:136606) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoyl-L-serine (CHEBI:143514) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoylglycine (CHEBI:58961) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoylphosphatidylethanolamine (CHEBI:52571) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoylphytosphingosine (CHEBI:85207) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoylserotonin (CHEBI:132255) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoylsphinganine (CHEBI:85206) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoylsphingosine (CHEBI:85198) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoyltaurine (CHEBI:132506) has functional parent arachidonic acid (CHEBI:15843)
AACOCF3 (CHEBI:2341) has functional parent arachidonic acid (CHEBI:15843)
anandamide (CHEBI:2700) has functional parent arachidonic acid (CHEBI:15843)
arachidonoyl amine (CHEBI:137830) has functional parent arachidonic acid (CHEBI:15843)
arachidonoyl bioconjugate (CHEBI:76180) has functional parent arachidonic acid (CHEBI:15843)
Arachidonoyl dopamine (CHEBI:31231) has functional parent arachidonic acid (CHEBI:15843)
arachidonoyl-CoA (CHEBI:15514) has functional parent arachidonic acid (CHEBI:15843)
arachidonoyl-containing glycerolipid (CHEBI:90077) has functional parent arachidonic acid (CHEBI:15843)
arachidonoylcholine (CHEBI:133694) has functional parent arachidonic acid (CHEBI:15843)
arachidonyl-2'-chloroethylamide (CHEBI:191854) has functional parent arachidonic acid (CHEBI:15843)
CDP-1,2-diarachidonoyl-sn-glycerol (CHEBI:85835) has functional parent arachidonic acid (CHEBI:15843)
CDP-1-palmitoyl-2-arachidonoyl-sn-glycerol (CHEBI:85830) has functional parent arachidonic acid (CHEBI:15843)
CDP-1-stearoyl-2-arachidonoyl-sn-glycerol (CHEBI:85829) has functional parent arachidonic acid (CHEBI:15843)
cholesteryl arachidonate (CHEBI:82751) has functional parent arachidonic acid (CHEBI:15843)
DHET (CHEBI:64005) has functional parent arachidonic acid (CHEBI:15843)
EET (CHEBI:64007) has functional parent arachidonic acid (CHEBI:15843)
ethyl arachidonate (CHEBI:84873) has functional parent arachidonic acid (CHEBI:15843)
lipoxin (CHEBI:6497) has functional parent arachidonic acid (CHEBI:15843)
methyl arachidonate (CHEBI:78033) has functional parent arachidonic acid (CHEBI:15843)
1-arachidonyl-2-palmityl-sn-glycero-3-phosphocholine (CHEBI:77695) is a arachidonic acid (CHEBI:15843)
arachidonate (CHEBI:32395) is conjugate base of arachidonic acid (CHEBI:15843)
IUPAC Name
(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
Synonyms Sources
(5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraenoic acid NIST Chemistry WebBook
(5Z,8Z,11Z,14Z)-Icosatetraenoic acid KEGG COMPOUND
AA ChEBI
all-cis-5,8,11,14-eicosatetraenoic acid ChEBI
ARA ChEBI
Arachidonate KEGG COMPOUND
Arachidonic acid KEGG COMPOUND
ARACHIDONIC ACID PDBeChem
Arachidonsäure ChEBI
cis-5,8,11,14-Eicosatetraenoic acid KEGG COMPOUND
cis-Δ5,8,11,14-eicosatetraenoic acid ChEBI
Manual Xrefs Databases
ACD PDBeChem
Arachidonic_acid Wikipedia
ARACHIDONIC_ACID MetaCyc
C00000388 KNApSAcK
C00219 KEGG COMPOUND
DB04557 DrugBank
HMDB0001043 HMDB
LMFA01030001 LIPID MAPS
View more database links
Registry Numbers Types Sources
1913991 Reaxys Registry Number Reaxys
1913991 Beilstein Registry Number Beilstein
506-32-1 CAS Registry Number KEGG COMPOUND
506-32-1 CAS Registry Number ChemIDplus
506-32-1 CAS Registry Number NIST Chemistry WebBook
58972 Gmelin Registry Number Gmelin
Citations Waiting for Citations Types Sources
15129302 PubMed citation Europe PMC
18931599 PubMed citation Europe PMC
18973997 PubMed citation Europe PMC
25584012 PubMed citation Europe PMC
2820055 PubMed citation Europe PMC
Last Modified
27 May 2022
General Comments
2011-03-24 It is one of the essential fatty acids required by most mammals, and the counterpart to the saturated arachidic acid found in peanut oil.
2011-03-24 Released from membrane phospholipids upon cell stimulation, arachidonic acid is converted by a 5-lipoxygenase to leukotrienes, which participate in host defense reactions and pathophysiological conditions such as immediate hypersensitivity and inflammation.