octadecanoic acid (CHEBI:28842)

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CHEBI:28842 - octadecanoic acid

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ChEBI Name	octadecanoic acid

ChEBI ID	CHEBI:28842

Definition	A C₁₈ straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:45710, CHEBI:25631

Supplier Information	ChemicalBook:CB2739302, ChemicalBook:CB2704227, eMolecules:476359, Selleckchem:Abitrexate, ZINC000001529323

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Wikipedia	License
Methotrexate, formerly known as amethopterin, is a chemotherapy agent and immune-system suppressant. It is used to treat cancer, autoimmune diseases, and ectopic pregnancies. Types of cancers it is used for include breast cancer, leukemia, lung cancer, lymphoma, gestational trophoblastic disease, and osteosarcoma. Types of autoimmune diseases it is used for include psoriasis, rheumatoid arthritis, and Crohn's disease. It can be given by mouth or by injection. Common side effects include nausea, feeling tired, fever, increased risk of infection, low white blood cell counts, and breakdown of the skin inside the mouth. Other side effects may include liver disease, lung disease, lymphoma, and severe skin rashes. People on long-term treatment should be regularly checked for side effects. It is not safe during breastfeeding. In those with kidney problems, lower doses may be needed. It acts by blocking the body's use of folic acid. Methotrexate was first made in 1947 and initially was used to treat cancer, as it was less toxic than the then-current treatments. In 1956 it provided the first cures of a metastatic cancer. It is on the World Health Organization's List of Essential Medicines. Methotrexate is available as a generic medication. In 2022, it was the 132nd most commonly prescribed medication in the United States, with more than 4 million prescriptions.
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Formula

C18H36O2

Net Charge

Average Mass

284.478

Monoisotopic Mass

284.27153

InChI

InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)

InChIKey

QIQXTHQIDYTFRH-UHFFFAOYSA-N

SMILES

C(CCCCCCCCCC)CCCCCCC(=O)O

Metabolite of Species	Details
Neolitsea daibuensis (IPNI:466954-1)	Found in root (BTO:0001188). Cold MeOH extract of dried root, obtained as a mixture of stearic acid and docosanoic acid See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055)	See: PubMed
Daphnia magna (NCBI:txid35525)	See: Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
Centella asiatica (NCBI:txid48106)	See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	See: PubMed

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):	Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). 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.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	octadecanoic acid (CHEBI:28842) has parent hydride octadecane (CHEBI:32926) octadecanoic acid (CHEBI:28842) has role Daphnia magna metabolite (CHEBI:83056) octadecanoic acid (CHEBI:28842) has role algal metabolite (CHEBI:84735) octadecanoic acid (CHEBI:28842) has role human metabolite (CHEBI:77746) octadecanoic acid (CHEBI:28842) has role plant metabolite (CHEBI:76924) octadecanoic acid (CHEBI:28842) is a long-chain fatty acid (CHEBI:15904) octadecanoic acid (CHEBI:28842) is a saturated fatty acid (CHEBI:26607) octadecanoic acid (CHEBI:28842) is a straight-chain saturated fatty acid (CHEBI:39418) octadecanoic acid (CHEBI:28842) is conjugate acid of octadecanoate (CHEBI:25629)

Incoming	α-D-Gal-(1→4)-β-D-Gal-(1→4)-β-D-Glc-(1↔1')-Cer(d18:1/18:0) (CHEBI:84690) has functional parent octadecanoic acid (CHEBI:28842) α-Neu5Ac-(2→3)-β-D-Gal-(1→3)-β-D-GalNAc-(1→4)-[α-Neu5Ac-(2→8)-α-Neu5Ac-(2→8)-α-Neu5Ac-(2→3)]-β-D-Gal-(1→4)-β-D-Glc-(1↔1')-Cer(d18:1/18:0) (CHEBI:84682) has functional parent octadecanoic acid (CHEBI:28842) α-Neu5Ac-(2→3)-β-D-Gal-(1→4)-β-D-Glc-(1↔1')-Cer(d18:1/18:0) (CHEBI:84675) has functional parent octadecanoic acid (CHEBI:28842) β-D-galactosyl-(1→4)-β-D-glucosyl-(1↔1)-N-octadecanoylsphingosine (CHEBI:84759) has functional parent octadecanoic acid (CHEBI:28842) β-D-galactosyl-(1↔1ʼ)-N-octadecanoylsphinganine (CHEBI:90498) has functional parent octadecanoic acid (CHEBI:28842) β-D-galactosyl-N-octadecanoylsphingosine (CHEBI:84720) has functional parent octadecanoic acid (CHEBI:28842) β-D-glucosyl-(1↔1ʼ)-N-octadecanoylsphinganine (CHEBI:84697) has functional parent octadecanoic acid (CHEBI:28842) β-D-glucosyl-N-octadecanoylsphingosine (CHEBI:84719) has functional parent octadecanoic acid (CHEBI:28842) β-GalNAc-(1→4)-[α-Neu5Ac-(2→8)-α-Neu5Ac-(2→8)-α-Neu5Ac-(2→3)]-β-Gal-(1→4)-β-Glc-(1→1')-Cer(d18:1/18:0) (CHEBI:84685) has functional parent octadecanoic acid (CHEBI:28842) (13Z)-8-hydroxyoctadecene-9,11-diynoic acid (CHEBI:73751) has functional parent octadecanoic acid (CHEBI:28842) (9R,10S)-dihydroxyoctadecanoic acid (CHEBI:136767) has functional parent octadecanoic acid (CHEBI:28842) (9S,10R)-10-hydroxy-9-(phosphonooxy)octadecanoic acid (CHEBI:85632) has functional parent octadecanoic acid (CHEBI:28842) (9S,10R)-dihydroxyoctadecanoic acid (CHEBI:85633) has functional parent octadecanoic acid (CHEBI:28842) (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoic acid (CHEBI:49253) has functional parent octadecanoic acid (CHEBI:28842) 1,2-dioctadecanoyl-sn-glycero-3-cytidine 5'-diphosphate (CHEBI:104121) has functional parent octadecanoic acid (CHEBI:28842) 1,2-dioctadecanoyl-sn-glycerol (CHEBI:41847) has functional parent octadecanoic acid (CHEBI:28842) 1,2-dioleoyl-3-stearoyl-sn-glycerol (CHEBI:77686) has functional parent octadecanoic acid (CHEBI:28842) 1,2-distearoyl-sn-glycero-3-phosphocholine (CHEBI:83718) has functional parent octadecanoic acid (CHEBI:28842) 1,2-distearoyl-sn-glycero-3-phosphoserine (CHEBI:84519) has functional parent octadecanoic acid (CHEBI:28842) 1,2-distearoylphosphatidylethanolamine (CHEBI:47764) has functional parent octadecanoic acid (CHEBI:28842) 1-O-stearoyl-N-acetylsphingosine (CHEBI:76074) has functional parent octadecanoic acid (CHEBI:28842) 1-[(7Z,10Z,13Z,16Z)-docosatetraenoyl]-2-octadecanoyl-sn-glycero-3-phosphocholine (CHEBI:86200) has functional parent octadecanoic acid (CHEBI:28842) 1-[(8Z,11Z,14Z,17Z)-icosatetraenoyl]-2-octadecanoyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:89250) has functional parent octadecanoic acid (CHEBI:28842) 1-[(9Z,12Z)-octadecadienoyl]-2-octadecanoyl-sn-glycero-3-phosphocholine (CHEBI:86112) has functional parent octadecanoic acid (CHEBI:28842) 1-[(9Z,12Z)-octadecadienoyl]-2-octadecanoyl-sn-glycerol (CHEBI:86337) has functional parent octadecanoic acid (CHEBI:28842) 1-acyl-2-octadecanoyl-sn-glycero-3-phosphate (CHEBI:64864) has functional parent octadecanoic acid (CHEBI:28842) 1-acyl-2-stearoyl-sn-glycero-3-phospho-(1D-myo-inositol) (CHEBI:84317) has functional parent octadecanoic acid (CHEBI:28842) 1-eicosanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine (CHEBI:86166) has functional parent octadecanoic acid (CHEBI:28842) 1-heptadecanoyl-2-stearoyl-sn-glycero-3-phosphate (CHEBI:85385) has functional parent octadecanoic acid (CHEBI:28842) 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine (CHEBI:73000) has functional parent octadecanoic acid (CHEBI:28842) 1-hexadecanoyl-2-octadecanoyl-sn-glycerol (CHEBI:86975) has functional parent octadecanoic acid (CHEBI:28842) 1-hexadecyl-2-octadecanoyl-sn-glycero-3-phosphocholine (CHEBI:86229) has functional parent octadecanoic acid (CHEBI:28842) 1-hexanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine (CHEBI:86282) has functional parent octadecanoic acid (CHEBI:28842) 1-myristoyl-2-stearoyl-sn-glycero-3-phosphocholine (CHEBI:86090) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine (CHEBI:84829) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoethanolamine (CHEBI:79109) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3- phosphocholine (CHEBI:73865) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-(5E,8E,11E,14E-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine (CHEBI:84837) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-(6Z,9Z,12Z,15Z,18Z-docosapentaenoyl)-sn-glycero-3- phosphocholine (CHEBI:84151) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phosphocholine (CHEBI:84565) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphate (CHEBI:75073) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-[(10Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholine (CHEBI:84819) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-[(11Z)-eicosenoyl]-sn-glycero-3-phosphocholine (CHEBI:86173) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-[(13Z)-docosenoyl]-sn-glycero-3-phosphocholine (CHEBI:86196) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-[(15Z)-tetracosenoyl]-sn-glycero-3-phosphocholine (CHEBI:86219) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-[(2E,4E)-octadecadienoyl]-sn-glycero-3-phosphocholine (CHEBI:84820) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-[(4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl]-sn-glycero-3-phosphoethanolamine (CHEBI:131665) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-[(5Z,8Z,11Z)-eicosatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:86176) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-[(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl]-sn-glycero-3-phosphocholine (CHEBI:86181) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-[(6Z,9Z)-octadecadienoyl]-sn-glycero-3-phosphocholine (CHEBI:84821) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:86117) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-[(6Z,9Z,12Z,15Z)-octadecatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:86134) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-[(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl]-sn-glycero-3-phosphocholine (CHEBI:86203) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-[(8Z,10Z,12Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:84823) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-[(8Z,11Z,14Z)-eicosatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:86177) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86097) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-[(9Z,11Z,13Z,15Z,17Z,19E)-docosahexaenoyl]-sn-glycero-3-phosphocholine (CHEBI:84830) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-[(9Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholine (CHEBI:84822) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:65090) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-docosanoyl-sn-glycerol (CHEBI:87241) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-dodecanoyl-sn-glycero-3-phosphocholine (CHEBI:138215) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholine (CHEBI:86167) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-hexanoyl-sn-glycero-3-phosphocholine (CHEBI:138212) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-nonanoyl-sn-glycero-3-phosphocholine (CHEBI:138214) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-octadecenoyl-sn-glycero-3-phosphocholine (CHEBI:84818) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-octanoyl-sn-glycero-3-phosphocholine (CHEBI:138213) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-pentadecanoyl-sn-glycero-3-phosphocholine (CHEBI:134076) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-pentanoyl-sn-glycero-3-phosphocholine (CHEBI:138211) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecanoyl-2-tetracosanoyl-sn-glycero-3-phosphocholine (CHEBI:86212) has functional parent octadecanoic acid (CHEBI:28842) 1-octadecyl-2-octadecanoyl-sn-glycero-3-phosphocholine (CHEBI:86239) has functional parent octadecanoic acid (CHEBI:28842) 1-oleoyl-2-stearoyl-sn-glycero-3-phospho-L-serine (CHEBI:75103) has functional parent octadecanoic acid (CHEBI:28842) 1-oleoyl-2-stearoyl-sn-glycero-3-phosphocholine (CHEBI:76073) has functional parent octadecanoic acid (CHEBI:28842) 1-oleoyl-2-stearoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85076) has functional parent octadecanoic acid (CHEBI:28842) 1-oleoyl-2-stearoyl-sn-glycerol (CHEBI:75448) has functional parent octadecanoic acid (CHEBI:28842) 1-palmitoleoyl-2-stearoyl-sn-glycero-3-phosphocholine (CHEBI:84570) has functional parent octadecanoic acid (CHEBI:28842) 1-palmitoleoyl-2-stearoyl-sn-glycerol (CHEBI:84418) has functional parent octadecanoic acid (CHEBI:28842) 1-palmitoyl-2-lauroyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol) (CHEBI:77122) has functional parent octadecanoic acid (CHEBI:28842) 1-palmitoyl-2-oleoyl-3-stearoyl-sn-glycerol (CHEBI:77623) has functional parent octadecanoic acid (CHEBI:28842) 1-palmitoyl-2-stearoyl-sn-glycero-3-phosphoserine (CHEBI:84520) has functional parent octadecanoic acid (CHEBI:28842) 1-palmitoyl-3-stearoyl-sn-glycerol (CHEBI:77624) has functional parent octadecanoic acid (CHEBI:28842) 1-palmityl-2-acetyl-3-stearoyl-sn-glycerol (CHEBI:77677) has functional parent octadecanoic acid (CHEBI:28842) 1-pentadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine (CHEBI:134075) has functional parent octadecanoic acid (CHEBI:28842) 1-pentadecanoyl-2-octadecanoyl-sn-glycero-3-phosphoethanolamine (CHEBI:136139) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl 2-acylglycerolipid (CHEBI:87007) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-(α-linolenoyl)-sn-glycero-3-phosphocholine (CHEBI:78022) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-sn-glycero-3-phosphate (CHEBI:77258) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-sn-glycerol (CHEBI:77129) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phosphoserine (CHEBI:84506) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycerol (CHEBI:84435) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-(8-epi-prostaglandin F_2α)-sn-glycero-3-phosphocholine (CHEBI:77329) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-(8Z,11Z,14Z-icosa-8,11,14-trienoyl)-sn-glycerol (CHEBI:84433) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-(8Z,11Z,14Z-icosatrienoyl)-sn-glycero-3-phosphoserine (CHEBI:84512) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-acetyl-sn-glycero-3-phosphocholine (CHEBI:75220) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-arachidonoyl-3-oleoyl-sn-glycerol (CHEBI:75729) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphate (CHEBI:77239) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol) (CHEBI:75646) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-(1D-myo-inositol 3,4,5-triphosphate) (CHEBI:83980) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:84153) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-biphosphate (CHEBI:77276) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol 4-phosphate (CHEBI:77271) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol 5-phosphate (CHEBI:77345) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:74965) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphoethanolamine (CHEBI:79110) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphoserine (CHEBI:79113) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-arachidonoyl-sn-glycerol (CHEBI:75728) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-arachidonoylglycerol (CHEBI:83288) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-arachidonoylphosphatidic acid (CHEBI:84165) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-linoleoyl-sn-glycero-3-phosphate (CHEBI:77248) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-linoleoyl-sn-glycero-3-phospho-1D-myo-inositol 5-phosphate (CHEBI:77344) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-linoleoyl-sn-glycero-3-phospho-L-serine (CHEBI:84513) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:133600) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-linoleoyl-sn-glycerol (CHEBI:77097) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-myristoyl-sn-glycero-3-phosphocholine (CHEBI:86089) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-oleoyl-sn-glycero-3-phosphate (CHEBI:74847) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-oleoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-biphosphate (CHEBI:77279) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-oleoyl-sn-glycero-3-phospho-1D-myo-inositol 4-phosphate (CHEBI:77277) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-oleoyl-sn-glycero-3-phospho-1D-myo-inositol 5-phosphate (CHEBI:77347) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-oleoyl-sn-glycero-3-phosphoserine (CHEBI:79096) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-oleoylglycerol (CHEBI:75590) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-2-palmitoyl-sn-glycero-3-phosphocholine (CHEBI:75026) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-sn-glycero-3-phosphate (CHEBI:74850) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:83054) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-sn-glycero-3-phosphocholine (CHEBI:73858) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-sn-glycero-3-phosphoethanolamine (CHEBI:83047) has functional parent octadecanoic acid (CHEBI:28842) 1-stearoyl-sn-glycero-3-phosphoserine (CHEBI:85403) has functional parent octadecanoic acid (CHEBI:28842) 1-tetracosanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine (CHEBI:86208) has functional parent octadecanoic acid (CHEBI:28842) 10-hydroxyoctadecanoic acid (CHEBI:143095) has functional parent octadecanoic acid (CHEBI:28842) 10-PAHSA (CHEBI:84460) has functional parent octadecanoic acid (CHEBI:28842) 11-PAHSA (CHEBI:84464) has functional parent octadecanoic acid (CHEBI:28842) 12-(octadecanoyloxy)octadecanoic acid (CHEBI:137089) has functional parent octadecanoic acid (CHEBI:28842) 12-(phosphonooxy)octadecanoic acid (CHEBI:85133) has functional parent octadecanoic acid (CHEBI:28842) 12-methyloctadecanoic acid (CHEBI:85058) has functional parent octadecanoic acid (CHEBI:28842) 12-PAHSA (CHEBI:84468) has functional parent octadecanoic acid (CHEBI:28842) 13-(octadecanoyloxy)octadecanoic acid (CHEBI:137091) has functional parent octadecanoic acid (CHEBI:28842) 13-PAHSA (CHEBI:84469) has functional parent octadecanoic acid (CHEBI:28842) 16-DOXYL-stearic acid (CHEBI:184306) has functional parent octadecanoic acid (CHEBI:28842) 16-methyloctadecanoic acid (CHEBI:84875) has functional parent octadecanoic acid (CHEBI:28842) 17-methyloctadecanoic acid (CHEBI:133136) has functional parent octadecanoic acid (CHEBI:28842) 2,3-distearoyl-sn-glycerol (CHEBI:77395) has functional parent octadecanoic acid (CHEBI:28842) 2-methyloctadecanoic acid (CHEBI:144310) has functional parent octadecanoic acid (CHEBI:28842) 2-octadecanoyl-sn-glycero-3-phosphoethanolamine (CHEBI:133145) has functional parent octadecanoic acid (CHEBI:28842) 2-oxooctadecanoic acid (CHEBI:30820) has functional parent octadecanoic acid (CHEBI:28842) 2-stearoyl-sn-glycero-3-phosphocholine (CHEBI:76076) has functional parent octadecanoic acid (CHEBI:28842) 2-stearoylglycerol (CHEBI:75456) has functional parent octadecanoic acid (CHEBI:28842) 3-oxooctadecanoic acid (CHEBI:50576) has functional parent octadecanoic acid (CHEBI:28842) 5-DOXYL-stearic acid (CHEBI:184308) has functional parent octadecanoic acid (CHEBI:28842) 5-PAHSA (CHEBI:84457) has functional parent octadecanoic acid (CHEBI:28842) 7-PAHSA (CHEBI:84479) has functional parent octadecanoic acid (CHEBI:28842) 8-PAHSA (CHEBI:84486) has functional parent octadecanoic acid (CHEBI:28842) 9-(octadecanoyloxy)octadecanoic acid (CHEBI:137097) has functional parent octadecanoic acid (CHEBI:28842) 9-PAHSA (CHEBI:84425) has functional parent octadecanoic acid (CHEBI:28842) all-trans-retinyl stearate (CHEBI:70761) has functional parent octadecanoic acid (CHEBI:28842) N-(octadecanoyl)-pentadecasphing-4-enine-1-phosphoethanolamine (CHEBI:86516) has functional parent octadecanoic acid (CHEBI:28842) N-(octadecanoyl)ethanolamine (CHEBI:85299) has functional parent octadecanoic acid (CHEBI:28842) N-(octadecanoyl)hexadecasphingosine-1-phosphocholine (CHEBI:136273) has functional parent octadecanoic acid (CHEBI:28842) N-octadecanoyl-(4E,14Z)-sphingadienine (CHEBI:136461) has functional parent octadecanoic acid (CHEBI:28842) N-octadecanoyl-15-methylhexadecasphingosine-1-phosphocholine (CHEBI:119713) has functional parent octadecanoic acid (CHEBI:28842) N-octadecanoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85668) has functional parent octadecanoic acid (CHEBI:28842) N-octadecanoylglycine (CHEBI:136623) has functional parent octadecanoic acid (CHEBI:28842) N-octadecanoylsphingadienine-1-phosphocholine (CHEBI:136281) has functional parent octadecanoic acid (CHEBI:28842) N-octadecanoylsphingosine (CHEBI:72961) has functional parent octadecanoic acid (CHEBI:28842) N-octadecanoylsphingosine 1-phosphate (CHEBI:73144) has functional parent octadecanoic acid (CHEBI:28842) N-octodecanoylsphinganine (CHEBI:67033) has functional parent octadecanoic acid (CHEBI:28842) N-stearoyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85791) has functional parent octadecanoic acid (CHEBI:28842) N-stearoyl-1-oleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85660) has functional parent octadecanoic acid (CHEBI:28842) N-stearoyl-D-galactosylsphingosine (CHEBI:83867) has functional parent octadecanoic acid (CHEBI:28842) N-stearoylhexadecasphinganine (CHEBI:82811) has functional parent octadecanoic acid (CHEBI:28842) N-stearoylserotonin (CHEBI:134065) has functional parent octadecanoic acid (CHEBI:28842) N-stearoylsphingosine-1-phosphocholine (CHEBI:83358) has functional parent octadecanoic acid (CHEBI:28842) N-stearoyltaurine (CHEBI:132479) has functional parent octadecanoic acid (CHEBI:28842) O-octadecanoyl-L-carnitine (CHEBI:84644) has functional parent octadecanoic acid (CHEBI:28842) O-stearoylcarnitine (CHEBI:73074) has functional parent octadecanoic acid (CHEBI:28842) butyl octadecanoate (CHEBI:85983) has functional parent octadecanoic acid (CHEBI:28842) CDP-1-stearoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-sn-glycerol (CHEBI:85846) has functional parent octadecanoic acid (CHEBI:28842) CDP-1-stearoyl-2-arachidonoyl-sn-glycerol (CHEBI:85829) has functional parent octadecanoic acid (CHEBI:28842) CDP-1-stearoyl-2-linoleoyl-sn-glycerol (CHEBI:85838) has functional parent octadecanoic acid (CHEBI:28842) CDP-1-stearoyl-2-oleoyl-sn-glycerol (CHEBI:85841) has functional parent octadecanoic acid (CHEBI:28842) cholesteryl stearate (CHEBI:82750) has functional parent octadecanoic acid (CHEBI:28842) epoxystearic acid (CHEBI:134617) has functional parent octadecanoic acid (CHEBI:28842) hydroxyoctadecanoic acid (CHEBI:24747) has functional parent octadecanoic acid (CHEBI:28842) monoacylglycerol 18:0 (CHEBI:87255) has functional parent octadecanoic acid (CHEBI:28842) octadecanamide (CHEBI:34900) has functional parent octadecanoic acid (CHEBI:28842) octadecanoate ester (CHEBI:75925) has functional parent octadecanoic acid (CHEBI:28842) stearonitrile (CHEBI:133638) has functional parent octadecanoic acid (CHEBI:28842) stearoyl-CoA (CHEBI:15541) has functional parent octadecanoic acid (CHEBI:28842) tristearoylglycerol (CHEBI:45956) has functional parent octadecanoic acid (CHEBI:28842) tuberculostearic acid (CHEBI:68565) has functional parent octadecanoic acid (CHEBI:28842) corn oil (CHEBI:195250) has part octadecanoic acid (CHEBI:28842) soybean oil (CHEBI:166975) has part octadecanoic acid (CHEBI:28842) octadecanoate (CHEBI:25629) is conjugate base of octadecanoic acid (CHEBI:28842)

IUPAC Name

octadecanoic acid

Synonyms	Sources
18:0	ChEBI
acide octadécanoïque	ChEBI
acide stéarique	ChEBI
C18:0	ChemIDplus
CH₃‒[CH₂]₁₆‒COOH	IUPAC
n-octadecanoic acid	NIST Chemistry WebBook
Octadecanoic acid	KEGG COMPOUND
Octadecansäure	ChemIDplus
octadecoic acid	ChEBI
Oktadekansäure	ChEBI
STEARIC ACID	PDBeChem
stearic acid	ChEBI
Stearinsäure	ChemIDplus

Manual Xrefs	Databases
4611	DrugCentral
C00001238	KNApSAcK
C01530	KEGG COMPOUND
D00119	KEGG DRUG
DB03193	DrugBank
HMDB0000827	HMDB
LMFA01010018	LIPID MAPS
STE	PDBeChem
Stearic_acid	Wikipedia
STEARIC_ACID	MetaCyc
View more database links

Registry Numbers	Types	Sources
11738	Gmelin Registry Number	Gmelin
57-11-4	CAS Registry Number	NIST Chemistry WebBook
57-11-4	CAS Registry Number	ChemIDplus
608585	Reaxys Registry Number	Reaxys

Citations

Wang ZJ, Li GM, Nie BM, Lu Y, Yin M (2006)
Neuroprotective effect of the stearic acid against oxidative stress via phosphatidylinositol 3-kinase pathway.
Chemico-biological interactions 160, 80-87 [PubMed:16448636]
[show Abstract]

Kim JY, Kinoshita M, Ohnishi M, Fukui Y (2001)
Lipid and fatty acid analysis of fresh and frozen-thawed immature and in vitro matured bovine oocytes.
Reproduction (Cambridge, England) 122, 131-138 [PubMed:11425337]
[show Abstract]
The lipid content and fatty acid composition of fresh immature and in vitro matured bovine oocytes cultured in media with or without serum, and also those of frozen-thawed immature oocytes were analysed. All oocytes were ranked (A or B) on the basis of their cytoplasmic quality. Fatty acid composition (mol %; w/w) in the total lipid fraction was analysed by gas chromatography. Triglyceride, total cholesterol, phospholipid (phosphocholine-containing phospholipid) and non-esterified fatty acid contents of immature and in vitro matured oocytes were determined using lipid analysis kits. Phosphocholine-containing phospholipid and non-esterified fatty acid contents were determined in frozen-thawed immature bovine oocytes. Palmitic acid was the most abundant fatty acid in immature oocytes (A: 35%, B: 36%), and in in vitro matured oocytes cultured in the medium containing serum (A: 36%, B: 35%) or polyvinyl alcohol (A: 33%, B: 36%). Oleic acid was the second most abundant fatty acid in all A ranked oocytes, whereas stearic acid was the second most abundant fatty acid in all B ranked oocytes. There were significant differences (P < 0.05) in linoleic and arachidonic acid fractions between A and B ranked immature oocytes. In vitro matured oocytes had significantly (P < 0.05) lower proportions of linoleic and arachidonic acids, and significantly (P < 0.01) lower contents of triglyceride and total cholesterol compared with those of immature oocytes. The fatty acid composition of in vitro matured oocytes cultured in medium containing fetal calf serum or polyvinyl alcohol was similar, but significant differences (P < 0.01) in triglyceride and the total cholesterol content were observed. There was a significant decrease (P < 0.05) in the arachidonic acid proportion in frozen-thawed immature oocytes compared with that in fresh immature oocytes. In addition, significant (P < 0.05) decreases in both phospholipid (15.8--10.6 pmol) and non-esterified fatty acid (11.0--4.1 pmol) were found in frozen--thawed immature oocytes. The results indicate that lipids are available for use as an energy source for maturation and that serum lipids are incorporated into the oocyte cytoplasm during in vitro maturation. The changes in the lipid content (mainly phospholipid) and fatty acid composition were also observed in frozen--thawed immature oocytes. The study indicates that the alteration of fatty acid composition in bovine oocytes might improve maturation and cryopreservation.

Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG (2007)
Growth control of the eukaryote cell: a systems biology study in yeast.
Journal of biology 6, 4 [PubMed:17439666]
[show Abstract]

Background

Cell growth underlies many key cellular and developmental processes, yet a limited number of studies have been carried out on cell-growth regulation. Comprehensive studies at the transcriptional, proteomic and metabolic levels under defined controlled conditions are currently lacking.

Results

Metabolic control analysis is being exploited in a systems biology study of the eukaryotic cell. Using chemostat culture, we have measured the impact of changes in flux (growth rate) on the transcriptome, proteome, endometabolome and exometabolome of the yeast Saccharomyces cerevisiae. Each functional genomic level shows clear growth-rate-associated trends and discriminates between carbon-sufficient and carbon-limited conditions. Genes consistently and significantly upregulated with increasing growth rate are frequently essential and encode evolutionarily conserved proteins of known function that participate in many protein-protein interactions. In contrast, more unknown, and fewer essential, genes are downregulated with increasing growth rate; their protein products rarely interact with one another. A large proportion of yeast genes under positive growth-rate control share orthologs with other eukaryotes, including humans. Significantly, transcription of genes encoding components of the TOR complex (a major controller of eukaryotic cell growth) is not subject to growth-rate regulation. Moreover, integrative studies reveal the extent and importance of post-transcriptional control, patterns of control of metabolic fluxes at the level of enzyme synthesis, and the relevance of specific enzymatic reactions in the control of metabolic fluxes during cell growth.

Conclusion

This work constitutes a first comprehensive systems biology study on growth-rate control in the eukaryotic cell. The results have direct implications for advanced studies on cell growth, in vivo regulation of metabolic fluxes for comprehensive metabolic engineering, and for the design of genome-scale systems biology models of the eukaryotic cell.

Last Modified

31 May 2023

CHEBI:28842 - octadecanoic acid

Background

Results

Conclusion

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