oleic acid (CHEBI:16196)

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CHEBI:16196 - oleic acid

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ChEBI Name	oleic acid

ChEBI ID	CHEBI:16196

Definition	An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.

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

Secondary ChEBI IDs	CHEBI:44741, CHEBI:104361, CHEBI:7741, CHEBI:25664

Supplier Information	eMolecules:979405

Download	Molfile XML SDF

more structures >>

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7.3204 3.3281 0.7314 C 0 0 0 0 0 0 0 0 0 0 0 0

6.3459 2.8131 -0.2075 C 0 0 0 0 0 0 0 0 0 0 0 0

7.1847 4.4223 1.2584 O 0 0 0 0 0 0 0 0 0 0 0 0

5.6303 1.5368 0.3043 C 0 0 0 0 0 0 0 0 0 0 0 0

4.6110 0.9559 -0.7052 C 0 0 0 0 0 0 0 0 0 0 0 0

3.9110 -0.3295 -0.1982 C 0 0 0 0 0 0 0 0 0 0 0 0

2.9257 -0.9212 -1.2342 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2107 -2.2093 -0.7568 C 0 0 0 0 0 0 0 0 0 0 0 0

1.3228 -2.8467 -1.8562 C 0 0 0 0 0 0 0 0 0 0 0 0

8.3177 2.6827 1.0327 O 0 0 0 0 0 0 0 0 0 0 0 0

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6.3747 0.7653 0.5232 H 0 0 0 0 0 0 0 0 0 0 0 0

3.8515 1.7128 -0.9219 H 0 0 0 0 0 0 0 0 0 0 0 0

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1.9621 -3.2818 -2.6288 H 0 0 0 0 0 0 0 0 0 0 0 0

8.4609 1.8877 0.6811 H 0 0 0 0 0 0 0 0 0 0 0 0

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M END): 22 ms

reading 54 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

54 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Molfile

Wikipedia	License
Indole-3-carbinol (I3C, C9H9N O) is produced by the breakdown of the glucosinolate glucobrassicin, which can be found at relatively high levels in cruciferous vegetables such as broccoli, cabbage, cauliflower, brussels sprouts, collard greens and kale. It is also available in dietary supplements. Indole-3-carbinol is the subject of on-going biomedical research into its possible anticarcinogenic, antioxidant, and anti-atherogenic effects. Research on indole-3-carbinol has been conducted primarily using laboratory animals and cultured cells. Limited and inconclusive human studies have been reported. A recent review of the biomedical research literature found that "evidence of an inverse association between cruciferous vegetable intake and breast or prostate cancer in humans is limited and inconsistent" and "larger randomized controlled trials are needed" to determine if supplemental indole-3-carbinol has health benefits.
Read full article at Wikipedia

Formula

C18H34O2

Net Charge

Average Mass

282.46140

Monoisotopic Mass

282.25588

InChI

InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-

InChIKey

ZQPPMHVWECSIRJ-KTKRTIGZSA-N

SMILES

CCCCCCCC\C=C/CCCCCCCC(O)=O

Metabolite of Species	Details
Neolitsea daibuensis (IPNI:466954-1)	Found in root (BTO:0001188). Cold MeOH extract of dried roots See: PubMed
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
Centella asiatica (NCBI:txid48106)	See: MetaboLights Study
Escherichia coli (NCBI:txid562)	See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Chemical Role(s):	solvent A liquid that can dissolve other substances (solutes) without any change in their chemical composition. antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. (via octadec-9-enoic acid ) 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). Daphnia galeata metabolite A Daphnia metabolite produced by the species Daphnia galeata.

Application(s):	solvent A liquid that can dissolve other substances (solutes) without any change in their chemical composition.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	oleic acid (CHEBI:16196) has parent hydride cis-octadec-9-ene (CHEBI:37604) oleic acid (CHEBI:16196) has role Daphnia galeata metabolite (CHEBI:83038) oleic acid (CHEBI:16196) has role Escherichia coli metabolite (CHEBI:76971) oleic acid (CHEBI:16196) has role antioxidant (CHEBI:22586) oleic acid (CHEBI:16196) has role EC 3.1.1.1 (carboxylesterase) inhibitor (CHEBI:78444) oleic acid (CHEBI:16196) has role mouse metabolite (CHEBI:75771) oleic acid (CHEBI:16196) has role plant metabolite (CHEBI:76924) oleic acid (CHEBI:16196) has role solvent (CHEBI:46787) oleic acid (CHEBI:16196) is a octadec-9-enoic acid (CHEBI:36021) oleic acid (CHEBI:16196) is conjugate acid of oleate (CHEBI:30823)

Incoming	β-D-glucosyl-N-(oleoyl)sphingosine (CHEBI:139140) has functional parent oleic acid (CHEBI:16196) (2S)-1-oleoyl-2-methylglycero-3-phosphothionate (CHEBI:139223) has functional parent oleic acid (CHEBI:16196) (9Z)-12-(phosphonooxy)octadecenoic acid (CHEBI:85140) has functional parent oleic acid (CHEBI:16196) (9Z)-12-hydroxyoctadec-9-enoic acid (CHEBI:85639) has functional parent oleic acid (CHEBI:16196) (9Z)-17-hydroxyoctadec-9-enoic acid (CHEBI:144923) has functional parent oleic acid (CHEBI:16196) (9Z,12R)-12,18-dihydroxyoctadecenoic acid (CHEBI:129091) has functional parent oleic acid (CHEBI:16196) (R)-oleoylcarnitine (CHEBI:84651) has functional parent oleic acid (CHEBI:16196) (R,R)-2-oleoylglycero-1-phospho-1'-glycerol (CHEBI:139585) has functional parent oleic acid (CHEBI:16196) (R,R)-bis(2-oleoylglycero)-3-phosphate (CHEBI:139583) has functional parent oleic acid (CHEBI:16196) (S,S)-2-oleoylglycero-1-phospho-1'-glycerol (CHEBI:139543) has functional parent oleic acid (CHEBI:16196) (S,S)-3-oleoylglycero-1-phospho-1'-glycerol (CHEBI:139540) has functional parent oleic acid (CHEBI:16196) (S,S)-bis(2-oleoylglycero)-1-phosphate (CHEBI:139541) has functional parent oleic acid (CHEBI:16196) (S,S)-bis-(3-oleoylglycero)-1-phosphate (CHEBI:139539) has functional parent oleic acid (CHEBI:16196) 1,1ʼ,2-trilinoleoyl-2ʼ-oleoyl cardiolipin (CHEBI:84399) has functional parent oleic acid (CHEBI:16196) 1,1'-dilinoleoyl-2-oleoyl monolysocardiolipin (CHEBI:84583) has functional parent oleic acid (CHEBI:16196) 1,1'-dioleyl 2,2'-dilysocardiolipin (CHEBI:77560) has functional parent oleic acid (CHEBI:16196) 1,2-di-[(9Z)-octadecenoyl]-sn-glycero-3-phosphoethanolamine (CHEBI:84839) has functional parent oleic acid (CHEBI:16196) 1,2-dioleoyl-3-lauroyl-sn-glycerol (CHEBI:77685) has functional parent oleic acid (CHEBI:16196) 1,2-dioleoyl-3-linoleoyl-sn-glycerol (CHEBI:77683) has functional parent oleic acid (CHEBI:16196) 1,2-dioleoyl-3-myristoyl-sn-glycerol (CHEBI:77684) has functional parent oleic acid (CHEBI:16196) 1,2-dioleoyl-3-palmitoylglycerol (CHEBI:75848) has functional parent oleic acid (CHEBI:16196) 1,2-dioleoyl-3-stearoyl-sn-glycerol (CHEBI:77686) has functional parent oleic acid (CHEBI:16196) 1,2-dioleoyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol) (CHEBI:75385) has functional parent oleic acid (CHEBI:16196) 1,2-dioleoyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol-3ʼ-phosphate) (CHEBI:82848) has functional parent oleic acid (CHEBI:16196) 1,2-dioleoyl-sn-glycero-3-phospho-1ʼ-(3ʼ-oleoyl)-sn-glycerol (CHEBI:139551) has functional parent oleic acid (CHEBI:16196) 1,2-dioleoyl-sn-glycero-3-phospho-N,N-dimethylethanolamine (CHEBI:85963) has functional parent oleic acid (CHEBI:16196) 1,2-dioleoyl-sn-glycero-3-phospho-N-methylethanolamine (CHEBI:85962) has functional parent oleic acid (CHEBI:16196) 1,2-dioleoyl-sn-glycero-3-phospho-L-serine (CHEBI:60568) has functional parent oleic acid (CHEBI:16196) 1,2-dioleoyl-sn-glycero-3-phosphocholine (CHEBI:74669) has functional parent oleic acid (CHEBI:16196) 1,3-dioleoyl-2-palmitoylglycerol (CHEBI:75846) has functional parent oleic acid (CHEBI:16196) 1,3-dioleoylglycerol (CHEBI:75735) has functional parent oleic acid (CHEBI:16196) 1,3-dipalmitoyl-2-oleoylglycerol (CHEBI:75688) has functional parent oleic acid (CHEBI:16196) 1-α-linolenoyl-2-oleoylglycerol (CHEBI:75609) has functional parent oleic acid (CHEBI:16196) 1-(1Z-hexadecenyl)-2-oleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:84533) has functional parent oleic acid (CHEBI:16196) 1-(1Z-octadecenyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine (CHEBI:79203) has functional parent oleic acid (CHEBI:16196) 1-(1Z-octadecenyl)-2-oleoyl-sn-glycero-3-phosphoserine (CHEBI:79206) has functional parent oleic acid (CHEBI:16196) 1-(1Z-octadecenyl)-sn-glycero-3-phospho-(N-oleoyl)ethanolamine (CHEBI:138095) has functional parent oleic acid (CHEBI:16196) 1-(9Z)-octadecenoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphate (CHEBI:75074) has functional parent oleic acid (CHEBI:16196) 1-(alk-1-enyl)-2-oleoyl-sn-glycero-3-phosphocholine (CHEBI:75148) has functional parent oleic acid (CHEBI:16196) 1-O-hexadecyl-2-oleoyl-sn-glycero-3-phosphocholine (CHEBI:34112) has functional parent oleic acid (CHEBI:16196) 1-O-oleoyl-N-acetylsphingosine (CHEBI:76054) has functional parent oleic acid (CHEBI:16196) 1-O-palmityl-3-oleoylglycerol (CHEBI:76062) has functional parent oleic acid (CHEBI:16196) 1-[(1Z)-octadecenyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86241) has functional parent oleic acid (CHEBI:16196) 1-[(1Z)-octadecenyl]-2-oleoyl-sn-glycero-3-phosphate (CHEBI:140595) has functional parent oleic acid (CHEBI:16196) 1-[(1Z,11Z)-octadecadienyl]-2-oleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85020) has functional parent oleic acid (CHEBI:16196) 1-[(2Z)-hexadecenoyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:84809) has functional parent oleic acid (CHEBI:16196) 1-[(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86183) has functional parent oleic acid (CHEBI:16196) 1-[(6Z,9Z,12Z)-octadecatrienoyl]-2-[(9Z)-octadecenoyl]-snglycero-3-phosphocholine (CHEBI:86123) has functional parent oleic acid (CHEBI:16196) 1-[(9Z)-hexadecenoyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:84811) has functional parent oleic acid (CHEBI:16196) 1-[(9Z)-octadecenoyl]-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-sn-glycero-3-phosphocholine (CHEBI:84814) has functional parent oleic acid (CHEBI:16196) 1-[(9Z)-octadecenoyl]-2-[(5Z,8Z,11Z)-eicosatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:86178) has functional parent oleic acid (CHEBI:16196) 1-[(9Z)-octadecenoyl]-2-[(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl]-sn-glycero-3-phosphocholine (CHEBI:86187) has functional parent oleic acid (CHEBI:16196) 1-[(9Z)-octadecenoyl]-2-[(6Z,9Z)-octadecadienoyl]-sn-glycero-3-phosphocholine (CHEBI:84831) has functional parent oleic acid (CHEBI:16196) 1-[(9Z)-octadecenoyl]-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:86130) has functional parent oleic acid (CHEBI:16196) 1-[(9Z)-octadecenoyl]-2-[(7Z,10Z,13Z,16Z)-docosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:86201) has functional parent oleic acid (CHEBI:16196) 1-[(9Z)-octadecenoyl]-2-[(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl]-sn-glycero-3-phosphocholine (CHEBI:86205) has functional parent oleic acid (CHEBI:16196) 1-[(9Z)-octadecenoyl]-2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86100) has functional parent oleic acid (CHEBI:16196) 1-[(9Z)-octadecenoyl]-2-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:86133) has functional parent oleic acid (CHEBI:16196) 1-[(9Z)-octadecenoyl]-2-docosanoyl-sn-glycero-3-phosphocholine (CHEBI:86190) has functional parent oleic acid (CHEBI:16196) 1-[(9Z)-octadecenoyl]-2-eicosanoyl-sn-glycero-3-phosphocholine (CHEBI:86172) has functional parent oleic acid (CHEBI:16196) 1-[(9Z)-octadecenoyl]-2-tetracosanoyl-sn-glycero-3-phosphocholine (CHEBI:86217) has functional parent oleic acid (CHEBI:16196) 1-[(9Z)-octadecenoyl]-2-tetradecanoyl-sn-glycero-3-phosphocholine (CHEBI:86092) has functional parent oleic acid (CHEBI:16196) 1-[(9Z,12Z,15Z)-octadecatrienoyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86127) has functional parent oleic acid (CHEBI:16196) 1-acyl-2-oleoyl-sn-glycero-3-phosphate (CHEBI:75109) has functional parent oleic acid (CHEBI:16196) 1-arachidonoyl-2-oleoyl-sn-glycero-3-phosphate (CHEBI:75141) has functional parent oleic acid (CHEBI:16196) 1-arachidonoyl-2-oleoylglycerol (CHEBI:75611) has functional parent oleic acid (CHEBI:16196) 1-butyryl-2-oleoyl-sn-glycerol (CHEBI:75443) has functional parent oleic acid (CHEBI:16196) 1-capryl-2-oleoyl-sn-glycerol (CHEBI:75505) has functional parent oleic acid (CHEBI:16196) 1-decanoyl-2-oleoyl-sn-glycero-3-phosphocholine (CHEBI:86410) has functional parent oleic acid (CHEBI:16196) 1-decanoyl-2-oleoylglycerol (CHEBI:85787) has functional parent oleic acid (CHEBI:16196) 1-eicosanoyl-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86171) has functional parent oleic acid (CHEBI:16196) 1-heptadecanoyl-2-oleoyl-sn-glycero-3-phosphate (CHEBI:74841) has functional parent oleic acid (CHEBI:16196) 1-heptadecanoyl-2-oleoyl-sn-glycero-3-phosphocholine (CHEBI:133624) has functional parent oleic acid (CHEBI:16196) 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine (CHEBI:73124) has functional parent oleic acid (CHEBI:16196) 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine (CHEBI:73001) has functional parent oleic acid (CHEBI:16196) 1-icosanoyl-2-oleoyl-sn-glycero-3-phosphate (CHEBI:74942) has functional parent oleic acid (CHEBI:16196) 1-icosanoyl-2-oleoyl-sn-glycerol (CHEBI:75470) has functional parent oleic acid (CHEBI:16196) 1-lauroyl-2-oleoylglycerol (CHEBI:75579) has functional parent oleic acid (CHEBI:16196) 1-linolenoyl-2-oleoyl-sn-glycero-3-phosphate (CHEBI:74833) has functional parent oleic acid (CHEBI:16196) 1-linoleoyl-2-oleoyl-sn-glycero-3-phosphate (CHEBI:74830) has functional parent oleic acid (CHEBI:16196) 1-linoleoyl-2-oleoylglycerol (CHEBI:75614) has functional parent oleic acid (CHEBI:16196) 1-myristoyl-2-oleoyl-sn-glycero-3-phosphate (CHEBI:74943) has functional parent oleic acid (CHEBI:16196) 1-myristoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85237) has functional parent oleic acid (CHEBI:16196) 1-myristoyl-2-oleoylglycerol (CHEBI:75582) has functional parent oleic acid (CHEBI:16196) 1-octanoyl-2-oleoyl-sn-glycerol (CHEBI:75462) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2,3-di-linoleoyl-sn-glycerol (CHEBI:84458) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-(α-linolenoyl)-sn-glycerol (CHEBI:75475) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-(11Z)-octadecenoyl-sn-glycero-3-phosphate (CHEBI:75357) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerol (CHEBI:84439) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-(6Z)-octadecenoyl-sn-glycero-3-phosphate (CHEBI:75363) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycerol (CHEBI:84438) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycerol (CHEBI:84437) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-O-arachidonyl-sn-glycerol (CHEBI:75914) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-sn-glycero-3-phosphate (CHEBI:139413) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-[(8Z,11Z,14Z)-icosatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:89618) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-acyl-sn-glycero-3-phosphocholine (CHEBI:78421) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-acyl-sn-glycero-3-phosphoserine(1−) (CHEBI:78422) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-arachidonoyl-sn-glycero-3-phosphate (CHEBI:75118) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:82762) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-arachidonoyl-sn-glycero-3-phospho-L-serine (CHEBI:75099) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:74671) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-arachidonoyl-sn-glycerol (CHEBI:75449) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-arachidonoyl-sn-glycerol-3-phosphoethanolamine (CHEBI:75169) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-decanoyl-sn-glycerol (CHEBI:75444) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-gondoyl-sn-glycerol (CHEBI:84436) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-heptadecanoyl-sn-glycero-3-phosphate (CHEBI:74845) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol-3ʼ-phosphate) (CHEBI:136816) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-icosanoyl-sn-glycero-3-phosphate (CHEBI:75134) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-lauroyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol) (CHEBI:77121) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-lauroyl-sn-glycerol (CHEBI:75445) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-linolenoyl-PAP (CHEBI:53754) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-linoleoyl-sn-glycero-3-phosphate (CHEBI:74849) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-linoleoyl-sn-glycero-3-phospho-L-serine (CHEBI:75096) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-linoleoyl-sn-glycero-3-phosphocholine (CHEBI:74670) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-linoleoyl-sn-glycerol (CHEBI:75450) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-linoleyl-sn-glycero-3-phosphoethanolamine (CHEBI:84543) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-myristoyl-sn-glycero-3-phosphate (CHEBI:74930) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-myristoyl-sn-glycero-3-phosphoethanolamine (CHEBI:82840) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-myristoyl-sn-glycerol (CHEBI:75446) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-palmitoleoyl-sn-glycero-3-phospho-L-serine (CHEBI:75101) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-palmitoleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:82837) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-palmitoyl-sn-glycero-3-phosphate (CHEBI:74836) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-palmitoyl-sn-glycero-3-phospho-L-serine (CHEBI:75106) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-palmitoyl-sn-glycero-3-phosphocholine (CHEBI:74667) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-palmitoyl-sn-glycero-3-phosphoethanolamine (CHEBI:82839) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-palmitoylglycerol (CHEBI:76065) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-pentadecanoyl-sn-glycero-3-phosphate (CHEBI:74852) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-stearoyl-sn-glycero-3-phosphate (CHEBI:74839) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-stearoyl-sn-glycero-3-phospho-L-serine (CHEBI:75103) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-stearoyl-sn-glycero-3-phosphocholine (CHEBI:76073) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-stearoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85076) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-stearoyl-sn-glycerol (CHEBI:75448) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-2-{6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl}-sn-glycero-3-phospho-L-serine (CHEBI:88338) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-3-linoleoylglycerol (CHEBI:133484) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-3-palmitoylglycerol (CHEBI:75869) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-sn-glycero-3-phospho-D-myo-inositol (CHEBI:82753) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:75168) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-sn-glycero-3-phosphoglycerol (CHEBI:85410) has functional parent oleic acid (CHEBI:16196) 1-oleoyl-sn-glycerol (CHEBI:75757) has functional parent oleic acid (CHEBI:16196) 1-oleoylglycerol (CHEBI:75342) has functional parent oleic acid (CHEBI:16196) 1-oleyl-2-linoleyl-PAP (CHEBI:53752) has functional parent oleic acid (CHEBI:16196) 1-palmitoyl-2-oleoyl-3-stearoyl-sn-glycerol (CHEBI:77623) has functional parent oleic acid (CHEBI:16196) 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoglycerol (CHEBI:34080) has functional parent oleic acid (CHEBI:16196) 1-palmitoyl-2-oleoylglycerol (CHEBI:75585) has functional parent oleic acid (CHEBI:16196) 1-palmityl-2-acetyl-3-oleoyl-sn-glycerol (CHEBI:76055) has functional parent oleic acid (CHEBI:16196) 1-palmityl-2-methyl-3-oleoyl-sn-glycerol (CHEBI:76064) has functional parent oleic acid (CHEBI:16196) 1-palmityl-2-oleoyl-sn-glycero-3-phosphate (CHEBI:77357) has functional parent oleic acid (CHEBI:16196) 1-palmityl-2-oleoyl-sn-glycerol (CHEBI:77185) has functional parent oleic acid (CHEBI:16196) 1-pentadecanoyl-2-oleoyl-sn-glycero-3-phosphocholine (CHEBI:133623) has functional parent oleic acid (CHEBI:16196) 1-stearoyl-2-arachidonoyl-3-oleoyl-sn-glycerol (CHEBI:75729) has functional parent oleic acid (CHEBI:16196) 1-stearoyl-2-oleoyl-sn-glycero-3-phosphate (CHEBI:74847) has functional parent oleic acid (CHEBI:16196) 1-stearoyl-2-oleoyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:77346) has functional parent oleic acid (CHEBI:16196) 1-stearoyl-2-oleoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-biphosphate (CHEBI:77279) has functional parent oleic acid (CHEBI:16196) 1-stearoyl-2-oleoyl-sn-glycero-3-phospho-1D-myo-inositol 4-phosphate (CHEBI:77277) has functional parent oleic acid (CHEBI:16196) 1-stearoyl-2-oleoyl-sn-glycero-3-phospho-1D-myo-inositol 5-phosphate (CHEBI:77347) has functional parent oleic acid (CHEBI:16196) 1-stearoyl-2-oleoyl-sn-glycero-3-phosphoserine (CHEBI:79096) has functional parent oleic acid (CHEBI:16196) 1-stearoyl-2-oleoylglycerol (CHEBI:75590) has functional parent oleic acid (CHEBI:16196) 1-tetracosanoyl-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86213) has functional parent oleic acid (CHEBI:16196) 1-tetradecanoyl-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:84808) has functional parent oleic acid (CHEBI:16196) 1-tetradecyl-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86424) has functional parent oleic acid (CHEBI:16196) 10-hydroperoxy-8E-octadecenoic acid (CHEBI:85589) has functional parent oleic acid (CHEBI:16196) 12-[(9Z)-octadecenoyloxy]octadecanoic acid (CHEBI:137082) has functional parent oleic acid (CHEBI:16196) 13-[(9Z)-octadecenoyloxy]octadecanoic acid (CHEBI:137083) has functional parent oleic acid (CHEBI:16196) 18-hydroxyoleic acid (CHEBI:79312) has functional parent oleic acid (CHEBI:16196) 18-hydroxyoleoyl-CoA (CHEBI:86053) has functional parent oleic acid (CHEBI:16196) 18-oxooleic acid (CHEBI:133357) has functional parent oleic acid (CHEBI:16196) 2,3-dioleoyl-sn-glycerol (CHEBI:75824) has functional parent oleic acid (CHEBI:16196) 2-hydroxyoleic acid (CHEBI:143096) has functional parent oleic acid (CHEBI:16196) 2-oleoyl-sn-glycero-3-phosphate (CHEBI:78270) has functional parent oleic acid (CHEBI:16196) 2-oleoyl-sn-glycero-3-phosphocholine (CHEBI:76071) has functional parent oleic acid (CHEBI:16196) 2-oleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:76231) has functional parent oleic acid (CHEBI:16196) 2-oleoyl-sn-glycero-3-phosphoethanolamine zwitterion (CHEBI:76088) has functional parent oleic acid (CHEBI:16196) 2-oleoyl-sn-glycero-3-phosphoserine (CHEBI:77646) has functional parent oleic acid (CHEBI:16196) 2-oleoylglycerol (CHEBI:73990) has functional parent oleic acid (CHEBI:16196) 2-palmitoyl-3-oleoyl-sn-glycerol (CHEBI:75870) has functional parent oleic acid (CHEBI:16196) 3-oleoyl-sn-glycerol (CHEBI:75938) has functional parent oleic acid (CHEBI:16196) 3-oxooleoyl-CoA (CHEBI:88007) has functional parent oleic acid (CHEBI:16196) 5-[(9Z)-octadecenoyloxy]octadecanoic acid (CHEBI:137106) has functional parent oleic acid (CHEBI:16196) 9-[(9Z)-octadecenoyloxy]octadecanoic acid (CHEBI:136996) has functional parent oleic acid (CHEBI:16196) 9-hydroperoxy-10E-octadecenoic acid (CHEBI:85587) has functional parent oleic acid (CHEBI:16196) all-trans-retinyl oleate (CHEBI:70760) has functional parent oleic acid (CHEBI:16196) N,1,2-trioleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85790) has functional parent oleic acid (CHEBI:16196) N,1-dioleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85664) has functional parent oleic acid (CHEBI:16196) N,O-dioleoylethanolamine (CHEBI:76068) has functional parent oleic acid (CHEBI:16196) N-(9Z-octadecenoyl)-(2S)-hydroxyglycine (CHEBI:142737) has functional parent oleic acid (CHEBI:16196) N-[(9Z)-octadecenoyl]sphinganine (CHEBI:74100) has functional parent oleic acid (CHEBI:16196) N-arachidonoyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85784) has functional parent oleic acid (CHEBI:16196) N-arachidonoyl-1-oleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85666) has functional parent oleic acid (CHEBI:16196) n-butyl oleate (CHEBI:82946) has functional parent oleic acid (CHEBI:16196) N-icosanoyl-1-oleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85667) has functional parent oleic acid (CHEBI:16196) N-lauroyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85794) has functional parent oleic acid (CHEBI:16196) N-myristoyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85793) has functional parent oleic acid (CHEBI:16196) N-oleoyl-(4E,14Z)-sphingadienine-1-phosphocholine (CHEBI:105799) has functional parent oleic acid (CHEBI:16196) N-oleoyl-1,2-diacyl-sn-glycero-3-phosphoethanolamine (CHEBI:138239) has functional parent oleic acid (CHEBI:16196) N-oleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85670) has functional parent oleic acid (CHEBI:16196) N-oleoyl-L-glutamic acid (CHEBI:136713) has functional parent oleic acid (CHEBI:16196) N-oleoyl-L-glutamine (CHEBI:136615) has functional parent oleic acid (CHEBI:16196) N-oleoyl-L-isoleucine (CHEBI:136711) has functional parent oleic acid (CHEBI:16196) N-oleoyl-L-leucine (CHEBI:136616) has functional parent oleic acid (CHEBI:16196) N-oleoyl-L-phenylalanine (CHEBI:134021) has functional parent oleic acid (CHEBI:16196) N-oleoyl-L-serine (CHEBI:136614) has functional parent oleic acid (CHEBI:16196) N-oleoyldopamine (CHEBI:31883) has functional parent oleic acid (CHEBI:16196) N-oleoylethanolamine phosphate (CHEBI:145794) has functional parent oleic acid (CHEBI:16196) N-oleoylglycine (CHEBI:73723) has functional parent oleic acid (CHEBI:16196) N-oleoylphytosphingosine (CHEBI:85204) has functional parent oleic acid (CHEBI:16196) N-oleoylserotonin (CHEBI:134064) has functional parent oleic acid (CHEBI:16196) N-oleoylsphinganine-1-phosphocholine (CHEBI:134074) has functional parent oleic acid (CHEBI:16196) N-oleoylsphingosine (CHEBI:77996) has functional parent oleic acid (CHEBI:16196) N-oleoylsphingosine 1-phosphate (CHEBI:85882) has functional parent oleic acid (CHEBI:16196) N-oleoylsphingosine-1-phosphocholine (CHEBI:84487) has functional parent oleic acid (CHEBI:16196) N-oleoyltaurine (CHEBI:146206) has functional parent oleic acid (CHEBI:16196) N-oleoylthreonine (CHEBI:131695) has functional parent oleic acid (CHEBI:16196) N-palmitoyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:78940) has functional parent oleic acid (CHEBI:16196) N-palmitoyl-1-oleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85654) has functional parent oleic acid (CHEBI:16196) N-stearoyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85791) has functional parent oleic acid (CHEBI:16196) N-stearoyl-1-oleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85660) has functional parent oleic acid (CHEBI:16196) O-oleoylanandamide (CHEBI:76070) has functional parent oleic acid (CHEBI:16196) arachidyl oleate (CHEBI:75628) has functional parent oleic acid (CHEBI:16196) CDP-1,2-dioleoyl-sn-glycerol (CHEBI:85856) has functional parent oleic acid (CHEBI:16196) CDP-1-stearoyl-2-oleoyl-sn-glycerol (CHEBI:85841) has functional parent oleic acid (CHEBI:16196) cholesteryl oleate (CHEBI:46898) has functional parent oleic acid (CHEBI:16196) decyl oleate (CHEBI:75620) has functional parent oleic acid (CHEBI:16196) egonol oleate (CHEBI:69548) has functional parent oleic acid (CHEBI:16196) ethyl oleate (CHEBI:84940) has functional parent oleic acid (CHEBI:16196) methyl oleate (CHEBI:27542) has functional parent oleic acid (CHEBI:16196) monooleoylglycerol (CHEBI:75937) has functional parent oleic acid (CHEBI:16196) oleonitrile (CHEBI:133637) has functional parent oleic acid (CHEBI:16196) oleoyl danshenxinkun A (CHEBI:66819) has functional parent oleic acid (CHEBI:16196) oleoyl ethanolamide (CHEBI:71466) has functional parent oleic acid (CHEBI:16196) oleoyl neocryptotanshinone (CHEBI:66820) has functional parent oleic acid (CHEBI:16196) oleoyl-containing glycerolipid (CHEBI:88240) has functional parent oleic acid (CHEBI:16196) oleoylcholine (CHEBI:133693) has functional parent oleic acid (CHEBI:16196) oleyl oleate (CHEBI:75626) has functional parent oleic acid (CHEBI:16196) oleylanilide (CHEBI:53721) has functional parent oleic acid (CHEBI:16196) palmitoleyl oleate (CHEBI:75624) has functional parent oleic acid (CHEBI:16196) palmityl oleate (CHEBI:75622) has functional parent oleic acid (CHEBI:16196) stearyl oleate (CHEBI:75625) has functional parent oleic acid (CHEBI:16196) triolein (CHEBI:53753) has functional parent oleic acid (CHEBI:16196) trioleoyl 2-monolysocardiolipin (CHEBI:77561) has functional parent oleic acid (CHEBI:16196) corn oil (CHEBI:195250) has part oleic acid (CHEBI:16196) soybean oil (CHEBI:166975) has part oleic acid (CHEBI:16196) 1-(γ-linolenoyl)-2-oleoyl-sn-glycero-3-phosphate (CHEBI:74936) is a oleic acid (CHEBI:16196) oleate (CHEBI:30823) is conjugate base of oleic acid (CHEBI:16196) oleoyl group (CHEBI:25667) is substituent group from oleic acid (CHEBI:16196)

IUPAC Name

(9Z)-octadec-9-enoic acid

Synonyms	Sources
(9Z)-Octadecenoic acid	KEGG COMPOUND
(Z)-Octadec-9-enoic acid	KEGG COMPOUND
18:1 n-9	ChEBI
18:1Δ9cis	ChEBI
C18:1 n-9	ChEBI
cis-9-octadecenoic acid	NIST Chemistry WebBook
cis-Δ⁹-octadecenoic acid	ChemIDplus
cis-oleic acid	ChEBI
FA 18:1	ChEBI
Octadec-9-enoic acid	ChEMBL
Oelsäure	ChEBI
Oleate	KEGG COMPOUND
Oleic acid	KEGG COMPOUND
OLEIC ACID	PDBeChem
Ölsäure	ChEBI

Manual Xrefs	Databases
3400	DrugCentral
C00001232	KNApSAcK
C00712	KEGG COMPOUND
D02315	KEGG DRUG
DB04224	DrugBank
ECMDB21348	ECMDB
HMDB0000207	HMDB
LMFA01030002	LIPID MAPS
OLA	PDBeChem
Oleic_acid	Wikipedia
View more database links

Registry Numbers	Types	Sources
109551	Gmelin Registry Number	Gmelin
112-80-1	CAS Registry Number	KEGG COMPOUND
112-80-1	CAS Registry Number	NIST Chemistry WebBook
112-80-1	CAS Registry Number	ChemIDplus
1726542	Reaxys Registry Number	Reaxys
57556	Gmelin Registry Number	Gmelin

Citations	Types	Sources
11304127	PubMed citation	Europe PMC
15325315	PubMed citation	Europe PMC
15723125	PubMed citation	Europe PMC
18772370	PubMed citation	Europe PMC
19761868	PubMed citation	Europe PMC
23844805	PubMed citation	Europe PMC
24819471	PubMed citation	Europe PMC
25584012	PubMed citation	Europe PMC
25794012	PubMed citation	Europe PMC
5332408	PubMed citation	Europe PMC
6205897	PubMed citation	Europe PMC

Last Modified

31 May 2023

General Comment
2011-01-15	Found in various animal and vegetable sources, it is reported to exert hypotensive effects.

CHEBI:16196 - oleic acid

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