CHEBI:50464 - cis-vaccenic acid

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ChEBI Name cis-vaccenic acid
ChEBI ID CHEBI:50464
ChEBI ASCII Name cis-vaccenic acid
Definition The cis isomer of vaccenic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:46425, CHEBI:30826
Supplier Information
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Formula C18H34O2
Net Charge 0
Average Mass 282.46136
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/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7-
InChIKey UWHZIFQPPBDJPM-FPLPWBNLSA-N
SMILES CCCCCC\C=C/CCCCCCCCCC(O)=O
Metabolite of Species Details
Daphnia galeata (NCBI:txid27404) See: DOI
Homo sapiens (NCBI:txid9606) Found in blood (UBERON:0000178). See: PubMed
Homo sapiens (NCBI:txid9606) Found in saliva (UBERON:0001836). See: DOI
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cis-vaccenic acid (CHEBI:50464) is a vaccenic acid (CHEBI:36023)
cis-vaccenic acid (CHEBI:50464) is conjugate acid of cis-vaccenate(1−) (CHEBI:30827)
Incoming (11Z)-octadecenoyl-CoA (CHEBI:75354) has functional parent cis-vaccenic acid (CHEBI:50464)
(11Z-octadecenoyl)-cholesterol (CHEBI:88768) has functional parent cis-vaccenic acid (CHEBI:50464)
1,2-di-[(11Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86114) has functional parent cis-vaccenic acid (CHEBI:50464)
1,2-di-[(11Z)-octadecenoyl]glycerol (CHEBI:131832) has functional parent cis-vaccenic acid (CHEBI:50464)
1-(11Z-octadecenoyl)-2-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-sn-glycero-3-phosphocholine (CHEBI:73868) has functional parent cis-vaccenic acid (CHEBI:50464)
1-[(11Z)-octadecenoyl]-2-[(4Z,7Z,10Z,13Z,16Z,19Z)]-docosahexaenoyl-sn-glycero-3-phosphocholine (CHEBI:84812) has functional parent cis-vaccenic acid (CHEBI:50464)
1-[(11Z)-octadecenoyl]-2-[(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl]-sn-glycero-3-phosphocholine (CHEBI:86186) has functional parent cis-vaccenic acid (CHEBI:50464)
1-[(11Z)-octadecenoyl]-2-docosanoyl-sn-glycero-3-phosphocholine (CHEBI:86189) has functional parent cis-vaccenic acid (CHEBI:50464)
1-[(11Z)-octadecenoyl]-2-hexadecanoyl-sn-glycerol (CHEBI:86346) has functional parent cis-vaccenic acid (CHEBI:50464)
1-[(11Z)-octadecenoyl]-2-octadecanoyl-sn-glycero-3-phosphocholine (CHEBI:86111) has functional parent cis-vaccenic acid (CHEBI:50464)
1-[(11Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86255) has functional parent cis-vaccenic acid (CHEBI:50464)
1-[(8Z,11Z,14Z,17Z)-icosatetraenoyl]-2-[(11Z)-octadecenoyl]-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:89251) has functional parent cis-vaccenic acid (CHEBI:50464)
1-[(9Z)-hexadecenoyl]-2-[(11Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:84810) has functional parent cis-vaccenic acid (CHEBI:50464)
1-eicosanoyl-2-[(11Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86170) has functional parent cis-vaccenic acid (CHEBI:50464)
1-hexadecanoyl-2-(11Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine (CHEBI:84833) has functional parent cis-vaccenic acid (CHEBI:50464)
1-hexadecanoyl-2-[(11Z)-octadec-9-enoyl]-sn-glycero-3-phospho-(1'-sn-glycerol) (CHEBI:44946) has functional parent cis-vaccenic acid (CHEBI:50464)
1-octadecanoyl-2-[(11Z)-octadecenoyl]-sn-glycerophosphochlonine (CHEBI:86109) has functional parent cis-vaccenic acid (CHEBI:50464)
1-oleoyl-2-(11Z)-octadecenoyl-sn-glycero-3-phosphate (CHEBI:75357) has functional parent cis-vaccenic acid (CHEBI:50464)
1-palmitoyl-2-(11Z-octadecenoyl)-sn-glycero-3-phosphocholine (CHEBI:85037) has functional parent cis-vaccenic acid (CHEBI:50464)
1-tetradecanoyl-2-(11Z-octadecenoyl)-sn-glycero-3-phosphocholine (CHEBI:73793) has functional parent cis-vaccenic acid (CHEBI:50464)
N-[(11Z)-octadecenoyl]sphinganine-1-phosphocholine (CHEBI:134073) has functional parent cis-vaccenic acid (CHEBI:50464)
ethyl cis-vaccenate (CHEBI:84942) has functional parent cis-vaccenic acid (CHEBI:50464)
cis-vaccenate(1−) (CHEBI:30827) is conjugate base of cis-vaccenic acid (CHEBI:50464)
cis-vaccenoyl group (CHEBI:23313) is substituent group from cis-vaccenic acid (CHEBI:50464)
IUPAC Name
(11Z)-octadec-11-enoic acid
Synonyms Sources
(Z)-11-octadecenoic acid ChemIDplus
(Z)-octadec-11-enoic acid ChEBI
asclepic acid LIPID MAPS
cis-11-octadecenoic acid ChEBI
cis-octadec-11-enoic acid ChEBI
trans-11-Octadecensäure ChEBI
VACCENIC ACID PDBeChem
Manual Xrefs Databases
LMFA01030076 LIPID MAPS
VCA PDBeChem
View more database links
Registry Numbers Types Sources
1726565 Beilstein Registry Number Beilstein
1726565 Reaxys Registry Number Reaxys
506-17-2 CAS Registry Number NIST Chemistry WebBook
506-17-2 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
7050094 PubMed citation Europe PMC
Last Modified
23 October 2023
General Comments
2010-04-23 Additional citation (no PMID) -- Kawahara K et al., (1994): Isolation of Sphingomonas Strains from Ears of Rice and Other Plants of Family Gramineae - Biosci. Biotech. Biochem. 58(3): 600-601.
2011-01-21 A component of microorganisms, animal tissues and human tissues; together with oleic acid, a common octadecenoic acid of fruit pulp liquids. --Shibahara et al. (1987) (http://www.springerlink.com/content/m6889066v5248447/fulltext.pdf).