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 282.256
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:27404) 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 )
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)
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 EuroFIR
cis-11-octadecenoic acid ChEBI
cis-octadec-11-enoic acid ChEBI
trans-11-Octadecensäure ChEBI
VACCENIC ACID PDBeChem
Database Links Databases
LMFA01030076 LIPID MAPS
VCA PDBeChem
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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
17 May 2017
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).