CHEBI:28194 - petroselinic acid

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ChEBI Name petroselinic acid
ChEBI ID CHEBI:28194
Definition The cis-isomer of octadec-6-enoic acid, a long-chain fatty acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:8032, CHEBI:25945
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Formulae C18H34O2
C18H34O2
Net Charge 0
Average Mass 282.462
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/h12-13H,2-11,14-17H2,1H3,(H,19,20)/b13-12-
InChIKey CNVZJPUDSLNTQU-SEYXRHQNSA-N
SMILES C(C/C=C\CCCCCCCCCCC)CCC(=O)O
Metabolite of Species Details
Carum carvi (NCBI:txid48032) Found in seed (BTO:0001226). See: DOI
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): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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ChEBI Ontology
Outgoing petroselinic acid (CHEBI:28194) has role plant metabolite (CHEBI:76924)
petroselinic acid (CHEBI:28194) is a octadec-6-enoic acid (CHEBI:36022)
petroselinic acid (CHEBI:28194) is conjugate acid of petroselinate (CHEBI:32375)
Incoming (6Z)-octadecenoyl-CoA (CHEBI:75360) has functional parent petroselinic acid (CHEBI:28194)
1,2-di-[(6Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86330) has functional parent petroselinic acid (CHEBI:28194)
1,2-di-[(6Z)-octadecenoyl]-sn-glycero-3-phosphoethanolamine (CHEBI:84845) has functional parent petroselinic acid (CHEBI:28194)
1-oleoyl-2-(6Z)-octadecenoyl-sn-glycero-3-phosphate (CHEBI:75363) has functional parent petroselinic acid (CHEBI:28194)
petroselinamide (CHEBI:146168) has functional parent petroselinic acid (CHEBI:28194)
petroselinate (CHEBI:32375) is conjugate base of petroselinic acid (CHEBI:28194)
petroselinoyl group (CHEBI:32376) is substituent group from petroselinic acid (CHEBI:28194)
IUPAC Name
(6Z)-octadec-6-enoic acid
Synonyms Sources
(6Z)-Octadecenoic acid KEGG COMPOUND
(6Z)-petroselinic acid ChEBI
(Z)-6-octadecenoic acid NIST Chemistry WebBook
cis-6-Octadecenoic acid KEGG COMPOUND
cis-Δ6-octadecenoic acid ChEBI
cis-octadec-6-enoic acid ChEBI
cis-ω-12-octadecenoic acid ChEBI
cis-petroselinic acid ChEBI
Octadec-6c-ensäre ChEBI
Petroseleninsäure ChEBI
Petroselinic acid KEGG COMPOUND
Petroselinic acid KEGG COMPOUND
Petroselinsäure ChEBI
Manual Xrefs Databases
C00001235 KNApSAcK
C08363 KEGG COMPOUND
HMDB0002080 HMDB
LMFA01030066 LIPID MAPS
Petroselinic_acid Wikipedia
View more database links
Registry Numbers Types Sources
1726527 Beilstein Registry Number Beilstein
1726527 Reaxys Registry Number Reaxys
593-39-5 CAS Registry Number KEGG COMPOUND
593-39-5 CAS Registry Number ChemIDplus
593-39-5 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
25148954 PubMed citation Europe PMC
9635505 PubMed citation Europe PMC
IND44686551 Agricola citation Europe PMC
Last Modified
19 February 2020
General Comment
2011-01-17 Exerts strong skin perturbation effects.