CHEBI:71466 - oleoyl ethanolamide

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ChEBI Name oleoyl ethanolamide
ChEBI ID CHEBI:71466
Definition An N-(long-chain-acyl)ethanolamine that is the ethanolamide of oleic acid. The monounsaturated analogue of the endocannabinoid anandamide
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Alan Bridge
Bijay
Secondary ChEBI IDs CHEBI:77362
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Formula C20H39NO2
Net Charge 0
Average Mass 325.52920
Monoisotopic Mass 325.29808
InChI InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-
InChIKey BOWVQLFMWHZBEF-KTKRTIGZSA-N
SMILES CCCCCCCC\C=C/CCCCCCCC(=O)NCCO
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 3.5.1.23 (ceramidase) inhibitor
An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the action of ceramidase (EC 3.5.1.23).
PPARalpha agonist
A PPAR modulator which activates the peroxisome proliferator-activated receptor-alpha.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via endocannabinoid )
cannabinoid receptor agonist
An agonist that binds to and activates cannabinoid receptors.
(via cannabinoid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing oleoyl ethanolamide (CHEBI:71466) has functional parent oleic acid (CHEBI:16196)
oleoyl ethanolamide (CHEBI:71466) has role EC 3.5.1.23 (ceramidase) inhibitor (CHEBI:71551)
oleoyl ethanolamide (CHEBI:71466) has role PPARα agonist (CHEBI:70782)
oleoyl ethanolamide (CHEBI:71466) is a N-(long-chain-acyl)ethanolamine (CHEBI:15897)
oleoyl ethanolamide (CHEBI:71466) is a N-acylethanolamine 18:1 (CHEBI:134158)
oleoyl ethanolamide (CHEBI:71466) is a endocannabinoid (CHEBI:67197)
Incoming N-oleoylethanolamine phosphate(2−) (CHEBI:145465) has part oleoyl ethanolamide (CHEBI:71466)
IUPAC Name
(9Z)-N-(2-hydroxyethyl)octadec-9-enamide
Synonyms Sources
N-(2-Hydroxyethyl)-9-octadecenamide ChemIDplus
N-(2-Hydroxyethyl)oleamide ChemIDplus
N-(9Z-octadecenoyl) ethanolamine UniProt
N-(9Z-octadecenoyl)-ethanolamine LIPID MAPS
N-(cis-9-octadecenoyl) ethanolamine LIPID MAPS
N-(hydroxyethyl)oleamide LIPID MAPS
N-oleoyl ethanolamine LIPID MAPS
N-Oleoylethanolamine ChemIDplus
OEA SUBMITTER
Oleamide MEA ChemIDplus
oleoyl 1-ethanolamide SUBMITTER
Oleoyl monoethanolamide ChemIDplus
oleoylethanolamide ChEBI
Manual Xrefs Databases
HMDB0002088 HMDB
LMFA08040015 LIPID MAPS
Oleoylethanolamide Wikipedia
View more database links
Registry Numbers Types Sources
111-58-0 CAS Registry Number ChemIDplus
2214880 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
27 November 2019