oleoyl ethanolamide (CHEBI:71466)

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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

Supplier Information

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Formula

C20H39NO2

Net Charge

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 )

Application(s):	geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

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 geroprotector (CHEBI:176497) 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

Last Modified

27 October 2021