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CHEBI:71466 - oleoyl ethanolamide

ChEBI IDCHEBI:71466
ChEBI Nameoleoyl ethanolamide
Stars
DefinitionAn N-(long-chain-acyl)ethanolamine that is the ethanolamide of oleic acid. The monounsaturated analogue of the endocannabinoid anandamide.
Secondary ChEBI IDCHEBI:77362
Last Modified27 October 2021
SubmitterAlan Bridge, Bijay
DownloadsMolfile
FormulaC20H39NO2
Net Charge0
Average Mass325.537
Monoisotopic Mass325.29808
SMILESCCCCCCCC/C=C\CCCCCCCC(=O)NCCO
InChIInChI=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-
InChIKeyBOWVQLFMWHZBEF-KTKRTIGZSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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-α.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
cannabinoid receptor agonist  An agonist that binds to and activates cannabinoid receptors.
cannabinoid receptor agonist  An agonist that binds to and activates cannabinoid receptors.
Application:
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
N-oleoylethanolamine phosphate(2−) (CHEBI:145465) has part oleoyl ethanolamide (CHEBI:71466)
IUPAC Name 
(9Z)-N-(2-hydroxyethyl)octadec-9-enamide
Synonyms  Source
oleoyl 1-ethanolamideSUBMITTER
OEASUBMITTER
N-(hydroxyethyl)oleamideLIPID MAPS
N-oleoyl ethanolamineLIPID MAPS
N-(9Z-octadecenoyl)-ethanolamineLIPID MAPS
N-(cis-9-octadecenoyl) ethanolamineLIPID MAPS
UniProt Name  Source
N-(9Z-octadecenoyl) ethanolamineUniProt
Manual XrefsDatabases
LMFA08040015LIPID MAPS
HMDB0002088HMDB
OleoylethanolamideWikipedia
LSM-2694LINCS
DB16495DrugBank
CPD-20398MetaCyc
FDB022839FooDB
Registry NumbersSources
Reaxys:2214880Reaxys
CAS:111-58-0ChemIDplus
Citations