CHEBI:71467 - (5Z,8Z,11Z,14Z,17Z)-icosapentaenoylethanolamine

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ChEBI Name (5Z,8Z,11Z,14Z,17Z)-icosapentaenoylethanolamine
ChEBI ID CHEBI:71467
ChEBI ASCII Name (5Z,8Z,11Z,14Z,17Z)-icosapentaenoylethanolamine
Definition An N-acylethanolamine 20:5 that is the ethanolamide of (5Z,8Z,11Z,14Z17Z)-eicosapentaenoic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Alan Bridge
Supplier Information
Download Molfile XML SDF
Formula C22H35NO2
Net Charge 0
Average Mass 345.527
Monoisotopic Mass 345.26678
InChI InChI=1S/C22H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h3-4,6-7,9-10,12-13,15-16,24H,2,5,8,11,14,17-21H2,1H3,(H,23,25)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChIKey OVKKNJPJQKTXIT-JLNKQSITSA-N
SMILES CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=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): PPARgamma agonist
A PPAR modulator which activates the peroxisome proliferator-activated receptor-gamma.
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 (5Z,8Z,11Z,14Z,17Z)-icosapentaenoylethanolamine (CHEBI:71467) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
(5Z,8Z,11Z,14Z,17Z)-icosapentaenoylethanolamine (CHEBI:71467) has role PPARγ agonist (CHEBI:71554)
(5Z,8Z,11Z,14Z,17Z)-icosapentaenoylethanolamine (CHEBI:71467) is a N-acylethanolamine 20:5 (CHEBI:134162)
(5Z,8Z,11Z,14Z,17Z)-icosapentaenoylethanolamine (CHEBI:71467) is a endocannabinoid (CHEBI:67197)
IUPAC Name
(5Z,8Z,11Z,14Z17Z)-N-(2-hydroxyethyl)icosa-5,8,11,14,17-pentaenamide
Synonyms Sources
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl ethanolamide ChEBI
(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl) ethanolamine UniProt
all-cis-eicosa-5,8,11,14,17-pentaenoyl ethanolamide ChEBI
all-cis-icosa-5,8,11,14,17-pentaenoyl ethanolamide ChEBI
Anandamide (20:5, n-3) LIPID MAPS
eicosapentaenoyl ethanolamide SUBMITTER
EPEA SUBMITTER
icosapentaenoyl ethanolamide ChEBI
N-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)ethanolamine LIPID MAPS
N-cis-5,8, 11,14,17-eicosapentaenoylethanolamine LIPID MAPS
Manual Xrefs Databases
HMDB0013649 HMDB
LMFA08040008 LIPID MAPS
View more database links
Registry Number Type Source
7649107 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
20601112 PubMed citation Europe PMC
20660502 PubMed citation Europe PMC
21562563 PubMed citation SUBMITTER
23168911 PubMed citation Europe PMC
Last Modified
24 March 2022