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CHEBI:52392 - 2-arachidonoylglycerol

ChEBI IDCHEBI:52392
ChEBI Name2-arachidonoylglycerol
Stars
DefinitionAn endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol.
Secondary ChEBI IDsCHEBI:34261, CHEBI:52365
Last Modified18 May 2017
SubmitterBijay, Marcus Ennis
DownloadsMolfile
FormulaC23H38O4
Net Charge0
Average Mass378.553
Monoisotopic Mass378.27701
SMILES[H]C(CO)(CO)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC
InChIInChI=1S/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3/b7-6-,10-9-,13-12-,16-15-
InChIKeyRCRCTBLIHCHWDZ-DOFZRALJSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606) - DOI (10.1038/nbt.2488)
Mus musculus (ncbitaxon:10090) - PubMed (12878451)
Roles Classification
Biological Roles:
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
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.
ChEBI Ontology
Outgoing Relation(s)
2-arachidonoylglycerol (CHEBI:52392) has functional parent arachidonic acid (CHEBI:15843)
2-arachidonoylglycerol (CHEBI:52392) has role human metabolite (CHEBI:77746)
2-arachidonoylglycerol (CHEBI:52392) is a 2-acylglycerol 20:4 (CHEBI:134144)
2-arachidonoylglycerol (CHEBI:52392) is a endocannabinoid (CHEBI:67197)
Incoming Relation(s)
12-HPETE 2-glyceryl ester (CHEBI:146254) has functional parent 2-arachidonoylglycerol (CHEBI:52392)
IUPAC Name 
1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Synonyms  Source
2-ArachidonoylglycerolKEGG COMPOUND
2-Ara-GlChemIDplus
2-Arachidonoyl-glycerolChemIDplus
2-Arachidonyl-glycerolChemIDplus
2-AGSUBMITTER
2-AGKEGG COMPOUND
UniProt Name  Source
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerolUniProt
Manual XrefsDatabases
C13856KEGG COMPOUND
CPD-12600MetaCyc
LMGL01010023LIPID MAPS
HMDB0004666HMDB
2-ArachidonoylglycerolWikipedia
Registry NumbersSources
Reaxys:8167264Reaxys
CAS:53847-30-6ChemIDplus
CAS:53847-30-6KEGG COMPOUND
Citations