CHEBI:52392 - 2-arachidonoylglycerol

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ChEBI Name 2-arachidonoylglycerol
ChEBI ID CHEBI:52392
Definition An endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Bijay
Secondary ChEBI IDs CHEBI:34261, CHEBI:52365
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Formula C23H38O4
Net Charge 0
Average Mass 378.54540
Monoisotopic Mass 378.27701
InChI InChI=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-
InChIKey RCRCTBLIHCHWDZ-DOFZRALJSA-N
SMILES [H]C(CO)(CO)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
Metabolite of Species Details
Mus musculus (NCBI:txid10090) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): 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.
(via endocannabinoid )
cannabinoid receptor agonist
An agonist that binds to and activates cannabinoid receptors.
(via cannabinoid )
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ChEBI Ontology
Outgoing 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 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 Sources
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol UniProt
2-AG SUBMITTER
2-AG KEGG COMPOUND
2-Ara-Gl ChemIDplus
2-Arachidonoyl-glycerol ChemIDplus
2-Arachidonoylglycerol KEGG COMPOUND
2-Arachidonyl-glycerol ChemIDplus
Manual Xrefs Databases
2-Arachidonoylglycerol Wikipedia
C13856 KEGG COMPOUND
CPD-12600 MetaCyc
HMDB0004666 HMDB
LMGL01010023 LIPID MAPS
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Registry Numbers Types Sources
53847-30-6 CAS Registry Number ChemIDplus
8167264 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12878451 PubMed citation Europe PMC
15543349 PubMed citation Europe PMC
18771906 PubMed citation Europe PMC
Last Modified
18 May 2017