1.0 2011-09-21 01:58:40 UTC 2025-11-19 02:58:00 UTC FDB029625 O-Arachidonoyl ethanolamine Arachidonoyl ethanolamide (AEA) was the first endogenous cannabinoid to be isolated and characterized as an agonist acting on the same receptors (CB1 and CB2) as tetrahydrocannabinols (THC). Since that time, a number of related endocannabinoids have been isolated, most notably 2-arachidonoyl glycerol (2-AG).O-Arachidonoyl ethanolamine hydrochloride (O-AEA) is a recently isolated constituent of human and rat brain wherein the ethanolamine moiety is attached ?backwards?, as an ester instead of an amide, as in AEA.1,2,4 O-AEA has mixed agonist/antagonist activity at the CB1 receptor and does not appear to be the native endogenous cannabinoid agonist at this receptor. This is in keeping with other observations that 2-AG is the primary endogenous CB1 receptor ligand [HMDB] Arachidonic Acid-(2-aminoethyl)-ester O-AEA Virodhamine C22H37NO2 347.5347 347.282429433 2-aminoethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate virodhamine 443129-35-9 CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCCN InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)25-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21,23H2,1H3/b7-6-,10-9-,13-12-,16-15- DLHLOYYQQGSXCC-DOFZRALJSA-N belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Fatty acid esters Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acid esters Aliphatic acyclic compounds Amino acids and derivatives Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Aliphatic acyclic compound Amine Amino acid or derivatives Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty acid ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Other Fatty Acyls Solid logp 6.27 ALOGPS logs -6.43 ALOGPS solubility 1.28e-04 g/l ALOGPS logp 5.94 ChemAxon pka_strongest_basic 9.23 ChemAxon iupac 2-aminoethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate ChemAxon average_mass 347.5347 ChemAxon mono_mass 347.282429433 ChemAxon smiles CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCCN ChemAxon formula C22H37NO2 ChemAxon inchi InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)25-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21,23H2,1H3/b7-6-,10-9-,13-12-,16-15- ChemAxon inchikey DLHLOYYQQGSXCC-DOFZRALJSA-N ChemAxon polar_surface_area 52.32 ChemAxon refractivity 112.67 ChemAxon polarizability 42.97 ChemAxon rotatable_bond_count 17 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 10575 Specdb::CMs 155276 Specdb::MsMs 289285 Specdb::MsMs 289286 Specdb::MsMs 289287 Specdb::MsMs 328672 Specdb::MsMs 328673 Specdb::MsMs 328674 Specdb::MsMs 2733099 Specdb::MsMs 2733100 Specdb::MsMs 2733101 Specdb::MsMs 2972409 Specdb::MsMs 2972410 Specdb::MsMs 2972411 HMDB13655