1.0 2011-09-21 01:58:33 UTC 2015-07-21 06:59:46 UTC FDB029620 Arachidonoyl serinol 2-Arachidonoyl glycerol (2-AG) has been isolated from porcine brain, and has been characterized as the natural endocannabinoid ligand for the CB1 receptor.1,2 Replacement of the sn-2 oxygen in the glycerol moiety of 2-AG with a nitrogen atom gives arachidonoyl serinol.3 Arachidonoyl serinol is much more stable than 2-AG. However, it is at least a log less potent as a CB1 receptor agonist than 2-AG. [HMDB] N-[(2-hydroxy-1-hydroxymethyl)ethyl]-5Z,8Z,11Z,14Z-eicosatetraenamide C23H39NO3 377.5607 377.292994119 (5Z,8Z,11Z,14Z)-N-(1,3-dihydroxypropan-2-yl)icosa-5,8,11,14-tetraenamide AA dihydroxypropylamine 183718-70-9 CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NC(CO)CO InChI=1S/C23H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(27)24-22(20-25)21-26/h6-7,9-10,12-13,15-16,22,25-26H,2-5,8,11,14,17-21H2,1H3,(H,24,27)/b7-6-,10-9-,13-12-,16-15- QHELXIATGZYOIB-DOFZRALJSA-N belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage. N-acyl amines Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty amides Aliphatic acyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Primary alcohols Secondary carboxylic acid amides Alcohol Aliphatic acyclic compound Carbonyl group Carboxamide group Carboxylic acid derivative Hydrocarbon derivative N-acyl-amine Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary alcohol Secondary carboxylic acid amide N-acyl amines Solid logp 5.35 ALOGPS logs -5.22 ALOGPS solubility 2.28e-03 g/l ALOGPS logp 4.68 ChemAxon pka_strongest_acidic 13.82 ChemAxon pka_strongest_basic -0.27 ChemAxon iupac (5Z,8Z,11Z,14Z)-N-(1,3-dihydroxypropan-2-yl)icosa-5,8,11,14-tetraenamide ChemAxon average_mass 377.5607 ChemAxon mono_mass 377.292994119 ChemAxon smiles CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NC(CO)CO ChemAxon formula C23H39NO3 ChemAxon inchi InChI=1S/C23H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(27)24-22(20-25)21-26/h6-7,9-10,12-13,15-16,22,25-26H,2-5,8,11,14,17-21H2,1H3,(H,24,27)/b7-6-,10-9-,13-12-,16-15- ChemAxon inchikey QHELXIATGZYOIB-DOFZRALJSA-N ChemAxon polar_surface_area 69.56 ChemAxon refractivity 118.93 ChemAxon polarizability 45.32 ChemAxon rotatable_bond_count 17 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 294493 Specdb::MsMs 294494 Specdb::MsMs 294495 Specdb::MsMs 335227 Specdb::MsMs 335228 Specdb::MsMs 335229 Specdb::MsMs 2778817 Specdb::MsMs 2778818 Specdb::MsMs 2778819 Specdb::MsMs 2903952 Specdb::MsMs 2903953 Specdb::MsMs 2903954 Specdb::CMs 12966 Specdb::CMs 40151 Specdb::CMs 150973 HMDB13650 #<Reference:0x000055ce328fdf80> #<Reference:0x000055ce328fdcd8> #<Reference:0x000055ce328fd800>