1.0 2011-09-21 01:58:44 UTC 2015-07-21 06:59:47 UTC FDB029629 (±)-8(9)-EET ethanolamide Arachidonoyl ethanolamide (AEA) is an endogenous lipid neurotransmitter with cannabingeric activity, binding to both the central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors.1,2 Fatty acid amide hydrolase (FAAH) is the enzyme responsible for the hydrolysis and inactivation of AEA.3 Metabolism of AEA by COX-2, lipoxygenases, and CYP450 enzymes has also been documented.4,5 (?)8(9)-EET ethanolamide is a cytochrome P450 (CYP450) metabolite of AEA, although specific stereochemistry rather than a racemic mixture would likely ensue from enzymatic metabolism.5 Human liver microsomes metabolize AEA to 5,6-, 8,9-, 11,12-, and 14,15-EET ethanolamides in a time and protein concentration dependent manner.5 (?)8(9)-EET reduces glomerular filtration rate through cyclooxygenase dependent preglomerular vasoconstriction.6 The physiological actions of (?)8(9)-EET ethanolamide have not been examined. [HMDB] (+/-)8(9)-epetre ethanolamide (±)8(9)-EpETrE Ethanolamide C22H37NO3 363.5341 363.277344055 (5Z)-N-(2-hydroxyethyl)-7-{3-[(2Z,5Z)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enamide 8(9)-EpETrE-EA CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(=O)NCCO InChI=1S/C22H37NO3/c1-2-3-4-5-6-7-8-9-12-15-20-21(26-20)16-13-10-11-14-17-22(25)23-18-19-24/h6-7,9-10,12-13,20-21,24H,2-5,8,11,14-19H2,1H3,(H,23,25)/b7-6-,12-9-,13-10- BXHPMUQFGGSDAK-TYAUOURKSA-N belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine. N-acylethanolamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aliphatic heteromonocyclic compounds Carbonyl compounds Dialkyl ethers Epoxides Hydrocarbon derivatives N-acyl amines Organic oxides Organopnictogen compounds Oxacyclic compounds Primary alcohols Secondary carboxylic acid amides Alcohol Aliphatic heteromonocyclic compound Carbonyl group Carboxamide group Carboxylic acid derivative Dialkyl ether Ether Fatty acyl Fatty amide Hydrocarbon derivative N-acyl-amine N-acylethanolamine Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Organopnictogen compound Oxacycle Oxirane Primary alcohol Secondary carboxylic acid amide N-acyl ethanolamines (endocannabinoids) Solid logp 5.42 ALOGPS logs -5.63 ALOGPS solubility 8.51e-04 g/l ALOGPS logp 4.38 ChemAxon pka_strongest_acidic 15.33 ChemAxon pka_strongest_basic -0.34 ChemAxon iupac (5Z)-N-(2-hydroxyethyl)-7-{3-[(2Z,5Z)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enamide ChemAxon average_mass 363.5341 ChemAxon mono_mass 363.277344055 ChemAxon smiles CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(=O)NCCO ChemAxon formula C22H37NO3 ChemAxon inchi InChI=1S/C22H37NO3/c1-2-3-4-5-6-7-8-9-12-15-20-21(26-20)16-13-10-11-14-17-22(25)23-18-19-24/h6-7,9-10,12-13,20-21,24H,2-5,8,11,14-19H2,1H3,(H,23,25)/b7-6-,12-9-,13-10- ChemAxon inchikey BXHPMUQFGGSDAK-TYAUOURKSA-N ChemAxon polar_surface_area 61.86 ChemAxon refractivity 111.37 ChemAxon polarizability 44.21 ChemAxon rotatable_bond_count 16 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 23693 Specdb::CMs 40159 Specdb::CMs 170272 Specdb::MsMs 318529 Specdb::MsMs 318530 Specdb::MsMs 318531 Specdb::MsMs 365323 Specdb::MsMs 365324 Specdb::MsMs 365325 Specdb::MsMs 2409478 Specdb::MsMs 2409479 Specdb::MsMs 2409480 Specdb::MsMs 2553307 Specdb::MsMs 2553308 Specdb::MsMs 2553309 HMDB13659 #<Reference:0x000055ce3218b1a8> #<Reference:0x000055ce3218aff0> #<Reference:0x000055ce3218ae38> #<Reference:0x000055ce3218ac80> #<Reference:0x000055ce3218aac8> #<Reference:0x000055ce3218a910>