1.0 2011-09-21 01:58:35 UTC 2015-07-21 06:59:47 UTC FDB029622 (±)-11(12)-EET ethanolamide Arachidonoyl ethanolamide (AEA; anandamide) is an endogenous lipid neurotransmitter with cannibingeric 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 cyclooxygenase-2, leading to formation of prostaglandin ethanolamides, and by lipoxygenases has also been documented.4 (?)11(12)-EET ethanolamide is a potential cytochrome P450 (CYP450) metabolite of AEA, although specific stereochemistry rather than a racemic mixture would likely ensue from enzymatic metabolism. CYP450 metabolism of AEA may be particularly relevant under conditions of FAAH inhibition. Evidence for the formation of 11(12)-EET ethanolamide in vivo has not been documented. [HMDB] (+/-)11(12)-epetre ethanolamide (±)11(12)-EpETrE Ethanolamide C22H37NO3 363.5341 363.277344055 (5Z,8Z)-N-(2-hydroxyethyl)-10-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienamide (5Z,8Z)-N-(2-hydroxyethyl)-10-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienamide CCCCC\C=C/CC1OC1C\C=C/C\C=C/CCCC(=O)NCCO InChI=1S/C22H37NO3/c1-2-3-4-5-9-12-15-20-21(26-20)16-13-10-7-6-8-11-14-17-22(25)23-18-19-24/h6,8-10,12-13,20-21,24H,2-5,7,11,14-19H2,1H3,(H,23,25)/b8-6-,12-9-,13-10- TYRRSRADDAROSO-KROJNAHFSA-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 5.43 ALOGPS logs -5.61 ALOGPS solubility 8.84e-04 g/l ALOGPS logp 4.38 ChemAxon pka_strongest_acidic 15.44 ChemAxon pka_strongest_basic -0.34 ChemAxon iupac (5Z,8Z)-N-(2-hydroxyethyl)-10-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienamide ChemAxon average_mass 363.5341 ChemAxon mono_mass 363.277344055 ChemAxon smiles CCCCC\C=C/CC1OC1C\C=C/C\C=C/CCCC(=O)NCCO ChemAxon formula C22H37NO3 ChemAxon inchi InChI=1S/C22H37NO3/c1-2-3-4-5-9-12-15-20-21(26-20)16-13-10-7-6-8-11-14-17-22(25)23-18-19-24/h6,8-10,12-13,20-21,24H,2-5,7,11,14-19H2,1H3,(H,23,25)/b8-6-,12-9-,13-10- ChemAxon inchikey TYRRSRADDAROSO-KROJNAHFSA-N ChemAxon polar_surface_area 61.86 ChemAxon refractivity 111.37 ChemAxon polarizability 44.05 ChemAxon rotatable_bond_count 16 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 26034 Specdb::CMs 40153 Specdb::CMs 134155 Specdb::CMs 141889 Specdb::MsMs 323686 Specdb::MsMs 323687 Specdb::MsMs 323688 Specdb::MsMs 371899 Specdb::MsMs 371900 Specdb::MsMs 371901 Specdb::MsMs 2712893 Specdb::MsMs 2712894 Specdb::MsMs 2712895 Specdb::MsMs 2965578 Specdb::MsMs 2965579 Specdb::MsMs 2965580 HMDB13652 #<Reference:0x000055ce30dbff48> #<Reference:0x000055ce30dbfcc8> #<Reference:0x000055ce30dbfae8> #<Reference:0x000055ce30dbf890>