1.0 2011-09-21 01:58:43 UTC 2015-07-21 06:59:47 UTC FDB029628 Docosahexaenoyl Ethanolamide Docosahexaenoic Acid (DHA) is an essential fatty acid and the most abundant ω-3 fatty acid in neural tissues, especially in the retina and brain. Docosahexaenoyl ethanolamide (DHEA) is the ethanolamine amide of DHA that has been detected in both brain and retina at concentrations similar to those for arachidonoyl ethanolamide (AEA).1,2 A 9.5 fold increase of DHEA was observed in brain lipid extracts from piglets fed a diet supplemented with DHA compared to a control diet without DHA.3 DHEA binds to the rat brain CB1 receptor with a Ki of 324 nM, which is approximately 10-fold higher than the Ki for AEA.4 DHEA inhibits shaker-related voltage-gated potassium channels in brain slightly better than AEA, with an IC50 of 1.5 ?M [HMDB] C24H37NO2 371.5561 371.282429433 (4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-hydroxyethyl)docosa-4,7,10,13,16,19-hexaenamide (4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-hydroxyethyl)docosa-4,7,10,13,16,19-hexaenamide 162758-94-3 CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)NCCO InChI=1S/C24H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(27)25-22-23-26/h3-4,6-7,9-10,12-13,15-16,18-19,26H,2,5,8,11,14,17,20-23H2,1H3,(H,25,27)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18- GEEHOLRSGZPBSM-KUBAVDMBSA-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 acyclic compounds Carbonyl compounds Hydrocarbon derivatives N-acyl amines Organic oxides Organopnictogen compounds Primary alcohols Secondary carboxylic acid amides Alcohol Aliphatic acyclic compound Carbonyl group Carboxamide group Carboxylic acid derivative Fatty acyl Fatty amide Hydrocarbon derivative N-acyl-amine N-acylethanolamine Organic oxide Organic oxygen compound Organooxygen compound Organopnictogen compound Primary alcohol Secondary carboxylic acid amide N-(long-chain-acyl)ethanolamine N-(polyunsaturated fatty acyl)ethanolamine N-acyl ethanolamines (endocannabinoids) endocannabinoid Solid logp 6.17 ALOGPS logs -5.80 ALOGPS solubility 5.90e-04 g/l ALOGPS logp 5.48 ChemAxon pka_strongest_acidic 15.45 ChemAxon pka_strongest_basic -0.48 ChemAxon iupac (4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-hydroxyethyl)docosa-4,7,10,13,16,19-hexaenamide ChemAxon average_mass 371.5561 ChemAxon mono_mass 371.282429433 ChemAxon smiles CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)NCCO ChemAxon formula C24H37NO2 ChemAxon inchi InChI=1S/C24H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(27)25-22-23-26/h3-4,6-7,9-10,12-13,15-16,18-19,26H,2,5,8,11,14,17,20-23H2,1H3,(H,25,27)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18- ChemAxon inchikey GEEHOLRSGZPBSM-KUBAVDMBSA-N ChemAxon polar_surface_area 49.33 ChemAxon refractivity 124.4 ChemAxon polarizability 44.14 ChemAxon rotatable_bond_count 16 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 9351 Specdb::CMs 40158 Specdb::CMs 133229 Specdb::CMs 140963 Specdb::MsMs 286642 Specdb::MsMs 286643 Specdb::MsMs 286644 Specdb::MsMs 325279 Specdb::MsMs 325280 Specdb::MsMs 325281 Specdb::MsMs 2236430 Specdb::MsMs 2238498 Specdb::MsMs 2239065 Specdb::MsMs 2241222 Specdb::MsMs 2659408 Specdb::MsMs 2659409 Specdb::MsMs 2659410 Specdb::MsMs 3019248 Specdb::MsMs 3019249 Specdb::MsMs 3019250 HMDB13658