1.02011-09-21 01:58:43 UTC2015-07-21 06:59:47 UTCFDB029628Docosahexaenoyl EthanolamideDocosahexaenoic 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]C24H37NO2371.5561371.282429433(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-hexaenamide162758-94-3CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)NCCOInChI=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-acylethanolaminesOrganic compoundsOrganic nitrogen compoundsOrganonitrogen compoundsAminesAliphatic acyclic compoundsCarbonyl compoundsHydrocarbon derivativesN-acyl aminesOrganic oxidesOrganopnictogen compoundsPrimary alcoholsSecondary carboxylic acid amidesAlcoholAliphatic acyclic compoundCarbonyl groupCarboxamide groupCarboxylic acid derivativeFatty acylFatty amideHydrocarbon derivativeN-acyl-amineN-acylethanolamineOrganic oxideOrganic oxygen compoundOrganooxygen compoundOrganopnictogen compoundPrimary alcoholSecondary carboxylic acid amideN-(long-chain-acyl)ethanolamineN-(polyunsaturated fatty acyl)ethanolamineN-acyl ethanolamines (endocannabinoids)endocannabinoidSolidlogp6.17logs-5.80solubility5.90e-04 g/llogp5.48pka_strongest_acidic15.45pka_strongest_basic-0.48iupac(4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-hydroxyethyl)docosa-4,7,10,13,16,19-hexaenamideaverage_mass371.5561mono_mass371.282429433smilesCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)NCCOformulaC24H37NO2inchiInChI=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-inchikeyGEEHOLRSGZPBSM-KUBAVDMBSA-Npolar_surface_area49.33refractivity124.4polarizability44.14rotatable_bond_count16acceptor_count2donor_count2physiological_charge0formal_charge0Specdb::CMs9351Specdb::CMs40158Specdb::CMs133229Specdb::CMs140963Specdb::MsMs286642Specdb::MsMs286643Specdb::MsMs286644Specdb::MsMs325279Specdb::MsMs325280Specdb::MsMs325281Specdb::MsMs2236430Specdb::MsMs2238498Specdb::MsMs2239065Specdb::MsMs2241222Specdb::MsMs2659408Specdb::MsMs2659409Specdb::MsMs2659410Specdb::MsMs3019248Specdb::MsMs3019249Specdb::MsMs3019250HMDB13658