1.02011-09-21 01:58:21 UTC2018-05-28 18:38:34 UTCFDB02960720-HETE ethanolamide20-HETE ethanolamide is a N-acylethanolamine. N-acylethanolamines (NAEs) constitute a class of lipid compounds naturally present in both animal and plant membranes as constituents of the membrane-bound phospholipid, N-acylphosphatidylethanolamine (NAPE). NAPE is composed of a third fatty acid moiety linked to the amino head group of the commonly occurring membrane phospholipid, phosphatidylethanolamine. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli. Transient NAE release and accumulation has been attributed a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. N-oleoylethanolamine is an inhibitor of the sphingolipid signaling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). N-oleoylethanolamine blocks the effects of TNF- and arachidonic acid on intracellular Ca concentration. (PMID: 12692337, 12056855, 12560208, 11997249) [HMDB]20-HETE EA20-HETE-EA20-HETE-ethanolamine20-hydroxy AEA20-hydroxy arachidonoyl ethanolamide20-hydroxyepoxyeicosatrienoate20-hydroxyepoxyeicosatrienoic acid20-hydroxyepoxyeicosatrienoic acid ethanolamideC22H37NO3363.5341363.277344055(5Z,8Z,11Z,14Z)-20-hydroxy-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide20-hete-EA942069-11-6OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCOInChI=1S/C22H37NO3/c24-20-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-22(26)23-19-21-25/h1,3-4,6-7,9-10,12,24-25H,2,5,8,11,13-21H2,(H,23,26)/b3-1-,6-4-,9-7-,12-10-QRMZDMUHHZLRMH-DTLRTWKJSA-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-acyl ethanolamines (endocannabinoids)Solidlogp4.88logs-5.11solubility2.81e-03 g/llogp3.88pka_strongest_acidic15.44pka_strongest_basic-1.2iupac(5Z,8Z,11Z,14Z)-20-hydroxy-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamideaverage_mass363.5341mono_mass363.277344055smilesOCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCOformulaC22H37NO3inchiInChI=1S/C22H37NO3/c24-20-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-22(26)23-19-21-25/h1,3-4,6-7,9-10,12,24-25H,2,5,8,11,13-21H2,(H,23,26)/b3-1-,6-4-,9-7-,12-10-inchikeyQRMZDMUHHZLRMH-DTLRTWKJSA-Npolar_surface_area69.56refractivity114.89polarizability44.19rotatable_bond_count17acceptor_count3donor_count3physiological_charge0formal_charge0Specdb::CMs13073Specdb::CMs40141Specdb::CMs147563Specdb::MsMs294727Specdb::MsMs294728Specdb::MsMs294729Specdb::MsMs335527Specdb::MsMs335528Specdb::MsMs335529Specdb::MsMs2720877Specdb::MsMs2720878Specdb::MsMs2720879Specdb::MsMs2958474Specdb::MsMs2958475Specdb::MsMs2958476HMDB13630#<Reference:0x00005556741072f8>#<Reference:0x00005556741070c8>#<Reference:0x0000555674106e98>#<Reference:0x0000555674106ce0>