1.02011-09-21 01:53:16 UTC2017-03-11 23:01:02 UTCFDB029286StearoylethanolamideStearoylethanolamide 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]Stearic acid monoethanolamideStearoyl ethanolamideC20H41NO2327.545327.313729561N-(2-hydroxyethyl)octadecanamidestearoyl-ethanolamine111-57-9CCCCCCCCCCCCCCCCCC(=O)NCCOInChI=1S/C20H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h22H,2-19H2,1H3,(H,21,23)OTGQIQQTPXJQRG-UHFFFAOYSA-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-(saturated fatty acyl)ethanolamineN-acyl ethanolamines (endocannabinoids)Solidlogp6.67logs-5.97solubility3.54e-04 g/llogp5.87pka_strongest_acidic15.46pka_strongest_basic-0.33iupacN-(2-hydroxyethyl)octadecanamideaverage_mass327.545mono_mass327.313729561smilesCCCCCCCCCCCCCCCCCC(=O)NCCOformulaC20H41NO2inchiInChI=1S/C20H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h22H,2-19H2,1H3,(H,21,23)inchikeyOTGQIQQTPXJQRG-UHFFFAOYSA-Npolar_surface_area49.33refractivity99.3polarizability44.34rotatable_bond_count18acceptor_count2donor_count2physiological_charge0formal_charge0Specdb::CMs15495Specdb::CMs40052Specdb::CMs170864Specdb::MsMs73863Specdb::MsMs73864Specdb::MsMs73865Specdb::MsMs133113Specdb::MsMs133114Specdb::MsMs133115Specdb::MsMs2355909Specdb::MsMs2355910Specdb::MsMs2355911Specdb::MsMs2607228Specdb::MsMs2607229Specdb::MsMs2607230Specdb::NmrOneD261108Specdb::NmrOneD261109Specdb::NmrOneD261110Specdb::NmrOneD261111Specdb::NmrOneD261112Specdb::NmrOneD261113Specdb::NmrOneD261114Specdb::NmrOneD261115Specdb::NmrOneD261116Specdb::NmrOneD261117Specdb::NmrOneD261118Specdb::NmrOneD261119Specdb::NmrOneD261120Specdb::NmrOneD261121Specdb::NmrOneD261122Specdb::NmrOneD261123Specdb::NmrOneD261124Specdb::NmrOneD261125Specdb::NmrOneD261126Specdb::NmrOneD261127HMDB13078#<Reference:0x0000555674709070>#<Reference:0x0000555674708eb8>#<Reference:0x0000555674708d00>#<Reference:0x0000555674708b48>