Showing metabocard for Linoleoyl ethanolamide (BMDB0012252)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:35:00 UTC
Update Date2020-04-22 15:49:18 UTC
BMDB IDBMDB0012252
Secondary Accession Numbers
  • BMDB12252
Metabolite Identification
Common NameLinoleoyl ethanolamide
DescriptionLinoleoyl ethanolamide, also known as linoleamide mea or anandamide (18:2, N-6), 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. Thus, linoleoyl ethanolamide is considered to be a fatty amide. Based on a literature review very few articles have been published on Linoleoyl ethanolamide.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(9Z,12Z)-N-(2-Hydroxyethyl)octadeca-9,12-dien-1-amideChEBI
Anandamide (18:2, N-6)ChEBI
Linoleamide meaChEBI
Linoleic ethanolamideChEBI
Linoleoyl monoethanolamideChEBI
Monoethanolamine linoleic acid amideChEBI
N-(2-Hydroxyethyl)-9,12-octadecadienamideChEBI
N-(2-Hydroxyethyl)linoleamideChEBI
N-(9Z,12Z-Octadecadienoyl)-ethanolamineChEBI
N-cis-9-cis-12-OctadecadienoylethanolamineChEBI
Monoethanolamine linoleate amideGenerator
LEAHMDB
N-(2-Hydroxyethyl)-linoleamideHMDB
LinoleoylethanolamideHMDB
Linoleoyl ethanolamideMeSH
Chemical FormulaC20H37NO2
Average Molecular Weight323.5133
Monoisotopic Molecular Weight323.282429433
IUPAC Name(9Z,12Z)-N-(2-hydroxyethyl)octadeca-9,12-dienamide
Traditional Namelinoleamide mea
CAS Registry Number68171-52-8
SMILES
CCCCC\C=C/C\C=C/CCCCCCCC(=O)NCCO
InChI Identifier
InChI=1S/C20H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h6-7,9-10,22H,2-5,8,11-19H2,1H3,(H,21,23)/b7-6-,10-9-
InChI KeyKQXDGUVSAAQARU-HZJYTTRNSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentN-acylethanolamines
Alternative Parents
Substituents
  • N-acylethanolamine
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Alcohol
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.26ALOGPS
logP5.15ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)15.47ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity101.53 m³·mol⁻¹ChemAxon
Polarizability41.41 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0012252
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028893
KNApSAcK IDNot Available
Chemspider ID4446566
KEGG Compound IDNot Available
BioCyc IDCPD6666-4
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283446
PDB IDNot Available
ChEBI ID64032
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available