Showing metabocard for N-Oleoylethanolamine (BMDB0002088)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:51:03 UTC
Update Date2020-05-11 20:39:49 UTC
BMDB IDBMDB0002088
Secondary Accession Numbers
  • BMDB02088
Metabolite Identification
Common NameN-Oleoylethanolamine
DescriptionOleoylethanolamide, also known as OEA or oleamide mea, 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, oleoylethanolamide is considered to be a fatty amide. Based on a literature review a significant number of articles have been published on Oleoylethanolamide.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-(2-Hydroxyethyl)-9-octadecenamideChEBI
N-(2-Hydroxyethyl)oleamideChEBI
N-(9Z-Octadecenoyl) ethanolamineChEBI
N-(9Z-Octadecenoyl)-ethanolamineChEBI
N-(cis-9-Octadecenoyl) ethanolamineChEBI
N-(Hydroxyethyl)oleamideChEBI
N-Oleoyl ethanolamineChEBI
N-OleoylethanolamineChEBI
OEAChEBI
Oleamide meaChEBI
Oleoyl 1-ethanolamideChEBI
Oleoyl monoethanolamideChEBI
N-Oleoyl ethanolamine, oleoyl monoethanolamide, oleoylethanolamideHMDB
N-Oleoyl-2-aminoethanolHMDB
NOEHMDB
Oleic acid ethanolamideHMDB
Oleic acid monoethanolamideHMDB
N-OEAHMDB
(9Z)-N-(2-Hydroxyethyl)-9-octadecenamideHMDB
N-(2-Hydroxyethyl)-9-Z-octadecenamideHMDB
N-OleoylethanolamideHMDB
Oleoyl ethanolamideHMDB
OleoylethanolamineHMDB
OleoylethanolamideChEBI
AEA(18:1)HMDB
Acylethanolamine 18:1HMDB
Chemical FormulaC20H39NO2
Average Molecular Weight325.5292
Monoisotopic Molecular Weight325.298079497
IUPAC Name(9Z)-N-(2-hydroxyethyl)octadec-9-enamide
Traditional Nameoleoylethanolamide
CAS Registry Number111-58-0
SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)NCCO
InChI Identifier
InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-
InChI KeyBOWVQLFMWHZBEF-KTKRTIGZSA-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
OriginNot Available
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
logP6.74ALOGPS
logP5.51ChemAxon
logS-6.1ALOGPS
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 Count17ChemAxon
Refractivity100.41 m³·mol⁻¹ChemAxon
Polarizability42.77 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 Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0002088
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022839
KNApSAcK IDNot Available
Chemspider ID4446574
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOleoylethanolamide
METLIN IDNot Available
PubChem Compound5283454
PDB IDNot Available
ChEBI ID71466
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available