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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2011-07-06 11:32:41 UTC
Update Date2020-03-26 17:28:30 UTC
HMDB IDHMDB0013648
Secondary Accession Numbers
  • HMDB13648
Metabolite Identification
Common NamePalmitoleoylethanolamde
DescriptionPalmitoleoylethanolamde (POEA), 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, palmitoleoylethanolamde is considered to be a fatty amide lipid molecule. Palmitoleoylethanolamde is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. During abstinence, young adults with a history of alcohol binge drinking had elevated plasma levels of monounsaturated and polyunsaturatedacylethanolamides, specifically oleoylethanolamide (OEA), palmitoleoylethanolamide (POEA), arachidonoylethanolamide (AEA), and dihomo-gamma-linolenoylethanolamide (DGLEA). Changes in these lipids positively correlated with mRNA upregulation of inflammatory markers in peripheral blood mononuclear cells (PBMCs), such as toll-like receptors (TLR4), pro-inflammatory cytokines/chemokines, and cyclooxygenase-2 (PMID: 29178411 ).
Structure
Data?1585243710
Synonyms
ValueSource
(Z)-Hexadec-9-enoyl ethanolamideChEBI
N-(2-Hydroxyethyl)palmitoleylamideChEBI
N-(9Z-Hexadecenoyl) ethanolamineChEBI
N-(9Z-Hexadecenoyl)-ethanolamineChEBI
Palmitoleoyl-eaChEBI
POEAChEBI
N-(9Z-Hexadecenoyl)-ethanolamideHMDB
Palmitoleoyl-ethanolamideHMDB
Palmitoleoyl-ethanolamineHMDB
PolyoxyethyleneamineHMDB
(9Z)-N-(2-Hydroxyethyl)-9-hexadecenamideHMDB
Palmitoleoyl ethanolamideHMDB
Chemical FormulaC18H35NO2
Average Molecular Weight297.476
Monoisotopic Molecular Weight297.266779369
IUPAC Name(9Z)-N-(2-hydroxyethyl)hexadec-9-enamide
Traditional Namepalmitoleoyl-EA
CAS Registry Number94421-67-7
SMILES
CCCCCC\C=C/CCCCCCCC(=O)NCCO
InChI Identifier
InChI=1S/C18H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)19-16-17-20/h7-8,20H,2-6,9-17H2,1H3,(H,19,21)/b8-7-
InChI KeyWFRLANWAASSSFV-FPLPWBNLSA-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
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0007 g/LALOGPS
logP6.07ALOGPS
logP4.62ChemAxon
logS-5.6ALOGPS
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 Count15ChemAxon
Refractivity91.21 m³·mol⁻¹ChemAxon
Polarizability38.49 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-9850000000-dca871694e1453ee1290Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9432000000-461ac4f924d74371dcfaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-3090000000-d6769586b97d92aec922Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9130000000-e2b3de7dda39a1a2b8e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9310000000-3a6ec9ee35e9c5b6fcb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-2bc9024817a3bec1dab5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r2-4090000000-29e8051940c6da6e4f7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9010000000-5d6e43f9124267c45344Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029618
KNApSAcK IDNot Available
Chemspider ID8011589
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9835868
PDB IDNot Available
ChEBI ID71465
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Syed SK, Bui HH, Beavers LS, Farb TB, Ficorilli J, Chesterfield AK, Kuo MS, Bokvist K, Barrett DG, Efanov AM: Regulation of GPR119 receptor activity with endocannabinoid-like lipids. Am J Physiol Endocrinol Metab. 2012 Dec 15;303(12):E1469-78. doi: 10.1152/ajpendo.00269.2012. Epub 2012 Oct 16. [PubMed:23074242 ]
  2. Anton M, Rodriguez-Gonzalez A, Rodriguez-Rojo IC, Pastor A, Correas A, Serrano A, Ballesta A, Alen F, Gomez de Heras R, de la Torre R, Rodriguez de Fonseca F, Orio L: Increased plasma oleoylethanolamide and palmitoleoylethanolamide levels correlate with inflammatory changes in alcohol binge drinkers: the case of HMGB1 in women. Addict Biol. 2018 Nov;23(6):1242-1250. doi: 10.1111/adb.12580. Epub 2017 Nov 27. [PubMed:29178411 ]