Palmitoleoyl ethanolamide (CHEM041404)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:28:09 UTC
Update Date2016-11-09 01:22:28 UTC
Accession NumberCHEM041404
Identification
Common NamePalmitoleoyl ethanolamide
ClassSmall Molecule
DescriptionAn N-(long-chain-acyl)ethanolamine that is the ethanolamide of palmitoleic acid.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(Z)-Hexadec-9-enoyl ethanolamideChEBI
N-(2-Hydroxyethyl)palmitoleylamideChEBI
N-(9Z-Hexadecenoyl) ethanolamineChEBI
N-(9Z-Hexadecenoyl)-ethanolamineChEBI
Palmitoleoyl-eaChEBI
POEAChEBI
PolyoxyethyleneamineMeSH
N-(9Z-Hexadecenoyl)-ethanolamideHMDB
Palmitoleoyl-ethanolamideHMDB
Palmitoleoyl-ethanolamineHMDB
(9Z)-N-(2-Hydroxyethyl)-9-hexadecenamideHMDB
Palmitoleoyl ethanolamideHMDB
Chemical FormulaC18H35NO2
Average Molecular Mass297.476 g/mol
Monoisotopic Mass297.267 g/mol
CAS Registry Number94421-67-7
IUPAC Name(9Z)-N-(2-hydroxyethyl)hexadec-9-enamide
Traditional Namepalmitoleoyl-EA
SMILESCCCCCC\C=C/CCCCCCCC(=O)NCCO
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-431ef9175cd6e2c98ac5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001j-3090000000-fd112625084534fd104fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-c67f4ac6eb06f01e12ffSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-9080000000-d5b6efef796a3944fdeeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9000000000-580ee14b795a28da936bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9000000000-0796fb6e81f9d4eed35fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-69f5cee9787e872ffdd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3190000000-42b64e70a801d7da5829Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059f-9110000000-ab8fbfe293d1e35072dbSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0013648
FooDB IDFDB029618
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8011589
ChEBI ID71465
PubChem Compound ID9835868
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21562563
2. 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.
3. 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.