Palmitoylethanolamide (CHEM017799)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:39:12 UTC
Update Date2016-11-09 01:15:40 UTC
Accession NumberCHEM017799
Identification
Common NamePalmitoylethanolamide
ClassSmall Molecule
DescriptionAn N-(long-chain-acyl)ethanolamine that is the ethanolamide of palmitic (hexadecanoic) acid.
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Anandamide (16:0)ChEBI
Hexadecanoyl ethanolamideChEBI
HydroxyethylpalmitamideChEBI
Monoethanolamine palmitic acid amideChEBI
N-(2-Hydroxyethyl)palmitamideChEBI
N-HexadecanoylethanolamineChEBI
N-PalmitoylethanolamineChEBI
PalmidrolChEBI
PalmidrolumChEBI
Palmitamide meaChEBI
Palmitic acid monoethanolamideChEBI
Palmitinsaeure-beta-hydroxyethylamidChEBI
Palmitoyl-eaChEBI
PEAChEBI
Palmdrol prodesKegg
Monoethanolamine palmitate amideGenerator
Palmitate monoethanolamideGenerator
Palmitinsaeure-b-hydroxyethylamidGenerator
Palmitinsaeure-β-hydroxyethylamidGenerator
ImpulsinMeSH
MimyXMeSH
N-(2-Hydroxyethyl)palmitateMeSH
PalmitylethanolamideMeSH
N-Hexadecanoyl ethanolamineChEBI, HMDB
Loramine P 256HMDB
N-(2-Hydroxyethyl)hexadecanamideHMDB
N-Hexadecyl-ethanolamineHMDB
Palmitoyl ethanolamideHMDB
PalmitoylethanolamideChEBI
Chemical FormulaC18H37NO2
Average Molecular Mass299.492 g/mol
Monoisotopic Mass299.282 g/mol
CAS Registry Number544-31-0
IUPAC NameN-(2-hydroxyethyl)hexadecanamide
Traditional Namepalmitoylethanolamide
SMILESCCCCCCCCCCCCCCCC(=O)NCCO
InChI IdentifierInChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)19-16-17-20/h20H,2-17H2,1H3,(H,19,21)
InChI KeyHXYVTAGFYLMHSO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboximidic acids and derivatives
Sub ClassCarboximidic acids
Direct ParentCarboximidic acids
Alternative Parents
Substituents
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid
  • Alkanolamine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • 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 Solubility0.0014 g/LALOGPS
logP5.74ALOGPS
logP4.98ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)15.46ChemAxon
pKa (Strongest Basic)-0.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity90.09 m³·mol⁻¹ChemAxon
Polarizability40.05 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, Positivesplash10-01ot-9550000000-2a81c82885f59140f22bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9342000000-ad8530134ab4732a0f8cSpectrum
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, Positivesplash10-0udi-0198000000-1cff41413d7ea5aa691eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03e9-9150000000-f699f2ee45fd83d20176Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-7179000000-22766d934944105dccf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9130000000-c6d2bfc2e68da1f5b0d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9410000000-d078025cabaaf62c59b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1090000000-5224a67dd0daaea79191Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ot-5090000000-dd9396934201d60f5af2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9010000000-d5bf936e945bfc965dfeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-86444a8ba84f59241172Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3190000000-31bf9918e08d5134f37cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9120000000-95f7b48f422a8476addbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-9008000000-4fe7f397e16e4c5cdf0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9000000000-e26f03daa120b23660dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-6cd5890dca5525a7b1e2Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
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 IDHMDB0002100
FooDB IDFDB001087
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPalmitoylethanolamide
Chemspider ID4509
ChEBI ID71464
PubChem Compound ID4671
Kegg Compound IDC16512
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16715117
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18501510
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19395322
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19535304
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19622239
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20462810
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21562563
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21564082
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21705689
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22172516
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22595021
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22912814
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23201387
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=4559625
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=4584774
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=4704121
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=5165412
18. Hoareau L, Ravanan P, Gonthier MP, Delarue P, Goncalves J, Cesari M, Festy F, Roche R: Effect of PEA on LPS inflammatory action in human adipocytes. Cytokine. 2006 Jun;34(5-6):291-6. Epub 2006 Aug 1.
19. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19.
20. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.