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Record Information
Version3.6
Creation Date2006-05-22 14:17:36 UTC
Update Date2017-03-02 21:26:52 UTC
HMDB IDHMDB02100
Secondary Accession NumbersNone
Metabolite Identification
Common NamePalmitoylethanolamide
DescriptionN-Palmitoylethanolamide (PEA) is present in the tissues of most mammals. It was initially described as an agonist of the type 2 cannabinoid receptor (CB2), although it is now universally recognized that PEA is in fact incapable of binding to cannabinoid receptors, or at least not to the known receptors. In addition to its anti-inflammatory activity, PEA also produces analgesia, neuroprotection, and possesses anti-epileptic properties. It also reduces gastrointestinal motility and cancer cell proliferation, as well as protecting the vascular endothelium in the ischemic heart. The physiological stimuli that regulate PEA levels in mammalian tissues are largely unknown, however, multiple studies indicate that this lipid accumulates during cellular stress, particularly following tissue injury. For example, PEA increases post-mortem in the pig brain. Similar elevations in PEA levels have been observed in the ischemic brain and PEA is also up-regulated in response to ultraviolet-B irradiation in mouse epidermal cells. Adipose tissue is highly implicated in the systemic secretion of IL-6 and leptin, and human mature adipocytes are able to secrete large quantity of PEA. Human adipose tissue can be subjected to modulation of its inflammatory state by lipopolysaccharide (LPS). LPS strongly inhibits adipose cell leptin release, with PEA acting as a potentiator of this inhibitory effect. These actions are not linked to a reduction in leptin gene transcription. Thus, PEA does not have an anti-inflammatory role in the secretion of IL-6 via NFkappaB at the adipocyte level, but instead seems to act at the heart of the LPS-stimulated pathway, which, independently of NFkappaB, inhibits the secretion of leptin. (PMID: 16884908 ).
Structure
Thumb
Synonyms
ValueSource
Anandamide (16:0)ChEBI
Hexadecanoyl ethanolamideChEBI
HydroxyethylpalmitamideChEBI
Monoethanolamine palmitic acid amideChEBI
N-(2-Hydroxyethyl)palmitamideChEBI
N-Hexadecanoyl ethanolamineChEBI
N-PalmitoylethanolamineChEBI
PalmidrolChEBI
PalmidrolumChEBI
Palmitamide meaChEBI
Palmitic acid monoethanolamideChEBI
Palmitinsaeure-beta-hydroxyethylamidChEBI
Palmitoyl-eaChEBI
PEAChEBI
Monoethanolamine palmitate amideGenerator
Palmitate monoethanolamideGenerator
Palmitinsaeure-b-hydroxyethylamidGenerator
Palmitinsaeure-β-hydroxyethylamidGenerator
Loramine P 256HMDB
N-(2-Hydroxyethyl)hexadecanamideHMDB
N-Hexadecyl-ethanolamineHMDB
Palmitoyl ethanolamideHMDB
ImpulsinMeSH
PalmitylethanolamideMeSH
MimyXMeSH
N-(2-Hydroxyethyl)palmitateMeSH
Chemical FormulaC18H37NO2
Average Molecular Weight299.4919
Monoisotopic Molecular Weight299.282429433
IUPAC NameN-(2-hydroxyethyl)hexadecanamide
Traditional Namepalmitoylethanolamide
CAS Registry Number544-31-0
SMILES
CCCCCCCCCCCCCCCC(=O)NCCO
InChI Identifier
InChI=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
DescriptionThis compound belongs to the class of chemical entities known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboximidic acids and derivatives
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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point98.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0014 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity90.09 m3·mol-1ChemAxon
Polarizability40.05 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-7179000000-22766d934944105dccf9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9130000000-c6d2bfc2e68da1f5b0d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9410000000-d078025cabaaf62c59b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1090000000-5224a67dd0daaea79191View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ot-5090000000-dd9396934201d60f5af2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9010000000-d5bf936e945bfc965dfeView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.013 (0.0094-0.0167) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified25.1 +/- 12 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00212 +/- 0.00072 uMNot SpecifiedNot Specifiednormal details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Not AvailableNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001087
KNApSAcK IDNot Available
Chemspider ID4509
KEGG Compound IDC16512
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02100
Metagene LinkHMDB02100
METLIN IDNot Available
PubChem Compound4671
PDB IDNot Available
ChEBI ID147261
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:16884908 ]