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Record Information
Version3.6
Creation Date2009-07-25 00:12:06 UTC
Update Date2013-02-09 00:29:42 UTC
HMDB IDHMDB13038
Secondary Accession NumbersNone
Metabolite Identification
Common NameProstaglandin E2 ethanolamide
Descriptionprostaglandin E2 ethanolamide is the major prostanoid product derived from anandamide. Incubation of anandamide with lysates and the intact cell line expressing COX-2 but not that of COX-1 produced prostaglandin E2 ethanolamide. This reaction demonstrates the existence of a COX-2-mediated pathway for anandamide metabolism, and the metabolites formed represent a novel class of prostaglandins. Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways.
Structure
Thumb
Synonyms
  1. PGE2EA
Chemical FormulaC22H37NO5
Average Molecular Weight395.5329
Monoisotopic Molecular Weight395.267173299
IUPAC Name(5Z)-7-[(1R,2R,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]-N-(2-hydroxyethyl)hept-5-enamide
Traditional IUPAC Name(5Z)-7-[(1R,2R,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]-N-(2-hydroxyethyl)hept-5-enamide
CAS Registry NumberNot Available
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@@H](O)CC(=O)[C@@H]1C\C=C/CCCC(=O)NCCO
InChI Identifier
InChI=1S/C22H37NO5/c1-2-3-6-9-17(25)12-13-19-18(20(26)16-21(19)27)10-7-4-5-8-11-22(28)23-14-15-24/h4,7,12-13,17-19,21,24-25,27H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4-,13-12+/t17-,18+,19+,21-/m0/s1
InChI KeyGKKWUSPPIQURFM-XXHBNTRVSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Amides
Sub ClassN-acyl Amines
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
Substituents
  • Allyl Alcohol
  • Carboxamide Group
  • Cyclic Alcohol
  • Ketone
  • N Acylethanolamine
  • Primary Alcohol
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct ParentN-acyl Amines
Ontology
StatusExpected and Not 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.062 g/LALOGPS
logP2.62ALOGPS
logP1.95ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-0.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity112.45ChemAxon
Polarizability46.17ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
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 IDFDB029263
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB13038
Metagene LinkHMDB13038
METLIN IDNot Available
PubChem Compound35021785
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available