Human Metabolome Database Version 3.5

Showing metabocard for Prostaglandin E2 ethanolamide (HMDB13038)

Record Information
Version 3.5
Creation Date 2009-07-24 18:12:06 -0600
Update Date 2013-02-08 17:29:42 -0700
Secondary Accession Numbers None
Metabolite Identification
Common Name Prostaglandin E2 ethanolamide
Description prostaglandin 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
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Display: 2D Structure | 3D Structure
  1. PGE2EA
Chemical Formula C22H37NO5
Average Molecular Weight 395.5329
Monoisotopic Molecular Weight 395.267173299
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 Number Not Available
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
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Amides
Sub Class N-acyl Amines
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • Allyl Alcohol
  • Carboxamide Group
  • Cyclic Alcohol
  • Ketone
  • N Acylethanolamine
  • Primary Alcohol
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct Parent N-acyl Amines
Status Expected and Not Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.062 g/L ALOGPS
LogP 2.62 ALOGPS
LogP 1.95 ChemAxon
LogS -3.80 ALOGPS
pKa (strongest acidic) 14.58 ChemAxon
pKa (strongest basic) -0.32 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 106.86 A2 ChemAxon
Rotatable Bond Count 14 ChemAxon
Refractivity 112.45 ChemAxon
Polarizability 46.17 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029263
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB13038 Link_out
Metagene Link HMDB13038 Link_out
METLIN ID Not Available
PubChem Compound 35021785 Link_out
PDB ID Not Available
ChEBI ID Not Available
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available