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Record Information
Creation Date2006-05-22 15:12:38 UTC
Update Date2017-03-02 21:27:12 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common Name15-Keto-prostaglandin E2
Description15-keto-PGE2 is one of the prostaglandin E2 metabolites. (PMID 7190512 ). It is a degradation product produced by 15-hydroxy prostaglandin dehydrogenase (PGDH or 15-PGDH). Dinoprostone is a naturally occurring prostaglandin E2 (PGE2) and the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bone's mineralized matrix). PGE2 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, to induce uterine contractions and to activate platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus; decreasing T-cell proliferation and lymphocyte migration and activating the secretion of IL-1alpha and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC), and PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype. (PMID: 16978535 ). 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.
15-Deoxy-15-oxo-prostaglandin e2ChEBI
15-Ketoprostaglandin e2ChEBI
(5Z)-(15S)-11a-Hydroxy-9,15-dioxoprosta-13-enoic acidGenerator
(5Z)-(15S)-11alpha-Hydroxy-9,15-dioxoprosta-13-enoic acidGenerator
(5Z)-(15S)-11α-hydroxy-9,15-dioxoprosta-13-enoic acidGenerator
(5Z,13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acidGenerator
(5Z,13E)-11alpha-Hydroxy-9,15-dioxoprost-13-enoic acidGenerator
(5Z,13E)-11α-hydroxy-9,15-dioxoprost-13-enoic acidGenerator
(5Z)-(13E)-11-alpha-Hydroxy-9,15-dioxoprosta-5,13-dienoic acidHMDB
(5Z,13E)-11-alpha-Hydroxy-9,15-dioxoprost-5,13-dienoic acidHMDB
9,15-dioxo-11-Hydroxyprosta-5,13-dienoic acidMeSH
15-Ketoprostaglandin e2, (11alpha)-isomerMeSH
Chemical FormulaC20H30O5
Average Molecular Weight350.4492
Monoisotopic Molecular Weight350.20932407
IUPAC Name(5Z)-7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional Name15-Keto-PGE2
CAS Registry Number26441-05-4
InChI Identifier
Chemical Taxonomy
ClassificationNot classified
StatusDetected and 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
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.058 mg/mLALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity98.54 m3·mol-1ChemAxon
Polarizability40.05 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified0.0006 (0.0002 - 0.0078) uMAdult (>18 years old)FemaleNormal 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 IDFDB023119
KNApSAcK IDNot Available
Chemspider ID4444303
KEGG Compound IDC04707
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03175
Metagene LinkHMDB03175
PubChem Compound5280719
PDB IDNot Available
ChEBI ID15547
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Fitzpatrick FA, Liggett WF, Wynalda MA: Albumin-eicosanoid interactions. A model system to determine their attributes and inhibition. J Biol Chem. 1984 Mar 10;259(5):2722-7. [PubMed:6698991 ]
  2. Yang P, Felix E, Madden T, Fischer SM, Newman RA: Quantitative high-performance liquid chromatography/electrospray ionization tandem mass spectrometric analysis of 2- and 3-series prostaglandins in cultured tumor cells. Anal Biochem. 2002 Sep 1;308(1):168-77. [PubMed:12234478 ]
  3. Harizi H, Gualde N: Pivotal role of PGE2 and IL-10 in the cross-regulation of dendritic cell-derived inflammatory mediators. Cell Mol Immunol. 2006 Aug;3(4):271-7. [PubMed:16978535 ]
  4. Gordon-Wright AP, Elder MG: Effect of prostaglandin E2 and its metabolites on lower segment myometrium in vitro. Eur J Obstet Gynecol Reprod Biol. 1980 Jun;10(5):297-302. [PubMed:7190512 ]