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Record Information
Version4.0
Creation Date2006-05-22 15:12:09 UTC
Update Date2017-09-27 08:24:18 UTC
HMDB IDHMDB0002776
Secondary Accession Numbers
  • HMDB02776
  • HMDB11650
Metabolite Identification
Common Name13,14-Dihydro-15-keto-PGE2
Description13,14-dihydro-15-keto-PGE2 is one of the prostaglandin E2 metabolites. (PMID 7190512 ) Human fetal lung in vitro has the competence to self-differentiate, as early as 12 weeks gestation and presence of high levels in fetal lung of the inactive metabolite 13,14-dihydro-15-keto-PGE2 relative to PGE2 suggests that active prostaglandin catabolism may be one of the mechanisms to retard this stage of maturation in vivo by limiting PGE2 availability. (PMID 8835315 )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.
Structure
Thumb
Synonyms
ValueSource
(5Z)-(15S)-11alpha-Hydroxy-9,15-dioxoprostanoateChEBI
13,14-dihydro-15-Ketoprostaglandin e2ChEBI
15-keto-13,14-dihydro-PGE2ChEBI
15-keto-13,14-Dihydroprostaglandin e2ChEBI
DHK-PGE2ChEBI
KH(2)PGE(2)ChEBI
PGEMChEBI
(5Z)-(15S)-11a-Hydroxy-9,15-dioxoprostanoateGenerator
(5Z)-(15S)-11a-Hydroxy-9,15-dioxoprostanoic acidGenerator
(5Z)-(15S)-11alpha-Hydroxy-9,15-dioxoprostanoic acidGenerator
(5Z)-(15S)-11α-hydroxy-9,15-dioxoprostanoateGenerator
(5Z)-(15S)-11α-hydroxy-9,15-dioxoprostanoic acidGenerator
11-alpha-Hydroxy-9,15-dioxoprost-5-enoateHMDB
11-alpha-Hydroxy-9,15-dioxoprost-5-enoic acidHMDB
15-keto-13,14-Dihydroprostaglandin e2, (11alpha)-isomerMeSH
PGEM (13,14-dihydro-15-keto-pge2)MeSH
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5Z)-7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid
Traditional NamePGEM
CAS Registry Number363-23-5
SMILES
CCCCCC(=O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,16-17,19,23H,2-3,5-6,8-14H2,1H3,(H,24,25)/b7-4-/t16-,17-,19-/m1/s1
InChI KeyCUJMXIQZWPZMNQ-XYYGWQPLSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Cyclopentanol
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Role

Industrial application:

Biological role:

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 Solubility0.072 g/LALOGPS
logP3.55ALOGPS
logP3.64ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)4.25ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity97.44 m³·mol⁻¹ChemAxon
Polarizability40.33 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00050 (0.00000 - 0.00870) uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.000397 +/- 6.2E-5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000389 +/- 0.000218 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00050 (0.00000 - 0.00825) uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.000136 +/- 0.000088 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.18 +/- 0.017 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.25 +/- 0.042 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000224 +/- 0.000057 uMAdult (>18 years old)BothSchizophrenia details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Mathe AA, Eberhard G, Saaf J, Wetterberg L: Plasma prostaglandin E2 metabolite--measured as 11-deoxy-15-keto-13,14-dihydro-11 beta,16 xi-cyclo-PGE2--in twins with schizophrenic disorder. Biol Psychiatry. 1986 Sep;21(11):1024-30. [PubMed:3741918 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023063
KNApSAcK IDNot Available
Chemspider ID4444296
KEGG Compound IDC04671
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID2311
PubChem Compound5280711
PDB IDNot Available
ChEBI ID15550
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. Hume R, Bell J, Cossar D, Giles M, Hallas A, Kelly R: Differential release of prostaglandins by organ cultures of human fetal trachea and lung. In Vitro Cell Dev Biol Anim. 1996 Jan;32(1):24-9. [PubMed:8835315 ]