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Human Metabolome Database Version 2.5

 

Showing metabocard for 15-Keto-prostaglandin E2 (HMDB03175)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-05-22 16:12:38
Update Date 2009-06-23 13:52:44
Accession Number HMDB03175
Secondary Accession Numbers Not Available
Common Name 15-Keto-prostaglandin E2
Description 15-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.
Synonyms
  1. 15-Keto-PGE2
  2. 15-Ketoprostaglandin E2
  3. 15-Oxo-PGE2
  4. (5Z)-(13E)-11-alpha-hydroxy-9,15-dioxoprosta-5,13-dienoate
  5. (5Z)-(13E)-11-alpha-hydroxy-9,15-dioxoprosta-5,13-dienoic acid
  6. (5Z,13E)-11-alpha-hydroxy-9,15-dioxoprost-5,13-dienoate
  7. (5Z,13E)-11-alpha-hydroxy-9,15-dioxoprost-5,13-dienoic acid
  8. 15-keto-PGE2-alpha
  9. 15-oxo-PGE2-alpha
Chemical IUPAC Name (E)-7-[(1R,2S,3R)-3-hydroxy-5-oxo-2-[(E)-3-oxooct-1-enyl]cyclopentyl]hept-5-enoic acid
Chemical Formula C20H30O5
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Prostanoids
Sub Class
  • Prostaglandins
Family
  • Mammalian Metabolite
Species
  • ketone
  • secondary alcohol
  • carboxylic acid
  • alkene
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 350.449
Monoisotopic Molecular Weight 350.209320
Isomeric SMILES CCCCCC(=O)C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CC=C/CCCC(O)=O
Canonical SMILES CCCCCC(=O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB03175 Link Image
Metagene Link HMDB03175 Link Image
METLIN ID 2309 Link Image
PubChem Compound 5280719 Link Image
PubChem Substance 737588 Link Image
ChEBI ID Not Available
CAS Registry Number 26441-05-4
InChI Identifier InChI=1/C20H30O5/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/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17-,19-/m1/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.0583 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 3.27 [Predicted by ALOGPS]; 2.48 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location
  • Blood
Tissue Location Not Available
Concentrations (Normal)
Biofluid Blood
Value 0.0006 (0.0002 - 0.0078) uM
Age Adult:>18 yrs old
Sex Female
Patient information After intra-vaginal insertion of 15-keto-Prostaglandin E2 (2mg - 5mg)
Comments Not Available
References
  • Gordon-Wright AP, Elder MG: The systemic absorption from the vagina of prostaglandin E2 administered for the induction of labour. Prostaglandins. 1979 Jul;18(1):153-60. [PubMed Link Image]
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways 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 Link Image]
  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 Link Image]