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Record Information
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:30 UTC
Update Date2020-02-26 21:23:41 UTC
Secondary Accession Numbers
  • HMDB01979
Metabolite Identification
Common Name6,15-Diketo,13,14-dihydro-PGF1a
Description6,15-diketo,13,14-dihydro-PGF1 alpha is a minor metabolite of prostacyclin (PGI2). Prostacyclin (PGI2) is one of the major vascular protectors against thrombosis and vasoconstriction, caused by thromboxane A(2). PGI2 inhibits platelet aggregation and vasoconstriction. PGI2 synthase (PGIS), a catalyst of PGI2 formation from prostaglandin H2, is widely distributed and predominantly found in vascular endothelial and smooth muscle cells. PGI2 plays an important cardioprotective role increasingly appreciated in recent years in light of adverse effects of COX-2 inhibitors in clinical trials. This cardioprotection is thought to be mediated, in part, by prostacyclin inhibition of platelet aggregation. Multiple lines of evidence suggest that prostacyclin additionally protects from cardiovascular disease by pleiotropic effects on vascular smooth muscle. PGI2 inhibits proliferation of cultured vascular SMCs by inhibiting cell cycle progression from G1 to S phase. Progression through G1 phase is regulated by the sequential activation of the G1 phase cyclin-dependent kinases (cdks). (PMID: 7000774 , 6231483 , 16303599 , 16533160 , 17073611 , 17164138 ).
6,15-Dioxo-9S,11R-dihydroxy-13E-prostenoic acidChEBI
6,15-Diketo,13,14-dihydroprostaglandin F1aHMDB
6,15-Diketo,13,14-dihydroprostaglandin F1αHMDB
Chemical FormulaC20H32O6
Average Molecular Weight368.4645
Monoisotopic Molecular Weight368.219888756
IUPAC Name7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]-6-oxoheptanoic acid
Traditional Name7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]-6-oxoheptanoic acid
CAS Registry Number63446-59-3
InChI Identifier
Chemical Taxonomy
Description 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
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Keto fatty acid
  • Cyclopentanol
  • Alpha,beta-unsaturated ketone
  • Cyclic alcohol
  • Enone
  • Acryloyl-group
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors

Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Biological role:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.16 g/LALOGPS
pKa (Strongest Acidic)4.14ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity99.1 m³·mol⁻¹ChemAxon
Polarizability41.09 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0g4r-3976000000-5bc2fe04581b9244d5b1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01b9-3543390000-25f79f833097c2d10877Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0019000000-8dca4677737c527f6a76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05ai-5279000000-1dac7223ee81fe387bedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059x-9341000000-25a9ad4937aaf25954d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-4147d0867aae1ef5ae18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aos-2297000000-13fed642b0d2cab3f6f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9541000000-2003f43a0d54db7a4ba5Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Normal Concentrations
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      Phenol Explorer Compound IDNot Available
      FooDB IDFDB022777
      KNApSAcK IDNot Available
      Chemspider ID4446160
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound5283033
      PDB IDNot Available
      ChEBI ID72595
      Food Biomarker OntologyNot Available
      VMH IDNot Available
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Rosenkranz B, Fischer C, Weimer KE, Frolich JC: Metabolism of prostacyclin and 6-keto-prostaglandin F1 alpha in man. J Biol Chem. 1980 Nov 10;255(21):10194-8. [PubMed:7000774 ]
      2. FitzGerald GA, Smith B, Pedersen AK, Brash AR: Increased prostacyclin biosynthesis in patients with severe atherosclerosis and platelet activation. N Engl J Med. 1984 Apr 26;310(17):1065-8. [PubMed:6231483 ]
      3. Kothapalli D, Flores-Stewart SA, Assoian RK: Antimitogenic effects of prostacyclin on the G1 phase cyclin-dependent kinases. Prostaglandins Other Lipid Mediat. 2005 Dec;78(1-4):3-13. Epub 2005 May 31. [PubMed:16303599 ]
      4. Ruan KH, Dogne JM: Implications of the molecular basis of prostacyclin biosynthesis and signaling in pharmaceutical designs. Curr Pharm Des. 2006;12(8):925-41. [PubMed:16533160 ]
      5. Nakayama T: Prostacyclin analogues: prevention of cardiovascular diseases. Cardiovasc Hematol Agents Med Chem. 2006 Oct;4(4):351-9. [PubMed:17073611 ]
      6. Fetalvero KM, Martin KA, Hwa J: Cardioprotective prostacyclin signaling in vascular smooth muscle. Prostaglandins Other Lipid Mediat. 2007 Jan;82(1-4):109-18. Epub 2006 Jul 7. [PubMed:17164138 ]