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Record Information
Creation Date2006-05-22 14:17:45 UTC
Update Date2016-02-11 01:05:32 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,3-Dinor-6-keto-prostaglandin F1 a
Description2,3-dinor-6-keto-prostaglandin F1 alpha is a major urinary prostacyclin metabolite, and is significantly higher in 9 patients with severe atherosclerosis and evidence of platelet activation. Prostacyclin is a potent vasodilator and platelet inhibitor produced by vascular endothelium. Endogenous production of prostacyclin under physiologic conditions is extremely low, far below the capacity of vascular tissue to generate this substance in response to stimulation in vitro. This may reflect a low frequency or intensity of stimulation of prostacyclin production. 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. (PMID: 6231483 , 7000774 , 6231483 , 16303599 , 16533160 , 17073611 , 17164138 )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.
2,3-Dinor-6-keto-prostaglandin F1 alphaHMDB
9S,11S,13S-Trihydroxy-2,3-dinor-5Z,13E-prostadienoic acidHMDB
Chemical FormulaC18H30O6
Average Molecular Weight342.4272
Monoisotopic Molecular Weight342.204238692
IUPAC Name5-[(1R,2R,3S,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-4-oxopentanoic acid
Traditional Name5-[(1R,2R,3S,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-4-oxopentanoic acid
CAS Registry NumberNot Available
InChI Identifier
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
  • Prostaglandin skeleton
  • Medium-chain keto acid
  • Fatty alcohol
  • Carbocyclic fatty acid
  • Gamma-keto acid
  • Keto acid
  • Cyclopentanol
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
StatusDetected and Quantified
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.91 mg/mLALOGPS
pKa (Strongest Acidic)4.26ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity90.79 m3·mol-1ChemAxon
Polarizability37.94 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified3.8E-5 +/- 8E-6 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0075 +/- 0.00079 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0063 +/- 0.0011 umol/mmol creatinineAdult (>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 IDFDB022942
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02277
Metagene LinkHMDB02277
METLIN IDNot Available
PubChem Compound53477747
PDB IDNot Available
ChEBI 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. [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. [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. [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. [16533160 ]
  5. Nakayama T: Prostacyclin analogues: prevention of cardiovascular diseases. Cardiovasc Hematol Agents Med Chem. 2006 Oct;4(4):351-9. [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. [17164138 ]