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Record Information
Version4.0
Creation Date2006-08-13 15:01:54 UTC
Update Date2017-09-27 08:24:27 UTC
HMDB IDHMDB0004241
Secondary Accession Numbers
  • HMDB04241
Metabolite Identification
Common Name6-Ketoprostaglandin E1
Description6-Ketoprostaglandin E1 (6-keto PGE1) is a biologically active and stable prostacyclin (PGI2) metabolite and a substrate for Adenylate cyclase type III. 6-keto PGE1 is a potent coronary vasodilator. 6-keto PGE1 could be elevated in plasma of patients with primary thrombocythaemia. 6-keto-PGE1 has approximately four times less potent antiplatelet activity than PGI2 on a molar basis in man. The cardiovascular and plasma renin activity (PRA) changes are less prominent for 6-keto-PGE1 than PGI2. Salt loading slightly increases urinary 6-keto PGE1. 6-keto-PGE1 elicits the same biological effects as PGI2 in human platelets and in rabbit aorta and mesenteric artery, being, however, less potent. 6-keto-PGE1 dose-dependently stimulates adenylate cyclase activity in membranes of human platelets and cultured myocytes from rabbit aorta and mesenteric artery. The extent of stimulation of the enzyme by 6-keto-PGE1 is the same as elicited by PGI2, while the apparent affinity is lower than that of prostacyclin, both in platelets and in vascular smooth muscle cells. At the level of platelet membranes, 6-keto-PGE1 interacts with the binding sites labelled by PGI2. However, in platelets as well as in mesenteric artery myocytes, 6-keto-PGE1 interacts with only one class of sites as demonstrated either by binding or by adenylate cyclase studies, whereas PGI2 in the same conditions recognizes two different classes. (PMID: 3186779 , 3075239 , 3472253 , 3912001 , 3881881 , 6391491 )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
6-keto-PGE1ChEBI
6-keto-Prostaglandin e1ChEBI
6-oxo-PGE1ChEBI
6-Oxoprostaglandin e1ChEBI
6,9-dioxo-11R,15S-Dihydroxy-13E-prostenoateHMDB
6,9-dioxo-11R,15S-Dihydroxy-13E-prostenoic acidHMDB
6-keto PGE1HMDB
6-KPGE1HMDB
6-oxo-Prostaglandin e1HMDB
Chemical FormulaC20H32O6
Average Molecular Weight368.4645
Monoisotopic Molecular Weight368.219888756
IUPAC Name7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]-6-oxoheptanoic acid
Traditional Name6-Keto-PGE1
CAS Registry Number67786-53-2
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CC(=O)CCCCC(O)=O
InChI Identifier
InChI=1S/C20H32O6/c1-2-3-4-7-14(21)10-11-16-17(19(24)13-18(16)23)12-15(22)8-5-6-9-20(25)26/h10-11,14,16-18,21,23H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14-,16+,17+,18+/m0/s1
InChI KeyROUDCKODIMKLNO-CTBSXBMHSA-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
  • Fatty alcohol
  • Hydroxy fatty acid
  • Keto fatty acid
  • Cyclopentanol
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    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 Solubility0.18 g/LALOGPS
logP2.02ALOGPS
logP2.41ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.1ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity98.96 m³·mol⁻¹ChemAxon
Polarizability42.05 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-005l-5920000000-5d82d8d407a98a19595aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-0040-5920000000-b930e702a5edfe6a21b8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005l-5920000000-5d82d8d407a98a19595aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0040-5920000000-b930e702a5edfe6a21b8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fbc-9785000000-e00c3d94ffc45296f22aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00xu-9010370000-39dd50540f235321f2afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0019000000-45e089848974d223c817View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ff0-4259000000-5a1d119bcb0808abb167View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zg3-9420000000-67d99bbd6776618bd2a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-0009000000-f8af87f67576792f65d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-2289000000-d9d9ce800ce279bd0e23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9531000000-3a8f481b219ca74ab254View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Acetaminophen Action PathwayPw000687Pw000687 greyscalePw000687 simpleNot Available
Acetylsalicylic Acid PathwayPw000128Pw000128 greyscalePw000128 simpleNot Available
Antipyrine Action PathwayPw000669Pw000669 greyscalePw000669 simpleNot Available
Antrafenine Action PathwayPw000670Pw000670 greyscalePw000670 simpleNot Available
Arachidonic Acid MetabolismPw000044Pw000044 greyscalePw000044 simpleMap00590
Displaying entries 1 - 5 of 41 in total
Normal Concentrations
Not Available
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 IDFDB023346
KNApSAcK IDNot Available
Chemspider ID4444412
KEGG Compound IDC05962
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7036
PubChem Compound5280889
PDB IDNot Available
ChEBI ID28269
References
Synthesis ReferenceTanaka, T.; Hazato, A.; Bannai, K.; Okamura, N.; Sugiura, S.; Manabe, K.; Kurozumi, S.; Suzuki, M.; Noyori, R. Prostaglandin chemistry. XXIII. Short synthesis of 6-oxoprostaglandin E1 and 6-oxoprostaglandin F1a Tetrahedron Letters (1984), 25(43), 4947-50.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mastacchi R, Fadda S, Tomasi V, Barnabei O: The effect of 6-keto-prostaglandin E1 on human lymphocyte cAMP levels. Prostaglandins Med. 1980 Dec;5(6):487-94. [PubMed:6258185 ]
  2. Stanton BJ, Coupar IM: Influence of the thromboxane-mimetic U-46619 and the prostacyclin metabolite 6-keto prostaglandin E1 on vasoconstriction induced by noradrenaline and 5-HT in rat mesenteric vasculature. Prostaglandins Leukot Essent Fatty Acids. 1988 Jul;33(1):7-12. [PubMed:3186779 ]
  3. Panzenbeck MJ, Hintze TH, Kaley G: 6-Keto-prostaglandin E1 is a potent coronary vasodilator and stimulates a vagal reflex in dogs. J Pharmacol Exp Ther. 1988 Mar;244(3):814-9. [PubMed:3075239 ]
  4. Gibson BE, Buchanan MR, Barr RD, White JG: Primary thrombocythaemia in childhood: symptomatic episodes and their relationship to thromboxane A2, 6-keto-PGE1 and 12-hydroxy-eicosatetraenoic acid production: a case report. Prostaglandins Leukot Med. 1987 Mar;26(3):221-31. [PubMed:3472253 ]
  5. Miyamori I, Morise T, Yasuhara S, Takeda Y, Koshida H, Takeda R: Single-blind study of epoprostenol and 6-keto-prostaglandin E1 in man: effects of platelet aggregation and plasma renin. Br J Clin Pharmacol. 1985 Dec;20(6):681-3. [PubMed:3912001 ]
  6. Ogihara T, Gotoh S, Tabuchi Y, Kumahara Y: Involvement of endogenous prostaglandins in salt-induced hypertension. Acta Endocrinol (Copenh). 1985 Jan;108(1):114-8. [PubMed:3881881 ]
  7. Oliva D, Bernini F, Corsini A, Nicosia S: 6-Keto-prostaglandin E1-sensitive adenylate cyclase and binding sites in membranes from platelets and cultured smooth muscle cells. Biochem Pharmacol. 1984 Dec 1;33(23):3755-8. [PubMed:6391491 ]