6-Ketoprostaglandin E1 (CHEM035660)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:58:00 UTC
Update Date2016-11-09 01:21:21 UTC
Accession NumberCHEM035660
Identification
Common Name6-Ketoprostaglandin E1
ClassSmall Molecule
DescriptionA prostaglandin E that is prostaglandin E1 bearing a keto substituent at the 6-position.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6-Keto-pge1ChEBI
6-Keto-prostaglandin e1ChEBI
6-oxo-PGE1ChEBI
6-Oxoprostaglandin e1ChEBI, HMDB, MeSH
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 Mass368.465 g/mol
Monoisotopic Mass368.220 g/mol
CAS Registry Number67786-53-2
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
SMILESCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CC(=O)CCCCC(O)=O
InChI IdentifierInChI=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
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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-005l-5920000000-5d82d8d407a98a19595aSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-0040-5920000000-b930e702a5edfe6a21b8Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005l-5920000000-5d82d8d407a98a19595aSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0040-5920000000-b930e702a5edfe6a21b8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fbc-9785000000-e00c3d94ffc45296f22aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00xu-9010370000-39dd50540f235321f2afSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0019000000-45e089848974d223c817Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ff0-4259000000-5a1d119bcb0808abb167Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zg3-9420000000-67d99bbd6776618bd2a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-0009000000-f8af87f67576792f65d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-2289000000-d9d9ce800ce279bd0e23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9531000000-3a8f481b219ca74ab254Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001j-0009000000-01c968c8cd4c28bf567aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-0295000000-093a8b0ed51f2cecd442Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9630000000-d9c29be766e2f8baf56eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-dfb0d2876bb26fdeafb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-7289000000-d599ab945a6d037940daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9500000000-62acdce350cfcd26aebfSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004241
FooDB IDFDB023346
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID7036
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4444412
ChEBI ID28269
PubChem Compound ID5280889
Kegg Compound IDC05962
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=2858551
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=3240016
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=3881101
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=6132981
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=6360281
6. Tanaka, 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.
13. 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.