Showing metabocard for 6-Ketoprostaglandin E1 (BMDB0004241)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:08:46 UTC
Update Date2020-04-22 15:13:35 UTC
BMDB IDBMDB0004241
Secondary Accession Numbers
  • BMDB04241
Metabolite Identification
Common Name6-Ketoprostaglandin E1
Description6-Ketoprostaglandin E1, also known as 6-keto-pge1, 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. Thus, 6-ketoprostaglandin E1 is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on 6-Ketoprostaglandin E1.
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 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
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001j-0009000000-01c968c8cd4c28bf567aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-0295000000-093a8b0ed51f2cecd442View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9630000000-d9c29be766e2f8baf56eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-dfb0d2876bb26fdeafb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-7289000000-d599ab945a6d037940daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9500000000-62acdce350cfcd26aebfView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004241
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 ReferencesNot Available