6,15-Diketo,13,14-dihydro-PGF1a (CHEM022516)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:38:14 UTC
Update Date2016-11-09 01:17:31 UTC
Accession NumberCHEM022516
Identification
Common Name6,15-Diketo,13,14-dihydro-PGF1a
ClassSmall Molecule
DescriptionA prostaglandin Falpha that is prostaglandin F1alpha bearing keto substituents at positions 6 and 15.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6,15-Dioxo-9S,11R-dihydroxy-13E-prostenoic acidChEBI
6,15DK,13,14DH-PGF1aChEBI
6,15-Dioxo-9S,11R-dihydroxy-13E-prostenoateGenerator
6,15-diketo,13,14-dihydro-PGF1alphaHMDB
6,15-diketo-13,14-dihydro-PGF1aHMDB
6,15-Diketo,13,14-dihydroprostaglandin F1aGenerator, HMDB
6,15-Diketo,13,14-dihydroprostaglandin F1αGenerator, HMDB
Chemical FormulaC20H32O6
Average Molecular Mass368.465 g/mol
Monoisotopic Mass368.220 g/mol
CAS Registry Number63446-59-3
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
SMILESCCCCCC(=O)\C=C\[C@H]1[C@H](O)C[C@H](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/h10-11,16-19,23-24H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t16-,17-,18-,19+/m1/s1
InChI KeyVKPWUQVGTPVEMU-QVPQFPIISA-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
  • 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
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 Solubility0.16 g/LALOGPS
logP2.04ALOGPS
logP2.21ChemAxon
logS-3.4ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fsi-0029000000-aaf0f6611d057ef21a2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9245000000-ac182ababaf86b60a84bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-99e5e4b43a6bcead6898Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-015a-0019000000-3e129a5512a3b7a729d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-103a-1395000000-170923c227f1323cc7f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9510000000-0487a84aaa4798546500Spectrum
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 IDHMDB0001979
FooDB IDFDB022777
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4446160
ChEBI ID72595
PubChem Compound ID5283033
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
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.
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.
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.
5. Nakayama T: Prostacyclin analogues: prevention of cardiovascular diseases. Cardiovasc Hematol Agents Med Chem. 2006 Oct;4(4):351-9.
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.