Back to Compounds

Showing Compound 6,15-Diketo,13,14-dihydro-PGF1a (FDB022777)

Record Information
Version1.0
Creation date2011-09-21 00:19:29 UTC
Update date2015-07-21 06:57:21 UTC
Primary IDFDB022777
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name6,15-Diketo,13,14-dihydro-PGF1a
Description6,15-diketo,13,14-dihydro-PGF1 alpha is a minor metabolite of prostacyclin (PGI2). Prostacyclin (PGI2) is one of the major vascular protectors against thrombosis and vasoconstriction, caused by thromboxane A(2). PGI2 inhibits platelet aggregation and vasoconstriction. 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. Progression through G1 phase is regulated by the sequential activation of the G1 phase cyclin-dependent kinases (cdks). (PMID: 7000774, 6231483, 16303599, 16533160, 17073611, 17164138) [HMDB]
CAS Number63446-59-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
6,15-dioxo-9S,11R-dihydroxy-13E-prostenoatehmdb
6,15-dioxo-9S,11R-dihydroxy-13E-prostenoic acidhmdb
6,15Dk,13,14dh-pgf1aChEBI
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H32O6
IUPAC name7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]-6-oxoheptanoic acid
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
Isomeric SMILESCCCCCC(=O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC(=O)CCCCC(O)=O
Average Molecular Weight368.4645
Monoisotopic Molecular Weight368.219888756
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS6,15-Diketo,13,14-dihydro-PGF1a, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0g4r-3976000000-5bc2fe04581b9244d5b1Spectrum
Predicted GC-MS6,15-Diketo,13,14-dihydro-PGF1a, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01b9-3543390000-25f79f833097c2d10877Spectrum
Predicted GC-MS6,15-Diketo,13,14-dihydro-PGF1a, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0019000000-8dca4677737c527f6a762016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05ai-5279000000-1dac7223ee81fe387bed2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059x-9341000000-25a9ad4937aaf25954d12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-4147d0867aae1ef5ae182016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aos-2297000000-13fed642b0d2cab3f6f62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9541000000-2003f43a0d54db7a4ba52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fsi-0029000000-aaf0f6611d057ef21a2e2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9245000000-ac182ababaf86b60a84b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-99e5e4b43a6bcead68982021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-015a-0019000000-3e129a5512a3b7a729d72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-103a-1395000000-170923c227f1323cc7f02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9510000000-0487a84aaa47985465002021-09-24View Spectrum
NMRNot Available
ChemSpider ID4446160
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5283033
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01979
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference