6-Keto-prostaglandin F1a (CHEM021670)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:09:36 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021670
Identification
Common Name6-Keto-prostaglandin F1a
ClassSmall Molecule
DescriptionA prostaglandin Falpha that is prostaglandin F1alpha bearing a keto substituent at the 6-position.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
6-Keto-PGF1aChEBI
6-Keto-PGF1alphaChEBI
6-Keto-prostaglandin F1alphaChEBI
6-Ketoprostaglandin F1alphaChEBI
6-oxo-PGF1alphaChEBI
6-oxo-Prostaglandin F1alphaChEBI
6-Keto-PGF1αGenerator
6-Keto-prostaglandin F1αGenerator
6-Ketoprostaglandin F1aGenerator
6-Ketoprostaglandin F1αGenerator
6-oxo-PGF1aGenerator
6-oxo-PGF1ΑGenerator
6-oxo-Prostaglandin F1aGenerator
6-oxo-Prostaglandin F1αGenerator
6 oxo PGF1 alphaMeSH
6 Oxoprostaglandin F1 alphaMeSH
6-Keto-PGF1 alphaMeSH
6-oxo-PGF1 alphaMeSH
F1 alpha, 6-OxoprostaglandinMeSH
alpha, 6-Keto-PGF1MeSH
alpha, 6-Oxoprostaglandin F1MeSH
6 Keto PGF1 alphaMeSH
6-Ketoprostaglandin F1 alphaMeSH
6-Oxoprostaglandin F1 alphaMeSH
F1 alpha, 6-KetoprostaglandinMeSH
alpha, 6-Ketoprostaglandin F1MeSH
alpha, 6-oxo-PGF1MeSH
6 Ketoprostaglandin F1 alphaMeSH
6-Oxoprostaglandin F1alphaChEBI, HMDB
6-Oxoprostaglandin F1aGenerator, HMDB
6-Oxoprostaglandin F1αGenerator, HMDB
6-oxo-9S,11R,15S-Trihydroxy-13E-prostenoateHMDB
6-oxo-9S,11R,15S-Trihydroxy-13E-prostenoic acidHMDB
Chemical FormulaC20H34O6
Average Molecular Mass370.480 g/mol
Monoisotopic Mass370.236 g/mol
CAS Registry Number58962-34-8
IUPAC Name7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-6-oxoheptanoic acid
Traditional Name6 keto PGF1 α
SMILESCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC(=O)CCCCC(O)=O
InChI IdentifierInChI=1S/C20H34O6/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/h10-11,14,16-19,21,23-24H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14-,16+,17+,18+,19-/m0/s1
InChI KeyKFGOFTHODYBSGM-ZUNNJUQCSA-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
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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 Solubility0.46 g/LALOGPS
logP1.75ALOGPS
logP1.79ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)4.14ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity100 m³·mol⁻¹ChemAxon
Polarizability42.48 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)splash10-0fj0-4920000000-106328b50f1f2f297ec4Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fj0-4920000000-106328b50f1f2f297ec4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fbc-7889000000-c51e44d63bd792b1ec6dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0006-4100279000-1636439cbaa3cd775a98Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0019000000-cc7bcdd01a8e316b6f16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3269000000-48cfefe23c0a5753c60bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-9451000000-dd83fb4bf88cd772a8c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0019000000-93edc1e964871bcde0a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pvi-2289000000-3e28055c2f4d8dfcd540Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9431000000-747a8063fb8f9cdcc3c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0019000000-704513759e9fd1ad8e9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-9366000000-7750caf5dc0451a37f06Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9400000000-21328656b96a98f4c9f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gc0-0009000000-b634e12e6a20562bd35fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-1030-0297000000-896903bc299e1df75493Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9640000000-b2f2f57806964f492154Spectrum
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 IDHMDB0002886
FooDB IDFDB023077
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6782
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4444411
ChEBI ID28158
PubChem Compound ID5280888
Kegg Compound IDC05961
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11034952
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11481608
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11510754
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11529335
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11798014
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=12535846
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=12912853
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=14735492
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15108967
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=15550787
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=15684771
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=15883739
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=18942642
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=6107345
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=6132981
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=7864124
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=9013819
18. de la Cruz JP, Guerrero A, Gonzalez-Correa JA, Marquez E, Nacle I, Sanchez de la Cuesta F: Effects of two preparations of 75-mg extended-release aspirin on platelet aggregation, prostanoids and nitric oxide production in humans. Eur J Clin Pharmacol. 2002 Jan;57(11):775-80.
19. Laitinen O, Seppala E, Nissila M, Vapaatalo H: Plasma levels and urinary excretion of prostaglandins in patients with rheumatoid arthritis. Clin Rheumatol. 1983 Dec;2(4):401-6.
20. Jawerbaum A, Rosello Catafau J, Gonzalez ET, Novaro V, Gomez G, Gelpi E, Gimeno MA: Eicosanoid production by placental and amnion tissues from control and non-insulin-dependent diabetic rats. Influence of oxytocin in the incubating medium. Prostaglandins Leukot Essent Fatty Acids. 1997 Jun;56(6):425-9.
21. Cerletti C, Dell'Elba G, Manarini S, Pecce R, Di Castelnuovo A, Scorpiglione N, Feliziani V, de Gaetano G: Pharmacokinetic and pharmacodynamic differences between two low dosages of aspirin may affect therapeutic outcomes. Clin Pharmacokinet. 2003;42(12):1059-70.
22. Katori M, Majima M, Harada Y: Possible background mechanisms of the effectiveness of cyclooxygenase-2 inhibitors in the treatment of rheumatoid arthritis. Inflamm Res. 1998 Oct;47 Suppl 2:S107-11.
23. Fain JN, Ballou LR, Bahouth SW: Obesity is induced in mice heterozygous for cyclooxygenase-2. Prostaglandins Other Lipid Mediat. 2001 Jul;65(4):199-209.
24. Rogov VA, Shilov EM, Kozlovskaia NL, Gordovskaia NB, Sidorova IS, Krylova MIu, Artem'eva VB: [Endothelium and platelets in pregnant women with chronic glomerulonephritis and therapeutic efficacy of acetylsalicylic acid and dipiridamol]. Ter Arkh. 2004;76(12):58-64.
25. Wubert J, Reder E, Kaser A, Weber PC, Lorenz RL: Simultaneous solid phase extraction, derivatization, and gas chromatographic mass spectrometric quantification of thromboxane and prostacyclin metabolites, prostaglandins, and isoprostanes in urine. Anal Chem. 1997 Jun 1;69(11):2143-6.
26. Wang GQ, Zou ZZ, Yu DP: [A study of the role of plasma thromboxane B2 and 6-keto-prostaglandin F1 alpha in epidemic hemorrhagic fever]. Zhonghua Nei Ke Za Zhi. 1990 Mar;29(3):138-40, 188.
27. Terada K, Hayashi G, Hokama Y: C-reactive protein and 6-keto prostaglandin F 1-alpha in patients with gynecologic cancer. Gynecol Oncol. 1990 Feb;36(2):212-4.
28. Miao XY: [Plasma level and effects of thromboxane A2 and 6-keto-PGF1 alpha in patients with acute obstructive suppurative cholangitis]. Zhonghua Wai Ke Za Zhi. 1990 Apr;28(4):228-30, 253-4.
29. Symons JD: Longitudinal and cross-sectional studies of the relationship between 6-keto PGF1 alpha and high density lipoproteins. Prostaglandins Leukot Essent Fatty Acids. 1990 Feb;39(2):159-65.