Prostaglandin F1a (CHEM035462)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:47:10 UTC
Update Date2016-11-09 01:21:19 UTC
Accession NumberCHEM035462
Identification
Common NameProstaglandin F1a
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(13E,15S)-9alpha,11alpha-9,11,15-Trihydroxyprost-13-en-1-Oic acidChEBI
PGF 1-alphaChEBI
Prostaglandin F1ChEBI
Prostaglandin F1-alphaChEBI
(13E,15S)-9a,11a-9,11,15-Trihydroxyprost-13-en-1-OateGenerator
(13E,15S)-9a,11a-9,11,15-Trihydroxyprost-13-en-1-Oic acidGenerator
(13E,15S)-9alpha,11alpha-9,11,15-Trihydroxyprost-13-en-1-OateGenerator
(13E,15S)-9Α,11α-9,11,15-trihydroxyprost-13-en-1-OateGenerator
(13E,15S)-9Α,11α-9,11,15-trihydroxyprost-13-en-1-Oic acidGenerator
PGF 1-aGenerator
PGF 1-ΑGenerator
Prostaglandin F1-aGenerator
Prostaglandin F1-αGenerator
3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)- (8ci)-cyclopentaneheptanoateHMDB
3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)- (8ci)-cyclopentaneheptanoic acidHMDB
9a,11a,15(S)-Trihydroxy-13-trans-prostenoateHMDB
9a,11a,15(S)-Trihydroxy-13-trans-prostenoic acidHMDB
Prostaglandin F1alphaHMDB, MeSH
PGF1MeSH, HMDB
Prostaglandin F1, (9alpha,11beta,13E,15S)-isomerMeSH, HMDB
PGF1alphaMeSH, HMDB
PGF1 alphaMeSH, HMDB
Prostaglandin F1, (9alpha,11alpha,13E,15S)-(+-)-isomerMeSH, HMDB
Prostaglandin F1, (8beta,9alpha,11alpha,13E,15S)-isomerMeSH, HMDB
Prostaglandin F1, (9alpha,11alpha,13E,15R)-isomerMeSH, HMDB
PGF1aGenerator, HMDB
PGF1ΑGenerator, HMDB
Chemical FormulaC20H36O5
Average Molecular Mass356.497 g/mol
Monoisotopic Mass356.256 g/mol
CAS Registry Number745-62-0
IUPAC Name7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]heptanoic acid
Traditional Nameprostaglandin f1α
SMILESCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CCCCCCC(O)=O
InChI IdentifierInChI=1S/C20H36O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-19,21-23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,18-,19+/m0/s1
InChI KeyDZUXGQBLFALXCR-CDIPTNKSSA-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
  • Cyclopentanol
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Alcohol
  • Organic oxygen 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 Solubility0.11 g/LALOGPS
logP3.95ALOGPS
logP2.97ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.41ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity99.35 m³·mol⁻¹ChemAxon
Polarizability42.53 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, Positivesplash10-01q0-7379000000-a80bb477130f4920e3f8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00c0-8210189000-df23bea8a59fa9bad99cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0009000000-ee4ad5913a757d21e80aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-3197000000-f2995d281bea49b8f8cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00vl-9160000000-66d373db3994a9b69253Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-0009000000-a68b82b30b1209712169Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-1039000000-0eb2b0c2f394df865d7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9631000000-3696ca86fef9e2d7e6c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-ca50430fcebead154dceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0059000000-f1ee0351b4eb7afd7ee2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0035-6093000000-26f9e8ca80319a072955Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0019000000-9fe4f88bef4300069cc6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9154000000-e93e360b803128be6ab5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9400000000-b045babce70118a4fad8Spectrum
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 IDHMDB0002685
FooDB IDFDB023044
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID3503
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4444441
ChEBI ID28852
PubChem Compound ID5280939
Kegg Compound IDC06475
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Schneider, William P.; Murray, Herbert C. Microbiological reduction and resolution of prostaglandins. Synthesis of natural PGF2a and ENT-PGF2b methyl esters. Journal of Organic Chemistry (1973), 38(2), 397-8.
2. Sutton JG, Bosley C, Rands A: The detection by enzyme linked immunosorbent assay of P30 and 19-OH prostaglandin F1/F2, in the presence of a range of possible contaminants. Sci Justice. 1998 Jul-Sep;38(3):157-64.
3. King SJ, Sutton JG, Trewsdale LA: Radioimmunoassay detection limits for 19-OH F1 alpha/F2 alpha prostaglandin in normal, infertile and vasectomized semen stains. Analysis of saliva, sweat and urine for possible non-specific or matrix effects. Forensic Sci Int. 1989 Mar;40(3):221-9.
4. O'Neill P, Walton S, Foy PM, Shaw MD: Role of prostaglandins in delayed cerebral ischemia after subarachnoid hemorrhage. Neurosurgery. 1992 Jan;30(1):17-22.
5. Beitz J, Forster W: Influence of human low density and high density lipoprotein cholesterol on the in vitro prostaglandin I2 synthetase activity. Biochim Biophys Acta. 1980 Dec 5;620(3):352-5.
6. Schweer H, Seyberth HW, Kuhl PG, Meese CO: Unusual metabolism of prostacyclin in infants with persistent septic pulmonary hypertension. Eicosanoids. 1990;3(4):237-42.
7. Barrow SE, Waddell KA, Ennis M, Dollery CT, Blair IA: Analysis of picomolar concentrations of 6-oxo-prostaglandin F1 alpha in biological fluids. J Chromatogr. 1982 Apr 30;239:71-80.