Showing metabocard for Prostaglandin F1a (BMDB0002685)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:01:15 UTC
Update Date2020-04-22 15:11:16 UTC
BMDB IDBMDB0002685
Secondary Accession Numbers
  • BMDB02685
Metabolite Identification
Common NameProstaglandin F1a
DescriptionProstaglandin F1a, also known as PGF 1-alpha or PGF 1-Α, 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, prostaglandin F1A is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on Prostaglandin F1a.
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 Weight356.4968
Monoisotopic Molecular Weight356.256274262
IUPAC Name7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]heptanoic acid
Traditional Nameprostaglandin f1α
CAS Registry Number745-62-0
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CCCCCCC(O)=O
InChI Identifier
InChI=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
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01q0-7379000000-a80bb477130f4920e3f8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00c0-8210189000-df23bea8a59fa9bad99cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0009000000-ee4ad5913a757d21e80aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-3197000000-f2995d281bea49b8f8cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00vl-9160000000-66d373db3994a9b69253View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-0009000000-a68b82b30b1209712169View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-1039000000-0eb2b0c2f394df865d7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9631000000-3696ca86fef9e2d7e6c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-ca50430fcebead154dceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0059000000-f1ee0351b4eb7afd7ee2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0035-6093000000-26f9e8ca80319a072955View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0019000000-9fe4f88bef4300069cc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9154000000-e93e360b803128be6ab5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9400000000-b045babce70118a4fad8View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002685
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023044
KNApSAcK IDNot Available
Chemspider ID4444441
KEGG Compound IDC06475
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3503
PubChem Compound5280939
PDB IDNot Available
ChEBI ID28852
References
Synthesis ReferenceSchneider, 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.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available