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Record Information
Version1.0
Creation Date2016-09-30 22:41:36 UTC
Update Date2020-05-21 16:28:39 UTC
BMDB IDBMDB0001139
Secondary Accession Numbers
  • BMDB01139
Metabolite Identification
Common NameProstaglandin F2a
DescriptionProstaglandin F2a, also known as 9a,11a-PGF2 or enzaprost, 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 F2A is considered to be an eicosanoid lipid molecule. Prostaglandin F2a is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
ValueSource
(+)-Prostaglandin F2aHMDB
(5Z,13E)-(15S)-9-alpha,11-alpha,15-Trihydroxyprosta-5,13-dienoateHMDB
(5Z,13E)-(15S)-9-alpha,11-alpha,15-Trihydroxyprosta-5,13-dienoic acidHMDB
(5Z,13E,15S)-9a,11a,15-Trihydroxyprosta-5,13-dien-1-OateHMDB
(5Z,13E,15S)-9a,11a,15-Trihydroxyprosta-5,13-dien-1-Oic acidHMDB
(5Z,9a,11a,13E,15S)-9,11,15-Trihydroxy-prosta-5,13-dien-1-OateHMDB
(5Z,9a,11a,13E,15S)-9,11,15-Trihydroxy-prosta-5,13-dien-1-Oic acidHMDB
(9alpha,11alpha,15)-Trihydroxyprosta-(5Z,13E)-dien-1-OateHMDB
(9alpha,11alpha,15)-Trihydroxyprosta-(5Z,13E)-dien-1-Oic acidHMDB
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoateHMDB
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acidHMDB
9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-OateHMDB
9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-Oic acidHMDB
9,11,15-Trihydroxyprosta-5Z,13E-dien-1-OateHMDB
9,11,15-Trihydroxyprosta-5Z,13E-dien-1-Oic acidHMDB
9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoateHMDB
9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoic acidHMDB
9a,11a-PGF2HMDB
9a,11a-PGF2aHMDB
AmoglandinHMDB
CyclosinHMDB
DinifertinHMDB
DinoprostHMDB
EnzaprostHMDB
Enzaprost FHMDB
F2a IsoprostaneHMDB
Glandin NHMDB
L-PGF2-alphaHMDB
L-Prostaglandin F2-alphaHMDB
PanacelanHMDB
PGF2aHMDB
Prostaglandin F2HMDB
ProstamateHMDB
Prostarmon FHMDB
Prostin F 2 alphaHMDB
ProtamodinHMDB
9alpha,11beta PGF2HMDB
9alpha,11beta-PGF2HMDB
EstrofanHMDB
F2 alpha, ProstaglandinHMDB
F2alpha, ProstaglandinHMDB
PGF2HMDB
PGF2 alphaHMDB
PGF2alphaHMDB
Prostaglandin F2 alphaHMDB
Prostaglandin F2alphaHMDB
alpha, PGF2HMDB
Chemical FormulaC20H34O5
Average Molecular Weight354.481
Monoisotopic Molecular Weight354.240624198
IUPAC Name(5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional Name5-trans-PGF2α
CAS Registry Number551-11-1
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O
InChI Identifier
InChI=1S/C20H34O5/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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4+,13-12+/t15-,16+,17+,18-,19+/m0/s1
InChI KeyPXGPLTODNUVGFL-UAAPODJFSA-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
  • Cyclopentanol
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Secondary alcohol
  • 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
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 Point30 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.39BODOR,H & HUANG,M (1992)
Predicted Properties
PropertyValueSource
logP3.11ALOGPS
logP2.61ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity100.47 m³·mol⁻¹ChemAxon
Polarizability41.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0019-6489000000-bf681ff653e664e9cde0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-9300188000-0fc1fbcf7464fb00c07eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0009000000-cd642664d59adb85ae59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0019000000-3c46ffbee46021b80901View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bi-2297000000-9fe530991fdc645e26f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0103-9170000000-0fa33343bc482bd6f5a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-0009000000-a337fc1b13431013f06aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1039000000-40b895b35529c4a81763View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9631000000-8dc66a223446641955e6View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Adrenal Gland
  • Epidermis
  • Placenta
  • Platelet
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal GlandExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001139
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022448
KNApSAcK IDNot Available
Chemspider ID4446204
KEGG Compound IDC00639
BioCyc IDNot Available
BiGG ID35568
Wikipedia LinkProstaglandin F2alpha
METLIN ID6032
PubChem Compound5283078
PDB IDNot Available
ChEBI ID15553
References
Synthesis ReferenceChen, Shaoqing; Janda, Kim D. Total synthesis of naturally occurring prostaglandin F2a on a non-crosslinked polystyrene support. Tetrahedron Letters (1998), 39(23), 3943-3946.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Lipid transport and metabolism
Specific function:
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione (By similarity).
Gene Name:
CBR1
Uniprot ID:
Q3SZD7
Molecular weight:
30533.0
Reactions
Prostaglandin E2 + NADPH → Prostaglandin F2a + NADPdetails
General function:
Not Available
Specific function:
Catalyzes the reduction of prostaglandin-ethanolamide H(2) (prostamide H(2)) to prostamide F(2alpha) with NADPH as proton donor. Also able to reduce prostaglandin H(2) to prostaglandin F(2alpha) (By similarity).
Gene Name:
PRXL2B
Uniprot ID:
Q58CY6
Molecular weight:
21497.0
Reactions
Prostaglandin H2 → Prostaglandin F2adetails