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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-15 09:54:55 UTC
Update Date2017-10-23 19:05:36 UTC
HMDB IDHMDB0010199
Secondary Accession Numbers
  • HMDB10199
Metabolite Identification
Common Name11b-PGF2a
Description11b-PGF2a is an intermediate metabolite in the arachadonic acid metabolic pathway. 11b-PGF2 is irreversibly produced from prostaglandin D2 via the enzyme prostaglandin-F synthase [EC:1.1.1.188].(KEGG)Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways.
Structure
Thumb
Synonyms
ValueSource
11-Epi-PGF2aChEBI
11-Epi-PGF2alphaChEBI
11-Epi-prostaglandin F2aChEBI
11beta-PGF2alphaChEBI
11beta-Prostaglandin F2alphaChEBI
11-Epi-PGF2αGenerator
11β-PGF2αGenerator
11b-Prostaglandin F2aGenerator
11β-prostaglandin F2αGenerator
(5Z,13E,15S)-9alpha,11beta,15-Trihydroxyprosta-5,13-dien-1-OateHMDB
(5Z,13E,15S)-9alpha,11beta,15-Trihydroxyprosta-5,13-dien-1-Oic acidHMDB
(Z)-7-[(1R,2R,3S,5S)-3,5-Dihydroxy-2-[(e,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoateHMDB
(Z)-7-[(1R,2R,3S,5S)-3,5-Dihydroxy-2-[(e,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acidHMDB
11-Epi-prostaglandin F2alphaHMDB
9S,11S,15S-Trihydroxy-5Z,13E-prostadienoateHMDB
9S,11S,15S-Trihydroxy-5Z,13E-prostadienoic acidHMDB
9alpha,11beta PGF2MeSH
Enzaprost FMeSH
F2 alpha, ProstaglandinMeSH
Prostaglandin F2 alphaMeSH
alpha, PGF2MeSH
PGF2MeSH
PGF2 alphaMeSH
Prostaglandin F2MeSH
9alpha,11beta-PGF2MeSH
DinoprostMeSH
F2alpha, ProstaglandinMeSH
Prostaglandin F2alphaMeSH
EstrofanMeSH
PGF2alphaMeSH
Chemical FormulaC20H34O5
Average Molecular Weight354.481
Monoisotopic Molecular Weight354.240624198
IUPAC Name(5Z)-7-[(1R,2R,3S,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional Name11β-prostaglandin F2α
CAS Registry NumberNot Available
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-ZWAKLXPCSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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
Physiological effect

Health effect:

  Health condition:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

    Multicellular process:

    Cellular process:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

  Molecular messenger:

  Modulator:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
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
Polarizability41.1 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00mp-1920000000-c63a1df66bf6eaea5769View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-002g-0910000000-5cc96e6cc98902f97cfbView in MoNA
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
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
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000213 +/- 4.8E-5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000149 +/- 0.0000100 uMAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.00024 (0.00011-0.00044) umol/mmol creatinineChildren (1-13 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.00021 (0.000099-0.00039) umol/mmol creatinineChildren (1-13 years old)BothAsthma details
UrineDetected and Quantified0.00044 (0.00016-0.00058) umol/mmol creatinineChildren (1-13 years old)BothAsthma details
Associated Disorders and Diseases
Disease References
Asthma
  1. Mai XM, Bottcher MF, Bruhammar M, Nilsson L, Zetterstrom O: Urinary inflammatory mediators and inhalation of hypertonic saline in children. Allergy. 2005 Jan;60(1):60-4. [PubMed:15575932 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027354
KNApSAcK IDNot Available
Chemspider ID4444409
KEGG Compound IDC05959
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280886
PDB IDNot Available
ChEBI ID27595
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:
AKR1C3
Uniprot ID:
P42330
Molecular weight:
36866.91