You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2008-09-15 09:54:55 UTC
Update Date2016-02-11 01:16:23 UTC
HMDB IDHMDB10199
Secondary Accession NumbersNone
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
11-Epi-prostaglandin F2αGenerator
11-Epi-PGF2αGenerator
11b-PGF2aGenerator
11β-PGF2αGenerator
(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
11beta-Prostaglandin F2alphaHMDB
9S,11S,15S-Trihydroxy-5Z,13E-prostadienoateHMDB
9S,11S,15S-Trihydroxy-5Z,13E-prostadienoic acidHMDB
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 KeyInChIKey=PXGPLTODNUVGFL-ZWAKLXPCSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Carbocyclic fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclopentanol
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Signaling
Application
  • Not Available
Cellular locations
  • Membrane (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity100.47 m3·mol-1ChemAxon
Polarizability41.1 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
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. [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
NuGOwiki LinkHMDB10199
Metagene LinkHMDB10199
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