Human Metabolome Database Version 3.5

Showing metabocard for 15-Keto-prostaglandin F2a (HMDB04240)

Record Information
Version 3.5
Creation Date 2006-08-13 09:01:23 -0600
Update Date 2013-05-29 13:40:02 -0600
HMDB ID HMDB04240
Secondary Accession Numbers None
Metabolite Identification
Common Name 15-Keto-prostaglandin F2a
Description 15-Keto-prostaglandin F2a is the oxidized product of prostaglandin F2a by 15-hydroxyprostaglandin dehydrogenase, which is present in lung, kidney, placenta and other tissues and catalyzes the NAD- or NADP-dependent dehydrogenation of 15-dydroxyl group. 15-Keto-prostaglandin F2a is further metabolized by its delta13-reduction, beta-oxidation and omega oxidation. The ultimate metabolite is 5a,7a-dihydroxy-11-keto-tetranorprosta-1,16-dioic acid, and excreted in urine. Prostaglandin F2a (PGF2) is one of the earliest discovered and most common prostaglandins is actively biosynthesized in various organs of mammals and exhibits a variety of biological activities, including contraction of pulmonary arteries. PGF2 is mainly synthesized directly from PGH2 by PGH2 9,11-endoperoxide reductase. A small amount of PGF2 is also produced from PGE2 by PGE2 9-ketoreductase. A PGF2 epimer has been reported to exhibit various biological activities, and its levels are increased in bronchoalveolar lavage fluid, plasma, and urine in patients with mastocytosis and bronchial asthma. PGF2 is synthesized from PGD2 by PGD2 11-ketoreductase. (PMID: 16475787 Link_out, 184496 Link_out, 5951401 Link_out, 12432938 Link_out)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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 15-Keto-PGF2a
  2. 15-Keto-PGF2alpha
  3. 15-Keto-prostaglandin F2a
  4. 15-Keto-prostaglandin F2alpha
  5. 15-Ketoprostaglandin F2alpha
  6. 15-Oxo PGF-2alpha
  7. 15-Oxo-prostaglandin F2alpha
  8. 9S,11R-Dihydroxy-15-oxo-5Z,13E-prostadienoate
  9. 9S,11R-Dihydroxy-15-oxo-5Z,13E-prostadienoic acid
Chemical Formula C20H32O5
Average Molecular Weight 352.4651
Monoisotopic Molecular Weight 352.224974134
IUPAC Name (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional IUPAC Name 15-keto-PGF2α
CAS Registry Number 35850-13-6
SMILES CCCCCC(=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/C20H32O5/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/h4,7,12-13,16-19,22-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17-,18+,19-/m1/s1
InChI Key LOLJEILMPWPILA-AMFHKTBMSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Prostaglandins and related compounds
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • Carbocyclic Fatty Acids
  • Keto Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Acryloyl Group
  • Carboxylic Acid
  • Cyclic Alcohol
  • Enone
  • Ketone
  • Secondary Alcohol
Direct Parent Prostaglandins and related compounds
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.093 g/L ALOGPS
LogP 3.03 ALOGPS
LogP 3.02 ChemAxon
LogS -3.58 ALOGPS
pKa (strongest acidic) 4.36 ChemAxon
pKa (strongest basic) -2.9 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 94.83 A2 ChemAxon
Rotatable Bond Count 12 ChemAxon
Refractivity 99.57 ChemAxon
Polarizability 40.62 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.000209 +/- 6E-6 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.000188 +/- 0.000111 uM Adult (>18 years old) Both Comment Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023345
KNApSAcK ID Not Available
Chemspider ID 4444410 Link_out
KEGG Compound ID C05960 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04240 Link_out
Metagene Link HMDB04240 Link_out
METLIN ID 7035 Link_out
PubChem Compound 5280887 Link_out
PDB ID Not Available
ChEBI ID 28442 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Cornette JC, Kirton KT, Schneider WP, Sun FF, Johnson RA, Nidy EG: Preparation and quantitation of urinary metabolites of prostaglandin F2alpha by radioimmunoassay. Prostaglandins. 1975 Feb;9(2):323-38. Pubmed: 1135444 Link_out
  2. Satoh K, Yasumizu T, Fukuoka H, Kinoshita K, Kaneko Y, Tsuchiya M, Sakamoto S: Prostaglandin F2 alpha metabolite levels in plasma, amniotic fluid, and urine during pregnancy and labor. Am J Obstet Gynecol. 1979 Apr 15;133(8):886-90. Pubmed: 434032 Link_out
  3. Komoto J, Yamada T, Watanabe K, Woodward DF, Takusagawa F: Prostaglandin F2alpha formation from prostaglandin H2 by prostaglandin F synthase (PGFS): crystal structure of PGFS containing bimatoprost. Biochemistry. 2006 Feb 21;45(7):1987-96. Pubmed: 16475787 Link_out
  4. Hansen HS: 15-hydroxyprostaglandin dehydrogenase. A review. Prostaglandins. 1976 Oct;12(4):647-79. Pubmed: 184496 Link_out
  5. Anggard E: The biological activities of three metabolites of prostaglandin E 1. Acta Physiol Scand. 1966 Apr;66(4):509-10. Pubmed: 5951401 Link_out
  6. Tai HH, Ensor CM, Tong M, Zhou H, Yan F: Prostaglandin catabolizing enzymes. Prostaglandins Other Lipid Mediat. 2002 Aug;68-69:483-93. Pubmed: 12432938 Link_out

Enzymes
Name: 15-hydroxyprostaglandin dehydrogenase [NAD(+)]
Reactions: Not Available
Gene Name: HPGD
Uniprot ID: P15428 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA