Human Metabolome Database Version 3.5

Showing metabocard for Prostaglandin F2a (HMDB01139)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:30:32 -0600
HMDB ID HMDB01139
Secondary Accession Numbers None
Metabolite Identification
Common Name Prostaglandin F2a
Description Prostaglandin F2a (PGF2) is one of the earliest discovered and most common prostaglandins. It is actively biosynthesized in various organs of mammals and exhibits a variety of biological activities, including contraction of pulmonary arteries. It is used in medicine to induce labor and as an abortifacient. PGF2a binds to the Prostaglandin F2 receptor (PTGFR) which is a member of the G-protein coupled receptor family. PGF2-alpha mediates luteolysis. Luteolysis is the structural and functional degradation of the corpus luteum (CL) that occurs at the end of the luteal phase of both the estrous and menstrual cycles in the absence of pregnancy. PGF2 may also be involved in modulating intraocular pressure and smooth muscle contraction in the uterus and gastrointestinal tract sphincters. 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). 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. (+)-Prostaglandin F2a
  2. (5Z,13E)-(15S)-9-alpha,11-alpha,15-trihydroxyprosta-5,13-dienoate
  3. (5Z,13E)-(15S)-9-alpha,11-alpha,15-trihydroxyprosta-5,13-dienoic acid
  4. (5Z,13E,15S)-9a,11a,15-trihydroxyprosta-5,13-dien-1-oate
  5. (5Z,13E,15S)-9a,11a,15-trihydroxyprosta-5,13-dien-1-oic acid
  6. (5Z,9a,11a,13E,15S)-9,11,15-trihydroxy-Prosta-5,13-dien-1-oate
  7. (5Z,9a,11a,13E,15S)-9,11,15-trihydroxy-Prosta-5,13-dien-1-oic acid
  8. (9alpha,11alpha,15)-trihydroxyprosta-(5Z,13E)-dien-1-oate
  9. (9alpha,11alpha,15)-trihydroxyprosta-(5Z,13E)-dien-1-oic acid
  10. 7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoate
  11. 7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-Heptenoic acid
  12. 9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-oate
  13. 9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-oic acid
  14. 9,11,15-Trihydroxyprosta-5Z,13E-dien-1-oate
  15. 9,11,15-Trihydroxyprosta-5Z,13E-dien-1-oic acid
  16. 9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoate
  17. 9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoic acid
  18. 9a,11a-PGF2
  19. 9a,11a-PGF2a
  20. Amoglandin
  21. Cyclosin
  22. Dinifertin
  23. Dinoprost
  24. Enzaprost
  25. Enzaprost F
  26. F2a Isoprostane
  27. Glandin N
  28. L-PGF2-alpha
  29. L-Prostaglandin F2-alpha
  30. Panacelan
  31. PGF2a
  32. Prostaglandin F2
  33. Prostaglandin F2a
  34. Prostamate
  35. Prostarmon F
  36. Prostin F 2 alpha
  37. Protamodin
Chemical Formula C20H34O5
Average Molecular Weight 354.481
Monoisotopic Molecular Weight 354.240624198
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 IUPAC Name 5-trans-PGF2α
CAS Registry Number 551-11-1
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 Key PXGPLTODNUVGFL-UAAPODJFSA-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
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Allyl Alcohol
  • Carboxylic Acid
  • Cyclic Alcohol
  • 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
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 30 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 4.39 BODOR,H & HUANG,M (1992)
Predicted Properties
Property Value Source
Water Solubility 0.12 g/L ALOGPS
LogP 3.11 ALOGPS
LogP 2.61 ChemAxon
LogS -3.48 ALOGPS
pKa (strongest acidic) 4.36 ChemAxon
pKa (strongest basic) -1.6 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 97.99 A2 ChemAxon
Rotatable Bond Count 12 ChemAxon
Refractivity 100.47 ChemAxon
Polarizability 41.7 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Placenta
  • Testes
  • Epidermis
  • Adrenal Gland
  • Adipose Tissue
  • Platelet
Pathways
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 map00590 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
5.3E-5 +/- 1.2E-5 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.000371 +/- 0.000144 uM Adult (>18 years old) Both Comment Normal
Blood Detected and Quantified
0.33 +/- 0.018 uM Adult (>18 years old) Not Specified Comment Normal
Blood Detected and Quantified
0.248 +/- 0.13 uM Adult (>18 years old) Not Specified Comment Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
7.340e-05 +/- 8.469e-06 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
7.340e-05 +/- 8.469e-06 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.002 (0.0-0.004) uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
0.00091 +/- 0.00008 uM Adult (>18 years old) Both Comment Normal
  • John W. Newm...
Urine Detected and Quantified
0.00021 +/- 0.000053 umol/mmol creatinine Adult (>18 years old) Female Normal
  • Geigy Scient...
Urine Detected and Quantified
0.00031 +/- 0.00012 umol/mmol creatinine Adult (>18 years old) Male Normal
  • Geigy Scient...
Urine Detected and Quantified
0.0000924 (0.0000588-0.000126) umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.0010 +/- 0.0002 uM Adult (>18 years old) Both Comment Cardiac arrest
Blood Detected and Quantified 0.0005 +/- 0.0001 uM Adult (>18 years old) Both Comment Cardiac arrest
Blood Detected and Quantified 0.0016 +/- 0.0004 uM Adult (>18 years old) Both Comment Cardiac arrest
Blood Detected and Quantified 0.0007 +/- 0.0001 uM Adult (>18 years old) Both Comment Cardiac arrest
Cerebrospinal Fluid (CSF) Detected and Quantified 0.000545 (4.799e-05-0.00192) uM Not Specified Not Specified HIV-Seropositive, Dementia
Cerebrospinal Fluid (CSF) Detected and Quantified 0.000500 (0.000452-0.000545) uM Not Specified Not Specified HIV-Seropositive (Neurologically normal)
Associated Disorders and Diseases
Disease References
Cardiac arrest
  • Strohmenger HU, Lindner KH, Keller A, Lindner IM, Bothner U, Georgieff M: Concentrations of prolactin and prostaglandins during and after cardiopulmonary resuscitation. Crit Care Med. 1995 Aug;23(8):1347-55. Pubmed: 7634804 Link_out
      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 FDB022448
      KNApSAcK ID Not Available
      Chemspider ID 4446204 Link_out
      KEGG Compound ID C00639 Link_out
      BioCyc ID 5Z13E-15S-9-ALPHA11-ALPHA15-TRIHY Link_out
      BiGG ID 35568 Link_out
      Wikipedia Link Not Available
      NuGOwiki Link HMDB01139 Link_out
      Metagene Link HMDB01139 Link_out
      METLIN ID 6032 Link_out
      PubChem Compound 5283078 Link_out
      PDB ID Not Available
      ChEBI ID 15553 Link_out
      References
      Synthesis Reference Chen, 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 References
      1. Grinsted J, Byskov AG: Meiosis-inducing and meiosis-preventing substances in human male reproductive organs. Fertil Steril. 1981 Feb;35(2):199-204. Pubmed: 7202743 Link_out
      2. Catanzarite VA: Prophylactic intramyometrial carboprost tromethamine does not substantially reduce blood loss relative to intramyometrial oxytocin at routine cesarean section. Am J Perinatol. 1990 Jan;7(1):39-42. Pubmed: 2403792 Link_out
      3. Carr BR, Milburn J Jr, Wright EE, Simpson ER: Adenylate cyclase activity in neocortex and fetal zone membrane fractions of the human fetal adrenal gland. J Clin Endocrinol Metab. 1985 Apr;60(4):718-22. Pubmed: 2982905 Link_out
      4. Negrel R, Gaillard D, Ailhaud G: Prostacyclin as a potent effector of adipose-cell differentiation. Biochem J. 1989 Jan 15;257(2):399-405. Pubmed: 2539085 Link_out
      5. Hammarstrom S, Hamberg M, Samuelsson B, Duell EA, Stawiski M, Voorhees JJ: Increased concentrations of nonesterified arachidonic acid, 12L-hydroxy-5,8,10,14-eicosatetraenoic acid, prostaglandin E2, and prostaglandin F2alpha in epidermis of psoriasis. Proc Natl Acad Sci U S A. 1975 Dec;72(12):5130-4. Pubmed: 1061097 Link_out
      6. Steele GL, Leung PC: Intragonadal signalling mechanisms in the control of steroid hormone production. J Steroid Biochem Mol Biol. 1992 Mar;41(3-8):515-22. Pubmed: 1562522 Link_out
      7. Ciabattoni G, Pugliese F, Spaldi M, Cinotti GA, Patrono C: Radioimmunoassay measurement of prostaglandins E2 and F2alpha in human urine. J Endocrinol Invest. 1979 Apr-Jun;2(2):173-82. Pubmed: 489926 Link_out
      8. Davi G, Chiarelli F, Santilli F, Pomilio M, Vigneri S, Falco A, Basili S, Ciabattoni G, Patrono C: Enhanced lipid peroxidation and platelet activation in the early phase of type 1 diabetes mellitus: role of interleukin-6 and disease duration. Circulation. 2003 Jul 1;107(25):3199-203. Epub 2003 Jun 16. Pubmed: 12810609 Link_out
      9. 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

      Enzymes
      Name: Carbonyl reductase [NADPH] 1
      Reactions:
      Prostaglandin F2a + NADP unknown Prostaglandin E2 + NADPH + Hydrogen Ion details
      Gene Name: CBR1
      Uniprot ID: P16152 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Carbonyl reductase [NADPH] 3
      Reactions:
      Prostaglandin F2a + NADP unknown Prostaglandin E2 + NADPH + Hydrogen Ion details
      Gene Name: CBR3
      Uniprot ID: O75828 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 15-hydroxyprostaglandin dehydrogenase [NAD(+)]
      Reactions: Not Available
      Gene Name: HPGD
      Uniprot ID: P15428 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA