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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-08-05 20:03:40 UTC
HMDB IDHMDB01139
Secondary Accession NumbersNone
Metabolite Identification
Common NameProstaglandin F2a
DescriptionProstaglandin 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 ). 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
  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 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
KingdomOrganic Compounds
Super ClassLipids
ClassEicosanoids
Sub ClassProstaglandins 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 ParentProstaglandins and related compounds
Ontology
StatusDetected 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
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
Water Solubility0.12ALOGPS
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
Polarizability41.7 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adipose Tissue
  • Adrenal Gland
  • Epidermis
  • Placenta
  • Platelet
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075map00590
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified5.3E-5 +/- 1.2E-5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000371 +/- 0.000144 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00033 +/- 0.000018 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.000248 +/- 0.00013 uMAdult (>18 years old)Not Specified
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified7.340e-05 +/- 8.469e-06 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified7.340e-05 +/- 8.469e-06 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.002 (0.0-0.004) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00091 +/- 0.00008 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
details
UrineDetected and Quantified0.00021 +/- 0.000053 umol/mmol creatinineAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.00031 +/- 0.00012 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.0000924 (0.0000588-0.000126) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0010 +/- 0.0002 uMAdult (>18 years old)Both
Cardiac arrest
details
BloodDetected and Quantified0.0005 +/- 0.0001 uMAdult (>18 years old)Both
Cardiac arrest
details
BloodDetected and Quantified0.0016 +/- 0.0004 uMAdult (>18 years old)Both
Cardiac arrest
details
BloodDetected and Quantified0.0007 +/- 0.0001 uMAdult (>18 years old)Both
Cardiac arrest
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000545 (4.799e-05-0.00192) uMNot SpecifiedNot SpecifiedHIV-Seropositive, Dementia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000500 (0.000452-0.000545) uMNot SpecifiedNot SpecifiedHIV-Seropositive (Neurologically normal) details
Associated Disorders and Diseases
Disease References
Cardiac arrest
  1. 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
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022448
KNApSAcK IDNot Available
Chemspider ID4446204
KEGG Compound IDC00639
BioCyc ID5Z13E-15S-9-ALPHA11-ALPHA15-TRIHY
BiGG ID35568
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01139
Metagene LinkHMDB01139
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 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
  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
  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
  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
  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
  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
  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
  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
  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

Enzymes

General function:
Involved in oxidoreductase activity
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.
Gene Name:
CBR1
Uniprot ID:
P16152
Molecular weight:
30374.73
Reactions
Prostaglandin F2a + NADP → Prostaglandin E2 + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Has low NADPH-dependent oxidoreductase activity towards 4-benzoylpyridine and menadione (in vitro).
Gene Name:
CBR3
Uniprot ID:
O75828
Molecular weight:
30849.97
Reactions
Prostaglandin F2a + NADP → Prostaglandin E2 + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Prostaglandin inactivation. Contributes to the regulation of events that are under the control of prostaglandin levels. Catalyzes the NAD-dependent dehydrogenation of lipoxin A4 to form 15-oxo-lipoxin A4. Inhibits in vivo proliferation of colon cancer cells.
Gene Name:
HPGD
Uniprot ID:
P15428
Molecular weight:
28977.105