PGF   Click here for help

GtoPdb Ligand ID: 1884

Synonyms: prostaglandin F
Immunopharmacology Ligand
Comment: PGF is a naturally-occurring prostanoid which functions as a potent vasoconstrictor. The synthetically produced drug, dinoprost, is chemically identical to the endogenous prostaglandin [3].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 5
Hydrogen bond donors 4
Rotatable bonds 12
Topological polar surface area 97.99
Molecular weight 354.24
XLogP 3.2
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CCCCCC(C=CC1C(O)CC(C1CC=CCCCC(=O)O)O)O
Isomeric SMILES CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O
InChI 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-YNNPMVKQSA-N
References
1. Abramovitz M, Adam M, Boie Y, Carrière M, Denis D, Godbout C, Lamontagne S, Rochette C, Sawyer N, Tremblay NM et al.. (2000)
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
Biochim Biophys Acta, 1483 (2): 285-93. [PMID:10634944]
2. Boie Y, Stocco R, Sawyer N, Slipetz DM, Ungrin MD, Neuschäfer-Rube F, Püschel GP, Metters KM, Abramovitz M. (1997)
Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes.
Eur J Pharmacol, 340 (2-3): 227-41. [PMID:9537820]
3. Coulthard G, Erb W, Aggarwal VK. (2012)
Stereocontrolled organocatalytic synthesis of prostaglandin PGF2α in seven steps.
Nature, 489 (7415): 278-81. [PMID:22895192]
4. Davis TL, Sharif NA. (2000)
Pharmacological characterization of [(3)H]-prostaglandin E(2) binding to the cloned human EP(4) prostanoid receptor.
Br J Pharmacol, 130: 1919-1926. [PMID:10952683]
5. Hata AN, Zent R, Breyer MD, Breyer RM. (2003)
Expression and molecular pharmacology of the mouse CRTH2 receptor.
J Pharmacol Exp Ther, 306 (2): 463-70. [PMID:12721327]
6. Kiriyama M, Ushikubi F, Kobayashi T, Hirata M, Sugimoto Y, Narumiya S. (1997)
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.
Br J Pharmacol, 122 (2): 217-24. [PMID:9313928]
7. Leduc M, Breton B, Galés C, Le Gouill C, Bouvier M, Chemtob S, Heveker N. (2009)
Functional selectivity of natural and synthetic prostaglandin EP4 receptor ligands.
J Pharmacol Exp Ther, 331 (1): 297-307. [PMID:19584306]
8. Neuschäfer-Rube F, Engemaier E, Koch S, Böer U, Püschel GP. (2003)
Identification by site-directed mutagenesis of amino acids contributing to ligand-binding specificity or signal transduction properties of the human FP prostanoid receptor.
Biochem J, 371 (Pt 2): 443-9. [PMID:12519077]
9. Sawyer N, Cauchon E, Chateauneuf A, Cruz RP, Nicholson DW, Metters KM, O'Neill GP, Gervais FG. (2002)
Molecular pharmacology of the human prostaglandin D2 receptor, CRTH2.
Br J Pharmacol, 137 (8): 1163-72. [PMID:12466225]
10. Sharif NA, Davis TL. (2002)
Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques.
J Pharm Pharmacol, 54 (4): 539-47. [PMID:11999132]
11. Stillman BA, Breyer MD, Breyer RM. (1999)
Importance of the extracellular domain for prostaglandin EP(2) receptor function.
Mol Pharmacol, 56 (3): 545-51. [PMID:10462542]
12. Wilson RJ, Giblin GM, Roomans S, Rhodes SA, Cartwright KA, Shield VJ, Brown J, Wise A, Chowdhury J, Pritchard S et al.. (2006)
GW627368X ((N-{2-[4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetyl} benzene sulphonamide): a novel, potent and selective prostanoid EP4 receptor antagonist.
Br J Pharmacol, 148 (3): 326-39. [PMID:16604093]
13. Wright DH, Metters KM, Abramovitz M, Ford-Hutchinson AW. (1998)
Characterization of the recombinant human prostanoid DP receptor and identification of L-644,698, a novel selective DP agonist.
Br J Pharmacol, 123 (7): 1317-24. [PMID:9579725]