PGD2   Click here for help

GtoPdb Ligand ID: 1881

Synonyms: 11-dehydroprostaglandin F2-α | BRN 2170623 | prostaglandin D2
PDB Ligand
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 12
Topological polar surface area 94.83
Molecular weight 352.22
XLogP 2.9
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CCCCCC(C=CC1C(=O)CC(C1CC=CCCCC(=O)O)O)O
Isomeric SMILES CCCCC[C@@H](/C=C/[C@H]1C(=O)C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O
InChI 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/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-/m0/s1
InChI Key BHMBVRSPMRCCGG-OUTUXVNYSA-N
References
1. Boie Y, Sawyer N, Slipetz DM, Metters KM, Abramovitz M. (1995)
Molecular cloning and characterization of the human prostanoid DP receptor.
J. Biol. Chem., 270 (32): 18910-6. [PMID:7642548]
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. 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]
4. Hata AN, Lybrand TP, Breyer RM. (2005)
Identification of determinants of ligand binding affinity and selectivity in the prostaglandin D2 receptor CRTH2.
J Biol Chem, 280: 32442-32451. [PMID:16030019]
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. Shichijo M, Sugimoto H, Nagao K, Inbe H, Encinas JA, Takeshita K, Bacon KB, Gantner F. (2003)
Chemoattractant receptor-homologous molecule expressed on Th2 cells activation in vivo increases blood leukocyte counts and its blockade abrogates 13,14-dihydro-15-keto-prostaglandin D2-induced eosinophilia in rats.
J. Pharmacol. Exp. Ther., 307 (2): 518-25. [PMID:12975488]
12. 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]
13. Sugimoto H, Shichijo M, Okano M, Bacon KB. (2005)
CRTH2-specific binding characteristics of [3H]ramatroban and its effects on PGD2-, 15-deoxy-Delta12, 14-PGJ2- and indomethacin-induced agonist responses.
Eur. J. Pharmacol., 524 (1-3): 30-7. [PMID:16256979]
14. 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]
15. 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]
16. Wright DH, Nantel F, Metters KM, Ford-Hutchinson AW. (1999)
A novel biological role for prostaglandin D2 is suggested by distribution studies of the rat DP prostanoid receptor.
Eur. J. Pharmacol., 377 (1): 101-15. [PMID:10448933]