PGD2   Click here for help

GtoPdb Ligand ID: 1881

Synonyms: 11-dehydroprostaglandin F2-α | BRN 2170623 | prostaglandin D2
PDB Ligand
Compound class: Metabolite
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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]