Ligand id: 1883

Name: PGE2

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View more information in the IUPHAR Pharmacology Education Project: prostaglandin e2

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 12
Topological polar surface area 94.83
Molecular weight 352.22
XLogP 2.79
No. Lipinski's rules broken 1

Molecular properties generated using the CDK

1. Abramovitz M, Adam M, Boie Y, Carriere M, Denis D, Godbout C, Lamontagne S, Rochette C, Sawyer N, Tremblay NM, Belley M, Gallant M, Dufresne C, Gareau Y, Ruel R, Juteau H, Labelle M, Ouimet N, Metters KM. (2000)
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogues.
Biochim. Biophys. Acta., 1483: 285-293. [PMID:10634944]
2. 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: 18910-18916. [PMID:7642548]
3. Boie Y, Stocco R, Sawyer N, Slipetz DM, Ungrin MD, Neuschafer-Rube F, Puschel GP, Metters KM, Abramovitz M. (1997)
Molecular cloning and characterisation of the four rat prostaglandin E2 prostanoid receptor subtypes.
Eur. J. Pharmacol., 304: 227-241. [PMID:9537820]
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: 463-470. [PMID:12721327]
6. Kimura H, Takeda M, Narikawa S, Enomoto A, Ichida K, Endou H. (2002)
Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins.
J. Pharmacol. Exp. Ther., 301 (1): 293-8. [PMID:11907186]
7. 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: 217-224. [PMID:9313928]
8. 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]
9. Lishko PV, Botchkina IL, Kirichok Y. (2011)
Progesterone activates the principal Ca2+ channel of human sperm.
Nature, 471 (7338): 387-91. [PMID:21412339]
10. Nakao K, Murase A, Ohshiro H, Okumura T, Taniguchi K, Murata Y, Masuda M, Kato T, Okumura Y, Takada J. (2007)
CJ-023,423, a novel, potent and selective prostaglandin EP4 receptor antagonist with antihyperalgesic properties.
J. Pharmacol. Exp. Ther., 322 (2): 686-94. [PMID:17495127]
11. Neuschäfer-Rube F, DeVries C, Hänecke K, Jungermann K, Püschel GP. (1994)
Molecular cloning and expression of a prostaglandin E2 receptor of the EP3 beta subtype from rat hepatocytes.
FEBS Lett., 351 (1): 119-22. [PMID:8076679]
12. 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: 443-449. [PMID:12519077]
13. Neuschäfer-Rube F, Hermosilla R, Kuna M, Pathe-Neuschäfer-Rube A, Schülein R, Püschel GP. (2005)
A Ser/Thr cluster within the C-terminal domain of the rat prostaglandin receptor EP3alpha is essential for agonist-induced phosphorylation, desensitization and internalization.
Br. J. Pharmacol., 145 (8): 1132-42. [PMID:15937517]
14. 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: 1163-1172. [PMID:12466225]
15. Sharif NA, Davis TL. (2002)
Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques.
J Pharm Pharmacol, 54: 539-547. [PMID:11999132]
16. Stillman BA, Breyer MD, Breyer RM. (1999)
Importance of the extracellular domain for prostaglandin EP(2) receptor function.
Mol Pharmacol, 56: 545-551. [PMID:10462542]
17. Su X, Leon LA, Wu CW, Morrow DM, Jaworski JP, Hieble JP, Lashinger ES, Jin J, Edwards RM, Laping NJ. (2008)
Modulation of bladder function by prostaglandin EP3 receptors in the central nervous system.
Am. J. Physiol. Renal Physiol., 295 (4): F984-94. [PMID:18632791]
18. Sugimoto Y, Nakato T, Kita A, Hatae N, Tabata H, Tanaka S, Ichikawa A. (2003)
Functional domains essential for Gs activity in prostaglandin EP2 and EP3 receptors.
Life Sci, 74: 135-141. [PMID:14607240]
19. Suzawa T, Miyaura C, Inada M, Maruyama T, Sugimoto Y, Ushikubi F, Ichikawa A, Narumiya S, Suda T. (2000)
The role of prostaglandin E receptor subtypes (EP1, EP2, EP3, and EP4) in bone resorption: an analysis using specific agonists for the respective EPs.
Endocrinology, 141: 1554-1559. [PMID:10746663]
20. Whittle BJ, Silverstein AM, Mottola DM, Clapp LH. (2012)
Binding and activity of the prostacyclin receptor (IP) agonists, treprostinil and iloprost, at human prostanoid receptors: treprostinil is a potent DP1 and EP2 agonist.
Biochem. Pharmacol., 84 (1): 68-75. [PMID:22480736]
21. Wilson RJ, Giblin GM, Roomans S, Rhodes SA, Cartwright KA, Shield VJ, Brown J, Wise A, Chowdhury J, Pritchard S, Coote J, Noel LS, Kenakin T, Burns-Kurtis CL, Morrison V, Gray DW, Giles H. (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: 326-339. [PMID:16604093]
22. Wright DH, Metters KM, Abramovitz M, Ford-Hutchinson AW. (1998)
Characterization of the recombinant human prostaglandin DP-receptor identifies L-644,698 a novel, DP-selective agonist.
Br. J. Pharmacol., 123: 1317-1324. [PMID:9579725]