PGE1   Click here for help

GtoPdb Ligand ID: 1882

Synonyms: Alprostadil® | MR-256 | prostaglandin E1
Approved drug PDB Ligand
PGE1 is an approved drug (FDA (1981))
Comment: PGE1 is an endogenous prostaglandin. Synthetic PGE1 is known as alprostadil. PGE1 activates prostanoid family GPCRs.
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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 13
Topological polar surface area 94.83
Molecular weight 354.24
XLogP 3.31
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CCCCCC(C=CC1C(O)CC(=O)C1CCCCCCC(=O)O)O
Isomeric SMILES CCCCC[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1
InChI Key GMVPRGQOIOIIMI-DWKJAMRDSA-N
References
1. Bastien L, Sawyer N, Grygorczyk R, Metters KM, Adam M. (1994)
Cloning, functional expression, and characterization of the human prostaglandin E2 receptor EP2 subtype.
J. Biol. Chem., 269 (16): 11873-7. [PMID:8163486]
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. 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]
5. 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]
6. Lishko PV, Botchkina IL, Kirichok Y. (2011)
Progesterone activates the principal Ca2+ channel of human sperm.
Nature, 471 (7338): 387-91. [PMID:21412339]
7. Maruyama T, Asada M, Shiraishi T, Ishida A, Egashira H, Yoshida H, Maruyama T, Ohuchida S, Nakai H, Kondo K et al.. (2001)
Design and synthesis of a highly selective EP4-receptor agonist. Part 1: 3,7-dithiaPG derivatives with high selectivity.
Bioorg. Med. Chem. Lett., 11 (15): 2029-31. [PMID:11454473]
8. 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]
9. Stitham J, Arehart E, Gleim SR, Li N, Douville K, Hwa J. (2007)
New insights into human prostacyclin receptor structure and function through natural and synthetic mutations of transmembrane charged residues.
Br. J. Pharmacol., 152 (4): 513-22. [PMID:17704830]
10. 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]