17-phenyl-ω-trinor-PGE2   Click here for help

GtoPdb Ligand ID: 1912

Synonyms: 17-Ph-ω-trinor-PGE2 | 17-phenyl-ω-trinor-prostaglandin E2 | 17-phenyl-PGE2 | 17-phenyl-trinor-PGE2 | 17-pt-PGE2
Compound class: Synthetic organic
Comment: 17-phenyl-ω-trinor-PGE2 can activate EP1, EP3 and EP4 prostanoid receptors [4]. The ligand was evaluated for biological activity in cell and animal models; no quantitative data for direct interaction with the EP4 receptor was determined.
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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 11
Topological polar surface area 94.83
Molecular weight 386.21
XLogP 2.53
No. Lipinski's rules broken 1
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Canonical SMILES OC(=O)CCCC=CCC1C(=O)CC(C1C=CC(CCc1ccccc1)O)O
Isomeric SMILES OC(=O)CCC/C=C\C[C@H]1C(=O)C[C@H]([C@@H]1/C=C/[C@H](CCc1ccccc1)O)O
InChI InChI=1S/C23H30O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,14-15,18-20,22,24,26H,2,7,10-13,16H2,(H,27,28)/b6-1-,15-14+/t18-,19+,20+,22+/m0/s1
1. 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]
2. 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]
3. 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]
4. Theiler A, Konya V, Pasterk L, Maric J, Bärnthaler T, Lanz I, Platzer W, Schuligoi R, Heinemann A. (2016)
The EP1/EP3 receptor agonist 17-pt-PGE2 acts as an EP4 receptor agonist on endothelial barrier function and in a model of LPS-induced pulmonary inflammation.
Vascul Pharmacol, 87: 180-189. [PMID:27664754]