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
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
EP3 receptor Mm Agonist Full agonist 8.4 pKi - 2
pKi 8.4 (Ki 3.7x10-9 M) [2]
EP3 receptor Rn Agonist Full agonist 8.4 pKi - 1
pKi 8.4 (Ki 4.3x10-9 M) EP3α isoform [1]
EP1 receptor Hs Agonist Full agonist 8.1 pKi - 3
pKi 8.1 [3]
EP1 receptor Mm Agonist Full agonist 7.9 pKi - 2
pKi 7.9 [2]
EP1 receptor Rn Agonist Full agonist 7.6 pKi - 1
pKi 7.6 [1]
EP2 receptor Rn Agonist Full agonist 6.1 pKi - 1
pKi 6.1 [1]
EP4 receptor Hs Agonist Agonist - - - 4
Ligand mentioned in the following text fields