GSK5182   Click here for help

GtoPdb Ligand ID: 8908

Synonyms: GSK 5182 | GSK-5182
PDB Ligand
Compound class: Synthetic organic
Comment: GSK5182 is an analogue of tamoxifen. It binds the ligand binding domain of the estrogen related receptor γ (ERRγ), acting as an inverse agonist [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 52.93
Molecular weight 417.23
XLogP 5.54
No. Lipinski's rules broken 1
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Canonical SMILES OCCCC(=C(c1ccc(cc1)O)c1ccc(cc1)OCCN(C)C)c1ccccc1
Isomeric SMILES OCCC/C(=C(\c1ccc(cc1)O)/c1ccc(cc1)OCCN(C)C)/c1ccccc1
InChI InChI=1S/C27H31NO3/c1-28(2)18-20-31-25-16-12-23(13-17-25)27(22-10-14-24(30)15-11-22)26(9-6-19-29)21-7-4-3-5-8-21/h3-5,7-8,10-17,29-30H,6,9,18-20H2,1-2H3/b27-26-
1. Chao EY, Collins JL, Gaillard S, Miller AB, Wang L, Orband-Miller LA, Nolte RT, McDonnell DP, Willson TM, Zuercher WJ. (2006)
Structure-guided synthesis of tamoxifen analogs with improved selectivity for the orphan ERRgamma.
Bioorg Med Chem Lett, 16 (4): 821-4. [PMID:16307879]
2. Kim DK, Gang GT, Ryu D, Koh M, Kim YN, Kim SS, Park J, Kim YH, Sim T, Lee IK et al.. (2013)
Inverse agonist of nuclear receptor ERRγ mediates antidiabetic effect through inhibition of hepatic gluconeogenesis.
Diabetes, 62 (9): 3093-102. [PMID:23775767]