compound 28 [Heitel et al., 2019]   Click here for help

GtoPdb Ligand ID: 10186

Compound class: Synthetic organic
Comment: Compound 28 is a retinoid X receptor agonist (rexinoid) [1] and is representative of a novel rexinoid chemotype that is proposed as a lead for the RXR-targeting medicinal chemistry pipeline.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 26.3
Molecular weight 302.13
XLogP 5.46
No. Lipinski's rules broken 1
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Canonical SMILES CC(=O)c1ccc(cc1)COc1ccccc1c1ccccc1
Isomeric SMILES CC(=O)c1ccc(cc1)COc1ccccc1c1ccccc1
InChI InChI=1S/C21H18O2/c1-16(22)18-13-11-17(12-14-18)15-23-21-10-6-5-9-20(21)19-7-3-2-4-8-19/h2-14H,15H2,1H3
Bioactivity Comments
Compound 28 is selectrive for retinoid X receptors and does not activate RARs [1]. In vitro it can activate PPARγ-RXR (EC50 1 μM) and synergistically promotes LXR-RXR activation by LXR agonist T0901317.
Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Retinoid X receptor-α Hs Agonist Agonist 7.0 pKd - 1
pKd 7.0 (Kd 9.5x10-8 M) [1]
Description: In a cell-free isothermal titration calorimetry (ITC) assay.
Retinoid X receptor-α Hs Agonist Agonist 6.6 pEC50 - 1
pEC50 6.6 (EC50 2.8x10-7 M) [1]
Description: In a whole cell reporter gene assay.
Retinoid X receptor-β Hs Agonist Agonist 6.5 pEC50 - 1
pEC50 6.5 (EC50 3.1x10-7 M) [1]
Retinoid X receptor-γ Hs Agonist Agonist 5.8 pEC50 - 1
pEC50 5.8 (EC50 1.6x10-6 M) [1]