compound 16g [PMID: 35507418]   Click here for help

GtoPdb Ligand ID: 12028

Compound class: Synthetic organic
Comment: This compound is reported as a thyroid receptor β (THRβ)-selective agonist [1]. It activates the wild type receptor and the subfunctional mutant receptor THRβH435R which has impaired sensitivity to thyroid hormones and underlies resistance to thyroid hormone in carriers.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 144.28
Molecular weight 548.16
XLogP 3.4
No. Lipinski's rules broken 0
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Canonical SMILES COc1cc(F)cc(c1)C(=O)c1cc(C)c(c(c1)C)Oc1ccc2c(c1)c(OC)nc(c2O)C(=O)NCC(=O)O
Isomeric SMILES O=C(NCC(=O)O)c1c(O)c2ccc(Oc3c(C)cc(C(=O)c4cc(OC)cc(F)c4)cc3C)cc2c(OC)n1
InChI InChI=1S/C29H25FN2O8/c1-14-7-16(25(35)17-9-18(30)11-20(10-17)38-3)8-15(2)27(14)40-19-5-6-21-22(12-19)29(39-4)32-24(26(21)36)28(37)31-13-23(33)34/h5-12,36H,13H2,1-4H3,(H,31,37)(H,33,34)
Bioactivity Comments
16g activates THRβ with the H435R mutation with an EC50 of ~1300 nM [1]. It does not activate THRα, or inhibit a range of CYP450 enzymes and has no hERG affinity.
Selectivity at nuclear hormone receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Thyroid hormone receptor-β Hs Agonist Agonist 7.7 pEC50 - 1
pEC50 7.7 (EC50 2.1x10-8 M) [1]