compound 24 [PMID: 26987013 ]   Click here for help

GtoPdb Ligand ID: 9252

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 24 is one of the clinical lead C-C motif chemokine receptor 9 (CCR9) antagonists reported in [2]. It is also one of the compounds claimed in patent WO2015097121 [1]. CCR9 modulators (e.g. antagonists, partial agonists or inverse agonists) are of clinical interest for their potential to treat, prevent or ameliorate condtions such as inflammatory bowel disease (IBD), in which CCR9 activation is believed to be associated with the pathology. Compound 24 exhibits an improved pharmacokinetic (PK) profile compared to the prototype CCR9 antagonist vercirnon.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 118.87
Molecular weight 499.1
XLogP 5.46
No. Lipinski's rules broken 1
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Canonical SMILES O=C1c2c(ccc(c2C(=O)N1c1ccc[n+](c1C)[O-])Cl)NS(=O)(=O)c1ccc(cc1)C(C)(C)C
Isomeric SMILES O=C1c2c(ccc(c2C(=O)N1c1ccc[n+](c1C)[O-])Cl)NS(=O)(=O)c1ccc(cc1)C(C)(C)C
InChI InChI=1S/C24H22ClN3O5S/c1-14-19(6-5-13-27(14)31)28-22(29)20-17(25)11-12-18(21(20)23(28)30)26-34(32,33)16-9-7-15(8-10-16)24(2,3)4/h5-13,26H,1-4H3
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Molecular structure representations generated using Open Babel