VRT-043198   Click here for help

GtoPdb Ligand ID: 9034

PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: VRT-043198 generated from the prodrug belnacasan (VX-765) is a potent and selective inhibitor of caspase-1 from Vertex. When administered orally to mice, it inhibits lipopolysaccharide-induced cytokine secretion and reduces disease severity and the expression of inflammatory mediators in models of rheumatoid arthritis and skin inflammation, suggesting that as a cytokine inhibitor it could be useful for treatment of inflammatory diseases [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 4
Rotatable bonds 12
Topological polar surface area 158.9
Molecular weight 480.18
XLogP 1.34
No. Lipinski's rules broken 0
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Canonical SMILES O=CC(NC(=O)C1CCCN1C(=O)C(C(C)(C)C)NC(=O)c1ccc(c(c1)Cl)N)CC(=O)O
Isomeric SMILES O=C[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](C(C)(C)C)NC(=O)c1ccc(c(c1)Cl)N)CC(=O)O
InChI InChI=1S/C22H29ClN4O6/c1-22(2,3)18(26-19(31)12-6-7-15(24)14(23)9-12)21(33)27-8-4-5-16(27)20(32)25-13(11-28)10-17(29)30/h6-7,9,11,13,16,18H,4-5,8,10,24H2,1-3H3,(H,25,32)(H,26,31)(H,29,30)/t13-,16-,18+/m0/s1
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Molecular structure representations generated using Open Babel