vercirnon   

GtoPdb Ligand ID: 9046

Synonyms: CCX282-B | GSK'786 | GSK1605786 | GSK1605786A | Traficet-EN
Compound class: Synthetic organic
Comment: Vercirnon (CCX282-B) is a selective, potent and orally bioavailable antagonist of the chemokine (C-C motif) receptor 9 (CCR9 chemokine receptor) [1]. It was developed for potential to treat inflammatory bowel disease.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 98.56
Molecular weight 444.09
XLogP 6.45
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES Clc1ccc(c(c1)C(=O)c1cc[n+](cc1)[O-])NS(=O)(=O)c1ccc(cc1)C(C)(C)C
Isomeric SMILES Clc1ccc(c(c1)C(=O)c1cc[n+](cc1)[O-])NS(=O)(=O)c1ccc(cc1)C(C)(C)C
InChI InChI=1S/C22H21ClN2O4S/c1-22(2,3)16-4-7-18(8-5-16)30(28,29)24-20-9-6-17(23)14-19(20)21(26)15-10-12-25(27)13-11-15/h4-14,24H,1-3H3
InChI Key JRWROCIMSDXGOZ-UHFFFAOYSA-N
References
1. Walters MJ, Wang Y, Lai N, Baumgart T, Zhao BN, Dairaghi DJ, Bekker P, Ertl LS, Penfold ME, Jaen JC et al.. (2010)
Characterization of CCX282-B, an orally bioavailable antagonist of the CCR9 chemokine receptor, for treatment of inflammatory bowel disease.
J. Pharmacol. Exp. Ther., 335 (1): 61-9. [PMID:20660125]