L873724   Click here for help

GtoPdb Ligand ID: 7860

Synonyms: L-873724
Compound class: Synthetic organic
Comment: This compound is a specific cathepsin K inhibitor [3] (compound 22 in the article), which is used as a functional probe in studying the effects of cathepsin K inhibition.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 107.44
Molecular weight 481.16
XLogP 5.15
No. Lipinski's rules broken 1
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Canonical SMILES CC(CC(C(=O)NCC#N)NC(C(F)(F)F)c1ccc(cc1)c1ccc(cc1)S(=O)(=O)C)C
Isomeric SMILES CC(C[C@@H](C(=O)NCC#N)N[C@H](C(F)(F)F)c1ccc(cc1)c1ccc(cc1)S(=O)(=O)C)C
InChI InChI=1S/C23H26F3N3O3S/c1-15(2)14-20(22(30)28-13-12-27)29-21(23(24,25)26)18-6-4-16(5-7-18)17-8-10-19(11-9-17)33(3,31)32/h4-11,15,20-21,29H,13-14H2,1-3H3,(H,28,30)/t20-,21-/m0/s1
1. Desmarais S, Massé F, Percival MD. (2009)
Pharmacological inhibitors to identify roles of cathepsin K in cell-based studies: a comparison of available tools.
Biol Chem, 390 (9): 941-8. [PMID:19453281]
2. Grabowskal U, Chambers TJ, Shiroo M. (2005)
Recent developments in cathepsin K inhibitor design.
Curr Opin Drug Discov Devel, 8 (5): 619-30. [PMID:16159024]
3. Li CS, Deschenes D, Desmarais S, Falgueyret JP, Gauthier JY, Kimmel DB, Léger S, Massé F, McGrath ME, McKay DJ et al.. (2006)
Identification of a potent and selective non-basic cathepsin K inhibitor.
Bioorg Med Chem Lett, 16 (7): 1985-9. [PMID:16413777]
4. Stroup GB, Lark MW, Veber DF, Bhattacharyya A, Blake S, Dare LC, Erhard KF, Hoffman SJ, James IE, Marquis RW et al.. (2001)
Potent and selective inhibition of human cathepsin K leads to inhibition of bone resorption in vivo in a nonhuman primate.
J Bone Miner Res, 16 (10): 1739-46. [PMID:11585335]