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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key VYFDSJLOCIGIKP-SFTDATJTSA-N
References
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]