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Compound Detail

CHEMBL251327

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N#CC1(NC(=O)[C@H](CS(=O)(=O)CC2CC2)N[C@@H](c2ccc(F)cc2)C(F)(F)F)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL251327
Phase Preclinical
Structure Type MOL
InChI Key NOTSCKFHTQJLMM-HOTGVXAUSA-N
10
Targets
13
Activities
1
Assay Types
3
PK Parameters
7
Publications
0
Known Names

Molecular Properties

447.4
MW (Da)
2.38
ALogP
5
HBA
2
HBD
99.1
PSA (Ų)
0.57
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H21F4N3O3S
MW 447.45
Aromatic Rings 1
Heavy Atoms 30
NP-Likeness -1.06

Activity Summary

IC50 13 meas. best 9.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cathepsin S
CHEMBL2954
 IC50 9.4 8.7267 0.4 3
Cathepsin S
CHEMBL4098
 IC50 9.05 9.05 0.9 1
Procathepsin L
CHEMBL3837
 IC50 7.21 6.97 62.0 2
Cathepsin B
CHEMBL5187
 IC50 6.6 6.6 253.0 1
Cathepsin B
CHEMBL2602
 IC50 6.57 6.57 272.0 1
Procathepsin L
CHEMBL5291
 IC50 6.48 6.48 332.0 1
Procathepsin L
CHEMBL2305
 IC50 6.13 6.13 738.0 1
Cathepsin S
CHEMBL1075217
 IC50 6.12 6.12 759.0 1
Cathepsin B
CHEMBL4072
 IC50 6.0 6.0 1000.0 1
Cathepsin K
CHEMBL268
 IC50 5.7 5.7 2003.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 2800.0 nM Rattus norvegicus
F 40.0 % Rattus norvegicus
T1/2 3.8 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cathepsin S IC50 = 0.4 nM 9.4 Inhibition of cathepsin S using FR-aminoluciferin as substrate preincubated for ... 23084902
Cathepsin S IC50 = 0.5 nM 9.3 Inhibition of human cathepsin S 17590332
Cathepsin S IC50 = 0.9 nM 9.05 Inhibition of mouse recombinant cathepsin S 17590332
Cathepsin S IC50 = 33.0 nM 7.48 Inhibition of cathepsin S-mediated antigen presentation in B/T hybridoma cells a... 23084902
Procathepsin L IC50 = 62.0 nM 7.21 Inhibition of cathepsin L using FR-aminoluciferin as substrate preincubated for ... 23084902
Procathepsin L IC50 = 188.0 nM 6.73 Inhibition of human cathepsin L 17590332
Cathepsin B IC50 = 253.0 nM 6.6 Inhibition of mouse recombinant cathepsin B 17590332
Cathepsin B IC50 = 272.0 nM 6.57 Inhibition of rat liver lysosomal cathepsin B 17590332
Procathepsin L IC50 = 332.0 nM 6.48 Inhibition of mouse recombinant cathepsin L 17590332
Procathepsin L IC50 = 738.0 nM 6.13 Inhibition of rat liver lysosomal cathepsin L 17590332
Cathepsin S IC50 = 759.0 nM 6.12 Inhibition of rat spleen cathepsin S 17590332
Cathepsin B IC50 = 1000.0 nM 6.0 Inhibition of human cathepsin B 17590332
Cathepsin K IC50 = 2003.0 nM 5.7 Inhibition of human cathepsin K 17590332

Literature References

PubMed DOI Target Context # Activities
17590332 10.1016/j.bmcl.2007.06.023 Cathepsin S 3
17590332 10.1016/j.bmcl.2007.06.023 Cathepsin B 3
17590332 10.1016/j.bmcl.2007.06.023 Procathepsin L 3
17590332 10.1016/j.bmcl.2007.06.023 Rattus norvegicus 3
17590332 10.1016/j.bmcl.2007.06.023 Cathepsin K 2
23084902 10.1016/j.bmcl.2012.09.054 Cathepsin S 2
23084902 10.1016/j.bmcl.2012.09.054 Procathepsin L 1

Data from ChEMBL 36 via Core Engine