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Compound Detail

CHEMBL249915

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CS(=O)(=O)C[C@H](N[C@@H](c1ccc(F)cc1)C(F)(F)F)C(=O)NC1(C#N)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL249915
Phase Preclinical
Structure Type MOL
InChI Key HBOZUMOKFHNMQI-STQMWFEESA-N
12
Targets
18
Activities
2
Assay Types
5
PK Parameters
15
Publications
0
Known Names

Molecular Properties

407.4
MW (Da)
1.60
ALogP
5
HBA
2
HBD
99.1
PSA (Ų)
0.67
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H17F4N3O3S
MW 407.39
Aromatic Rings 1
Heavy Atoms 27
NP-Likeness -1.29

Activity Summary

IC50 15 meas. best 9.22
Ki 3 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cathepsin S
CHEMBL4098
 IC50 9.22 9.22 0.6 1
Cathepsin S
CHEMBL2954
 Ki 9.0 9.0 1.0 1
Cathepsin S
CHEMBL2954
 IC50 8.74 8.5467 1.8 3
Unchecked
CHEMBL612545
 IC50 7.36 7.36 44.0 1
Procathepsin L
CHEMBL3837
 IC50 6.64 6.315 230.0 2
Cathepsin B
CHEMBL5187
 IC50 6.63 6.63 233.0 1
Cathepsin B
CHEMBL2602
 IC50 6.5 6.5 319.0 1
Cathepsin K
CHEMBL268
 IC50 6.39 6.39 405.0 1
Cathepsin S
CHEMBL1075217
 IC50 6.37 6.37 426.0 1
Cathepsin B
CHEMBL4072
 IC50 5.96 5.96 1104.0 1
Cathepsin K
CHEMBL1075277
 IC50 5.78 5.78 1646.0 1
Cathepsin B
CHEMBL4072
 Ki 5.78 5.78 1670.0 1
Procathepsin L
CHEMBL5291
 IC50 5.52 5.52 3037.0 1
Procathepsin L
CHEMBL2305
 IC50 5.5 5.5 3159.0 1
Procathepsin L
CHEMBL3837
 Ki 5.15 5.15 7106.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 43.0 uM Mus musculus
AUC 111.0 uM Mus musculus
Cmax 6300.0 nM Rattus norvegicus
F 48.0 % Rattus norvegicus
T1/2 5.2 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cathepsin S IC50 = 0.6 nM 9.22 Inhibition of mouse recombinant cathepsin S 17590332
Cathepsin S Ki = 1.0 nM 9.0 Inhibition of recombinant Cathepsin S (unknown origin) expressed in Escherichia ... 38894911
Cathepsin S IC50 = 1.8 nM 8.74 Inhibition of human cathepsin S 17590332
Cathepsin S IC50 = 2.5 nM 8.6 Inhibition of cathepsin S using FR-aminoluciferin as substrate preincubated for ... 23084902
Cathepsin S IC50 = 5.0 nM 8.3 Inhibition of cathepsin S-mediated antigen presentation in B/T hybridoma cells a... 23084902
Unchecked IC50 = 44.0 nM 7.36 Inhibition of antigen presentation in mouse B cells 17590332
Procathepsin L IC50 = 230.0 nM 6.64 Inhibition of cathepsin L using FR-aminoluciferin as substrate preincubated for ... 23084902
Cathepsin B IC50 = 233.0 nM 6.63 Inhibition of mouse recombinant cathepsin B 17590332
Cathepsin B IC50 = 319.0 nM 6.5 Inhibition of rat liver lysosomal cathepsin B 17590332
Cathepsin K IC50 = 405.0 nM 6.39 Inhibition of human cathepsin K 17590332
Cathepsin S IC50 = 426.0 nM 6.37 Inhibition of rat spleen cathepsin S 17590332
Procathepsin L IC50 = 1013.0 nM 5.99 Inhibition of human cathepsin L 17590332
Cathepsin B IC50 = 1104.0 nM 5.96 Inhibition of human cathepsin B 17590332
Cathepsin K IC50 = 1646.0 nM 5.78 Inhibition of mouse recombinant cathepsin K 17590332
Cathepsin B Ki = 1670.0 nM 5.78 Inhibition of human Cathepsin B using Z-Phe-Arg-AMC as substrate by fluorescence... 38894911
Procathepsin L IC50 = 3037.0 nM 5.52 Inhibition of mouse recombinant cathepsin L 17590332
Procathepsin L IC50 = 3159.0 nM 5.5 Inhibition of rat liver lysosomal cathepsin L 17590332
Procathepsin L Ki = 7106.0 nM 5.15 Inhibition of human Cathepsin L using Z-Phe-Arg-AMC as substrate by fluorescence... 38894911

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
17590332 10.1016/j.bmcl.2007.06.023 Mus musculus 2
23084902 10.1016/j.bmcl.2012.09.054 Cathepsin S 2
38894911 10.1021/acsmedchemlett.4c00050 Cathepsin S 2
17590332 10.1016/j.bmcl.2007.06.023 Hepatocyte 1
17590332 10.1016/j.bmcl.2007.06.023 Unchecked 1
23084902 10.1016/j.bmcl.2012.09.054 Procathepsin L 1
38894911 10.1021/acsmedchemlett.4c00050 Cathepsin B 1
38894911 10.1021/acsmedchemlett.4c00050 Procathepsin L 1
38894911 10.1021/acsmedchemlett.4c00050 Unchecked 1
38894911 10.1021/acsmedchemlett.4c00050 ADMET 1

Data from ChEMBL 36 via Core Engine