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Compound Detail

CHEMBL288365

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CC(C)C[C@@H](C=O)NC(=O)[C@@H](NS(=O)(=O)c1ccc(F)cc1)C(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL288365
Phase Preclinical
Structure Type MOL
InChI Key WSJWUIDLGZAXID-HOCLYGCPSA-N
10
Targets
16
Activities
2
Assay Types
7
PK Parameters
20
Publications
0
Known Names

Molecular Properties

372.5
MW (Da)
1.86
ALogP
4
HBA
2
HBD
92.3
PSA (Ų)
0.65
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 C17H25FN2O4S
MW 372.46
Aromatic Rings 1
Heavy Atoms 25
NP-Likeness -0.63

Activity Summary

IC50 14 meas. best 8.8
EC50 2 meas. best 7.42

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Procathepsin L
CHEMBL3837
 IC50 8.8 8.8 1.6 1
Calpain-1 catalytic subunit
CHEMBL3747
 IC50 8.12 8.12 7.5 1
Calpain-1 catalytic subunit
CHEMBL3891
 IC50 8.12 7.8133 7.5 3
Calpain-1 catalytic subunit
CHEMBL4062
 IC50 8.12 7.79 7.5 2
Cathepsin B
CHEMBL4072
 IC50 7.82 7.82 15.0 1
SARS-CoV-2
CHEMBL4303835
 EC50 7.42 6.65 37.7 2
Calpain-2 catalytic subunit
CHEMBL4143
 IC50 7.31 7.21 49.0 2
Calpain-2 catalytic subunit
CHEMBL2382
 IC50 7.11 7.11 78.0 1
Unchecked
CHEMBL612545
 IC50 7.1 6.995 80.0 2
Calpain-9
CHEMBL4523126
 IC50 5.65 5.65 2230.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 16760.7 ng.hr.mL-1 Rattus norvegicus
AUC 558.69 ng.hr.mL-1 Rattus norvegicus
CL 89.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 9400.0 nM Rattus norvegicus
F 18.0 % Rattus norvegicus
T1/2 0.7 hr Rattus norvegicus
Tmax 1.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Procathepsin L IC50 = 1.6 nM 8.8 Affinity Biochemical interaction: (Colorimetric assay, lysis of casein substrate... -
Calpain-1 catalytic subunit IC50 = 7.5 nM 8.12 Inhibition of pig CAPN1 18571418
Calpain-1 catalytic subunit IC50 = 7.5 nM 8.12 Inhibition of rat CAPN1 using BODIPY-labeled casein substrate by fluorometric an... 21955158
Calpain-1 catalytic subunit IC50 = 7.5 nM 8.12 Affinity Biochemical interaction: (Colorimetric assay, lysis of casein substrate... -
Cathepsin B IC50 = 15.0 nM 7.82 Affinity Biochemical interaction: (Colorimetric assay, lysis of casein substrate... -
Calpain-1 catalytic subunit IC50 = 22.0 nM 7.66 Inhibition of human erythrocyte mu calpain 16789748
Calpain-1 catalytic subunit IC50 = 22.0 nM 7.66 Inhibition of human Calpain-1 incubated for 60 mins by Bio-Rad protein assay dye... 34288674
Calpain-1 catalytic subunit IC50 = 35.0 nM 7.46 Tested for inhibitory activity against porcine erythrocyte Mu-calpain 12039572
SARS-CoV-2 EC50 = 37.7 nM 7.42 Antiviral activity against SARS CoV-2 GFP infected in african green monkey Vero ... 38630165
Calpain-2 catalytic subunit IC50 = 49.0 nM 7.31 Inhibition of porcein kidney m calpain 16789748
Calpain-2 catalytic subunit IC50 = 78.0 nM 7.11 Inhibition of pig CAPN2 18571418
Calpain-2 catalytic subunit IC50 = 78.0 nM 7.11 Affinity Biochemical interaction: (Colorimetric assay, lysis of casein substrate... -
Unchecked IC50 = 80.0 nM 7.1 Inhibition of ovine CAPN2 using BODIPY-labeled casein substrate by fluorometric ... 21955158
Unchecked IC50 = 130.0 nM 6.89 Inhibition of ovine CAPN1 using BODIPY-labeled casein substrate by fluorometric ... 21955158
SARS-CoV-2 EC50 = 1334.0 nM 5.88 Antiviral activity against SARS CoV-2 GFP infected in african green monkey Vero ... 38630165
Calpain-9 IC50 = 2230.0 nM 5.65 Inhibition of human recombinant mini-CAPN9 pre-incubated for 10 mins before calp... -

Literature References

PubMed DOI Target Context # Activities
16789748 10.1021/jm060157n Rattus norvegicus 9
12039572 10.1016/s0960-894x(02)00226-3 ADMET 4
- 10.6019/CHEMBL5724709 HEK-293T 2
- 10.6019/CHEMBL5724709 U2OS 2
- 10.6019/CHEMBL5724709 Fibroblast 2
38630165 10.1021/acs.jmedchem.3c02351 SARS-CoV-2 2
21955158 10.1021/jm200471r Unchecked 2
16789748 10.1021/jm060157n No relevant target 2
16789748 10.1021/jm060157n Calpain-1 catalytic subunit 1
18571418 10.1016/j.bmc.2008.05.048 Calpain-2 catalytic subunit 1
18571418 10.1016/j.bmc.2008.05.048 Calpain-1 catalytic subunit 1
21955158 10.1021/jm200471r Calpain-1 catalytic subunit 1
16789748 10.1021/jm060157n Calpain-2 catalytic subunit 1
34288674 10.1021/acs.jmedchem.1c00628 Calpain-1 catalytic subunit 1
33191083 10.1016/j.bmc.2020.115860 Replicase polyprotein 1ab 1
16789748 10.1021/jm060157n Homo sapiens 1
38630165 10.1021/acs.jmedchem.3c02351 Procathepsin L 1
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1
- 10.6019/CHEMBL5723035 Procathepsin L 1
16789748 10.1021/jm060157n Caco-2 1

Data from ChEMBL 36 via Core Engine