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Compound Detail

CHEMBL5174111

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O=C(NCc1cccs1)[C@@H]1CN(C(=O)c2cccnc2)CCN1c1ccc(Cl)c(Cl)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5174111
Phase Preclinical
Structure Type MOL
InChI Key XEFYJHCPILXFKJ-FQEVSTJZSA-N
8
Targets
15
Activities
2
Assay Types
15
PK Parameters
20
Publications
0
Known Names

Molecular Properties

475.4
MW (Da)
4.10
ALogP
5
HBA
1
HBD
65.5
PSA (Ų)
0.60
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H20Cl2N4O2S
MW 475.40
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -2.23

Activity Summary

IC50 11 meas. best 9.4
EC50 4 meas. best 7.48

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Replicase polyprotein 1ab
CHEMBL4523582
 IC50 9.4 9.4 0.4 1
SARS-CoV-2
CHEMBL4303835
 EC50 7.48 6.4325 33.0 4
SARS-CoV-2
CHEMBL4303835
 IC50 5.96 5.96 1100.0 1
Unchecked
CHEMBL612545
 IC50 5.34 5.34 4610.0 1
Caspase-3
CHEMBL2334
 IC50 4.3 4.3 50000.0 1
Cathepsin F
CHEMBL2517
 IC50 4.3 4.3 50000.0 1
Cathepsin K
CHEMBL268
 IC50 4.3 4.3 50000.0 1
Procathepsin L
CHEMBL3837
 IC50 4.3 4.3 50000.0 1
Cathepsin B
CHEMBL4072
 IC50 4.3 4.3 50000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 627.0 ng.hr.mL-1 Rattus norvegicus
AUC 637.0 ng.hr.mL-1 Rattus norvegicus
AUC 235.0 ng.hr.mL-1 Rattus norvegicus
AUC 230.0 ng.hr.mL-1 Rattus norvegicus
CL 994.0 mL.min-1.kg-1 Homo sapiens
CL 52.33 mL.min-1.kg-1 Rattus norvegicus
Cmax 2755.57 nM Rattus norvegicus
Cmax 156.92 nM Rattus norvegicus
F 72.0 % Rattus norvegicus
MRT 0.4 hr Rattus norvegicus
MRT 2.45 hr Rattus norvegicus
T1/2 0.36 hr Rattus norvegicus
T1/2 1.73 hr Rattus norvegicus
Tmax 0.08 hr Rattus norvegicus
Tmax 0.5 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Replicase polyprotein 1ab IC50 = 0.4 nM 9.4 Inhibition of SARS-CoV-2 main protease using MCA-AVLQSGFR-Lys(Dnp)-Lys-NH2 as fl... 36107752
SARS-CoV-2 EC50 = 33.0 nM 7.48 Antiviral activity against SARS-CoV-2 Omicron assessed as reduction of viral gro... 37229831
SARS-CoV-2 EC50 = 400.0 nM 6.4 Antiviral activity against SARS-CoV-2 infected in Vero E6 cells preincubated for... 36475694
SARS-CoV-2 EC50 = 1100.0 nM 5.96 Antiviral activity against SARS-CoV-2 infected in African green monkey Vero E6 c... 37244162
SARS-CoV-2 IC50 = 1100.0 nM 5.96 Antiviral activity against SARS-CoV-2 infected in Vero E6 cells assessed as inhi... 36107752
SARS-CoV-2 EC50 = 1300.0 nM 5.89 Antiviral activity against SARS-CoV-2 infected in African green monkey Vero E6 c... 37992202
Unchecked IC50 = 4610.0 nM 5.34 Inhibition of SARS-CoV-1 main protease 36107752
Caspase-3 IC50 = 50000.0 nM 4.3 Inhibition of human caspase-3 using Ac-Asp-Glu-Val-Asp-pNA as substrate incubate... 36107752
Procathepsin L IC50 = 50000.0 nM 4.3 Inhibition of human Cathepsin L using Z-Leu-Arg-AMC as fluorogenic substrate inc... 36107752
Cathepsin F IC50 = 50000.0 nM 4.3 Inhibition of human Cathepsin F using Z-Phe-Arg-AMC as fluorogenic substrate inc... 36107752
Cathepsin K IC50 = 50000.0 nM 4.3 Inhibition of human Cathepsin K using Ac-LR-AMC as fluorogenic substrate incubat... 36107752
Cathepsin B IC50 = 50000.0 nM 4.3 Inhibition of human Cathepsin B using Z-Leu-Arg-AMC as fluorogenic substrate inc... 36107752

Literature References

PubMed DOI Target Context # Activities
36107752 10.1021/acs.jmedchem.2c01146 ADMET 16
36475694 10.1021/acs.jmedchem.2c01716 Replicase polyprotein 1ab 2
36107752 10.1021/acs.jmedchem.2c01146 No relevant target 1
37992202 10.1021/acs.jmedchem.3c01876 Vero C1008 1
37992202 10.1021/acs.jmedchem.3c01876 SARS-CoV-2 1
37992202 10.1021/acs.jmedchem.3c01876 Replicase polyprotein 1ab 1
37244162 10.1016/j.ejmech.2023.115491 SARS-CoV-2 1
37244162 10.1016/j.ejmech.2023.115491 Replicase polyprotein 1ab 1
37229831 10.1016/j.ejmech.2023.115503 SARS-CoV-2 1
36475694 10.1021/acs.jmedchem.2c01716 Vero C1008 1
36475694 10.1021/acs.jmedchem.2c01716 SARS-CoV-2 1
36107752 10.1021/acs.jmedchem.2c01146 Caspase-3 1
36107752 10.1021/acs.jmedchem.2c01146 Unchecked 1
36107752 10.1021/acs.jmedchem.2c01146 Vero C1008 1
36107752 10.1021/acs.jmedchem.2c01146 SARS-CoV-2 1
36107752 10.1021/acs.jmedchem.2c01146 Cathepsin B 1
36107752 10.1021/acs.jmedchem.2c01146 Cathepsin K 1
36107752 10.1021/acs.jmedchem.2c01146 Cathepsin F 1
36107752 10.1021/acs.jmedchem.2c01146 Procathepsin L 1
36107752 10.1021/acs.jmedchem.2c01146 Replicase polyprotein 1ab 1

Data from ChEMBL 36 via Core Engine