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Compound Detail

CHEMBL295844

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COc1ccc2c(O[C@@H]3C[C@H]4C(=O)N[C@]5(C(=O)O)C[C@H]5/C=C\CCCCC[C@H](NC(=O)OC(C)(C)C)C(=O)N4C3)cc(-c3ccccc3)nc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL295844
Phase Preclinical
Structure Type MOL
InChI Key XAZOEZNXZFURMS-WCBFGBOISA-N
3
Targets
10
Activities
3
Assay Types
5
PK Parameters
10
Publications
0
Known Names

Molecular Properties

698.8
MW (Da)
5.63
ALogP
8
HBA
3
HBD
156.4
PSA (Ų)
0.28
QED
2
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C39H46N4O8
MW 698.82
Aromatic Rings 3
Heavy Atoms 51
NP-Likeness 0.14

Activity Summary

EC50 4 meas. best 8.92
IC50 4 meas. best 8.52
Ki 2 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus
CHEMBL379
 Ki 9.0 9.0 1.0 1
Hepatitis C virus
CHEMBL379
 EC50 8.92 7.8225 1.2 4
Unchecked
CHEMBL612545
 Ki 8.85 8.85 1.4 1
Hepatitis C virus serine protease, NS3/NS4A
CHEMBL2095231
 IC50 8.52 8.24 3.0 2
Unchecked
CHEMBL612545
 IC50 7.96 7.96 11.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 139.76 ng.hr.mL-1 Rattus norvegicus
CL 13.0 mL.min-1.kg-1 Rattus norvegicus
F 2.0 % Rattus norvegicus
F 42.0 % Rattus norvegicus
T1/2 0.4 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus Ki = 1.0 nM 9.0 Inhibition of HCV 1b NS3 protease 21381769
Hepatitis C virus EC50 = 1.2 nM 8.92 Antiviral activity against Hepatitis C virus 27501244
Unchecked Ki = 1.4 nM 8.85 Inhibition of HCV 1a NS3 protease 21381769
Hepatitis C virus serine protease, NS3/NS4A IC50 = 3.0 nM 8.52 Inhibition of HCV NS4A-NS3 protease 27501244
Hepatitis C virus EC50 = 7.0 nM 8.15 Antiviral activity against HCV by cell based replicon assay 21381769
Unchecked IC50 = 11.0 nM 7.96 Inhibitory concentration against hepatitis C virus NS3 protease 15027850
Unchecked IC50 = 11.0 nM 7.96 Inhibition of full length HCV NS3/4A protease 18954982
Hepatitis C virus serine protease, NS3/NS4A IC50 = 11.0 nM 7.96 Inhibition of C-terminal HCV NS4A-NS3 protease 27501244
Hepatitis C virus EC50 = 77.0 nM 7.11 Inhibition of hepatitis C virus in a cell based HCV replicon assay. 15027850
Hepatitis C virus EC50 = 77.0 nM 7.11 Antiviral activity against HCV infected in human Huh7 cells after 48 hrs by luci... 18954982

Literature References

PubMed DOI Target Context # Activities
15027850 10.1021/jm0342414 Rattus norvegicus 4
21381769 10.1021/jm1012374 Hepatitis C virus 2
27501244 10.1021/acs.jmedchem.6b00915 Hepatitis C virus serine protease, NS3/NS4A 2
15027850 10.1021/jm0342414 Unchecked 1
15027850 10.1021/jm0342414 Hepatitis C virus 1
18954982 10.1016/j.bmcl.2008.10.004 Unchecked 1
18954982 10.1016/j.bmcl.2008.10.004 Hepatitis C virus 1
21381769 10.1021/jm1012374 Unchecked 1
27501244 10.1021/acs.jmedchem.6b00915 Hepatitis C virus 1
27501244 10.1021/acs.jmedchem.6b00915 ADMET 1

Data from ChEMBL 36 via Core Engine