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Compound Detail

CHEMBL2208400

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COc1ccc2c(O[C@@H]3C[C@H]4C(=O)N[C@]5(C(=O)NS(=O)(=O)C6CC6)C[C@H]5/C=C\CCCCC[C@H](NC(=O)C5(OC)CCC5)C(=O)N4C3)cc(-c3nc(C4CC4)cs3)nc2c1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2208400
Phase Preclinical
Structure Type MOL
InChI Key SSESGVKMGZOAFR-TXTQRQSWSA-N
2
Targets
10
Activities
2
Assay Types
5
PK Parameters
4
Publications
0
Known Names

Molecular Properties

875.1
MW (Da)
4.96
ALogP
12
HBA
3
HBD
195.2
PSA (Ų)
0.22
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C44H54N6O9S2
MW 875.08
Aromatic Rings 3
Heavy Atoms 61
NP-Likeness 0.01

Activity Summary

EC50 9 meas. best 10.4
IC50 1 meas. best 8.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus
CHEMBL379
 EC50 10.4 8.3744 0.0 9
Unchecked
CHEMBL612545
 IC50 8.7 8.7 2.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 49.1 ng.hr.mL-1 Rattus norvegicus
AUC 117.0 ng.hr.mL-1 Rattus norvegicus
CL 143.92 mL.min-1.kg-1 Rattus norvegicus
F 8.2 % Rattus norvegicus
T1/2 0.99 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus EC50 = 0.04 nM 10.4 Antiviral activity against HCV subtype 1b expressing wild type NS3/4A protease i... 23142614
Hepatitis C virus EC50 = 0.1 nM 10.0 Antiviral activity against HCV subtype 1b infected in human hepatoma cells 23142614
Hepatitis C virus EC50 = 0.2 nM 9.7 Antiviral activity against HCV subtype 1a infected in human hepatoma cells 23142614
Hepatitis C virus EC50 = 0.3 nM 9.52 Antiviral activity against HCV subtype 1b expressing NS3/4A A156S mutant proteas... 23142614
Unchecked IC50 = 2.0 nM 8.7 Inhibition of HCV subtype 1a NS3/4A protease (Ac-DE-Dap(QXL520)-EE-Abu-psi-[COO]... 23142614
Hepatitis C virus EC50 = 20.0 nM 7.7 Antiviral activity against HCV subtype 1b expressing NS3/4A A156T mutant proteas... 23142614
Hepatitis C virus EC50 = 44.0 nM 7.36 Antiviral activity against HCV subtype 1b expressing NS3/4A R115K mutant proteas... 23142614
Hepatitis C virus EC50 = 85.0 nM 7.07 Antiviral activity against HCV subtype 1b expressing NS3/4A A156V mutant proteas... 23142614
Hepatitis C virus EC50 = 91.0 nM 7.04 Antiviral activity against HCV subtype 1b expressing NS3/4A D168A mutant proteas... 23142614
Hepatitis C virus EC50 = 263.0 nM 6.58 Antiviral activity against HCV subtype 1b expressing NS3/4A D168V mutant proteas... 23142614

Literature References

PubMed DOI Target Context # Activities
23142614 10.1016/j.bmcl.2012.10.075 Hepatitis C virus 9
23142614 10.1016/j.bmcl.2012.10.075 Rattus norvegicus 5
23142614 10.1016/j.bmcl.2012.10.075 Portal vein 1
23142614 10.1016/j.bmcl.2012.10.075 Unchecked 1

Data from ChEMBL 36 via Core Engine