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Compound Detail

CHEMBL2403888

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C=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H](Oc2nccc3cc(OC)ccc23)CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)C(=O)NS(=O)(=O)C1CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2403888
Phase Preclinical
Structure Type MOL
InChI Key IYWRCNFZPNEADN-CXODAYGWSA-N
4
Targets
14
Activities
2
Assay Types
23
PK Parameters
20
Publications
0
Known Names

Molecular Properties

713.9
MW (Da)
3.20
ALogP
10
HBA
3
HBD
182.3
PSA (Ų)
0.29
QED
1
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C35H47N5O9S
MW 713.85
Aromatic Rings 2
Heavy Atoms 50
NP-Likeness -0.18

Activity Summary

IC50 8 meas. best 9.0
EC50 6 meas. best 8.55

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 9.0 8.775 1.0 4
Hepatitis C virus serine protease, NS3/NS4A
CHEMBL2095231
 IC50 8.7 7.4833 2.0 3
Hepatitis C virus
CHEMBL379
 EC50 8.55 8.1517 2.8 6
Cytochrome P450 3A4
CHEMBL340
 IC50 5.7 5.7 2000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 10065.28 ng.hr.mL-1 Rattus norvegicus
AUC 7424.04 ng.hr.mL-1 Rattus norvegicus
AUC 10065.28 ng.hr.mL-1 Rattus norvegicus
AUC 7424.04 ng.hr.mL-1 Rattus norvegicus
AUC 10065.28 ng.hr.mL-1 Rattus norvegicus
AUC 7423.0 ng.hr.mL-1 Rattus norvegicus
CL 4.4 mL.min-1.kg-1 Rattus norvegicus
CL 4.4 mL.min-1.kg-1 Rattus norvegicus
CL 4.4 mL.min-1.kg-1 Rattus norvegicus
F 1.0 % Macaca fascicularis
F 51.0 % Canis lupus familiaris
F 18.0 % Rattus norvegicus
F 18.0 % Rattus norvegicus
F 18.0 % Rattus norvegicus
t1/2 - - Rattus norvegicus
t1/2 - - Homo sapiens
T1/2 4.0 hr Homo sapiens
T1/2 1.0 hr Rattus norvegicus
T1/2 4.4 hr Rattus norvegicus
T1/2 0.55 hr Homo sapiens
T1/2 4.4 hr Rattus norvegicus
T1/2 4.4 hr Rattus norvegicus
Tmax 1.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 1.0 nM 9.0 Inhibition of HCV genotype 1a NS3/4A protease 28011221
Unchecked IC50 = 2.0 nM 8.7 Inhibition of Hepatitis C virus NS3 protease 23773863
Unchecked IC50 = 2.0 nM 8.7 Inhibition of Hepatitis C virus genotype 1a H77 recombinant NS3/4A protease expr... 24555570
Unchecked IC50 = 2.0 nM 8.7 Inhibition of HCV genotype 1a NS3 protease using RET S1 as substrate incubated f... 27564532
Hepatitis C virus serine protease, NS3/NS4A IC50 = 2.0 nM 8.7 Inhibition of N-terminal poly-His tagged recombinant HCV genotype 1a NS3/4A prot... 29650290
Hepatitis C virus EC50 = 2.8 nM 8.55 Antiviral activity against Hepatitis C virus genotype 1b Con1 after 4 days by ce... 24555570
Hepatitis C virus EC50 = 3.0 nM 8.52 Antiviral activity against Hepatitis C virus 23773863
Hepatitis C virus EC50 = 8.3 nM 8.08 Antiviral activity against Hepatitis C virus genotype 1a H77 assessed as inhibit... 24555570
Hepatitis C virus EC50 = 12.0 nM 7.92 Antiviral activity against HCV genotype 1b Con1 expressing NS3 protease infected... 27564532
Hepatitis C virus EC50 = 12.0 nM 7.92 Antiviral activity against HCV genotype 1b by cell based replicon assay 28011221
Hepatitis C virus EC50 = 12.0 nM 7.92 Antiviral activity against HCV genotype 1b infected in human Huh7.5 replicon cel... 29650290
Hepatitis C virus serine protease, NS3/NS4A IC50 = 95.0 nM 7.02 Inhibition of N-terminal poly-His tagged recombinant HCV genotype 3a NS3/4A prot... 29650290
Hepatitis C virus serine protease, NS3/NS4A IC50 = 187.0 nM 6.73 Inhibition of N-terminal poly-His tagged recombinant HCV genotype 2b NS3/4A prot... 29650290
Cytochrome P450 3A4 IC50 = 2000.0 nM 5.7 Inhibition of CYP3A4 (unknown origin) 24555570

Literature References

PubMed DOI Target Context # Activities
24555570 10.1021/jm401840s Homo sapiens 8
27564532 10.1021/acs.jmedchem.6b00821 ADMET 6
28011221 10.1016/j.bmcl.2016.12.013 Heart 6
28011221 10.1016/j.bmcl.2016.12.013 Rattus norvegicus 5
24555570 10.1021/jm401840s Rattus norvegicus 4
24555570 10.1021/jm401840s Hepatitis C virus 4
29650290 10.1016/j.bmcl.2018.04.009 Hepatitis C virus serine protease, NS3/NS4A 3
24555570 10.1021/jm401840s ADMET 3
24555570 10.1021/jm401840s Plasma 3
24555570 10.1021/jm401840s Liver 3
24555570 10.1021/jm401840s Nucleic Acid 2
24555570 10.1021/jm401840s Hepatocyte 2
24555570 10.1021/jm401840s Unchecked 2
27564532 10.1021/acs.jmedchem.6b00821 Molecular identity unknown 2
28011221 10.1016/j.bmcl.2016.12.013 Liver 2
29650290 10.1016/j.bmcl.2018.04.009 ADMET 2
23773863 10.1016/j.bmcl.2013.05.045 No relevant target 2
28011221 10.1016/j.bmcl.2016.12.013 No relevant target 2
29650290 10.1016/j.bmcl.2018.04.009 Hepatitis C virus 2
23773863 10.1016/j.bmcl.2013.05.045 Liver microsomes 2

Data from ChEMBL 36 via Core Engine