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Compound Detail

CHEMBL414993

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C=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H](Oc2cc(-c3ccccc3)nc3cc(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 CHEMBL414993
Phase Preclinical
Structure Type MOL
InChI Key YMHQYWPVQDRYSQ-LMPQEXDPSA-N
5
Targets
12
Activities
3
Assay Types
16
PK Parameters
17
Publications
0
Known Names

Molecular Properties

790.0
MW (Da)
4.87
ALogP
10
HBA
3
HBD
182.3
PSA (Ų)
0.21
QED
1
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C41H51N5O9S
MW 789.95
Aromatic Rings 3
Heavy Atoms 56
NP-Likeness -0.20

Activity Summary

IC50 6 meas. best 9.0
EC50 5 meas. best 9.05
Ki 1 meas. best 10.24

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 10.24 10.24 0.1 1
Hepatitis C virus
CHEMBL379
 EC50 9.05 8.5175 0.9 4
Non-structural protein 4b
CHEMBL6066153
 IC50 9.0 9.0 1.0 1
Unchecked
CHEMBL612545
 IC50 9.0 9.0 1.0 2
SARS-CoV-2
CHEMBL4303835
 EC50 8.4 8.4 4.0 1
Hepatitis C virus serine protease, NS3/NS4A
CHEMBL2095231
 IC50 8.35 7.95 4.5 3

Pharmacokinetic Data

Parameter Value Units Species
AUC 455.8 ng.hr.mL-1 Rattus norvegicus
AUC 1579.9 ng.hr.mL-1 Canis lupus familiaris
AUC 576.66 ng.hr.mL-1 Rattus norvegicus
AUC 60.83 ng.hr.mL-1 Rattus norvegicus
AUC 61.0 ng.hr.mL-1 Rattus norvegicus
CL 16.0 mL.min-1.kg-1 Canis lupus familiaris
CL 55.0 mL.min-1.kg-1 Rattus norvegicus
F 9.0 % Rattus norvegicus
F 20.0 % Canis lupus familiaris
F 9.0 % Rattus norvegicus
T1/2 2.833 hr Canis lupus familiaris
T1/2 2.7 hr Rattus norvegicus
T1/2 0.6 hr Canis lupus familiaris
T1/2 1.0 hr Rattus norvegicus
T1/2 2.833 hr Canis lupus familiaris
T1/2 2.7 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.058 nM 10.24 Inhibition of HCV NS3 protease in presence of pH 7.5 HEPES buffer 17449253
Hepatitis C virus EC50 = 0.9 nM 9.05 Inhibition of HCV by subgenomic HCV replication assay 17449253
Unchecked IC50 = 1.0 nM 9.0 Inhibition of HCV NS3 protease 21413808
Unchecked IC50 = 1.0 nM 9.0 Inhibition of Hepatitis C virus genotype 1a H77 recombinant NS3/4A protease expr... 24555570
Non-structural protein 4b IC50 = 1.0 nM 9.0 Inhibition of Hepatitis C virus genotype 1a NS4B 38179950
Hepatitis C virus EC50 = 4.0 nM 8.4 Antiviral activity against Hepatitis C virus genotype 1b Con1 after 4 days by ce... 24555570
Hepatitis C virus EC50 = 4.0 nM 8.4 Antiviral activity against Hepatitis C virus 27501244
SARS-CoV-2 EC50 = 4.0 nM 8.4 Antiviral activity against SARS-CoV-2 infected in human Huh-7 cells assessed as ... 38179950
Hepatitis C virus serine protease, NS3/NS4A IC50 = 4.5 nM 8.35 Inhibition of N-terminal poly-His tagged recombinant HCV genotype 1a NS3/4A prot... 29650290
Hepatitis C virus EC50 = 6.0 nM 8.22 Antiviral activity against HCV genotype 1b infected in human Huh7.5 replicon cel... 29650290
Hepatitis C virus serine protease, NS3/NS4A IC50 = 18.0 nM 7.75 Inhibition of N-terminal poly-His tagged recombinant HCV genotype 2b NS3/4A prot... 29650290
Hepatitis C virus serine protease, NS3/NS4A IC50 = 18.0 nM 7.75 Inhibition of N-terminal poly-His tagged recombinant HCV genotype 3a NS3/4A prot... 29650290

Literature References

PubMed DOI Target Context # Activities
24555570 10.1021/jm401840s Rattus norvegicus 6
24555570 10.1021/jm401840s Canis familiaris 4
24555570 10.1021/jm401840s Plasma 3
24555570 10.1021/jm401840s Liver 3
29650290 10.1016/j.bmcl.2018.04.009 Hepatitis C virus serine protease, NS3/NS4A 3
24555570 10.1021/jm401840s Liver microsome 2
27501244 10.1021/acs.jmedchem.6b00915 ADMET 2
29650290 10.1016/j.bmcl.2018.04.009 ADMET 2
24555570 10.1021/jm401840s Hepatitis C virus 1
38179950 10.1021/acs.jmedchem.3c01971 SARS-CoV-2 1
38179950 10.1021/acs.jmedchem.3c01971 Non-structural protein 4b 1
27501244 10.1021/acs.jmedchem.6b00915 Hepatitis C virus 1
29650290 10.1016/j.bmcl.2018.04.009 Hepatitis C virus 1
24555570 10.1021/jm401840s Unchecked 1
17449253 10.1016/j.bmc.2007.03.089 Unchecked 1
21413808 10.1021/jm1013693 Unchecked 1
17449253 10.1016/j.bmc.2007.03.089 Hepatitis C virus 1

Data from ChEMBL 36 via Core Engine