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Compound Detail

CHEMBL3785323

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COc1ccc2nc(C(F)(F)F)c3c(c2c1)CC[C@]1(C[C@H]2C(=O)N[C@]4(C(=O)NS(=O)(=O)C5(C)CC5)C[C@H]4/C=C\CCCCC[C@H](NC(=O)OCC(C)C)C(=O)N2C1)O3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3785323
Phase Preclinical
Structure Type MOL
InChI Key GBJKXZJNFVRHCK-XPTVTBSVSA-N
3
Targets
24
Activities
2
Assay Types
3
PK Parameters
14
Publications
0
Known Names

Molecular Properties

833.9
MW (Da)
5.07
ALogP
10
HBA
3
HBD
182.3
PSA (Ų)
0.32
QED
2
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C40H50F3N5O9S
MW 833.93
Aromatic Rings 2
Heavy Atoms 58
NP-Likeness 0.12

Activity Summary

IC50 15 meas. best 11.0
EC50 9 meas. best 9.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus serine protease, NS3/NS4A
CHEMBL2095231
 IC50 11.0 11.0 0.0 2
Unchecked
CHEMBL612545
 IC50 11.0 9.8255 0.0 11
Hepatitis C virus
CHEMBL379
 EC50 9.15 8.81 0.7 9

Pharmacokinetic Data

Parameter Value Units Species
AUC 7505.37 ng.hr.mL-1 Rattus norvegicus
F 31.0 % Rattus norvegicus
F 17.0 % Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus serine protease, NS3/NS4A IC50 = 0.01 nM 11.0 Inhibition of HCV genotype 1b NS3/4A protease R155K mutant using Ac-C(Eu)DDMEEAb... 26819676
Unchecked IC50 = 0.01 nM 11.0 Inhibition of HCV genotype 1a NS3/4A protease assessed as substrate cleavage usi... 27994759
Unchecked IC50 = 0.01 nM 11.0 Inhibition of HCV genotype 1b NS3/4A protease assessed as substrate cleavage usi... 27994759
Hepatitis C virus serine protease, NS3/NS4A IC50 = 0.01 nM 11.0 Inhibition of HCV genotype 1b NS3/4A protease R155K mutant assessed as substrate... 27994759
Unchecked IC50 = 0.02 nM 10.7 Inhibition of HCV genotype 2a NS3/4A protease assessed as substrate cleavage usi... 27994759
Unchecked IC50 = 0.023 nM 10.64 Inhibition of HCV genotype 1b NS3/4A protease D168Y mutant using Ac-C(Eu)DDMEEAb... 26819676
Unchecked IC50 = 0.03 nM 10.52 Inhibition of HCV genotype 1b NS3/4A protease D168Y mutant assessed as substrate... 27994759
Unchecked IC50 = 0.41 nM 9.39 Inhibition of HCV genotype 3a full length NS3/4A protease using Ac-C(Eu)DDMEEAbu... 26819676
Unchecked IC50 = 0.483 nM 9.32 Inhibition of HCV genotype 1b NS3/4A protease A156T mutant using Ac-C(Eu)DDMEEAb... 26819676
Unchecked IC50 = 0.53 nM 9.28 Inhibition of HCV genotype 3a NS3/4A protease assessed as substrate cleavage usi... 27994759
Unchecked IC50 = 0.59 nM 9.23 Inhibition of HCV genotype 1b NS3/4A protease A156T mutant assessed as substrate... 27994759
Hepatitis C virus EC50 = 0.7 nM 9.15 Antiviral activity against HCV genotype 1a infected in human HuH7 cells assessed... 26819676
Hepatitis C virus EC50 = 0.8 nM 9.1 Antiviral activity against HCV genotype 1b infected in human HuH7 cells assessed... 26819676
Hepatitis C virus EC50 = 0.9 nM 9.05 Antiviral activity against HCV genotype 2a infected in human HuH7 cells assessed... 26819676
Hepatitis C virus EC50 = 1.2 nM 8.92 Antiviral activity against HCV genotype 1b infected in human HuH7 cells assessed... 27994759
Hepatitis C virus EC50 = 1.7 nM 8.77 Antiviral activity against HCV genotype 3a infected in human HuH7 cells assessed... 26819676
Hepatitis C virus EC50 = 2.0 nM 8.7 Antiviral activity against HCV genotype 3a infected in human HuH7 cells assessed... 27994759
Hepatitis C virus EC50 = 2.0 nM 8.7 Antiviral activity against HCV genotype 2a infected in human HuH7 cells assessed... 27994759
Unchecked IC50 = 2.76 nM 8.56 Inhibition of HCV genotype 1b NS3/4A protease A156V mutant using Ac-C(Eu)DDMEEAb... 26819676
Hepatitis C virus EC50 = 3.4 nM 8.47 Antiviral activity against HCV genotype 2b infected in human HuH7 cells assessed... 26819676

Literature References

PubMed DOI Target Context # Activities
26819676 10.1021/acsmedchemlett.5b00425 Hepatitis C virus 9
26819676 10.1021/acsmedchemlett.5b00425 Canis familiaris 8
27994759 10.1021/acsmedchemlett.6b00321 Unchecked 7
26819676 10.1021/acsmedchemlett.5b00425 Unchecked 6
26819676 10.1021/acsmedchemlett.5b00425 Rattus norvegicus 6
27994759 10.1021/acsmedchemlett.6b00321 Hepatitis C virus 4
26819676 10.1021/acsmedchemlett.5b00425 Hepatitis C virus serine protease, NS3/NS4A 1
26819676 10.1021/acsmedchemlett.5b00425 Cytochrome P450 3A4 1
26819676 10.1021/acsmedchemlett.5b00425 Cytochrome P450 2C9 1
26819676 10.1021/acsmedchemlett.5b00425 Cytochrome P450 2D6 1
26819676 10.1021/acsmedchemlett.5b00425 Salmonella typhimurium 1
26819676 10.1021/acsmedchemlett.5b00425 Liver 1
26819676 10.1021/acsmedchemlett.5b00425 Cytochrome P450 2C8 1
27994759 10.1021/acsmedchemlett.6b00321 Hepatitis C virus serine protease, NS3/NS4A 1

Data from ChEMBL 36 via Core Engine