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Compound Detail

CHEMBL176058

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CC(C)CCn1c(=O)c(C2=NS(=O)(=O)c3ccccc3N2)c(O)c2ccccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL176058
Phase Preclinical
Structure Type MOL
InChI Key MQFPIRFODWNQIO-UHFFFAOYSA-N
4
Targets
26
Activities
2
Assay Types
8
PK Parameters
20
Publications
0
Known Names

Molecular Properties

411.5
MW (Da)
3.31
ALogP
6
HBA
2
HBD
100.8
PSA (Ų)
0.69
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H21N3O4S
MW 411.48
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -0.76

Activity Summary

IC50 17 meas. best 7.52
EC50 9 meas. best 6.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus
CHEMBL379
 IC50 7.52 6.8773 30.0 11
RNA-directed RNA polymerase
CHEMBL4296320
 IC50 7.5 7.1 32.0 2
Unchecked
CHEMBL612545
 IC50 7.5 6.885 32.0 2
Hepatitis C virus
CHEMBL379
 EC50 6.6 5.9586 250.0 7
RNA-directed RNA polymerase
CHEMBL4296320
 EC50 6.38 6.38 417.0 1
Genome polyprotein
CHEMBL4620
 IC50 6.1 6.1 800.0 1
Unchecked
CHEMBL612545
 EC50 6.05 6.05 900.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 10.1 mL.min-1.kg-1 Rattus norvegicus
CL 0.5 mL.min-1.kg-1 Canis lupus familiaris
Cmax 2.664 nM Rattus norvegicus
Cmax 5419.46 nM Canis lupus familiaris
F 70.0 % Rattus norvegicus
F 89.0 % Canis lupus familiaris
T1/2 0.6067 hr Rattus norvegicus
T1/2 14.32 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus IC50 = 30.0 nM 7.52 Inhibition of HCV 1b J4 NS5B Cdelta 21polymerase over expressed in Escherichia c... 19447623
Hepatitis C virus IC50 = 32.0 nM 7.5 Inhibition of HCV1b Cdelta-21-truncated NS5B by enzymatic assay 19515564
Unchecked IC50 = 32.0 nM 7.5 Inhibition of HCV isolate BK NS5B deltaC21 polymerase 19502055
RNA-directed RNA polymerase IC50 = 32.0 nM 7.5 Inhibitory activity against HCV delta 21 NS5B RNA polymerase by SPA assay 16451063
Hepatitis C virus IC50 = 32.0 nM 7.5 Inhibition of HCV 1b NS5B polymerase 18242088
Hepatitis C virus IC50 = 32.0 nM 7.5 Inhibition of HCV 1b NS5B RNA polymerase 18487044
Hepatitis C virus IC50 = 32.0 nM 7.5 Inhibition of HCV 1b NS5B polymerase expressed in Sf9 cells 19505821
Hepatitis C virus IC50 = 85.0 nM 7.07 Inhibition of N-terminal His-tagged recombinant Hepatitis C virus subtype 1b NS5... 23409936
RNA-directed RNA polymerase IC50 = 200.0 nM 6.7 Inhibition of HCV NS5B RNA dependent RNA polymerase 16455253
Hepatitis C virus EC50 = 250.0 nM 6.6 Antiviral activity against HCV 1b in presence of 5% fetal calf serum by replicon... 18599294
RNA-directed RNA polymerase EC50 = 417.0 nM 6.38 Inhibition of HCV RNA replication in Huh7 cells 16451063
Hepatitis C virus IC50 = 417.0 nM 6.38 Antiviral activity against HCV 1b after 72 hrs by replicon assay 19515564
Hepatitis C virus IC50 = 417.0 nM 6.38 Antiviral activity against HCV 1b infected in human hepatoma cells by replicon a... 19505821
Hepatitis C virus IC50 = 420.0 nM 6.38 Inhibition of HCV 1b NS5B polymerase 18599294
Hepatitis C virus EC50 = 417.0 nM 6.38 Antiviral activity against HCV 1b infected in human HuH7 cells after 46 to 50 hr... 19502055
Unchecked IC50 = 540.0 nM 6.27 Inhibition of HCV 1a NS5B polymerase 18599294
Hepatitis C virus EC50 = 600.0 nM 6.22 Antiviral activity against Hepatitis C virus genotype 1b infected in human Huh-9... 18625766
Genome polyprotein IC50 = 800.0 nM 6.1 Inhibitory concentration against hepatitis C virus polymerase 15633995
Hepatitis C virus EC50 = 870.0 nM 6.06 Antiviral activity against HCV 1b replication in human 2209-23 cells assessed as... 19447623
Unchecked EC50 = 900.0 nM 6.05 Inhibition of replication in Huh-9-13 cells containing Wild type HCV replicons a... 17088480

Literature References

PubMed DOI Target Context # Activities
16451063 10.1021/jm050855s Rattus norvegicus 5
16451063 10.1021/jm050855s Canis familiaris 5
18625766 10.1128/aac.01534-07 ADMET 4
18625766 10.1128/aac.01534-07 Hepatitis C virus 4
17088480 10.1128/aac.00498-06 Unchecked 4
16451063 10.1021/jm050855s RNA-directed RNA polymerase 3
19515564 10.1016/j.bmcl.2009.05.091 Hepatitis C virus 3
19447623 10.1016/j.bmcl.2009.04.119 Hepatitis C virus 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
19505821 10.1016/j.bmcl.2009.05.080 Hepatitis C virus 2
18599294 10.1016/j.bmcl.2008.06.043 Hepatitis C virus 2
19070486 10.1016/j.bmcl.2008.11.060 Hepatitis C virus 1
18599294 10.1016/j.bmcl.2008.06.043 Unchecked 1
18487044 10.1016/j.bmcl.2008.04.066 Hepatitis C virus 1
19505821 10.1016/j.bmcl.2009.05.080 Albumin 1
19502055 10.1016/j.bmcl.2009.05.063 Unchecked 1
19502055 10.1016/j.bmcl.2009.05.063 Hepatitis C virus 1
18242088 10.1016/j.bmcl.2008.01.007 Hepatitis C virus 1
16455253 10.1016/j.bmcl.2006.01.034 Hepatitis C virus 1
16455253 10.1016/j.bmcl.2006.01.034 RNA-directed RNA polymerase 1

Data from ChEMBL 36 via Core Engine