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Compound Detail

CHEMBL372357

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O=c1c(C2=Nc3ccccc3S(=O)(=O)N2)c(O)c2cc(F)ccc2n1CCC1CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL372357
Phase Preclinical
Structure Type MOL
InChI Key QEMCDXCXSVPAAB-UHFFFAOYSA-N
4
Targets
19
Activities
2
Assay Types
15
PK Parameters
19
Publications
0
Known Names

Molecular Properties

427.5
MW (Da)
3.02
ALogP
6
HBA
2
HBD
100.8
PSA (Ų)
0.67
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H18FN3O4S
MW 427.46
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -0.94

Activity Summary

IC50 13 meas. best 8.0
EC50 6 meas. best 7.42

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus
CHEMBL379
 IC50 8.0 7.1357 10.0 7
RNA-directed RNA polymerase
CHEMBL4296320
 IC50 8.0 7.8 10.0 4
Hepatitis C virus
CHEMBL379
 EC50 7.42 6.41 38.0 4
RNA-directed RNA polymerase
CHEMBL4296320
 EC50 7.42 7.42 38.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 6.08 6.04 840.0 2
Nuclear receptor subfamily 1 group I member 2
CHEMBL3401
 EC50 5.28 5.28 5300.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.4 mL.min-1.kg-1 Rattus norvegicus
CL 0.86 mL.min-1.kg-1 Canis lupus familiaris
CL 0.76 mL.min-1.kg-1 Macaca fascicularis
Cmax 9687.46 nM Rattus norvegicus
Cmax 10422.03 nM Canis lupus familiaris
Cmax 12719.32 nM Macaca fascicularis
F 44.0 % Rattus norvegicus
F 35.0 % Canis lupus familiaris
F 53.0 % Macaca fascicularis
F 10.0 % Rattus norvegicus
F 44.0 % Rattus norvegicus
T1/2 3.037 hr Rattus norvegicus
T1/2 1.725 hr Canis lupus familiaris
T1/2 1.615 hr Macaca fascicularis
T1/2 3.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus IC50 = 10.0 nM 8.0 Inhibition of HCV1b Cdelta-21-truncated NS5B by enzymatic assay 19515564
Hepatitis C virus IC50 = 10.0 nM 8.0 Inhibition of HCV 1b J4 NS5B Cdelta 21polymerase over expressed in Escherichia c... 19447623
RNA-directed RNA polymerase IC50 = 10.0 nM 8.0 Inhibitory activity against HCV delta 21 NS5B RNA polymerase by SPA assay 16451063
RNA-directed RNA polymerase IC50 = 10.0 nM 8.0 Inhibitory activity against HCV 1b NS5B RNA polymerase 16451063
RNA-directed RNA polymerase IC50 = 13.0 nM 7.89 Inhibitory activity against HCV 2a NS5B RNA polymerase 16451063
Hepatitis C virus IC50 = 30.0 nM 7.52 Inhibition of HCV 1b isolate BK NS5B Cdelta21 polymerase expressed in Escherichi... 19457662
Hepatitis C virus EC50 = 38.0 nM 7.42 Protein binding in Huh7 cells using HCV 1b replicon by a replicon cell assay 16451063
Hepatitis C virus IC50 = 38.0 nM 7.42 Antiviral activity against HCV 1b after 72 hrs by replicon assay 19515564
RNA-directed RNA polymerase EC50 = 38.0 nM 7.42 Inhibition of HCV RNA replication in Huh7 cells 16451063
Hepatitis C virus IC50 = 40.0 nM 7.4 Antiviral activity against HCV in human HuH7 cells by replicon assay 19447623
RNA-directed RNA polymerase IC50 = 49.0 nM 7.31 Inhibitory activity against HCV 1a NS5B RNA polymerase 16451063
Hepatitis C virus IC50 = 100.0 nM 7.0 Inhibition of HCV 1b NS5B polymerase 19447623
Hepatitis C virus EC50 = 180.0 nM 6.75 Protein binding in Huh7 cells using HCV 1b replicon by a replicon cell assay in ... 16451063
Hepatitis C virus EC50 = 260.0 nM 6.58 Antiviral activity against HCV 1b replication in human 2209-23 cells assessed as... 19447623
Cytochrome P450 2C9 IC50 = 840.0 nM 6.08 Inhibition of CYP2C9 19515564
Cytochrome P450 2C9 IC50 = 1000.0 nM 6.0 Inhibition of CYP2C9 isozyme 16451063
Nuclear receptor subfamily 1 group I member 2 EC50 = 5300.0 nM 5.28 Effect on PXR activity 16451063
Hepatitis C virus EC50 = 13000.0 nM 4.89 Protein binding in Huh7 cells using HCV 1b replicon by a replicon cell assay in ... 16451063
Hepatitis C virus IC50 = 24461.0 nM 4.61 Antiviral activity against HCV 1b after 72 hrs by replicon assay in presence of ... 19515564

Literature References

PubMed DOI Target Context # Activities
16451063 10.1021/jm050855s RNA-directed RNA polymerase 7
16451063 10.1021/jm050855s Rattus norvegicus 5
16451063 10.1021/jm050855s Canis familiaris 5
16451063 10.1021/jm050855s Cynomolgus monkey 5
16451063 10.1021/jm050855s Hepatitis C virus 4
19447623 10.1016/j.bmcl.2009.04.119 Hepatitis C virus 4
19515564 10.1016/j.bmcl.2009.05.091 Hepatitis C virus 3
19515564 10.1016/j.bmcl.2009.05.091 Rattus norvegicus 2
16451063 10.1021/jm050855s Cytochrome P450 3A4 1
19515564 10.1016/j.bmcl.2009.05.091 Cytochrome P450 2C9 1
19515564 10.1016/j.bmcl.2009.05.091 Plasma 1
19457662 10.1016/j.bmcl.2009.05.004 Rattus norvegicus 1
19457662 10.1016/j.bmcl.2009.05.004 No relevant target 1
19457662 10.1016/j.bmcl.2009.05.004 Hepatitis C virus 1
16451063 10.1021/jm050855s Nuclear receptor subfamily 1 group I member 2 1
16451063 10.1021/jm050855s Cytochrome P450 2C9 1
16451063 10.1021/jm050855s DNA polymerase beta 1
16451063 10.1021/jm050855s Genome polyprotein 1
16451063 10.1021/jm050855s DNA polymerase alpha catalytic subunit 1

Data from ChEMBL 36 via Core Engine