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Compound Detail

CHEMBL559638

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O=C1c2cccc3c(NCCO)ccc(c23)C(=O)N1c1cccc(Br)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL559638
Phase Preclinical
Structure Type MOL
InChI Key JZCUVYNOSDWORZ-UHFFFAOYSA-N
3
Targets
26
Activities
2
Assay Types
5
PK Parameters
9
Publications
0
Known Names

Molecular Properties

411.3
MW (Da)
3.81
ALogP
4
HBA
2
HBD
69.6
PSA (Ų)
0.64
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 C20H15BrN2O3
MW 411.26
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -1.17

Activity Summary

IC50 18 meas. best 7.7
EC50 8 meas. best 5.34

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus
CHEMBL379
 IC50 7.7 7.7 20.0 1
RNA-directed RNA polymerase
CHEMBL4296320
 IC50 7.7 7.405 20.0 2
Unchecked
CHEMBL612545
 IC50 7.7 5.868 20.0 15
Hepatitis C virus
CHEMBL379
 EC50 5.34 5.1038 4600.0 8

Pharmacokinetic Data

Parameter Value Units Species
AUC 3989.22 ng.hr.mL-1 Rattus norvegicus
CL 12.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 4000.0 nM Rattus norvegicus
F 83.0 % Rattus norvegicus
T1/2 0.7 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 20.0 nM 7.7 Inhibition of HCV1b BK NS5B Cdelta21 RNA dependent RNA polymerase 19877603
RNA-directed RNA polymerase IC50 = 20.0 nM 7.7 Inhibition of HCV1b BK NS5B Cdelta21 RNA dependent RNA polymerase Thumb site 1 P... 19877603
Hepatitis C virus IC50 = 20.0 nM 7.7 Inhibition of HCV genotype 1b NS5B polymerase deltaC21 mutant 20363140
Unchecked IC50 = 64.0 nM 7.19 Inhibition of HCV1a RB5 NS5B Cdelta21 RNA dependent RNA polymerase 19877603
RNA-directed RNA polymerase IC50 = 78.0 nM 7.11 Inhibition of HCV1b BK NS5B Cdelta21 RNA dependent RNA polymerase Palm site 1 an... 19877603
Unchecked IC50 = 180.0 nM 6.75 Inhibition of HCV2b.2 NS5B Cdelta21 RNA dependent RNA polymerase 19877603
Unchecked IC50 = 180.0 nM 6.75 Inhibition of HCV genotype 2b NS5B polymerase deltaC21 mutant 20363140
Unchecked IC50 = 490.0 nM 6.31 Inhibition of HCV6a NS5B Cdelta21 RNA dependent RNA polymerase 19877603
Unchecked IC50 = 500.0 nM 6.3 Inhibition of HCV1b BK NS5B Cdelta21 RNA dependent RNA polymerase Thumb site 2 R... 19877603
Unchecked IC50 = 540.0 nM 6.27 Inhibition of HCV4a NS5B Cdelta21 RNA dependent RNA polymerase 19877603
Unchecked IC50 = 760.0 nM 6.12 Inhibition of HCV3a.7 NS5B Cdelta21 RNA dependent RNA polymerase 19877603
Unchecked IC50 = 770.0 nM 6.11 Inhibition of HCV2a.4 NS5B Cdelta21 RNA dependent RNA polymerase 19877603
Unchecked IC50 = 3200.0 nM 5.5 Selectivity for IC50 for HCV1a RB5 NS5B Cdelta21 RNA dependent RNA polymerase to... 19877603
Hepatitis C virus EC50 = 4600.0 nM 5.34 Antiviral activity against HCV1b BK infected in human Huh7 cells by replicon cel... 19877603
Hepatitis C virus EC50 = 4700.0 nM 5.33 Antiviral activity against HCV H77-1a infected in human Huh7 cells by replicon c... 19877603
Hepatitis C virus EC50 = 6400.0 nM 5.19 Antiviral activity against HCV1b Con1 infected in human Huh7 cells by replicon c... 19877603
Hepatitis C virus EC50 = 7100.0 nM 5.15 Antiviral activity against HCV infected in human HBI10A cells 20363140
Hepatitis C virus EC50 = 7100.0 nM 5.15 Antiviral activity against HCV1b Con1 infected in human Huh7 clone HBI10A cells ... 19877603
Unchecked IC50 = 9500.0 nM 5.02 Selectivity for IC50 for HCV2b.2 NS5B Cdelta21 RNA dependent RNA polymerase to I... 19877603
Hepatitis C virus EC50 = 11000.0 nM 4.96 Antiviral activity against HCV1b BK infected in human H2B2 cells expressing HEPR... 19877603

Literature References

PubMed DOI Target Context # Activities
19877603 10.1021/jm900517t Unchecked 26
19877603 10.1021/jm900517t Hepatitis C virus 6
19877603 10.1021/jm900517t Rattus norvegicus 6
20363140 10.1016/j.bmc.2010.03.024 Hepatitis C virus 4
19877603 10.1021/jm900517t RNA-directed RNA polymerase 3
19877603 10.1021/jm900517t No relevant target 2
20363140 10.1016/j.bmc.2010.03.024 Unchecked 2
19877603 10.1021/jm900517t ADMET 1
20363140 10.1016/j.bmc.2010.03.024 ADMET 1

Data from ChEMBL 36 via Core Engine