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Compound Detail

CHEMBL181653

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O=C(O)c1nc(-c2cccs2)nc(O)c1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL181653
Phase Preclinical
Structure Type MOL
InChI Key SSOGKSFNCMYOPA-UHFFFAOYSA-N
8
Targets
16
Activities
2
Assay Types
4
PK Parameters
17
Publications
0
Known Names

Molecular Properties

238.2
MW (Da)
1.31
ALogP
6
HBA
3
HBD
103.5
PSA (Ų)
0.73
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C9H6N2O4S
MW 238.22
Aromatic Rings 2
Heavy Atoms 16
NP-Likeness -1.47

Activity Summary

IC50 14 meas. best 6.82
EC50 2 meas. best 5.03

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus
CHEMBL379
 IC50 6.82 6.2 150.0 2
RNA-directed RNA polymerase
CHEMBL4296320
 IC50 6.62 5.43 240.0 7
Tripartite terminase subunit 3
CHEMBL4879551
 IC50 5.92 5.92 1200.0 1
Hepatitis C virus NS5B RNA-dependent RNA polymerase
CHEMBL5375
 IC50 5.58 5.58 2600.0 1
DNA excision repair protein ERCC-1/DNA repair endonuclease XPF
CHEMBL3883316
 IC50 5.54 5.54 2900.0 1
Hepatitis C virus
CHEMBL379
 EC50 5.03 5.03 9300.0 1
Flap endonuclease 1
CHEMBL5027
 IC50 4.98 4.98 10400.0 1
Cytomegalovirus
CHEMBL613134
 EC50 4.74 4.74 18200.0 1
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 IC50 4.34 4.34 46000.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 24.0 hr Homo sapiens
T1/2 24.0 hr Mus musculus
T1/2 120.0 hr Homo sapiens
T1/2 120.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus IC50 = 150.0 nM 6.82 Antiviral activity against HCV in human HBI10A cells by ELISA 18835180
RNA-directed RNA polymerase IC50 = 240.0 nM 6.62 Inhibitory activity against HCV 1b BK NS5B deltaC55 RNA polymerase involving man... 16509585
Tripartite terminase subunit 3 IC50 = 1200.0 nM 5.92 Inhibition of human cytomegalovirus pHAR-UL89C expressed in Escherichia coli Ros... 35377638
RNA-directed RNA polymerase IC50 = 2600.0 nM 5.58 inhibitory concentration against RNA dependent RNA polymerase Nonstructural prot... 15380204
RNA-directed RNA polymerase IC50 = 2600.0 nM 5.58 Inhibitory activity against HCV 1b BK NS5B deltaC55 RNA polymerase 16509585
RNA-directed RNA polymerase IC50 = 2600.0 nM 5.58 Inhibitory activity against HCV 1b BK NS5B deltaC55 RNA polymerase involving mag... 16509585
Hepatitis C virus IC50 = 2600.0 nM 5.58 Inhibition of HCV1b Cdelta55 NS5B polymerase 19800789
RNA-directed RNA polymerase IC50 = 2600.0 nM 5.58 Inhibition of deltaC55 truncated Hepatitis C virus NS5B expressed in Escherichia... 35377638
Hepatitis C virus NS5B RNA-dependent RNA polymerase IC50 = 2600.0 nM 5.58 Inhibition of Hepatitis C virus NS5B polymerase 37827528
DNA excision repair protein ERCC-1/DNA repair endonuclease XPF IC50 = 2900.0 nM 5.54 Inhibition of ERCC1-XPF (unknown origin) by high-throughput fluorescence based i... 26321360
Hepatitis C virus EC50 = 9300.0 nM 5.03 Antiviral activity against HCV in human HBI10A cells by ELISA 18835180
RNA-directed RNA polymerase IC50 = 9300.0 nM 5.03 Inhibitory activity against HCV 1b BK NS5B deltaC55-R158M mutant RNA polymerase 16509585
Flap endonuclease 1 IC50 = 10400.0 nM 4.98 Inhibition of FEN1 (unknown origin) 26321360
Cytomegalovirus EC50 = 18200.0 nM 4.74 Antiviral activity against human cytomegalovirus expressing ADCREGFP infected in... 35377638
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 46000.0 nM 4.34 Inhibition of HIV1 reverse transcriptase p66/p51 polymerase using PPT57 DNA/Cy5-... 29478802
RNA-directed RNA polymerase IC50 = 92000.0 nM 4.04 Inhibitory activity against HCV 1b BK NS5B deltaC55-R158K mutant RNA polymerase 16509585

Literature References

PubMed DOI Target Context # Activities
35377638 10.1021/acs.jmedchem.2c00203 ADMET 8
16509585 10.1021/jm051064t RNA-directed RNA polymerase 6
35377638 10.1021/acs.jmedchem.2c00203 Tripartite terminase subunit 3 3
16509585 10.1021/jm051064t No relevant target 2
18835180 10.1016/j.bmc.2008.09.006 Hepatitis C virus 2
37827528 10.1021/acs.jmedchem.3c01280 Hepatitis C virus NS5B RNA-dependent RNA polymerase 1
15380204 10.1016/j.bmcl.2004.07.075 RNA-directed RNA polymerase 1
35377638 10.1021/acs.jmedchem.2c00203 RNA-directed RNA polymerase 1
35377638 10.1021/acs.jmedchem.2c00203 No relevant target 1
35377638 10.1021/acs.jmedchem.2c00203 HFF 1
35377638 10.1021/acs.jmedchem.2c00203 Cytomegalovirus 1
29478802 10.1016/j.bmc.2018.02.017 Human immunodeficiency virus type 1 reverse transcriptase 1
26321360 10.1016/j.bmcl.2015.08.024 Deoxyribonuclease-1 1
26321360 10.1016/j.bmcl.2015.08.024 DNA excision repair protein ERCC-1/DNA repair endonuclease XPF 1
26321360 10.1016/j.bmcl.2015.08.024 Flap endonuclease 1 1
19800789 10.1016/j.bmcl.2009.06.106 Hepatitis C virus 1
17107799 10.1016/j.bmcl.2006.10.054 Unchecked 1

Data from ChEMBL 36 via Core Engine