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Compound Detail

CHEMBL73809

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C[C@@]1(O)[C@H](O)[C@@H](CO)O[C@H]1n1cnc2c(N)ncnc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL73809
Phase Preclinical
Structure Type MOL
InChI Key PASOFFRBGIVJET-YRKGHMEHSA-N
12
Targets
34
Activities
3
Assay Types
8
PK Parameters
20
Publications
0
Known Names

Molecular Properties

281.3
MW (Da)
-1.59
ALogP
9
HBA
4
HBD
139.5
PSA (Ų)
0.52
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C11H15N5O4
MW 281.27
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 1.42

Activity Summary

EC50 23 meas. best 6.92
Ki 6 meas. best 6.13
IC50 5 meas. best 5.75

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus
CHEMBL379
 EC50 6.92 6.4718 120.0 17
Nucleic Acid
CHEMBL345
 EC50 6.58 6.58 260.0 1
RNA-directed RNA polymerase
CHEMBL4296320
 EC50 6.52 6.52 300.0 1
Adenosine receptor A1
CHEMBL318
 Ki 6.13 6.13 740.0 1
Adenosine receptor A1
CHEMBL4975
 Ki 6.13 6.04 740.0 2
dengue virus type 2
CHEMBL613966
 EC50 5.95 5.675 1120.0 2
Zika virus
CHEMBL4296612
 IC50 5.75 5.75 1760.0 1
Hepatitis C virus
CHEMBL379
 IC50 5.72 5.445 1900.0 2
RNA-directed RNA polymerase
CHEMBL4296320
 IC50 5.72 5.72 1900.0 1
Adenosine receptor A2a
CHEMBL251
 Ki 5.47 5.355 3420.0 2
Adenosine receptor A2a
CHEMBL302
 Ki 5.47 5.47 3400.0 1
West Nile virus
CHEMBL613730
 EC50 5.29 5.29 5100.0 1
Tick-borne encephalitis virus
CHEMBL4296604
 EC50 5.15 5.15 7100.0 1
K562
CHEMBL385
 IC50 4.8 4.8 16000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 200.0 mL.min-1.kg-1 Rattus norvegicus
CL 200.0 mL.min-1.kg-1 Rattus norvegicus
Cmax - nM Rattus norvegicus
F - % Rattus norvegicus
F - % Rattus norvegicus
F - % Rattus norvegicus
T1/2 0.3 hr Rattus norvegicus
Tmax - hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus EC50 = 120.0 nM 6.92 Antiviral activity against Hepatitis C virus genotype 1b infected in human Huh5-... 18625766
Hepatitis C virus EC50 = 150.0 nM 6.82 Antiviral activity against HCV in ET cells assessed as activity of luciferase re... 19072694
Hepatitis C virus EC50 = 200.0 nM 6.7 Antiviral activity against HCV genotype 1b in Huh7 cells assessed as inhibition ... 17521911
Hepatitis C virus EC50 = 200.0 nM 6.7 Antiviral activity against HCV genotype 1b infected in human HuH7 cells after 3 ... 22100256
Hepatitis C virus EC50 = 230.0 nM 6.64 Antiviral activity against HCV 1b Con1 replicon in Huh7 cells 17997319
Hepatitis C virus EC50 = 230.0 nM 6.64 Antiviral activity against Hepatitis C virus 1b after 3 days 18078757
Hepatitis C virus EC50 = 250.0 nM 6.6 Antiviral activity against HCV genotype 1b in Huh7 cells assessed as inhibition ... 17521911
Hepatitis C virus EC50 = 250.0 nM 6.6 Antiviral activity against HCV assessed as inhibition of viral replicon replicat... 19523820
Nucleic Acid EC50 = 260.0 nM 6.58 Inhibition of HCV RNA replication in a subgenomic bicistronic replicon assay in ... 15456273
Hepatitis C virus EC50 = 290.0 nM 6.54 Antiviral activity against Hepatitis C virus genotype 1b infected in human HuH6 ... 18625766
RNA-directed RNA polymerase EC50 = 300.0 nM 6.52 Inhibition HCV RNA replication 15084127
Hepatitis C virus EC50 = 300.0 nM 6.52 Antiviral activity against HCV by viral replicon assay 19523820
Hepatitis C virus EC50 = 300.0 nM 6.52 Inhibition of hepatitis C virus RNA replication in a subgenomic replicon cell li... 15664842
Hepatitis C virus EC50 = 350.0 nM 6.46 Antiviral activity against HCV genotype 1b infected in human HuH7 cells assessed... 22578461
Hepatitis C virus EC50 = 400.0 nM 6.4 Antiviral activity against Hepatitis C virus genotype 1b infected in human Huh-9... 18625766
Hepatitis C virus EC50 = 618.0 nM 6.21 Antiviral activity against Hepatitis C virus genotype 1b in luciferase encoding ... 20516274
Hepatitis C virus EC50 = 733.0 nM 6.13 Antiviral activity against Hepatitis C virus genotype 1a in luciferase encoding ... 20516274
Adenosine receptor A1 Ki = 740.0 nM 6.13 Inhibition of [3H]CHA (N6-cyclohexyl adenosine) to rat brain membrane Adenosine ... 11881988
Adenosine receptor A1 Ki = 740.0 nM 6.13 Inhibitory activity at Adenosine A1 receptor by inhibition of [3H]CHA binding to... 9572897
dengue virus type 2 EC50 = 1120.0 nM 5.95 Antiviral activity against at 0.3 MOI Dengue virus 2 infected in human A549 cell... 20457821

Literature References

PubMed DOI Target Context # Activities
15456273 10.1021/jm040068f ADMET 5
18625766 10.1128/aac.01534-07 Hepatitis C virus 4
18625766 10.1128/aac.01534-07 ADMET 4
16610805 10.1021/jm051250z MDBK441 3
9572897 10.1021/jm9707737 Unchecked 3
22748708 10.1016/j.bmc.2012.05.066 Hepatitis C virus 2
16134952 10.1021/jm050335x Hepatitis C virus 2
16033277 10.1021/jm048944c K562 2
16610805 10.1021/jm051250z Bovine viral diarrhea virus 1 2
22578461 10.1016/j.bmcl.2012.04.065 Hepatitis C virus 2
15664842 10.1016/j.bmcl.2004.11.020 Hepatitis C virus 2
17521911 10.1016/j.bmc.2007.05.020 Hepatitis C virus 2
22100256 10.1016/j.bmc.2011.10.058 Hepatitis C virus 2
22100256 10.1016/j.bmc.2011.10.058 Huh-7 2
20516274 10.1128/aac.00289-10 Hepatitis C virus 2
22578461 10.1016/j.bmcl.2012.04.065 Rattus norvegicus 2
19523820 10.1016/j.bmcl.2009.05.122 Hepatitis C virus 2
15084127 10.1021/jm030424e RNA-directed RNA polymerase 2
11881988 10.1021/jm0102755 Adenosine receptor A2a and A3 1
37801825 10.1016/j.ejmech.2023.115852 Zika virus 1

Data from ChEMBL 36 via Core Engine