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Compound Detail

CHEMBL2031678

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C[C@@]1(O)[C@H](O)[C@@H](CO)O[C@H]1c1ccc2c(N)ncnn12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2031678
Phase Preclinical
Structure Type MOL
InChI Key RLGAXHNBEXKRIZ-MWGHHZFTSA-N
2
Targets
18
Activities
2
Assay Types
20
PK Parameters
20
Publications
0
Known Names

Molecular Properties

280.3
MW (Da)
-1.14
ALogP
8
HBA
4
HBD
126.1
PSA (Ų)
0.55
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 C12H16N4O4
MW 280.28
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 0.74

Activity Summary

EC50 11 meas. best 6.39
IC50 7 meas. best 6.51

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus
CHEMBL379
 IC50 6.51 6.51 310.0 1
Unchecked
CHEMBL612545
 IC50 6.43 6.2983 370.0 6
Hepatitis C virus
CHEMBL379
 EC50 6.39 6.054 410.0 10
Unchecked
CHEMBL612545
 EC50 4.96 4.96 11100.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3643.64 ng.hr.mL-1 Rattus norvegicus
AUC 6978.97 ng.hr.mL-1 Canis lupus familiaris
AUC 1401.4 ng.hr.mL-1 Macaca fascicularis
CL 6.667 mL.min-1.kg-1 Canis lupus familiaris
CL 18.8 mL.min-1.kg-1 Rattus norvegicus
CL 11.4 mL.min-1.kg-1 Canis lupus familiaris
CL 20.5 mL.min-1.kg-1 Macaca fascicularis
Cmax 2380.0 nM Rattus norvegicus
Cmax 8360.0 nM Canis lupus familiaris
Cmax 820.0 nM Macaca fascicularis
F 70.0 % Canis lupus familiaris
F 50.0 % Rattus norvegicus
F 83.0 % Rattus norvegicus
F 96.0 % Canis lupus familiaris
F 33.0 % Macaca fascicularis
T1/2 7.0 hr Canis lupus familiaris
T1/2 4.0 hr Rattus norvegicus
T1/2 7.6 hr Canis lupus familiaris
T1/2 4.3 hr Macaca fascicularis
Vd 1.66 L.kg-1 Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus IC50 = 310.0 nM 6.51 Inhibition of HCV genotype 1b NS5B after 90 mins 22578461
Unchecked IC50 = 370.0 nM 6.43 Inhibition of N-terminal His6-tagged Hepatitis C virus genotype 1b isolate Con1 ... 24944743
Unchecked IC50 = 390.0 nM 6.41 Inhibition of C-terminal His6-tagged and C-terminal 21 amino acids truncated Hep... 24944743
Hepatitis C virus EC50 = 410.0 nM 6.39 Antiviral activity against Hepatitis C virus genotype 2b infected in human HuH7 ... 24944743
Hepatitis C virus EC50 = 420.0 nM 6.38 Antiviral activity against Hepatitis C virus genotype 3a infected in human HuH7 ... 24944743
Unchecked IC50 = 480.0 nM 6.32 Inhibition of C-terminal His6-tagged and C-terminal 21 amino acids truncated Hep... 24944743
Unchecked IC50 = 500.0 nM 6.3 Inhibition of C-terminal His6-tagged and C-terminal 21 amino acids truncated Hep... 24944743
Unchecked IC50 = 570.0 nM 6.24 Inhibition of C-terminal His6-tagged and C-terminal 21 amino acids truncated Hep... 24944743
Hepatitis C virus EC50 = 630.0 nM 6.2 Antiviral activity against Hepatitis C virus genotype 2a infected in human HuH7 ... 24944743
Hepatitis C virus EC50 = 760.0 nM 6.12 Antiviral activity against Hepatitis C virus genotype 1a infected in human HuH7 ... 24944743
Unchecked IC50 = 810.0 nM 6.09 Inhibition of C-terminal His6-tagged and C-terminal 21 amino acids truncated Hep... 24944743
Hepatitis C virus EC50 = 820.0 nM 6.09 Antiviral activity against Hepatitis C virus genotype 5a infected in human HuH7 ... 24944743
Hepatitis C virus EC50 = 880.0 nM 6.06 Antiviral activity against Hepatitis C virus genotype 4a infected in human HuH7 ... 24944743
Hepatitis C virus EC50 = 1000.0 nM 6.0 Antiviral activity against Hepatitis C virus genotype 6a infected in human HuH7 ... 24944743
Hepatitis C virus EC50 = 1600.0 nM 5.8 Antiviral activity against Hepatitis C virus genotype 1b in human HuH7 cells ass... 25288185
Hepatitis C virus EC50 = 1600.0 nM 5.8 Antiviral activity against Hepatitis C virus genotype 1b infected in human HuH7 ... 24944743
Hepatitis C virus EC50 = 1980.0 nM 5.7 Antiviral activity against HCV genotype 1b infected in human HuH7 cells assessed... 22578461
Unchecked EC50 = 11100.0 nM 4.96 Antiviral activity against murine Norovirus infected in mouse RAW264.7 cells ass... 32294613

Literature References

PubMed DOI Target Context # Activities
24944743 10.1021/ml500077j ADMET 15
24944743 10.1021/ml500077j Hepatocyte 8
24944743 10.1021/ml500077j Hepatitis C virus 8
24944743 10.1021/ml500077j Rattus norvegicus 7
24944743 10.1021/ml500077j Cynomolgus monkey 6
24944743 10.1021/ml500077j Canis familiaris 6
24944743 10.1021/ml500077j Unchecked 6
22578461 10.1016/j.bmcl.2012.04.065 Canis familiaris 4
32294613 10.1016/j.ejmech.2020.112198 Unchecked 2
22578461 10.1016/j.bmcl.2012.04.065 Hepatitis C virus 2
23547794 10.1021/jm400201a Rattus norvegicus 2
22578461 10.1016/j.bmcl.2012.04.065 Rattus norvegicus 2
22578461 10.1016/j.bmcl.2012.04.065 Huh-7 2
23547794 10.1021/jm400201a DNA-directed RNA polymerase, mitochondrial 1
22578461 10.1016/j.bmcl.2012.04.065 Syrian golden hamster 1
22578461 10.1016/j.bmcl.2012.04.065 Hepatocyte 1
22578461 10.1016/j.bmcl.2012.04.065 ADMET 1
24944743 10.1021/ml500077j Epithelial cell 1
24944743 10.1021/ml500077j Salmonella typhimurium 1
25288185 10.1016/j.bmcl.2014.09.030 Hepatitis C virus 1

Data from ChEMBL 36 via Core Engine