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Compound Detail

CHEMBL438605

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C[C@@]1(O)[C@H](O)[C@@H](CO)O[C@H]1n1ccc(N)nc1=O

Basic Information

ChEMBL ID CHEMBL438605
Phase Preclinical
Structure Type MOL
InChI Key PPUDLEUZKVJXSZ-VPCXQMTMSA-N
19
Targets
72
Activities
2
Assay Types
7
PK Parameters
20
Publications
0
Known Names

Molecular Properties

257.2
MW (Da)
-2.17
ALogP
8
HBA
4
HBD
130.8
PSA (Ų)
0.47
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 C10H15N3O5
MW 257.25
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness 1.77

Activity Summary

EC50 63 meas. best 7.52
IC50 9 meas. best 6.14

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Norovirus
CHEMBL4296584
EC50 7.52 5.7383 30.0 6
Hepatitis C virus
CHEMBL379
EC50 7.4 5.8916 40.0 37
Hepatitis C virus
CHEMBL379
IC50 6.14 6.025 730.0 2
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
IC50 5.98 5.98 1050.0 1
Unchecked
CHEMBL612545
IC50 5.78 5.3025 1670.0 4
Unchecked
CHEMBL612545
EC50 5.7 5.7 2000.0 1
dengue virus type 3
CHEMBL612717
EC50 5.62 5.62 2400.0 1
dengue virus type 4
CHEMBL613728
EC50 5.58 5.58 2600.0 1
dengue virus type 2
CHEMBL613966
EC50 5.55 5.25 2800.0 2
RNA-directed RNA polymerase
CHEMBL4296320
EC50 5.55 5.55 2800.0 1
dengue virus type 1
CHEMBL613360
EC50 5.54 5.54 2900.0 1
NON-PROTEIN TARGET
CHEMBL3879801
EC50 5.22 4.874 6000.0 5
Poliovirus 1
CHEMBL613556
EC50 5.14 5.14 7300.0 1
Tick-borne encephalitis virus
CHEMBL4296604
EC50 4.85 4.85 14200.0 1
Mammalian orthoreovirus 1
CHEMBL612927
EC50 4.8 4.8 16000.0 1
Reovirus sp.
CHEMBL613721
EC50 4.8 4.8 16000.0 1
Coxsackievirus B5
CHEMBL613555
EC50 4.75 4.75 18000.0 1
PBMC
CHEMBL613107
IC50 4.32 4.32 47400.0 1
Human immunodeficiency virus 1
CHEMBL378
EC50 4.32 4.32 47500.0 1
CCRF-CEM
CHEMBL382
IC50 4.26 4.26 54400.0 1
Coxsackievirus B3
CHEMBL613554
EC50 4.03 4.03 94000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 30000.0 ng.hr.mL-1 Rattus norvegicus
AUC 74400.0 ng.hr.mL-1 Rattus norvegicus
Cmax 23790.09 nM Rattus norvegicus
Cmax 293877.55 nM Rattus norvegicus
F 33.6 % Rattus norvegicus
T1/2 7.1 hr Rattus norvegicus
Tmax 2.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Norovirus EC50 = 30.0 nM 7.52 Antiviral activity against human Norovirus infected in BJAB cells assessed as re... 32294613
Hepatitis C virus EC50 = 40.0 nM 7.4 Antiviral activity against BILN 2061-resistant HCV genotype 1b infected in human... 19104013
Hepatitis C virus EC50 = 110.0 nM 6.96 Antiviral activity against compound-resistant HCV genotype 1b infected in human ... 19104013
Hepatitis C virus EC50 = 210.0 nM 6.68 Antiviral activity against cyclosporine-resistant HCV genotype 1b infected in hu... 19104013
Hepatitis C virus EC50 = 230.0 nM 6.64 Antiviral activity against Hepatitis C virus isolate Con1 transfected with NS5B ... 18694956
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 = 410.0 nM 6.39 Antiviral activity against HCV genotype 1b infected in human Huh-9-13 cells asse... 19104013
Hepatitis C virus EC50 = 480.0 nM 6.32 Antiviral activity against Hepatitis C virus isolate Con1 transfected with NS5B ... 18694956
Hepatitis C virus EC50 = 620.0 nM 6.21 Antiviral activity against Hepatitis C virus isolate Con1 transfected with NS5B ... 18694956
Hepatitis C virus EC50 = 700.0 nM 6.16 Antiviral activity against Hepatitis C virus genotype 1b infected in human HuH6 ... 18625766
Hepatitis C virus EC50 = 700.0 nM 6.16 Antiviral activity against Hepatitis C virus genotype 1b infected in human Huh-M... 18625766
Hepatitis C virus IC50 = 730.0 nM 6.14 Inhibition of HCV genotype 1b NS5B after 90 mins 22578461
Hepatitis C virus EC50 = 1010.0 nM 6.0 Antiviral activity against VX 950-resistant HCV genotype 1b infected in human Hu... 19104013
Hepatitis C virus EC50 = 1000.0 nM 6.0 Antiviral activity against Hepatitis C virus genotype 2a JFH1 infected in human ... 18694956
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 1050.0 nM 5.98 Inhibition of HIV-1 reverse transcriptase associated RNA-dependent DNA polymeras... 37229831
Hepatitis C virus EC50 = 1100.0 nM 5.96 Antiviral activity against Hepatitis C virus genotype 1a H77 infected in human H... 18694956
Hepatitis C virus EC50 = 1160.0 nM 5.94 Antiviral activity against R479-resistant HCV genotype 1b infected in human Huh-... 19104013
Hepatitis C virus EC50 = 1143.0 nM 5.94 Antiviral activity against Hepatitis C virus genotype 1b Con1 infected in human ... 18936191
Hepatitis C virus IC50 = 1230.0 nM 5.91 Antiviral activity against HCV 1b replicon in human 2209-23 cells 17317178
Hepatitis C virus EC50 = 1230.0 nM 5.91 Antiviral activity against Hepatitis C virus subtype 1b Con1 infected in human H... 18285474

Literature References

PubMed DOI Target Context # Activities
18694956 10.1128/aac.00533-08 Hepatitis C virus 16
18710916 10.1128/aac.00078-08 Hepatitis C virus 9
19104013 10.1128/aac.00939-08 Hepatitis C virus 7
17064080 10.1021/jm0603623 Rattus norvegicus 7
17064080 10.1021/jm0603623 No relevant target 5
18625766 10.1128/aac.01534-07 Hepatitis C virus 4
18625766 10.1128/aac.01534-07 ADMET 4
17101674 10.1128/aac.00400-06 Deoxycytidine kinase 3
18710916 10.1128/aac.00078-08 Unchecked 3
18710916 10.1128/aac.00078-08 ADMET 3
31604163 10.1016/j.ejmech.2019.111733 Norovirus 3
18936191 10.1128/aac.01081-08 Hepatitis C virus 3
17999967 10.1128/aac.01184-07 Cytidine deaminase 3
19072694 10.1021/jm801418v Hepatitis C virus 2
21621997 10.1016/j.bmcl.2011.05.012 Hepatitis C virus 2
22014549 10.1016/j.bmcl.2011.09.089 Human immunodeficiency virus 1 2
17317178 10.1016/j.bmcl.2007.02.004 ADMET 2
22014549 10.1016/j.bmcl.2011.09.089 Hepatitis C virus 2
16107149 10.1021/jm0502788 Huh-7 2
16107149 10.1021/jm0502788 NON-PROTEIN TARGET 2

Data from ChEMBL 36 via Core Engine