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Compound Detail

CHEMBL1630221

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C#C[C@@]1(O)[C@H](O)[C@@H](CO)O[C@H]1n1ccc2c(N)ncnc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1630221
Phase Preclinical
Structure Type MOL
InChI Key NKRAIOQPSBRMOV-NRMKKVEVSA-N
16
Targets
91
Activities
3
Assay Types
10
PK Parameters
20
Publications
0
Known Names

Molecular Properties

290.3
MW (Da)
-1.37
ALogP
8
HBA
4
HBD
126.7
PSA (Ų)
0.50
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 C13H14N4O4
MW 290.28
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness 0.94

Activity Summary

EC50 79 meas. best 7.62
IC50 11 meas. best 6.64
Kd 1 meas. best 5.46

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Zika virus
CHEMBL4296612
 EC50 7.62 6.3529 24.0 28
dengue virus type 4
CHEMBL613728
 EC50 7.52 6.935 30.0 4
dengue virus type 2
CHEMBL613966
 EC50 7.04 5.9441 91.0 32
dengue virus type 3
CHEMBL612717
 EC50 6.92 6.32 120.0 4
NS5
CHEMBL4523952
 EC50 6.86 6.86 137.0 4
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 6.77 6.47 170.0 2
Tick-borne encephalitis virus
CHEMBL4296604
 EC50 6.7 6.7 200.0 1
enterovirus D68
CHEMBL613204
 IC50 6.64 6.64 230.0 1
Unchecked
CHEMBL612545
 IC50 6.51 6.51 310.0 1
Enterovirus A71
CHEMBL612436
 IC50 6.3 6.28 500.0 2
Enterovirus A71
CHEMBL612436
 EC50 6.2 6.2 625.0 1
Coxsackievirus A16
CHEMBL5209663
 IC50 6.15 6.15 710.0 1
dengue virus type 1
CHEMBL613360
 EC50 6.07 5.9067 860.0 3
Zika virus
CHEMBL4296612
 IC50 6.07 5.93 850.0 2
Coxsackievirus
CHEMBL613750
 IC50 6.04 6.04 920.0 1
Yellow fever virus
CHEMBL613731
 IC50 5.72 5.72 1910.0 1
Japanese encephalitis virus
CHEMBL613729
 IC50 5.51 5.51 3090.0 1
NS5
CHEMBL4523952
 Kd 5.46 5.46 3430.0 1
Dengue virus
CHEMBL613757
 IC50 5.3 5.3 5050.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1968.0 ng.hr.mL-1 Mus musculus
AUC 2705.0 ng.hr.mL-1 Mus musculus
AUC 2080.0 ng.hr.mL-1 Mus musculus
AUC 2792.0 ng.hr.mL-1 Mus musculus
Cmax 23277.53 nM Mus musculus
Cmax 1994.63 nM Mus musculus
T1/2 9.1 hr Mus musculus
T1/2 5.09 hr Mus musculus
Tmax 0.033 hr Mus musculus
Tmax 0.83 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Zika virus EC50 = 24.0 nM 7.62 Functional immunofluorescence assay to measure dose dependent changes in antivir... -
dengue virus type 4 EC50 = 30.0 nM 7.52 Antiviral activity against clinical isolates of Dengue virus 4 Martinique 017 in... 26774922
dengue virus type 4 EC50 = 80.0 nM 7.1 Antiviral activity against clinical isolates of Dengue virus 4 Dakar HD34460 inf... 26774922
Zika virus EC50 = 86.0 nM 7.07 Functional immunofluorescence assay to measure dose dependent changes in antivir... -
dengue virus type 2 EC50 = 91.0 nM 7.04 Functional immunofluorescence assay to measure dose dependent changes in antivir... -
dengue virus type 4 EC50 = 110.0 nM 6.96 Antiviral activity Dengue virus 4 by cell based assay 38382389
Zika virus EC50 = 115.0 nM 6.94 Functional immunofluorescence assay to measure dose dependent changes in antivir... -
dengue virus type 3 EC50 = 120.0 nM 6.92 Antiviral activity against clinical isolates of Dengue virus 3 Bolivia 4025 infe... 26774922
Zika virus EC50 = 120.0 nM 6.92 Antiviral activity Zika virus by cell based assay 38382389
Zika virus EC50 = 121.0 nM 6.92 Functional immunofluorescence assay to measure dose dependent changes in antivir... -
Zika virus EC50 = 136.0 nM 6.87 Functional immunofluorescence assay to measure dose dependent changes in antivir... -
NS5 EC50 = 137.0 nM 6.86 Inhibition of RNA-dependent RNA polymerase in Zika virus FSS13025/2010 infected ... 31549836
NS5 EC50 = 137.0 nM 6.86 Inhibition of RNA-dependent RNA polymerase in Zika virus FSS13025/2010 infected ... 31549836
NS5 EC50 = 137.0 nM 6.86 Inhibition of RNA-dependent RNA polymerase in Zika virus GZ01/2016 infected in A... 31549836
NS5 EC50 = 137.0 nM 6.86 Inhibition of RNA-dependent RNA polymerase in Zika virus GZ01/2016 infected in A... 31549836
dengue virus type 2 EC50 = 148.0 nM 6.83 Functional immunofluorescence assay to measure dose dependent changes in antivir... -
Zika virus EC50 = 161.0 nM 6.79 Functional immunofluorescence assay to measure dose dependent changes in antivir... -
NON-PROTEIN TARGET EC50 = 170.0 nM 6.77 Antiviral activity against EV71 assessed as reduction in viral replication after... 27776325
Zika virus EC50 = 200.0 nM 6.7 Antiviral activity against Zika virus H/PF/2013 infected in human Huh-7 cells as... 33208235
Tick-borne encephalitis virus EC50 = 200.0 nM 6.7 Antiviral activity against TBEV infected in human A549 cells assessed as reducti... 38128296

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5661943 Zika virus 54
- 10.6019/CHEMBL5661955 ADMET 50
- 10.6019/CHEMBL5661943 dengue virus type 2 46
20457821 10.1128/aac.00140-10 dengue virus type 2 23
34560428 10.1016/j.ejmech.2021.113852 ADMET 12
35598412 10.1016/j.ejmech.2022.114436 ADMET 7
20457821 10.1128/aac.00140-10 Blood 6
20516277 10.1128/aac.00397-10 dengue virus type 2 4
38382389 10.1016/j.ejmech.2024.116213 dengue virus type 2 4
35598412 10.1016/j.ejmech.2022.114436 Unchecked 4
31549836 10.1021/acs.jmedchem.9b00775 NS5 4
38493729 10.1016/j.bmc.2024.117682 Zika virus 3
35598412 10.1016/j.ejmech.2022.114436 RD 3
37801825 10.1016/j.ejmech.2023.115852 Zika virus 3
27776325 10.1016/j.ejmech.2016.10.019 NON-PROTEIN TARGET 3
32435384 10.1021/acsmedchemlett.9b00619 Unchecked 2
33208235 10.1016/j.ejmech.2020.112992 Unchecked 2
35306290 10.1016/j.ejmech.2022.114275 Zika virus 2
26774922 10.1016/j.ejmech.2015.12.046 dengue virus type 4 2
26774922 10.1016/j.ejmech.2015.12.046 dengue virus type 2 2

Data from ChEMBL 36 via Core Engine