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Compound Detail

CHEMBL266573

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COc1ccc(N2C(N)=NC(N)=NC2(C)C)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL266573
Phase Preclinical
Structure Type MOL
InChI Key KLCSZLKQTXQCTD-UHFFFAOYSA-N
7
Targets
12
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

247.3
MW (Da)
0.88
ALogP
6
HBA
2
HBD
89.2
PSA (Ų)
0.81
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 C12H17N5O
MW 247.30
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness -0.28

Activity Summary

EC50 7 meas. best 5.82
Ki 3 meas. best 6.48
IC50 1 meas. best 4.05
Kd 1 meas. best 4.76

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL2575
 Ki 6.48 6.48 331.1 1
Respiratory syncytial virus
CHEMBL612679
 EC50 5.82 5.82 1500.0 1
Unchecked
CHEMBL612545
 EC50 5.7 4.7467 2000.0 3
Dihydrofolate reductase
CHEMBL1809
 Ki 5.4 5.4 4020.0 1
Influenza B virus
CHEMBL613129
 EC50 5.09 5.09 8200.0 1
Dihydrofolate reductase
CHEMBL1809
 Kd 4.76 4.76 17230.0 1
Influenza A virus
CHEMBL613740
 EC50 4.43 4.315 37000.0 2
Dihydrofolate reductase
CHEMBL2902
 Ki 4.1 4.1 79432.8 1
Dihydrofolate reductase
CHEMBL1809
 IC50 4.05 4.05 89100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase Ki = 331.13 nM 6.48 Inhibitory activity against isolated chicken liver dihydrofolate reductase (DHFR... 6420569
Respiratory syncytial virus EC50 = 1500.0 nM 5.82 Antiviral activity against Respiratory syncytial virus infected in human HeLa ce... 28477572
Unchecked EC50 = 2000.0 nM 5.7 Antiviral activity against Influenza B virus B/Ned/537/05 infected in MDCK cells... 28477572
Dihydrofolate reductase Ki = 4020.0 nM 5.4 Inhibition of Escherichia coli DHFR assessed as NADP formation by quadratic Morr... 26414808
Influenza B virus EC50 = 8200.0 nM 5.09 Antiviral activity against Influenza B virus B/Ned/537/05 infected in MDCK cells... 28477572
Dihydrofolate reductase Kd = 17230.0 nM 4.76 Binding affinity to Escherichia coli DHFR at 500 uM using spyro orange reporter ... 26414808
Influenza A virus EC50 = 37000.0 nM 4.43 Antiviral activity against Influenza A virus A/Ned/378/05(H1N1) infected in MDCK... 28477572
Unchecked EC50 = 49000.0 nM 4.31 Antiviral activity against Influenza A virus A/Virginia/ATCC3/2009(H1N1) infecte... 28477572
Unchecked EC50 = 59000.0 nM 4.23 Antiviral activity against Influenza A virus A/Virginia/ATCC3/2009(H1N1) infecte... 28477572
Influenza A virus EC50 = 63000.0 nM 4.2 Antiviral activity against Influenza A virus A/Ned/378/05(H1N1) infected in MDCK... 28477572
Dihydrofolate reductase Ki = 79432.82 nM 4.1 Inhibitory activity against Lactobacillus casei dihydrofolate reductase (DHFR) 6420569
Dihydrofolate reductase IC50 = 89100.0 nM 4.05 Inhibition of Escherichia coli DHFR assessed as NADP formation 26414808

Literature References

PubMed DOI Target Context # Activities
26414808 10.1016/j.ejmech.2015.08.021 Dihydrofolate reductase 4
28477572 10.1016/j.ejmech.2017.04.070 Unchecked 3
7241512 10.1021/jm00137a013 Dihydrofolate reductase 2
6699880 10.1021/jm00369a019 Dihydrofolate reductase 2
6420569 10.1021/jm00368a006 Dihydrofolate reductase 2
28477572 10.1016/j.ejmech.2017.04.070 Influenza A virus 2
28477572 10.1016/j.ejmech.2017.04.070 MDCK 2
28477572 10.1016/j.ejmech.2017.04.070 Coxsackievirus B4 2
28477572 10.1016/j.ejmech.2017.04.070 Influenza B virus 1
28477572 10.1016/j.ejmech.2017.04.070 Respiratory syncytial virus 1
28477572 10.1016/j.ejmech.2017.04.070 Yellow fever virus 1
28477572 10.1016/j.ejmech.2017.04.070 Punta Toro virus 1
28477572 10.1016/j.ejmech.2017.04.070 Sindbis virus 1
28477572 10.1016/j.ejmech.2017.04.070 Mammalian orthoreovirus 1 1
28477572 10.1016/j.ejmech.2017.04.070 Human respirovirus 3 1
28477572 10.1016/j.ejmech.2017.04.070 HeLa 1
28477572 10.1016/j.ejmech.2017.04.070 Vesicular stomatitis virus 1
6737433 10.1021/jm00373a016 Dihydrofolate reductase 1
9379435 10.1021/jm970211n Dihydrofolate reductase 1
6864738 10.1021/jm00361a012 Dihydrofolate reductase 1

Data from ChEMBL 36 via Core Engine