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Compound Detail

CHEMBL22148

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CCc1nc(N)nc(N)c1-c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL22148
Phase Preclinical
Structure Type MOL
InChI Key XREDUPOVEQDQQS-UHFFFAOYSA-N
7
Targets
23
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

214.3
MW (Da)
1.87
ALogP
4
HBA
2
HBD
77.8
PSA (Ų)
0.80
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 C12H14N4
MW 214.27
Aromatic Rings 2
Heavy Atoms 16
NP-Likeness -0.67

Activity Summary

IC50 11 meas. best 6.16
Ki 11 meas. best 8.64
EC50 1 meas. best 5.81

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.64 8.0388 2.3 8
Unchecked
CHEMBL612545
 Ki 8.64 8.07 2.3 2
Dihydrofolate reductase
CHEMBL202
 Ki 7.98 7.98 10.4 1
Plasmodium falciparum
CHEMBL364
 IC50 6.16 6.15 700.0 2
Plasmodium falciparum
CHEMBL364
 EC50 5.81 5.81 1553.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 5.48 5.48 3300.0 1
Beta-N-acetyl-D-hexosaminidase-A/B
CHEMBL3038485
 IC50 4.96 4.6375 11000.0 4
Beta-hexosaminidase subunit beta
CHEMBL5877
 IC50 4.82 4.62 15000.0 2
Beta-hexosaminidase subunit alpha
CHEMBL1250415
 IC50 4.57 4.57 27000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 2.3 nM 8.64 Competitive inhibition of wild type Plasmodium falciparum dihydrofolate reductas... 31685330
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.3 nM 8.64 Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falcipa... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.3 nM 8.64 Inhibition of the wild-type dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 3.0 nM 8.52 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) o... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 4.5 nM 8.35 Inhibition of the S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 8.7 nM 8.06 Inhibition of the C59R+S108N mutant of dihydrofolate reductase (DHFR) 11881993
Dihydrofolate reductase Ki = 10.4 nM 7.98 Inhibition of human dihydrofolate reductase using dihydrofolate as substrate in ... 31685330
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 25.0 nM 7.6 Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) ... 14736247
Unchecked Ki = 31.9 nM 7.5 Competitive inhibition of Plasmodium falciparum dihydrofolate reductase N51I/C59... 31685330
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 32.0 nM 7.5 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N+I164L D... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 100.0 nM 7.0 Inhibition constant against Plasmodium falciparum dihydrofolate reductase 15293997
Plasmodium falciparum IC50 = 700.0 nM 6.16 In vitro antiplasmodial activity (IC50) against Plasmodium falciparum wtTM4/8.2 11881993
Plasmodium falciparum IC50 = 720.0 nM 6.14 Antimalarial activity against Plasmodium falciparum TM4/8.2 infected in human er... 31685330
Plasmodium falciparum EC50 = 1553.0 nM 5.81 NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati... 18579783
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 3300.0 nM 5.48 Antiplasmodial activity IC50 against Plasmodium falciparum K1CB1 DHFR double-mut... 11881993
Beta-N-acetyl-D-hexosaminidase-A/B IC50 = 11000.0 nM 4.96 Inhibition of human placental HexA using MUGS substrate incubated for 1 to 2 hrs... 25984755
Beta-hexosaminidase subunit beta IC50 = 15000.0 nM 4.82 Inhibition of human placental HexB using MUGS substrate incubated for 1 to 2 hrs... 25984755
Beta-N-acetyl-D-hexosaminidase-A/B IC50 = 27000.0 nM 4.57 Inhibition of HexA in normal human fibroblasts using MUGS substrate incubated fo... 25984755
Beta-hexosaminidase subunit alpha IC50 = 27000.0 nM 4.57 Inhibition of HexA alpha G269S mutant in ATSD patient fibroblasts using MUGS sub... 25984755
Beta-N-acetyl-D-hexosaminidase-A/B IC50 = 30000.0 nM 4.52 Inhibition of human placental HexA using MUGS substrate incubated for 1 to 2 hrs... 25984755

Literature References

PubMed DOI Target Context # Activities
25984755 10.1021/jm5017895 Beta-hexosaminidase subunit alpha 10
11881993 10.1021/jm010131q Bifunctional dihydrofolate reductase-thymidylate synthase 8
31685330 10.1016/j.bmc.2019.115158 Unchecked 7
14736247 10.1021/jm030165t Bifunctional dihydrofolate reductase-thymidylate synthase 7
11881993 10.1021/jm010131q Plasmodium falciparum 5
25984755 10.1021/jm5017895 Beta-N-acetyl-D-hexosaminidase-A/B 5
11881993 10.1021/jm010131q NON-PROTEIN TARGET 5
20485427 10.1038/nature09107 Plasmodium falciparum 4
31685330 10.1016/j.bmc.2019.115158 Plasmodium falciparum 4
25984755 10.1021/jm5017895 ADMET 3
18579783 10.1073/pnas.0802982105 Plasmodium falciparum 2
25984755 10.1021/jm5017895 Beta-hexosaminidase subunit beta 2
11881993 10.1021/jm010131q BC 1
15293997 10.1021/jm040769c Bifunctional dihydrofolate reductase-thymidylate synthase 1
31685330 10.1016/j.bmc.2019.115158 Vero 1
20485427 10.1038/nature09107 Unchecked 1
18579783 10.1073/pnas.0802982105 Huh-7 1
18579783 10.1073/pnas.0802982105 Unchecked 1
22096101 10.1126/science.1211936 Plasmodium yoelii 1
11881993 10.1021/jm010131q KB 1

Data from ChEMBL 36 via Core Engine