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Compound Detail

CHEMBL329687

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NC1=NC(c2ccccc2)N(c2cccc(Cl)c2)C(N)=N1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL329687
Phase Preclinical
Structure Type MOL
InChI Key XWGKYMBFBXACSF-UHFFFAOYSA-N
3
Targets
19
Activities
2
Assay Types
0
PK Parameters
7
Publications
0
Known Names

Molecular Properties

299.8
MW (Da)
2.49
ALogP
5
HBA
2
HBD
80.0
PSA (Ų)
0.89
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 C15H14ClN5
MW 299.76
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -0.81

Activity Summary

IC50 12 meas. best 7.7
Ki 7 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.0 7.3529 10.0 7
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 7.7 6.6433 20.0 6
Plasmodium falciparum
CHEMBL364
 IC50 7.62 6.6533 24.0 3
KB
CHEMBL398
 IC50 4.06 4.06 87000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 10.0 nM 8.0 Evaluated for inhibition constant (Ki mut) against A16V+S108T Mutant dihydrofola... 10893311
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 10.5 nM 7.98 Binding affinity towards mutant dihydrofolate reductase (A16V+S108T DHFR) of Pla... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 11.7 nM 7.93 Evaluated for inhibition constant (Ki wt) against Wild-type dihydrofolate reduct... 10893311
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 11.7 nM 7.93 Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falcipa... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 20.0 nM 7.7 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Plasmodium falciparum IC50 = 24.0 nM 7.62 Inhibition of Plasmodium falciparum T9/94 mutant 10893311
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 111.0 nM 6.96 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) o... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 200.0 nM 6.7 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 217.0 nM 6.66 Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) ... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 250.0 nM 6.6 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 310.0 nM 6.51 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Plasmodium falciparum IC50 = 455.0 nM 6.34 Growth inhibition (IC50) against Plasmodium falciparum wild-type TM4/8.2 10893311
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 560.0 nM 6.25 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 800.0 nM 6.1 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 984.0 nM 6.01 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N+I164L D... 14736247
Plasmodium falciparum IC50 = 1000.0 nM 6.0 Antimicrobial activity against Plasmodium falciparum 20185316
KB IC50 = 87000.0 nM 4.06 In vitro cytotoxicity against Plasmodium falciparum infected KB cell line 14736247

Literature References

PubMed DOI Target Context # Activities
14736247 10.1021/jm030165t Bifunctional dihydrofolate reductase-thymidylate synthase 15
10893311 10.1021/jm0009181 Bifunctional dihydrofolate reductase-thymidylate synthase 6
14736247 10.1021/jm030165t Vero 5
14736247 10.1021/jm030165t KB 4
14736247 10.1021/jm030165t BC 3
10893311 10.1021/jm0009181 Plasmodium falciparum 2
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine