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Compound Detail

CHEMBL21921

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Nc1nc(N)c(-c2cccc(Cl)c2)c(CCCc2ccccc2)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL21921
Phase Preclinical
Structure Type MOL
InChI Key CZDYZPVAAIFLQU-UHFFFAOYSA-N
5
Targets
18
Activities
2
Assay Types
0
PK Parameters
8
Publications
0
Known Names

Molecular Properties

338.8
MW (Da)
4.14
ALogP
4
HBA
2
HBD
77.8
PSA (Ų)
0.73
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H19ClN4
MW 338.84
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness -0.63

Activity Summary

IC50 10 meas. best 6.17
Ki 8 meas. best 8.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.92 8.5225 1.2 8
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 6.17 5.548 670.0 5
Plasmodium falciparum
CHEMBL364
 IC50 6.16 5.69 700.0 2
KB
CHEMBL398
 IC50 5.8 5.8 1600.0 1
BC
CHEMBL613535
 IC50 5.8 5.8 1600.0 1
Vero
CHEMBL391
 IC50 5.68 5.68 2100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.2 nM 8.92 Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falcipa... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.2 nM 8.92 Inhibition of the wild-type dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.0 nM 8.7 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N+I164L D... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.0 nM 8.7 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) o... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.2 nM 8.66 Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) ... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 3.0 nM 8.52 Inhibition of the S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 4.2 nM 8.38 Inhibition of the C59R+S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 42.0 nM 7.38 Inhibition constant against Plasmodium falciparum dihydrofolate reductase 15293997
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 670.0 nM 6.17 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Plasmodium falciparum IC50 = 700.0 nM 6.16 In vitro antiplasmodial activity (IC50) against Plasmodium falciparum wtTM4/8.2 11881993
BC IC50 = 1600.0 nM 5.8 In vitro cytotoxicity against Plasmodium falciparum infected BC cell line. 14736247
KB IC50 = 1600.0 nM 5.8 In vitro cytotoxicity against Plasmodium falciparum infected KB cell line 14736247
Vero IC50 = 2100.0 nM 5.68 In vitro cytotoxicity against Plasmodium falciparum infected vero cell line. 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 3000.0 nM 5.52 Antiplasmodial activity IC50 against Plasmodium falciparum K1CB1 DHFR double-mut... 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 3600.0 nM 5.44 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 4300.0 nM 5.37 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 5700.0 nM 5.24 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Plasmodium falciparum IC50 = 6000.0 nM 5.22 Antimicrobial activity against Plasmodium falciparum 20185316

Literature References

PubMed DOI Target Context # Activities
14736247 10.1021/jm030165t Bifunctional dihydrofolate reductase-thymidylate synthase 11
11881993 10.1021/jm010131q Bifunctional dihydrofolate reductase-thymidylate synthase 9
14736247 10.1021/jm030165t Vero 5
14736247 10.1021/jm030165t KB 4
14736247 10.1021/jm030165t BC 3
11881993 10.1021/jm010131q Plasmodium falciparum 2
15293997 10.1021/jm040769c Bifunctional dihydrofolate reductase-thymidylate synthase 1
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine