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Compound Detail

CHEMBL422005

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

Basic Information

ChEMBL ID CHEMBL422005
Phase Preclinical
Structure Type MOL
InChI Key URNIAKXYUQJBFB-UHFFFAOYSA-N
5
Targets
12
Activities
2
Assay Types
0
PK Parameters
5
Publications
0
Known Names

Molecular Properties

278.7
MW (Da)
1.89
ALogP
5
HBA
3
HBD
98.0
PSA (Ų)
0.79
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C13H15ClN4O
MW 278.74
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -0.51

Activity Summary

IC50 8 meas. best 6.0
Ki 4 meas. best 8.64

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.64 7.865 2.3 4
Plasmodium falciparum
CHEMBL364
 IC50 6.0 6.0 1000.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 5.96 5.56 1100.0 4
KB
CHEMBL398
 IC50 5.0 5.0 10100.0 1
BC
CHEMBL613535
 IC50 4.82 4.82 15000.0 1
Vero
CHEMBL391
 IC50 4.65 4.65 22300.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.3 nM 8.64 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) o... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 9.2 nM 8.04 Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falcipa... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 29.0 nM 7.54 Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) ... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 57.0 nM 7.24 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
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 1100.0 nM 5.96 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 1900.0 nM 5.72 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 4500.0 nM 5.35 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 6200.0 nM 5.21 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
KB IC50 = 10100.0 nM 5.0 In vitro cytotoxicity against Plasmodium falciparum infected KB cell line 14736247
BC IC50 = 15000.0 nM 4.82 In vitro cytotoxicity against Plasmodium falciparum infected BC cell line. 14736247
Vero IC50 = 22300.0 nM 4.65 In vitro cytotoxicity against Plasmodium falciparum infected vero cell line. 14736247

Literature References

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

Data from ChEMBL 36 via Core Engine