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Compound Detail

CHEMBL444605

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CC(=O)OCCCc1nc(N)nc(N)c1-c1cccc(Cl)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL444605
Phase Preclinical
Structure Type MOL
InChI Key YRAOVTHKXFGTRW-UHFFFAOYSA-N
5
Targets
12
Activities
2
Assay Types
0
PK Parameters
5
Publications
0
Known Names

Molecular Properties

320.8
MW (Da)
2.46
ALogP
6
HBA
2
HBD
104.1
PSA (Ų)
0.65
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 C15H17ClN4O2
MW 320.78
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.45

Activity Summary

IC50 8 meas. best 5.8
Ki 4 meas. best 8.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.74 8.31 1.8 4
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 5.8 5.6275 1600.0 4
Plasmodium falciparum
CHEMBL364
 IC50 5.7 5.7 2000.0 1
BC
CHEMBL613535
 IC50 5.0 5.0 10000.0 1
KB
CHEMBL398
 IC50 4.77 4.77 17000.0 1
Vero
CHEMBL391
 IC50 4.3 4.3 50000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.8 nM 8.74 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) o... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 3.1 nM 8.51 Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falcipa... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 3.2 nM 8.49 Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) ... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 31.4 nM 7.5 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N+I164L D... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 1600.0 nM 5.8 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 1800.0 nM 5.75 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Plasmodium falciparum IC50 = 2000.0 nM 5.7 Antimicrobial activity against Plasmodium falciparum 20185316
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 2100.0 nM 5.68 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 5300.0 nM 5.28 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
BC IC50 = 10000.0 nM 5.0 In vitro cytotoxicity against Plasmodium falciparum infected BC cell line. 14736247
KB IC50 = 17000.0 nM 4.77 In vitro cytotoxicity against Plasmodium falciparum infected KB cell line 14736247
Vero IC50 = 50000.0 nM 4.3 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