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Compound Detail

CHEMBL346982

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CCCOc1ccc(C2N=C(N)N=C(N)N2c2cccc(Cl)c2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL346982
Phase Preclinical
Structure Type MOL
InChI Key KNQLUUYDCOXNAX-UHFFFAOYSA-N
4
Targets
14
Activities
2
Assay Types
0
PK Parameters
5
Publications
0
Known Names

Molecular Properties

357.9
MW (Da)
3.28
ALogP
6
HBA
2
HBD
89.2
PSA (Ų)
0.86
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 C18H20ClN5O
MW 357.85
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.90

Activity Summary

IC50 9 meas. best 8.4
Ki 5 meas. best 9.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 9.3 8.612 0.5 5
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 8.4 6.4167 4.0 6
Plasmodium falciparum
CHEMBL364
 IC50 5.52 5.52 3000.0 1
KB
CHEMBL398
 IC50 5.22 5.22 6000.0 1
BC
CHEMBL613535
 IC50 4.52 4.52 30000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.5 nM 9.3 Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) ... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.1 nM 8.68 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) o... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.7 nM 8.57 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N+I164L D... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 3.3 nM 8.48 Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falcipa... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 4.0 nM 8.4 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 9.3 nM 8.03 Binding affinity towards mutant dihydrofolate reductase (A16V+S108T DHFR) of Pla... 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 = 380.0 nM 6.42 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 1000.0 nM 6.0 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 2900.0 nM 5.54 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 2900.0 nM 5.54 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Plasmodium falciparum IC50 = 3000.0 nM 5.52 Antimicrobial activity against Plasmodium falciparum 20185316
KB IC50 = 6000.0 nM 5.22 In vitro cytotoxicity against Plasmodium falciparum infected KB cell line 14736247
BC IC50 = 30000.0 nM 4.52 In vitro cytotoxicity against Plasmodium falciparum infected BC cell line. 14736247

Literature References

PubMed DOI Target Context # Activities
14736247 10.1021/jm030165t Bifunctional dihydrofolate reductase-thymidylate synthase 15
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