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Compound Detail

CHEMBL354011

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NC1=NC(c2cccc(OCc3ccccc3)c2)N(c2cccc(Cl)c2)C(N)=N1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL354011
Phase Preclinical
Structure Type MOL
InChI Key JQLXDOJOBIARNA-UHFFFAOYSA-N
4
Targets
14
Activities
2
Assay Types
0
PK Parameters
5
Publications
0
Known Names

Molecular Properties

405.9
MW (Da)
4.07
ALogP
6
HBA
2
HBD
89.2
PSA (Ų)
0.67
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 C22H20ClN5O
MW 405.89
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -0.84

Activity Summary

IC50 9 meas. best 6.72
Ki 5 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 8.434 2.3 5
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 6.72 5.52 190.0 6
Plasmodium falciparum
CHEMBL364
 IC50 5.1 5.1 8000.0 1
KB
CHEMBL398
 IC50 5.1 5.1 8000.0 1
BC
CHEMBL613535
 IC50 4.66 4.66 22000.0 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 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 (N51I+C59R+S108N DHFR) o... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 3.2 nM 8.49 Binding affinity towards mutant dihydrofolate reductase (A16V+S108T DHFR) of Pla... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 3.6 nM 8.44 Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) ... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 7.7 nM 8.11 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N+I164L D... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 190.0 nM 6.72 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 3300.0 nM 5.48 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 4000.0 nM 5.4 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 4900.0 nM 5.31 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 7500.0 nM 5.12 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
KB IC50 = 8000.0 nM 5.1 In vitro cytotoxicity against Plasmodium falciparum infected KB cell line 14736247
Plasmodium falciparum IC50 = 8000.0 nM 5.1 Antimicrobial activity against Plasmodium falciparum 20185316
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 8200.0 nM 5.09 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
BC IC50 = 22000.0 nM 4.66 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