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Compound Detail

CHEMBL4558959

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Cl.Nc1nc(N)c(-c2cccc(Cl)c2)c(CCCCOc2ccccc2)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4558959
Phase Preclinical
Structure Type MOL
InChI Key WQLQDJDDBITRRP-UHFFFAOYSA-N
Parent Compound CHEMBL4596911
Active Moiety CHEMBL4596911
4
Targets
6
Activities
2
Assay Types
0
PK Parameters
4
Publications
0
Known Names

Molecular Properties

368.9
MW (Da)
4.36
ALogP
5
HBA
2
HBD
87.0
PSA (Ų)
0.60
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H22Cl2N4O
MW 405.33
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -0.80

Activity Summary

IC50 3 meas. best 6.47
Ki 3 meas. best 9.42

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 9.42 9.125 0.4 2
Dihydrofolate reductase
CHEMBL202
 Ki 7.89 7.89 12.8 1
Plasmodium falciparum
CHEMBL364
 IC50 6.47 5.815 340.0 2
Vero
CHEMBL391
 IC50 5.29 5.29 5150.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.38 nM 9.42 Competitive inhibition of wild type Plasmodium falciparum dihydrofolate reductas... 31685330
Unchecked Ki = 1.49 nM 8.83 Competitive inhibition of Plasmodium falciparum dihydrofolate reductase N51I/C59... 31685330
Dihydrofolate reductase Ki = 12.77 nM 7.89 Inhibition of human dihydrofolate reductase using dihydrofolate as substrate in ... 31685330
Plasmodium falciparum IC50 = 340.0 nM 6.47 Antimalarial activity against Plasmodium falciparum TM4/8.2 infected in human er... 31685330
Vero IC50 = 5150.0 nM 5.29 Cytotoxicity against African green monkey Vero cells by sulforhodamine B assay 31685330
Plasmodium falciparum IC50 = 6940.0 nM 5.16 Antimalarial activity against pyrimethamine-resistant Plasmodium falciparum V1/S... 31685330

Literature References

PubMed DOI Target Context # Activities
31685330 10.1016/j.bmc.2019.115158 Unchecked 9
31685330 10.1016/j.bmc.2019.115158 Plasmodium falciparum 4
31685330 10.1016/j.bmc.2019.115158 Dihydrofolate reductase 1
31685330 10.1016/j.bmc.2019.115158 Vero 1

Data from ChEMBL 36 via Core Engine