Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL22403

Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
Nc1nc(N)c(-c2cccc(Cl)c2)c(CCOCCCOc2ccccc2)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL22403
Phase Preclinical
Structure Type MOL
InChI Key CRGQDUYGPMHVEY-UHFFFAOYSA-N
5
Targets
21
Activities
2
Assay Types
0
PK Parameters
12
Publications
0
Known Names

Molecular Properties

398.9
MW (Da)
3.99
ALogP
6
HBA
2
HBD
96.3
PSA (Ų)
0.53
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H23ClN4O2
MW 398.89
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -0.88

Activity Summary

IC50 13 meas. best 6.46
Ki 8 meas. best 9.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 9.4 8.87 0.4 8
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 6.46 5.634 350.0 5
Plasmodium falciparum
CHEMBL364
 IC50 6.4 6.4 400.0 1
BC
CHEMBL613535
 IC50 5.31 5.26 4900.0 2
KB
CHEMBL398
 IC50 5.19 5.14 6400.0 2
Vero
CHEMBL391
 IC50 4.82 4.82 15000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.4 nM 9.4 Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falcipa... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.4 nM 9.4 Inhibition of the wild-type dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.7 nM 9.15 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) o... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.3 nM 8.89 Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) ... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.7 nM 8.77 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N+I164L D... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.8 nM 8.74 Inhibition of the S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.9 nM 8.72 Inhibition of the C59R+S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 13.0 nM 7.89 Inhibition constant against Plasmodium falciparum dihydrofolate reductase 15293997
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 350.0 nM 6.46 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Plasmodium falciparum IC50 = 400.0 nM 6.4 In vitro antiplasmodial activity (IC50) against Plasmodium falciparum wtTM4/8.2 11881993
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 = 3300.0 nM 5.48 Antiplasmodial activity IC50 against Plasmodium falciparum K1CB1 DHFR double-mut... 11881993
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 = 4600.0 nM 5.34 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
BC IC50 = 4900.0 nM 5.31 In vitro cytotoxicity against Plasmodium falciparum infected BC cell line. 14736247
BC IC50 = 6100.0 nM 5.21 Cytotoxicity against human breast cancer cells. 11881993
KB IC50 = 6400.0 nM 5.19 In vitro cytotoxicity against Plasmodium falciparum infected KB cell line 14736247
KB IC50 = 8100.0 nM 5.09 Cytotoxicity against human epidermoid carcinoma KB cell. 11881993
Vero IC50 = 15000.0 nM 4.82 Cytotoxicity by the selective inhibition against African green monkey kidney fib... 11881993
Vero IC50 = 15000.0 nM 4.82 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
11881993 10.1021/jm010131q Bifunctional dihydrofolate reductase-thymidylate synthase 9
11881993 10.1021/jm010131q NON-PROTEIN TARGET 5
14736247 10.1021/jm030165t Vero 5
14736247 10.1021/jm030165t KB 4
11881993 10.1021/jm010131q Plasmodium falciparum 3
14736247 10.1021/jm030165t BC 3
11881993 10.1021/jm010131q Vero 1
11881993 10.1021/jm010131q KB 1
11881993 10.1021/jm010131q BC 1
15293997 10.1021/jm040769c Bifunctional dihydrofolate reductase-thymidylate synthase 1
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine