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Compound Detail

CHEMBL278813

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COc1ccc(CCCc2nc(N)nc(N)c2-c2cccc(Cl)c2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL278813
Phase Preclinical
Structure Type MOL
InChI Key NGXOWQSZWYMAKV-UHFFFAOYSA-N
5
Targets
20
Activities
2
Assay Types
0
PK Parameters
12
Publications
0
Known Names

Molecular Properties

368.9
MW (Da)
4.15
ALogP
5
HBA
2
HBD
87.0
PSA (Ų)
0.68
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H21ClN4O
MW 368.87
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -0.60

Activity Summary

IC50 12 meas. best 6.4
Ki 8 meas. best 8.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.89 8.5038 1.3 8
Plasmodium falciparum
CHEMBL364
 IC50 6.4 6.4 400.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 6.39 5.652 410.0 5
Vero
CHEMBL391
 IC50 5.52 5.52 3000.0 2
BC
CHEMBL613535
 IC50 5.52 5.52 3000.0 1
KB
CHEMBL398
 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 = 1.3 nM 8.89 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) o... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.0 nM 8.7 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N+I164L D... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.2 nM 8.66 Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falcipa... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.2 nM 8.66 Inhibition of the wild-type dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.9 nM 8.54 Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) ... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 4.0 nM 8.4 Inhibition of the S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 6.0 nM 8.22 Inhibition of the C59R+S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 11.0 nM 7.96 Inhibition constant against Plasmodium falciparum dihydrofolate reductase 15293997
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 = 410.0 nM 6.39 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 2700.0 nM 5.57 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 2700.0 nM 5.57 Antiplasmodial activity IC50 against Plasmodium falciparum K1CB1 DHFR double-mut... 11881993
BC IC50 = 3000.0 nM 5.52 In vitro cytotoxicity against Plasmodium falciparum infected BC cell line. 14736247
Vero IC50 = 3000.0 nM 5.52 In vitro cytotoxicity against Plasmodium falciparum infected vero cell line. 14736247
Vero IC50 = 3000.0 nM 5.52 Cytotoxicity by the selective inhibition against African green monkey kidney fib... 11881993
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 = 4700.0 nM 5.33 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
KB IC50 = 15000.0 nM 4.82 In vitro cytotoxicity against Plasmodium falciparum infected KB cell line 14736247
KB IC50 = 15000.0 nM 4.82 Cytotoxicity against human epidermoid carcinoma KB cell. 11881993

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
14736247 10.1021/jm030165t Vero 5
14736247 10.1021/jm030165t KB 4
14736247 10.1021/jm030165t BC 3
11881993 10.1021/jm010131q Plasmodium falciparum 2
11881993 10.1021/jm010131q Dihydrofolate reductase 1
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