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Compound Detail

CHEMBL21691

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Nc1nc(N)c(-c2ccc(Cl)cc2)c(CCCc2ccccc2)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL21691
Phase Preclinical
Structure Type MOL
InChI Key PEDYEMSEQIYDBQ-UHFFFAOYSA-N
2
Targets
10
Activities
2
Assay Types
0
PK Parameters
4
Publications
0
Known Names

Molecular Properties

338.8
MW (Da)
4.14
ALogP
4
HBA
2
HBD
77.8
PSA (Ų)
0.73
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 C19H19ClN4
MW 338.84
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness -0.55

Activity Summary

Ki 8 meas. best 9.15
IC50 2 meas. best 7.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 9.15 8.0888 0.7 8
Plasmodium falciparum
CHEMBL364
 IC50 7.3 7.3 50.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 4.97 4.97 10600.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.7 nM 9.15 Inhibition of the wild-type dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.7 nM 9.15 Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falcipa... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.74 nM 9.13 Inhibition constant against Plasmodium falciparum dihydrofolate reductase 15293997
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 13.9 nM 7.86 Inhibition of the S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 15.1 nM 7.82 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) o... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 23.3 nM 7.63 Inhibition of the C59R+S108N mutant of dihydrofolate reductase (DHFR) 11881993
Plasmodium falciparum IC50 = 50.0 nM 7.3 In vitro antiplasmodial activity (IC50) against Plasmodium falciparum wtTM4/8.2 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 63.0 nM 7.2 Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) ... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 170.0 nM 6.77 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N+I164L D... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 10600.0 nM 4.97 Antiplasmodial activity IC50 against Plasmodium falciparum K1CB1 DHFR double-mut... 11881993

Literature References

PubMed DOI Target Context # Activities
11881993 10.1021/jm010131q Bifunctional dihydrofolate reductase-thymidylate synthase 9
14736247 10.1021/jm030165t Bifunctional dihydrofolate reductase-thymidylate synthase 7
11881993 10.1021/jm010131q Plasmodium falciparum 2
15293997 10.1021/jm040769c Bifunctional dihydrofolate reductase-thymidylate synthase 1

Data from ChEMBL 36 via Core Engine