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Compound Detail

CHEMBL21494

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COC(=O)CCCc1nc(N)nc(N)c1-c1cccc(Cl)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL21494
Phase Preclinical
Structure Type MOL
InChI Key NKROAACUFYYULW-UHFFFAOYSA-N
2
Targets
9
Activities
2
Assay Types
0
PK Parameters
3
Publications
0
Known Names

Molecular Properties

320.8
MW (Da)
2.46
ALogP
6
HBA
2
HBD
104.1
PSA (Ų)
0.82
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 C15H17ClN4O2
MW 320.78
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.63

Activity Summary

Ki 7 meas. best 9.3
IC50 2 meas. best 6.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 9.3 8.9057 0.5 7
Plasmodium falciparum
CHEMBL364
 IC50 6.1 6.1 800.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 4.44 4.44 36300.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.5 nM 9.3 Inhibition of the wild-type dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.5 nM 9.3 Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falcipa... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.77 nM 9.11 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) o... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.7 nM 8.77 Inhibition of the S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.8 nM 8.74 Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) ... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.7 nM 8.57 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N+I164L D... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.8 nM 8.55 Inhibition of the C59R+S108N mutant of dihydrofolate reductase (DHFR) 11881993
Plasmodium falciparum IC50 = 800.0 nM 6.1 In vitro antiplasmodial activity (IC50) against Plasmodium falciparum wtTM4/8.2 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 36300.0 nM 4.44 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

Data from ChEMBL 36 via Core Engine