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Compound Detail

CHEMBL21407

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COC(=O)CCCc1nc(N)nc(N)c1-c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL21407
Phase Preclinical
Structure Type MOL
InChI Key CSSVOQROYPHQPU-UHFFFAOYSA-N
2
Targets
10
Activities
2
Assay Types
0
PK Parameters
4
Publications
0
Known Names

Molecular Properties

286.3
MW (Da)
1.80
ALogP
6
HBA
2
HBD
104.1
PSA (Ų)
0.81
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 C15H18N4O2
MW 286.33
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -0.31

Activity Summary

Ki 8 meas. best 9.22
IC50 2 meas. best 6.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 9.22 8.42 0.6 8
Plasmodium falciparum
CHEMBL364
 IC50 6.4 6.4 400.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 4.5 4.5 31300.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.6 nM 9.22 Inhibition of the wild-type dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.6 nM 9.22 Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falcipa... 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 = 3.3 nM 8.48 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) o... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 5.5 nM 8.26 Inhibition of the C59R+S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 10.0 nM 8.0 Inhibition constant against Plasmodium falciparum dihydrofolate reductase 15293997
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 15.0 nM 7.82 Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) ... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 24.0 nM 7.62 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N+I164L D... 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 = 31300.0 nM 4.5 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