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Compound Detail

CHEMBL416552

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CCCCCCc1nc(N)nc(N)c1-c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL416552
Phase Preclinical
Structure Type MOL
InChI Key DBCDYKFZHWOABJ-UHFFFAOYSA-N
4
Targets
22
Activities
2
Assay Types
0
PK Parameters
13
Publications
0
Known Names

Molecular Properties

270.4
MW (Da)
3.43
ALogP
4
HBA
2
HBD
77.8
PSA (Ų)
0.79
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 C16H22N4
MW 270.38
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness -0.21

Activity Summary

IC50 13 meas. best 7.22
Ki 9 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 9.52 9.0638 0.3 8
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 7.22 5.892 60.0 5
Plasmodium falciparum
CHEMBL364
 IC50 7.22 7.22 60.0 1
Dihydrofolate reductase
CHEMBL202
 Ki 4.82 4.82 15000.0 1
Vero
CHEMBL391
 IC50 4.26 4.26 55000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.3 nM 9.52 Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falcipa... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.3 nM 9.52 Inhibition of the wild-type dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.4 nM 9.4 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) o... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.7 nM 9.15 Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) ... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.7 nM 9.15 Inhibition of the C59R+S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.2 nM 8.92 Inhibition of the S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.4 nM 8.85 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N+I164L D... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 10.0 nM 8.0 Inhibition constant against Plasmodium falciparum dihydrofolate reductase 15293997
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 60.0 nM 7.22 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Plasmodium falciparum IC50 = 60.0 nM 7.22 In vitro antiplasmodial activity (IC50) against Plasmodium falciparum wtTM4/8.2 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 1300.0 nM 5.89 Antiplasmodial activity IC50 against Plasmodium falciparum K1CB1 DHFR double-mut... 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 2300.0 nM 5.64 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 3000.0 nM 5.52 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 6400.0 nM 5.19 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Dihydrofolate reductase Ki = 15000.0 nM 4.82 Cytotoxicity by selective inhibition against human dihydrofolate reductase (DHFR... 11881993
Vero IC50 = 55000.0 nM 4.26 In vitro cytotoxicity against Plasmodium falciparum infected vero cell line. 14736247
Vero IC50 = 55000.0 nM 4.26 Cytotoxicity by the selective inhibition against African green monkey kidney fib... 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
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 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