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Compound Detail

CHEMBL161009

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CCCCCCC1(C)N=C(N)N=C(N)N1c1cccc(Cl)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL161009
Phase Preclinical
Structure Type MOL
InChI Key VSXVVMCROPSSBG-UHFFFAOYSA-N
4
Targets
14
Activities
2
Assay Types
0
PK Parameters
5
Publications
0
Known Names

Molecular Properties

321.9
MW (Da)
3.48
ALogP
5
HBA
2
HBD
80.0
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 C16H24ClN5
MW 321.86
Aromatic Rings 1
Heavy Atoms 22
NP-Likeness -0.36

Activity Summary

IC50 9 meas. best 7.22
Ki 5 meas. best 8.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.62 7.92 2.4 5
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 7.22 6.328 60.0 5
BC
CHEMBL613535
 IC50 5.66 5.66 2200.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.52 5.52 3000.0 1
KB
CHEMBL398
 IC50 5.4 5.4 4000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.4 nM 8.62 Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falcipa... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 5.5 nM 8.26 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) o... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 12.1 nM 7.92 Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) ... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 15.9 nM 7.8 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N+I164L D... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 60.0 nM 7.22 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 101.0 nM 7.0 Binding affinity towards mutant dihydrofolate reductase (A16V+S108T DHFR) of Pla... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 480.0 nM 6.32 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 490.0 nM 6.31 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 510.0 nM 6.29 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
BC IC50 = 2200.0 nM 5.66 In vitro cytotoxicity against Plasmodium falciparum infected BC cell line. 14736247
Plasmodium falciparum IC50 = 3000.0 nM 5.52 Antimicrobial activity against Plasmodium falciparum 20185316
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 3200.0 nM 5.5 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
KB IC50 = 4000.0 nM 5.4 In vitro cytotoxicity against Plasmodium falciparum infected KB cell line 14736247

Literature References

PubMed DOI Target Context # Activities
14736247 10.1021/jm030165t Bifunctional dihydrofolate reductase-thymidylate synthase 15
14736247 10.1021/jm030165t Vero 5
14736247 10.1021/jm030165t KB 4
14736247 10.1021/jm030165t BC 3
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine