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Compound Detail

CHEMBL158639

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CCCC1(C)N=C(N)N=C(N)N1c1cccc(Cl)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL158639
Phase Preclinical
Structure Type MOL
InChI Key SKJYINOHXUZOKK-UHFFFAOYSA-N
2
Targets
13
Activities
2
Assay Types
0
PK Parameters
5
Publications
0
Known Names

Molecular Properties

279.8
MW (Da)
2.31
ALogP
5
HBA
2
HBD
80.0
PSA (Ų)
0.89
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C13H18ClN5
MW 279.78
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness -0.60

Activity Summary

IC50 8 meas. best 6.75
Ki 5 meas. best 8.34

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.34 7.514 4.6 5
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 6.75 6.51 180.0 5
BC
CHEMBL613535
 IC50 4.19 4.19 64000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 4.6 nM 8.34 Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falcipa... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 9.7 nM 8.01 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) o... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 33.1 nM 7.48 Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) ... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 39.4 nM 7.41 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N+I164L D... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 180.0 nM 6.75 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 180.0 nM 6.75 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 280.0 nM 6.55 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 290.0 nM 6.54 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 471.0 nM 6.33 Binding affinity towards mutant dihydrofolate reductase (A16V+S108T DHFR) of Pla... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 1100.0 nM 5.96 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
BC IC50 = 64000.0 nM 4.19 In vitro cytotoxicity against Plasmodium falciparum infected BC 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