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Compound Detail

CHEMBL161034

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NC1=NC(c2ccc(Oc3ccccc3)cc2)N(c2ccc(Cl)cc2)C(N)=N1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL161034
Phase Preclinical
Structure Type MOL
InChI Key SHTBKDRNGQHNDH-UHFFFAOYSA-N
4
Targets
14
Activities
2
Assay Types
0
PK Parameters
5
Publications
0
Known Names

Molecular Properties

391.9
MW (Da)
4.28
ALogP
6
HBA
2
HBD
89.2
PSA (Ų)
0.69
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H18ClN5O
MW 391.86
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -0.60

Activity Summary

IC50 9 meas. best 7.4
Ki 5 meas. best 9.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 9.4 7.768 0.4 5
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 7.4 5.9683 40.0 6
Plasmodium falciparum
CHEMBL364
 IC50 5.16 5.16 7000.0 1
KB
CHEMBL398
 IC50 5.16 5.16 7000.0 1
BC
CHEMBL613535
 IC50 5.07 5.07 8600.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.4 nM 9.4 Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falcipa... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 3.8 nM 8.42 Binding affinity towards mutant dihydrofolate reductase (A16V+S108T DHFR) of Pla... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 29.3 nM 7.53 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) o... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 40.0 nM 7.4 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 120.0 nM 6.92 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 145.0 nM 6.84 Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) ... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 222.0 nM 6.65 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N+I164L D... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 3100.0 nM 5.51 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 3200.0 nM 5.5 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 4800.0 nM 5.32 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 6900.0 nM 5.16 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
KB IC50 = 7000.0 nM 5.16 In vitro cytotoxicity against Plasmodium falciparum infected KB cell line 14736247
Plasmodium falciparum IC50 = 7000.0 nM 5.16 Antimicrobial activity against Plasmodium falciparum 20185316
BC IC50 = 8600.0 nM 5.07 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