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Compound Detail

CHEMBL279509

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COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL279509
Phase Preclinical
Structure Type MOL
InChI Key NEBFMAAUKXSAAC-UHFFFAOYSA-N
4
Targets
7
Activities
2
Assay Types
0
PK Parameters
5
Publications
0
Known Names

Molecular Properties

366.4
MW (Da)
2.83
ALogP
7
HBA
2
HBD
105.5
PSA (Ų)
0.66
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H22N4O3
MW 366.42
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -0.17

Activity Summary

IC50 4 meas. best 7.85
Ki 3 meas. best 8.38

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.38 7.5767 4.2 3
Dihydrofolate reductase
CHEMBL1809
 IC50 7.85 7.85 14.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.38 5.38 4200.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 4.52 4.52 30100.0 1
Dihydrofolate reductase
CHEMBL2363
 IC50 4.33 4.33 47000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 4.2 nM 8.38 Inhibition of the wild-type dihydrofolate reductase (DHFR) 11881993
Dihydrofolate reductase IC50 = 14.0 nM 7.85 Inhibitory activity against Dihydrofolate reductase of Escherichia coli 7035668
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 61.9 nM 7.21 Inhibition of the S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 71.9 nM 7.14 Inhibition of the C59R+S108N mutant of dihydrofolate reductase (DHFR) 11881993
Plasmodium falciparum IC50 = 4200.0 nM 5.38 In vitro antiplasmodial activity (IC50) against Plasmodium falciparum wtTM4/8.2 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 30100.0 nM 4.52 Antiplasmodial activity IC50 against Plasmodium falciparum K1CB1 DHFR double-mut... 11881993
Dihydrofolate reductase IC50 = 47000.0 nM 4.33 Inhibition of rat liver Dihydrofolate reductase. 7035668

Literature References

PubMed DOI Target Context # Activities
7035668 10.1021/jm00140a005 Dihydrofolate reductase 10
11881993 10.1021/jm010131q Bifunctional dihydrofolate reductase-thymidylate synthase 4
11881993 10.1021/jm010131q Plasmodium falciparum 2
28327306 10.1016/j.bmcl.2016.10.051 Escherichia coli 1
28327306 10.1016/j.bmcl.2016.10.051 Staphylococcus aureus 1

Data from ChEMBL 36 via Core Engine