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Compound Detail

CHEMBL22146

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COc1cc(Cc2cnc(N)nc2N)ccc1OCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL22146
Phase Preclinical
Structure Type MOL
InChI Key KRZXDTYOZAQOGL-UHFFFAOYSA-N
5
Targets
17
Activities
2
Assay Types
0
PK Parameters
11
Publications
0
Known Names

Molecular Properties

336.4
MW (Da)
2.82
ALogP
6
HBA
2
HBD
96.3
PSA (Ų)
0.72
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 C19H20N4O2
MW 336.40
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -0.30

Activity Summary

Ki 10 meas. best 8.66
IC50 7 meas. best 6.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.66 7.2557 2.2 7
Dihydrofolate reductase
CHEMBL4888
 Ki 7.53 7.53 29.5 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 6.68 5.436 210.0 5
Dihydrofolate reductase
CHEMBL2902
 Ki 6.5 6.5 316.2 1
Plasmodium falciparum
CHEMBL364
 IC50 5.33 5.315 4700.0 2
Dihydrofolate reductase
CHEMBL2575
 Ki 4.72 4.72 19054.6 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.2 nM 8.66 Inhibitory activity against wild-type dihydrofolate reductase (S108N DHFR) 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.2 nM 8.66 Inhibition of the wild-type dihydrofolate reductase (DHFR) 11881993
Dihydrofolate reductase Ki = 29.51 nM 7.53 Inhibitory activity against Escherichia coli dihydrofolate reductase 1899453
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 34.9 nM 7.46 Inhibition of the S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 60.7 nM 7.22 Inhibition of the C59R+S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 60.7 nM 7.22 Inhibitory activity against double mutant dihydrofolate reductase (C59R+S108N DH... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 210.0 nM 6.68 In vitro antimalarial activity against Plasmodium falciparum Csl-2 triple DHFR m... 14711307
Dihydrofolate reductase Ki = 316.23 nM 6.5 Inhibitory activity against Lactobacillus casei dihydrofolate reductase 2502631
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 700.0 nM 6.16 In vitro antimalarial activity relative to trimethoprim against Plasmodium falci... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1375.7 nM 5.86 Inhibitory activity against quadruple mutant dihydrofolate reductase (N51I C59R ... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1974.1 nM 5.71 Inhibitory activity against triple mutant dihydrofolate reductase (C59R S108N I1... 14711307
Plasmodium falciparum IC50 = 4700.0 nM 5.33 In vitro antiplasmodial activity (IC50) against Plasmodium falciparum wtTM4/8.2 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 4660.0 nM 5.33 In vitro antimalarial activity against Plasmodium falciparum TM4/8.2 wtDHFR 14711307
Plasmodium falciparum IC50 = 5000.0 nM 5.3 Antimicrobial activity against Plasmodium falciparum 20185316
Dihydrofolate reductase Ki = 19054.61 nM 4.72 Inhibitory activity against chicken liver dihydrofolate reductase 2502631
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 25610.0 nM 4.59 In vitro antimalarial activity against Plasmodium falciparum Csl-2 triple DHFR m... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 38020.0 nM 4.42 In vitro antimalarial activity against Plasmodium falciparum Vl/S with quadruple... 14711307

Literature References

PubMed DOI Target Context # Activities
14711307 10.1021/jm0303352 Bifunctional dihydrofolate reductase-thymidylate synthase 16
11881993 10.1021/jm010131q Bifunctional dihydrofolate reductase-thymidylate synthase 4
3276891 10.1021/jm00397a017 Escherichia coli 2
11881993 10.1021/jm010131q Plasmodium falciparum 2
2502631 10.1021/jm00128a035 Dihydrofolate reductase 2
11495588 10.1021/jm000226c Dihydrofolate reductase 1
1899453 10.1021/jm00105a008 Dihydrofolate reductase 1
1507206 10.1021/jm00095a016 Dihydrofolate reductase 1
3276891 10.1021/jm00397a017 Dihydrofolate reductase 1
2502631 10.1021/jm00128a035 No relevant target 1
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine