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Compound Detail

CHEMBL325533

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COc1cc(Cc2c(C)nc(N)nc2N)cc(OC)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL325533
Phase Preclinical
Structure Type MOL
InChI Key KUPCMNHSRONILW-UHFFFAOYSA-N
4
Targets
15
Activities
2
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

304.4
MW (Da)
1.57
ALogP
7
HBA
2
HBD
105.5
PSA (Ų)
0.86
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H20N4O3
MW 304.35
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.15

Activity Summary

IC50 11 meas. best 7.0
Ki 4 meas. best 7.42

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 7.42 6.34 38.2 4
Dihydrofolate reductase
CHEMBL1809
 IC50 7.0 7.0 100.0 3
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL3963
 IC50 6.47 6.47 340.0 2
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 6.3 5.314 500.0 5
Plasmodium falciparum
CHEMBL364
 IC50 4.64 4.64 23000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 38.2 nM 7.42 Inhibitory activity against wild-type dihydrofolate reductase (S108N DHFR) 14711307
Dihydrofolate reductase IC50 = 100.0 nM 7.0 Compound was tested for inhibition of Escherichia coli Dihydrofolate reductase. 8941396
Dihydrofolate reductase IC50 = 100.0 nM 7.0 Inhibition against dihydrofolate reductase enzyme of Escherichia coli 6991695
Dihydrofolate reductase IC50 = 100.0 nM 7.0 Inhibitory activity against Dihydrofolate reductase enzyme purified from Escheri... 6991692
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 340.0 nM 6.47 Compound was tested for its inhibition against dihydrofolate reductase enzyme of... 6991695
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 340.0 nM 6.47 Inhibitory activity against Dihydrofolate reductase enzyme purified from Plasmod... 6991692
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 500.0 nM 6.3 In vitro antimalarial activity relative to trimethoprim against Plasmodium falci... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 520.3 nM 6.28 Inhibitory activity against double mutant dihydrofolate reductase (C59R+S108N DH... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 760.0 nM 6.12 In vitro antimalarial activity against Plasmodium falciparum Csl-2 triple DHFR m... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1364.3 nM 5.87 Inhibitory activity against triple mutant dihydrofolate reductase (C59R S108N I1... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1634.3 nM 5.79 Inhibitory activity against quadruple mutant dihydrofolate reductase (N51I C59R ... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 3410.0 nM 5.47 In vitro antimalarial activity relative to trimethoprim against Plasmodium falci... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 22730.0 nM 4.64 In vitro antimalarial activity against Plasmodium falciparum TM4/8.2 wtDHFR 14711307
Plasmodium falciparum IC50 = 23000.0 nM 4.64 Antimicrobial activity against Plasmodium falciparum 20185316
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 90810.0 nM 4.04 In vitro antimalarial activity against Plasmodium falciparum Csl-2 triple DHFR m... 14711307

Literature References

PubMed DOI Target Context # Activities
14711307 10.1021/jm0303352 Bifunctional dihydrofolate reductase-thymidylate synthase 16
6991695 10.1021/jm00179a012 Dihydrofolate reductase 2
6991692 10.1021/jm00178a007 Dihydrofolate reductase 2
6991692 10.1021/jm00178a007 Streptococcus pyogenes 1
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1
6991692 10.1021/jm00178a007 Proteus vulgaris 1
6991692 10.1021/jm00178a007 Serratia marcescens 1
6991692 10.1021/jm00178a007 Shigella dysenteriae 1
6991692 10.1021/jm00178a007 Klebsiella pneumoniae 1
6991692 10.1021/jm00178a007 Escherichia coli 1
6991692 10.1021/jm00178a007 Salmonella 1
6991692 10.1021/jm00178a007 Staphylococcus aureus 1
6991692 10.1021/jm00178a007 Bifunctional dihydrofolate reductase-thymidylate synthase 1
6991695 10.1021/jm00179a012 Bifunctional dihydrofolate reductase-thymidylate synthase 1
8941396 10.1021/jm960491r No relevant target 1
8941396 10.1021/jm960491r Dihydrofolate reductase 1
7277386 10.1021/jm00139a010 Dihydrofolate reductase type 1 1

Data from ChEMBL 36 via Core Engine