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Compound Detail

CHEMBL1181

4-HYDROXYTRIMETHOPRIM
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COc1cc(Cc2cnc(N)nc2N)cc(OC)c1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1181
Name 4-HYDROXYTRIMETHOPRIM
Phase Preclinical
Structure Type MOL
InChI Key HPOCGNHBIFZCAN-UHFFFAOYSA-N
4
Targets
10
Activities
1
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

276.3
MW (Da)
0.95
ALogP
7
HBA
3
HBD
116.5
PSA (Ų)
0.76
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 C13H16N4O3
MW 276.30
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 0.26

Activity Summary

IC50 10 meas. best 7.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL1809
 IC50 7.96 7.96 11.0 4
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL3963
 IC50 6.52 6.52 300.0 2
Dihydrofolate reductase
CHEMBL3565
 IC50 6.48 6.48 330.0 1
Dihydrofolate reductase
CHEMBL2363
 IC50 4.04 4.04 92000.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase IC50 = 11.0 nM 7.96 Inhibitory activity against dihydrofolate reductase (DHFR) from Escherichia coli 3100802
Dihydrofolate reductase IC50 = 10.96 nM 7.96 Compound was tested for inhibition of Escherichia coli Dihydrofolate reductase. 8941396
Dihydrofolate reductase IC50 = 11.0 nM 7.96 Inhibitory activity against Dihydrofolate reductase of Escherichia coli 7035668
Dihydrofolate reductase IC50 = 11.0 nM 7.96 Inhibitory activity against Dihydrofolate reductase enzyme purified from Escheri... 6991692
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 300.0 nM 6.52 Inhibitory activity against dihydrofolate reductase (DHFR) of Plasmodium berghei 3100802
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 300.0 nM 6.52 Inhibitory activity against Dihydrofolate reductase enzyme purified from Plasmod... 6991692
Dihydrofolate reductase IC50 = 330.0 nM 6.48 Inhibitory activity against dihydrofolate reductase (DHFR) of Neisseria gonorrho... 3100802
Dihydrofolate reductase IC50 = 92000.0 nM 4.04 Inhibitory activity against dihydrofolate reductase (DHFR) from rat liver 3100802
Dihydrofolate reductase IC50 = 92000.0 nM 4.04 Inhibition of rat liver Dihydrofolate reductase. 7035668
Dihydrofolate reductase IC50 = 92000.0 nM 4.04 Inhibitory activity against Dihydrofolate reductase enzyme purified from rat liv... 6991692

Literature References

PubMed DOI Target Context # Activities
7035668 10.1021/jm00140a005 Dihydrofolate reductase 10
3100802 10.1021/jm00385a017 Dihydrofolate reductase 3
36423825 10.1016/j.bmcl.2022.129086 Acinetobacter baumannii 2
36423825 10.1016/j.bmcl.2022.129086 Enterococcus faecium 2
36423825 10.1016/j.bmcl.2022.129086 Staphylococcus aureus 2
6991692 10.1021/jm00178a007 Dihydrofolate reductase 2
8941396 10.1021/jm960491r No relevant target 1
6991692 10.1021/jm00178a007 Bifunctional dihydrofolate reductase-thymidylate synthase 1
6991692 10.1021/jm00178a007 Streptococcus pyogenes 1
6991692 10.1021/jm00178a007 Staphylococcus aureus 1
6991692 10.1021/jm00178a007 Salmonella 1
6991692 10.1021/jm00178a007 Escherichia coli 1
6991692 10.1021/jm00178a007 Proteus vulgaris 1
319234 10.1021/jm00211a020 Dihydrofolate reductase 1
28327306 10.1016/j.bmcl.2016.10.051 Escherichia coli 1
28327306 10.1016/j.bmcl.2016.10.051 Staphylococcus aureus 1
8941396 10.1021/jm960491r Dihydrofolate reductase 1
3100802 10.1021/jm00385a017 Bifunctional dihydrofolate reductase-thymidylate synthase 1
6737433 10.1021/jm00373a016 Dihydrofolate reductase 1

Data from ChEMBL 36 via Core Engine