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Compound Detail

CHEMBL220937

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

Basic Information

ChEMBL ID CHEMBL220937
Phase Preclinical
Structure Type MOL
InChI Key WGUCJULKGMTPOP-UHFFFAOYSA-N
5
Targets
13
Activities
2
Assay Types
0
PK Parameters
10
Publications
0
Known Names

Molecular Properties

358.4
MW (Da)
1.71
ALogP
8
HBA
2
HBD
114.7
PSA (Ų)
0.78
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 C18H22N4O4
MW 358.40
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness -0.16

Activity Summary

IC50 10 meas. best 6.5
Ki 3 meas. best 5.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL2329
 IC50 6.5 6.5 320.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL2425
 IC50 6.26 6.26 550.0 1
Dihydrofolate reductase
CHEMBL202
 IC50 5.91 5.91 1220.0 2
Dihydrofolate reductase
CHEMBL5270
 Ki 5.7 5.3033 2000.0 3
Dihydrofolate reductase
CHEMBL5270
 IC50 5.56 4.86 2760.0 4
Unchecked
CHEMBL612545
 IC50 5.3 5.3 5000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase IC50 = 320.0 nM 6.5 Inhibition of Candida albicans DHFR expressed in Escherichia coli BL21 (DE3) ass... 19560363
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 550.0 nM 6.26 Inhibition of Toxoplasma gondii DHFR-TS 17269758
Dihydrofolate reductase IC50 = 1220.0 nM 5.91 Inhibition of human DHFR assessed as rate of enzyme-dependent NADPH oxidation 19007108
Dihydrofolate reductase IC50 = 1220.0 nM 5.91 Inhibition of human DHFR assessed as rate of NADPH consumption using dihydrofola... 19560363
Dihydrofolate reductase Ki = 2000.0 nM 5.7 Inhibition of Bacillus anthracis recombinant DHFR Y102F mutant 20882962
Dihydrofolate reductase IC50 = 2760.0 nM 5.56 Inhibition of Bacillus anthracis recombinant DHFR F96I mutant 20882962
Unchecked IC50 = 5000.0 nM 5.3 Inhibition of Cryptosporidium hominis DHFR-TS expressed in Escherichia coli 17269758
Dihydrofolate reductase Ki = 6350.0 nM 5.2 Inhibition of Bacillus anthracis recombinant DHFR F96I mutant 20882962
Dihydrofolate reductase Ki = 9810.0 nM 5.01 Inhibition of wild type Bacillus anthracis recombinant DHFR 20882962
Dihydrofolate reductase IC50 = 15800.0 nM 4.8 Inhibition of Bacillus anthracis recombinant DHFR Y102F mutant 20882962
Dihydrofolate reductase IC50 = 29100.0 nM 4.54 Inhibition of Bacillus anthracis recombinant DHFR expressed in mouse M15 cells a... 19007108
Dihydrofolate reductase IC50 = 29100.0 nM 4.54 Inhibition of wild type Bacillus anthracis recombinant DHFR 20882962

Literature References

PubMed DOI Target Context # Activities
20882962 10.1021/jm100727t Dihydrofolate reductase 6
19007108 10.1021/jm800776a Dihydrofolate reductase 2
19560363 10.1016/j.bmc.2009.06.021 Dihydrofolate reductase 2
20882962 10.1021/jm100727t Unchecked 2
17269758 10.1021/jm061027h Unchecked 1
17269758 10.1021/jm061027h Bifunctional dihydrofolate reductase-thymidylate synthase 1
19007108 10.1021/jm800776a Unchecked 1
19560363 10.1016/j.bmc.2009.06.021 Unchecked 1
19560363 10.1016/j.bmc.2009.06.021 Candida albicans 1
19560363 10.1016/j.bmc.2009.06.021 ADMET 1

Data from ChEMBL 36 via Core Engine