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Compound Detail

CHEMBL222461

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

Basic Information

ChEMBL ID CHEMBL222461
Phase Preclinical
Structure Type MOL
InChI Key RUQVXLIOJPKNCM-UHFFFAOYSA-N
5
Targets
13
Activities
2
Assay Types
0
PK Parameters
10
Publications
0
Known Names

Molecular Properties

342.4
MW (Da)
2.13
ALogP
7
HBA
2
HBD
105.5
PSA (Ų)
0.82
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 C18H22N4O3
MW 342.40
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.19

Activity Summary

IC50 10 meas. best 6.96
Ki 3 meas. best 6.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL2329
 IC50 6.96 6.96 110.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL2425
 IC50 6.92 6.92 120.0 1
Dihydrofolate reductase
CHEMBL5270
 Ki 6.77 5.41 170.0 3
Unchecked
CHEMBL612545
 IC50 6.77 6.77 169.0 1
Dihydrofolate reductase
CHEMBL5270
 IC50 5.88 4.9375 1330.0 4
Dihydrofolate reductase
CHEMBL202
 IC50 5.86 5.86 1380.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase IC50 = 110.0 nM 6.96 Inhibition of Candida albicans DHFR expressed in Escherichia coli BL21 (DE3) ass... 19560363
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 120.0 nM 6.92 Inhibition of Toxoplasma gondii DHFR-TS 17269758
Unchecked IC50 = 169.0 nM 6.77 Inhibition of Cryptosporidium hominis DHFR-TS expressed in Escherichia coli 17269758
Dihydrofolate reductase Ki = 170.0 nM 6.77 Inhibition of Bacillus anthracis recombinant DHFR Y102F mutant 20882962
Dihydrofolate reductase IC50 = 1330.0 nM 5.88 Inhibition of Bacillus anthracis recombinant DHFR Y102F mutant 20882962
Dihydrofolate reductase IC50 = 1380.0 nM 5.86 Inhibition of human DHFR assessed as rate of enzyme-dependent NADPH oxidation 19007108
Dihydrofolate reductase IC50 = 1380.0 nM 5.86 Inhibition of human DHFR assessed as rate of NADPH consumption using dihydrofola... 19560363
Dihydrofolate reductase Ki = 10200.0 nM 4.99 Inhibition of wild type Bacillus anthracis recombinant DHFR 20882962
Dihydrofolate reductase IC50 = 14800.0 nM 4.83 Inhibition of Bacillus anthracis recombinant DHFR F96I mutant 20882962
Dihydrofolate reductase IC50 = 30300.0 nM 4.52 Inhibition of Bacillus anthracis recombinant DHFR expressed in mouse M15 cells a... 19007108
Dihydrofolate reductase IC50 = 30300.0 nM 4.52 Inhibition of wild type Bacillus anthracis recombinant DHFR 20882962
Dihydrofolate reductase Ki = 34100.0 nM 4.47 Inhibition of Bacillus anthracis recombinant DHFR F96I mutant 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