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Compound Detail

CHEMBL220159

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

Basic Information

ChEMBL ID CHEMBL220159
Phase Preclinical
Structure Type MOL
InChI Key WJIMEKODTQDGFJ-UHFFFAOYSA-N
5
Targets
13
Activities
2
Assay Types
0
PK Parameters
10
Publications
0
Known Names

Molecular Properties

328.4
MW (Da)
1.57
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 C17H20N4O3
MW 328.37
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness -0.13

Activity Summary

IC50 10 meas. best 6.75
Ki 3 meas. best 7.31

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL5270
 Ki 7.31 6.3833 49.0 3
Dihydrofolate reductase
CHEMBL2329
 IC50 6.75 6.75 180.0 1
Dihydrofolate reductase
CHEMBL5270
 IC50 6.41 5.8925 389.0 4
Dihydrofolate reductase
CHEMBL202
 IC50 6.4 6.4 400.0 2
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL2425
 IC50 6.06 6.06 880.0 1
Unchecked
CHEMBL612545
 IC50 4.99 4.99 10200.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase Ki = 49.0 nM 7.31 Inhibition of Bacillus anthracis recombinant DHFR Y102F mutant 20882962
Dihydrofolate reductase IC50 = 180.0 nM 6.75 Inhibition of Candida albicans DHFR expressed in Escherichia coli BL21 (DE3) ass... 19560363
Dihydrofolate reductase IC50 = 389.0 nM 6.41 Inhibition of Bacillus anthracis recombinant DHFR Y102F mutant 20882962
Dihydrofolate reductase IC50 = 400.0 nM 6.4 Inhibition of human DHFR assessed as rate of enzyme-dependent NADPH oxidation 19007108
Dihydrofolate reductase IC50 = 400.0 nM 6.4 Inhibition of human DHFR assessed as rate of NADPH consumption using dihydrofola... 19560363
Dihydrofolate reductase IC50 = 500.0 nM 6.3 Inhibition of Bacillus anthracis recombinant DHFR F96I mutant 20882962
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 880.0 nM 6.06 Inhibition of Toxoplasma gondii DHFR-TS 17269758
Dihydrofolate reductase Ki = 1150.0 nM 5.94 Inhibition of Bacillus anthracis recombinant DHFR F96I mutant 20882962
Dihydrofolate reductase Ki = 1250.0 nM 5.9 Inhibition of wild type Bacillus anthracis recombinant DHFR 20882962
Dihydrofolate reductase IC50 = 3700.0 nM 5.43 Inhibition of Bacillus anthracis recombinant DHFR expressed in mouse M15 cells a... 19007108
Dihydrofolate reductase IC50 = 3700.0 nM 5.43 Inhibition of wild type Bacillus anthracis recombinant DHFR 20882962
Unchecked IC50 = 10200.0 nM 4.99 Inhibition of Cryptosporidium hominis DHFR-TS expressed in Escherichia coli 17269758

Literature References

PubMed DOI Target Context # Activities
20882962 10.1021/jm100727t Dihydrofolate reductase 6
17269758 10.1021/jm061027h Unchecked 3
17269758 10.1021/jm061027h Bifunctional dihydrofolate reductase-thymidylate synthase 3
19007108 10.1021/jm800776a Dihydrofolate reductase 2
19560363 10.1016/j.bmc.2009.06.021 Dihydrofolate reductase 2
20882962 10.1021/jm100727t Unchecked 2
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