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Compound Detail

CHEMBL221172

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

Basic Information

ChEMBL ID CHEMBL221172
Phase Preclinical
Structure Type MOL
InChI Key MRGVCWULZNEIIL-UHFFFAOYSA-N
4
Targets
13
Activities
2
Assay Types
0
PK Parameters
10
Publications
0
Known Names

Molecular Properties

344.4
MW (Da)
1.06
ALogP
8
HBA
3
HBD
125.7
PSA (Ų)
0.70
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 C17H20N4O4
MW 344.37
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.06

Activity Summary

IC50 10 meas. best 6.01
Ki 3 meas. best 6.41

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL5270
 Ki 6.41 5.6933 390.0 3
Dihydrofolate reductase
CHEMBL2329
 IC50 6.01 6.01 980.0 1
Dihydrofolate reductase
CHEMBL5270
 IC50 5.72 5.2275 1910.0 4
Dihydrofolate reductase
CHEMBL202
 IC50 5.24 5.24 5710.0 2
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL2425
 IC50 5.04 5.04 9100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase Ki = 390.0 nM 6.41 Inhibition of Bacillus anthracis recombinant DHFR Y102F mutant 20882962
Dihydrofolate reductase IC50 = 980.0 nM 6.01 Inhibition of Candida albicans DHFR expressed in Escherichia coli BL21 (DE3) ass... 19560363
Dihydrofolate reductase IC50 = 1910.0 nM 5.72 Inhibition of Bacillus anthracis recombinant DHFR F96I mutant 20882962
Dihydrofolate reductase IC50 = 3070.0 nM 5.51 Inhibition of Bacillus anthracis recombinant DHFR Y102F mutant 20882962
Dihydrofolate reductase Ki = 4390.0 nM 5.36 Inhibition of Bacillus anthracis recombinant DHFR F96I mutant 20882962
Dihydrofolate reductase Ki = 4890.0 nM 5.31 Inhibition of wild type Bacillus anthracis recombinant DHFR 20882962
Dihydrofolate reductase IC50 = 5710.0 nM 5.24 Inhibition of human DHFR assessed as rate of enzyme-dependent NADPH oxidation 19007108
Dihydrofolate reductase IC50 = 5710.0 nM 5.24 Inhibition of human DHFR assessed as rate of NADPH consumption using dihydrofola... 19560363
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 9100.0 nM 5.04 Inhibition of Toxoplasma gondii DHFR-TS 17269758
Dihydrofolate reductase IC50 = 14500.0 nM 4.84 Inhibition of Bacillus anthracis recombinant DHFR expressed in mouse M15 cells a... 19007108
Dihydrofolate reductase IC50 = 14500.0 nM 4.84 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