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Compound Detail

CHEMBL520358

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COc1cc(-c2ccccc2)cc(C(C)C#Cc2c(C)nc(N)nc2N)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL520358
Phase Preclinical
Structure Type MOL
InChI Key JPENSYBRTSIYGO-UHFFFAOYSA-N
7
Targets
19
Activities
2
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

358.4
MW (Da)
3.78
ALogP
5
HBA
2
HBD
87.0
PSA (Ų)
0.70
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C22H22N4O
MW 358.45
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -0.49

Activity Summary

IC50 15 meas. best 8.74
Ki 4 meas. best 6.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL2366489
 IC50 8.74 8.74 1.8 1
Unchecked
CHEMBL612545
 IC50 8.74 8.44 1.8 2
Dihydrofolate reductase
CHEMBL2329
 IC50 7.26 7.26 55.0 2
Dihydrofolate reductase
CHEMBL1681620
 IC50 7.21 7.0467 61.0 3
Dihydrofolate reductase
CHEMBL1681620
 Ki 6.96 6.96 110.0 1
Dihydrofolate reductase
CHEMBL5270
 IC50 6.32 5.5033 476.0 3
Dihydrofolate reductase
CHEMBL5270
 Ki 5.99 5.8433 1030.0 3
Dihydrofolate reductase
CHEMBL202
 IC50 5.77 5.77 1700.0 3
ADMET
CHEMBL612558
 IC50 4.05 4.05 90000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 1.8 nM 8.74 Spectrophotometric Enzyme Assay: Compounds were evaluated in spectrophotometric ... -
Unchecked IC50 = 1.8 nM 8.74 Inhibition of Cryptosporidium hominis dihydrofolate reductase expressed in Esche... 18834108
Unchecked IC50 = 7.3 nM 8.14 Inhibition of Candida glabrata DHFR using dihydrofolate as substrate preincubate... 24568657
Dihydrofolate reductase IC50 = 55.0 nM 7.26 Inhibition of Candida albicans DHFR expressed in Escherichia coli BL21 (DE3) ass... 19560363
Dihydrofolate reductase IC50 = 55.0 nM 7.26 Inhibition of Candida albicans DHFR using dihydrofolate as substrate preincubate... 24568657
Dihydrofolate reductase IC50 = 61.0 nM 7.21 Inhibition of methicillin-resistant Staphylococcus aureus DHFR -
Dihydrofolate reductase IC50 = 61.0 nM 7.21 Inhibition of Staphylococcus aureus DHFR assessed as reduction in rate of NADPH ... 22815313
Dihydrofolate reductase Ki = 110.0 nM 6.96 Inhibition of methicillin-resistant Staphylococcus aureus DHFR F98Y/H30N double ... -
Dihydrofolate reductase IC50 = 190.0 nM 6.72 Inhibition of methicillin-resistant Staphylococcus aureus DHFR F98Y mutant -
Dihydrofolate reductase IC50 = 476.0 nM 6.32 Inhibition of Bacillus anthracis recombinant DHFR F96I mutant 20882962
Dihydrofolate reductase Ki = 1030.0 nM 5.99 Inhibition of Bacillus anthracis recombinant DHFR Y102F mutant 20882962
Dihydrofolate reductase Ki = 1100.0 nM 5.96 Inhibition of Bacillus anthracis recombinant DHFR F96I mutant 20882962
Dihydrofolate reductase IC50 = 1700.0 nM 5.77 Inhibition of human dihydrofolate reductase by spectrophotometry 18834108
Dihydrofolate reductase IC50 = 1700.0 nM 5.77 Spectrophotometric Enzyme Assay: Compounds were evaluated in spectrophotometric ... -
Dihydrofolate reductase IC50 = 1700.0 nM 5.77 Inhibition of human DHFR assessed as rate of NADPH consumption using dihydrofola... 19560363
Dihydrofolate reductase Ki = 2660.0 nM 5.58 Inhibition of wild type Bacillus anthracis recombinant DHFR 20882962
Dihydrofolate reductase IC50 = 7900.0 nM 5.1 Inhibition of wild type Bacillus anthracis recombinant DHFR 20882962
Dihydrofolate reductase IC50 = 8090.0 nM 5.09 Inhibition of Bacillus anthracis recombinant DHFR Y102F mutant 20882962
ADMET IC50 = 90000.0 nM 4.05 Cytotoxicity against human MCF10A cells after 4 hrs by alamar blue assay 19560363

Literature References

PubMed DOI Target Context # Activities
20882962 10.1021/jm100727t Dihydrofolate reductase 6
- 10.1039/C3MD00104K Dihydrofolate reductase 3
18834108 10.1021/jm8009124 Unchecked 2
19560363 10.1016/j.bmc.2009.06.021 Dihydrofolate reductase 2
20882962 10.1021/jm100727t Unchecked 2
22815313 10.1124/dmd.112.046870 No relevant target 1
22815313 10.1124/dmd.112.046870 Staphylococcus aureus 1
22815313 10.1124/dmd.112.046870 Dihydrofolate reductase 1
24568657 10.1021/jm401916j Candida albicans 1
24568657 10.1021/jm401916j Nakaseomyces glabratus 1
24568657 10.1021/jm401916j Dihydrofolate reductase 1
24568657 10.1021/jm401916j Unchecked 1
- 10.1039/C3MD00104K Staphylococcus aureus 1
19560363 10.1016/j.bmc.2009.06.021 ADMET 1
19560363 10.1016/j.bmc.2009.06.021 Candida albicans 1
19560363 10.1016/j.bmc.2009.06.021 Unchecked 1
18834108 10.1021/jm8009124 Dihydrofolate reductase 1

Data from ChEMBL 36 via Core Engine