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Compound Detail

CHEMBL2335419

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CCc1nc(N)nc(N)c1C#CC(C)c1cc(OC)cc(-c2ccncc2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2335419
Phase Preclinical
Structure Type MOL
InChI Key KEPLBUUTAQCZOE-UHFFFAOYSA-N
5
Targets
15
Activities
2
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

373.5
MW (Da)
3.43
ALogP
6
HBA
2
HBD
99.9
PSA (Ų)
0.68
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 C22H23N5O
MW 373.46
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -0.58

Activity Summary

IC50 9 meas. best 7.72
Ki 6 meas. best 8.55

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL1681620
 Ki 8.55 7.15 2.8 6
Dihydrofolate reductase
CHEMBL1681620
 IC50 7.72 7.4825 19.0 4
Dihydrofolate reductase
CHEMBL2329
 IC50 7.22 7.22 60.0 1
Unchecked
CHEMBL612545
 IC50 7.05 7.05 89.0 1
Dihydrofolate reductase
CHEMBL3988594
 IC50 6.75 6.75 180.0 1
Dihydrofolate reductase
CHEMBL202
 IC50 5.89 5.89 1300.0 2

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.5667 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase Ki = 2.83 nM 8.55 Inhibition of TMP/methicillin-resistant Staphylococcus aureus wild type DHFR ass... 27308944
Dihydrofolate reductase Ki = 12.98 nM 7.89 Inhibition of TMP/methicillin-resistant Staphylococcus aureus recombinant DHFR H... 27308944
Dihydrofolate reductase Ki = 13.14 nM 7.88 Inhibition of TMP/methicillin-resistant Staphylococcus aureus recombinant DHFR F... 27308944
Dihydrofolate reductase IC50 = 19.0 nM 7.72 Inhibition of methicillin-resistant Staphylococcus aureus DHFR -
Dihydrofolate reductase IC50 = 19.0 nM 7.72 Inhibition of Staphylococcus aureus DHFR assessed as reduction in rate of NADPH ... 22815313
Dihydrofolate reductase IC50 = 19.0 nM 7.72 Enzyme Inhibition Assay: Heterocyclic analogs of propargyl-linked inhibitors of ... -
Dihydrofolate reductase IC50 = 60.0 nM 7.22 Inhibition of Candida albicans DHFR 23375226
Unchecked IC50 = 89.0 nM 7.05 Inhibition of Candida glabrata DHFR 23375226
Dihydrofolate reductase IC50 = 170.0 nM 6.77 Inhibition of methicillin-resistant Staphylococcus aureus DHFR F98Y mutant -
Dihydrofolate reductase IC50 = 180.0 nM 6.75 Enzyme Inhibition Assay: Heterocyclic analogs of propargyl-linked inhibitors of ... -
Dihydrofolate reductase Ki = 191.7 nM 6.72 Inhibition of TMP/methicillin-resistant Staphylococcus aureus recombinant DHFR H... 27308944
Dihydrofolate reductase Ki = 681.7 nM 6.17 Inhibition of TMP/methicillin-resistant Staphylococcus aureus recombinant DHFR H... 27308944
Dihydrofolate reductase IC50 = 1300.0 nM 5.89 Inhibition of human DHFR 23375226
Dihydrofolate reductase IC50 = 1300.0 nM 5.89 Enzyme Inhibition Assay: Heterocyclic analogs of propargyl-linked inhibitors of ... -
Dihydrofolate reductase Ki = 2059.0 nM 5.69 Inhibition of TMP/methicillin-resistant Staphylococcus aureus recombinant DHFR F... 27308944

Literature References

PubMed DOI Target Context # Activities
27308944 10.1021/acs.jmedchem.6b00688 Staphylococcus aureus 12
22815313 10.1124/dmd.112.046870 ADMET 8
27308944 10.1021/acs.jmedchem.6b00688 Dihydrofolate reductase 6
23375226 10.1016/j.bmcl.2013.01.008 Unchecked 4
- 10.1039/C3MD00104K Staphylococcus aureus 4
23375226 10.1016/j.bmcl.2013.01.008 Dihydrofolate reductase 3
22815313 10.1124/dmd.112.046870 No relevant target 2
22815313 10.1124/dmd.112.046870 Liver 2
24568657 10.1021/jm401916j Candida albicans 2
- 10.1039/C3MD00104K Dihydrofolate reductase 2
- 10.6019/CHEMBL4513161 Pseudomonas aeruginosa 2
22815313 10.1124/dmd.112.046870 Dihydrofolate reductase 1
22815313 10.1124/dmd.112.046870 Staphylococcus aureus 1
24568657 10.1021/jm401916j Nakaseomyces glabratus 1
- 10.6019/CHEMBL4513161 Candida albicans 1
- 10.6019/CHEMBL4513161 Cryptococcus neoformans 1
- 10.6019/CHEMBL4513161 Escherichia coli 1
- 10.6019/CHEMBL4513161 Klebsiella pneumoniae 1
- 10.6019/CHEMBL4513161 Acinetobacter baumannii 1
- 10.6019/CHEMBL4513161 Staphylococcus aureus 1

Data from ChEMBL 36 via Core Engine