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Compound Detail

CHEMBL560502

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CCCC1c2ccccc2C=NN1C(=O)/C=C/c1cc(Cc2cnc(N)nc2N)cc(O)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL560502
Phase Preclinical
Structure Type MOL
InChI Key DYKJZIGXLIOJIF-MDZDMXLPSA-N
4
Targets
11
Activities
2
Assay Types
0
PK Parameters
12
Publications
0
Known Names

Molecular Properties

472.6
MW (Da)
3.68
ALogP
8
HBA
3
HBD
139.9
PSA (Ų)
0.45
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C26H28N6O3
MW 472.55
Aromatic Rings 3
Heavy Atoms 35
NP-Likeness 0.17

Activity Summary

IC50 9 meas. best 8.28
Ki 2 meas. best 9.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL1681620
 Ki 9.05 8.8 0.9 2
Dihydrofolate reductase
CHEMBL1681620
 IC50 8.28 8.005 5.2 4
Bacillus anthracis
CHEMBL613904
 IC50 7.27 7.27 54.0 1
Unchecked
CHEMBL612545
 IC50 6.57 6.57 270.0 1
Dihydrofolate reductase
CHEMBL2363
 IC50 4.6 4.6 25000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase Ki = 0.9 nM 9.05 Inhibition of Staphylococcus aureus DHFR F98Y mutant by MTS assay 20606069
Dihydrofolate reductase Ki = 2.8 nM 8.55 Inhibition of Staphylococcus aureus wild type recombinant DHFR by MTS assay 20606069
Dihydrofolate reductase IC50 = 5.2 nM 8.28 Inhibition of Staphylococcus aureus wild type recombinant DHFR by MTS assay 20606069
Dihydrofolate reductase IC50 = 8.8 nM 8.06 Inhibition of Staphylococcus aureus DHFR F98Y mutant by MTS assay 20606069
Dihydrofolate reductase IC50 = 9.4 nM 8.03 Inhibition of Staphylococcus aureus wild type recombinant DHFR by MTS assay 20606069
Dihydrofolate reductase IC50 = 22.6 nM 7.65 Inhibition of Staphylococcus aureus DHFR F98Y mutant by MTS assay 20606069
Bacillus anthracis IC50 = 54.0 nM 7.27 Inhibition of histidine-tagged Bacillus anthracis Sterne recombinant DHFR expres... 17875993
Unchecked IC50 = 270.0 nM 6.57 Inhibition of Bacillus cereus recombinant DHFR expressed in Escherichia coli BL2... 17875993
Dihydrofolate reductase IC50 = 25000.0 nM 4.6 Inhibition of rat DHFR 17875993

Literature References

PubMed DOI Target Context # Activities
20606069 10.1128/aac.00361-10 Staphylococcus aureus 7
20606069 10.1128/aac.00361-10 Dihydrofolate reductase 7
17875993 10.1128/aac.00628-07 Bacillus anthracis 3
17875993 10.1128/aac.00628-07 Dihydrofolate reductase 2
17875993 10.1128/aac.00628-07 Unchecked 2
20606069 10.1128/aac.00361-10 Unchecked 2
17875993 10.1128/aac.00628-07 Bacillus cereus 1
20606069 10.1128/aac.00361-10 NON-PROTEIN TARGET 1
20606069 10.1128/aac.00361-10 Yersinia pestis 1
20606069 10.1128/aac.00361-10 Brucella abortus 1
20606069 10.1128/aac.00361-10 Bacillus anthracis 1
20606069 10.1128/aac.00361-10 Enterococcus faecalis 1

Data from ChEMBL 36 via Core Engine