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Compound Detail

CHEMBL4854181

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Cc1[nH]c(C(=O)Nc2nc3c(OCc4ccccc4)cc(C(=O)O)cc3s2)c(Cl)c1Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4854181
Phase Preclinical
Structure Type MOL
InChI Key QJJVAUMJKWWKTD-UHFFFAOYSA-N
5
Targets
13
Activities
1
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

476.3
MW (Da)
5.77
ALogP
5
HBA
3
HBD
104.3
PSA (Ų)
0.33
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H15Cl2N3O4S
MW 476.34
Aromatic Rings 4
Heavy Atoms 31
NP-Likeness -1.40

Activity Summary

IC50 13 meas. best 9.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
DNA gyrase
CHEMBL2094139
 IC50 9.1 9.1 0.8 1
DNA gyrase
CHEMBL3038482
 IC50 9.1 8.45 0.8 2
Unchecked
CHEMBL612545
 IC50 8.29 6.9514 5.1 7
DNA topoisomerase 2-alpha
CHEMBL1806
 IC50 5.71 5.71 1950.0 1
HepG2
CHEMBL395
 IC50 4.99 4.55 10300.0 2

Pharmacokinetic Data

Parameter Value Units Species
Fu 0.001 - Homo sapiens
Fu 0.001 - Mus musculus
T1/2 1.183 hr Homo sapiens
T1/2 2.2 hr Mus musculus
T1/2 2.367 hr Homo sapiens
T1/2 1.65 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
DNA gyrase IC50 = 0.8 nM 9.1 Inhibition of Staphylococcus aureus DNA gyrase incubated for 30 mins by fluoresc... 36634346
DNA gyrase IC50 = 0.8 nM 9.1 Inhibition of Escherichia coli DNA gyrase incubated for 30 mins by fluorescence ... 36634346
Unchecked IC50 = 5.1 nM 8.29 Inhibition of Mycobacterium tuberculosis DNA gyrase B 39053193
DNA gyrase IC50 = 16.0 nM 7.8 Inhibition of Staphylococcus aureus DNA gyrase assessed reduction in relaxation ... 33524686
Unchecked IC50 = 64.0 nM 7.19 Inhibition of Acinetobacter baumannii 1419130 full length wildtype DNA topoisome... 36634346
Unchecked IC50 = 68.0 nM 7.17 Inhibition of Staphylococcus aureus topoisomerase assessed as reduction in relax... 33524686
Unchecked IC50 = 235.0 nM 6.63 Inhibition of Pseudomonas aeruginosa PAO1 full length wildtype DNA topoisomerase... 36634346
Unchecked IC50 = 350.0 nM 6.46 Inhibition of Escherichia coli topoisomerase assessed as reduction in relaxation... 33524686
Unchecked IC50 = 350.0 nM 6.46 Inhibition of Escherichia coli DNA topoisomerase 4 relaxation 36877255
Unchecked IC50 = 350.0 nM 6.46 Inhibition of Escherichia coli topoisomerase IV assessed as reduction in decaten... 36634346
DNA topoisomerase 2-alpha IC50 = 1950.0 nM 5.71 Inhibition of human topoisomerase II alpha 36634346
HepG2 IC50 = 10300.0 nM 4.99 Cytotoxicity in human HepG2 cells incubated for 2 hrs by FMC assay 36634346
HepG2 IC50 = 78000.0 nM 4.11 Cytotoxicity in human HepG2 cells incubated for 0.5 to 4 hrs by MTS assay 36634346

Literature References

PubMed DOI Target Context # Activities
36634346 10.1021/acs.jmedchem.2c01597 ADMET 13
36634346 10.1021/acs.jmedchem.2c01597 Acinetobacter baumannii 6
36634346 10.1021/acs.jmedchem.2c01597 Pseudomonas aeruginosa 6
36634346 10.1021/acs.jmedchem.2c01597 HepG2 6
36634346 10.1021/acs.jmedchem.2c01597 Unchecked 5
36634346 10.1021/acs.jmedchem.2c01597 No relevant target 4
36634346 10.1021/acs.jmedchem.2c01597 Escherichia coli 3
36634346 10.1021/acs.jmedchem.2c01597 Klebsiella pneumoniae 3
36634346 10.1021/acs.jmedchem.2c01597 DNA gyrase subunit B 3
36877255 10.1021/acs.jmedchem.2c01905 Staphylococcus aureus 3
36634346 10.1021/acs.jmedchem.2c01597 DNA gyrase 2
33524686 10.1016/j.ejmech.2021.113200 DNA gyrase 2
33524686 10.1016/j.ejmech.2021.113200 Staphylococcus aureus 2
33524686 10.1016/j.ejmech.2021.113200 Unchecked 2
36877255 10.1021/acs.jmedchem.2c01905 Unchecked 1
36877255 10.1021/acs.jmedchem.2c01905 Escherichia coli 1
36877255 10.1021/acs.jmedchem.2c01905 DNA gyrase 1
36877255 10.1021/acs.jmedchem.2c01905 Enterococcus faecalis 1
39053193 10.1016/j.ejmech.2024.116693 Unchecked 1
33524686 10.1016/j.ejmech.2021.113200 Pseudomonas aeruginosa 1

Data from ChEMBL 36 via Core Engine