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Compound Detail

CHEMBL2158050

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COc1ccc2ncc(F)c([C@@H](O)CC[C@@H]3CCN(CCSc4cccs4)C[C@@H]3C(=O)O)c2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2158050
Phase Preclinical
Structure Type MOL
InChI Key USGHRRVFKSLEJT-WVBUVRCRSA-N
9
Targets
25
Activities
2
Assay Types
8
PK Parameters
20
Publications
0
Known Names

Molecular Properties

504.6
MW (Da)
5.07
ALogP
7
HBA
2
HBD
82.9
PSA (Ų)
0.37
QED
2
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H29FN2O4S2
MW 504.65
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness -0.65

Activity Summary

IC50 24 meas. best 6.9
EC50 1 meas. best 4.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
DNA gyrase subunit A
CHEMBL2424506
 IC50 6.9 6.45 125.0 2
DNA gyrase
CHEMBL3038482
 IC50 6.9 6.3933 125.0 3
Unchecked
CHEMBL612545
 IC50 6.7 5.3929 200.0 7
Topoisomerase IV
CHEMBL3038508
 IC50 6.52 5.79 300.0 2
DNA topoisomerase 4 subunit A
CHEMBL1895
 IC50 5.66 5.66 2200.0 1
DNA gyrase
CHEMBL2094139
 IC50 5.41 5.41 3900.0 1
DNA gyrase subunit A
CHEMBL1858
 IC50 4.96 4.96 11000.0 2
DNA topoisomerase 4 subunit A
CHEMBL4088
 IC50 4.75 4.75 18000.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.63 4.63 23600.0 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 EC50 4.62 4.62 24000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 32.7 mL.min-1.kg-1 Rattus norvegicus
F 31.5 % Rattus norvegicus
Fu 0.15 - Rattus norvegicus
Fu 0.0945 - Rattus norvegicus
Fu 0.672 - Rattus norvegicus
Fu 0.19 - Rattus norvegicus
Fu 0.191 - Rattus norvegicus
Fu 0.132 - Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
DNA gyrase IC50 = 125.0 nM 6.9 Inhibition of wild type Staphylococcus aureus DNA gyrase subunit 2GyrA/2GyrB ass... 23968485
DNA gyrase subunit A IC50 = 125.0 nM 6.9 Inhibition of quinolone-resistant Staphylococcus aureus A-798 DNA gyrase S84L mu... 23968485
Unchecked IC50 = 200.0 nM 6.7 Inhibition of Escherichia coli DNA topoisomerase 4 using supercoiled pBR322 DNA ... 32027491
Topoisomerase IV IC50 = 300.0 nM 6.52 Inhibition of Staphylococcus aureus RN4220 DNA topoisomerase 4 expressed in Esch... 32027491
DNA gyrase IC50 = 340.0 nM 6.47 Inhibition of Staphylococcus aureus DNA gyrase supercoiling activity using pNO1 ... 34906671
DNA gyrase subunit A IC50 = 1000.0 nM 6.0 Inhibition of Staphylococcus aureus DNA gyrase A assessed as reduction in enzyme... 31276392
Unchecked IC50 = 1000.0 nM 6.0 Inhibition of Staphylococcus aureus N-terminal His6-tagged DNA gyrase B expresse... 32027491
DNA gyrase IC50 = 1560.0 nM 5.81 Inhibition of Staphylococcus aureus DNA gyrase 23566517
Unchecked IC50 = 1560.0 nM 5.81 Inhibition of Staphylococcus aureus DNA gyrase 28610977
Unchecked IC50 = 2000.0 nM 5.7 Inhibition of wild type Escherichia coli ATCC 25922 DNA topoisomerase-4 subunit ... 23968485
DNA topoisomerase 4 subunit A IC50 = 2200.0 nM 5.66 Inhibition of Escherichia coli DNA topoisomerase 4 subunit ParC assessed as redu... 31276392
DNA gyrase IC50 = 3900.0 nM 5.41 Inhibition of Escherichia coli DNA gyrase by fluorescence based microtiter plate... 34906671
Topoisomerase IV IC50 = 8800.0 nM 5.06 Inhibition of Staphylococcus aureus topoisomerase 4 using pNO1 plasmid DNA as su... 34906671
DNA gyrase subunit A IC50 = 11000.0 nM 4.96 Inhibition of Escherichia coli DNA gyrase A assessed as reduction in enzyme-medi... 31276392
DNA gyrase subunit A IC50 = 11000.0 nM 4.96 Inhibition of Escherichia coli N-terminal His6-tagged DNA gyrase A expressed in ... 32027491
DNA topoisomerase 4 subunit A IC50 = 18000.0 nM 4.75 Inhibition of Staphylococcus aureus DNA topoisomerase 4 subunit ParC assessed as... 31276392
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 23600.0 nM 4.63 Inhibition of human ERG channel in HEK293 cells by voltage-gated patch clamp tec... 23566517
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 23600.0 nM 4.63 Inhibition of human ERG 28610977
Voltage-gated inwardly rectifying potassium channel KCNH2 EC50 = 24000.0 nM 4.62 Inhibition of hERG by fluorescence polarization assay 34906671
Unchecked IC50 = 30400.0 nM 4.52 Inhibition of Staphylococcus aureus DNA topoisomerase 4 23566517

Literature References

PubMed DOI Target Context # Activities
31732255 10.1016/j.ejmech.2019.111813 ADMET 18
23566517 10.1016/j.bmcl.2013.03.047 Staphylococcus aureus 6
28610977 10.1016/j.bmcl.2017.06.009 Staphylococcus aureus 5
23566517 10.1016/j.bmcl.2013.03.047 Unchecked 4
34906671 10.1016/j.bmcl.2021.128499 Staphylococcus aureus 4
23566517 10.1016/j.bmcl.2013.03.047 Rattus norvegicus 3
23968485 10.1021/jm400963y Staphylococcus aureus 3
23968485 10.1021/jm400963y Unchecked 2
31276392 10.1021/acs.jmedchem.9b00394 DNA topoisomerase 4 subunit A 2
28610977 10.1016/j.bmcl.2017.06.009 Unchecked 2
31276392 10.1021/acs.jmedchem.9b00394 DNA gyrase subunit A 2
34906671 10.1016/j.bmcl.2021.128499 DNA gyrase 2
23968485 10.1021/jm400963y DNA gyrase subunit A 2
32027491 10.1021/acs.jmedchem.9b01738 Unchecked 2
23566517 10.1016/j.bmcl.2013.03.047 Streptococcus pyogenes 2
21443219 10.1021/jm2002124 Staphylococcus aureus 2
34906671 10.1016/j.bmcl.2021.128499 Topoisomerase IV 1
23968485 10.1021/jm400963y Pseudomonas aeruginosa 1
21443219 10.1021/jm2002124 Voltage-gated inwardly rectifying potassium channel KCNH2 1
23968485 10.1021/jm400963y Topoisomerase IV 1

Data from ChEMBL 36 via Core Engine