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Compound Detail

CHEMBL224214

CARBONYL CYANIDE M-CHLOROPHENYLHYDRAZONE
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N#CC(C#N)=NNc1cccc(Cl)c1

Basic Information

ChEMBL ID CHEMBL224214
Name CARBONYL CYANIDE M-CHLOROPHENYLHYDRAZONE
Phase Preclinical
Structure Type MOL
InChI Key UGTJLJZQQFGTJD-UHFFFAOYSA-N
5
Targets
14
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

204.6
MW (Da)
2.16
ALogP
4
HBA
1
HBD
72.0
PSA (Ų)
0.59
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C9H5ClN4
MW 204.62
Aromatic Rings 1
Heavy Atoms 14
NP-Likeness -1.52

Activity Summary

IC50 8 meas. best 5.52
EC50 5 meas. best 7.0
Ki 1 meas. best 5.83

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Liver
CHEMBL613580
EC50 7.0 7.0 100.0 1
Unchecked
CHEMBL612545
EC50 6.7 6.5275 200.0 4
CDGSH iron-sulfur domain-containing protein 1
CHEMBL1795168
Ki 5.83 5.83 1497.0 1
Mycobacterium tuberculosis
CHEMBL360
IC50 5.52 5.52 3000.0 1
Unchecked
CHEMBL612545
IC50 5.32 5.32 4800.0 1
HepG2
CHEMBL395
IC50 5.22 4.894 6000.0 5
CDGSH iron-sulfur domain-containing protein 1
CHEMBL1795168
IC50 4.46 4.46 35040.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Liver EC50 = 100.0 nM 7.0 Mitochondrial uncoupling activity in mouse liver mitochondria assessed as effect... 29156129
Unchecked EC50 = 200.0 nM 6.7 Induction of proton motive force collapse in Escherichia coli inverted membrane ... 28248504
Unchecked EC50 = 210.0 nM 6.68 Induction of proton motive force collapse in Escherichia coli inverted membrane ... 29459278
Unchecked EC50 = 400.0 nM 6.4 Induction of proton motive force collapse in Escherichia coli inverted membrane ... 28248504
Unchecked EC50 = 470.0 nM 6.33 Induction of proton motive force collapse in Escherichia coli inverted membrane ... 29459278
CDGSH iron-sulfur domain-containing protein 1 Ki = 1497.0 nM 5.83 Displacement of [3H]rosiglitazone from recombinant human C-terminal His-tagged M... 27687671
Mycobacterium tuberculosis IC50 = 3000.0 nM 5.52 Induction of membrane damage in Mycobacterium bovis BCG incubated for 60 mins un... -
Unchecked IC50 = 4800.0 nM 5.32 Inhibition of ATP synthase in Mycobacterium smegmatis inverted membrane vesicles... -
HepG2 IC50 = 6000.0 nM 5.22 Hepatotoxicity in human HepG2 cells assessed as decrease in cell viability after... 27598234
HepG2 IC50 = 7200.0 nM 5.14 Hepatotoxicity in human HepG2 cells assessed as intracellular ATP level after 48... 27598234
HepG2 IC50 = 9800.0 nM 5.01 Hepatotoxicity in human HepG2 cells assessed as intracellular ATP level after 24... 27598234
HepG2 IC50 = 22000.0 nM 4.66 Hepatotoxicity in human HepG2 cells assessed as decrease in cell viability after... 27598234
CDGSH iron-sulfur domain-containing protein 1 IC50 = 35040.0 nM 4.46 Displacement of [3H]rosiglitazone from recombinant human C-terminal His-tagged M... 27687671
HepG2 IC50 = 36000.0 nM 4.44 Hepatotoxicity in human HepG2 cells assessed as loss of mitochondrial membrane p... 27598234

Literature References

PubMed DOI Target Context # Activities
19029333 10.1128/aac.00485-08 Acinetobacter pittii 15
36716281 10.1021/acs.jmedchem.2c01630 SH-SY5Y 11
36958177 10.1016/j.ejmech.2023.115224 Cell membrane 9
34953341 10.1016/j.bmc.2021.116580 Quinolone resistance protein NorA 8
17548499 10.1128/aac.00339-07 Escherichia coli 7
27598234 10.1016/j.ejmech.2016.08.059 HepG2 7
30190182 10.1016/j.bmc.2018.08.034 Multidrug efflux pump LfrA 6
24368029 10.1016/j.bmc.2013.12.007 CCRF-CEM 6
38283226 10.1039/d3md00483j Morganella morganii 6
17210767 10.1128/aac.01048-06 Escherichia coli 6
23539337 10.1039/c2md20127e Bacillus subtilis 5
27490025 10.1016/j.ejmech.2016.07.028 Mycolicibacterium smegmatis 4
34425202 10.1016/j.bmcl.2021.128334 Quinolone resistance protein NorA 4
30523084 10.1126/science.aat9446 Plasmodium berghei 4
38283226 10.1039/d3md00483j Klebsiella pneumoniae 3
18591276 10.1128/aac.00475-08 Escherichia coli 3
19164140 10.1128/aac.00822-08 Unchecked 3
38911153 10.1039/d4md00002a Cell membrane 3
18086841 10.1128/aac.00642-07 Trypanosoma brucei brucei 3
20713660 10.1128/aac.00009-10 Beta-lactamase 3

Data from ChEMBL 36 via Core Engine