CLIOQUINOL

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
ATC D08AH30 D09AA10 G01AC02 P01AA02 S02AA05
UNII 7BHQ856EJ5
EPA CompTox DTXSID7022837

Structure

InChI Key QCDFBFJGMNKBDO-UHFFFAOYSA-N
Smiles Oc1c(I)cc(Cl)c2cccnc12
InChI
InChI=1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H

Physicochemical Descriptors

Property Name Value
Molecular Formula C9H5ClINO
Molecular Weight 305.5
AlogP 3.2
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 0.0
Polar Surface Area 33.12
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 13.0

Bioactivity

Mechanism of Action Action Reference
Copper chelating agent CHELATING AGENT PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Lyase
- - - 2330 -
Enzyme Protease Metallo protease Metallo protease MAE clan Metallo protease M27 family
- 20300 - - -
Enzyme Transferase
- 4786 - - -
Membrane receptor
- 100000 - - 2-75
Unclassified protein
- - - - 0-55
Assay Description Organism Bioactivity Reference
Inhibition of polyhistidine tagged yeast prion protein Sup35 expressed in Escherichia coli BL21 (DE3) assessed as inhibition of amyloid polymerization at 50 uM by thioflavin T fluorescence assay relative to untreated control Saccharomyces cerevisiae 54.7 %
Inhibition of polyhistidine tagged yeast prion protein Sup35 expressed in Escherichia coli BL21 (DE3) assessed as inhibition of amyloid polymerization at 50 uM in presence of 5 mg/ml BSA by thioflavin T fluorescence assay relative to untreated control Saccharomyces cerevisiae 0.0 %
Inhibition of mouse prion protein (89-230) assessed as inhibition of amyloid polymerization at 50 uM by thioflavin T fluorescence assay relative to untreated control Mus musculus 0.0 %
Inhibition of Beta-lactamase at 25 uM by nitrocefin hydrolysis assay None 51.6 %
Inhibition of Beta-lactamase at 25 uM in presence of 0.01% Triton X-100 by nitrocefin hydrolysis assay None 6.4 %
Inhibition of Cu2+-induced amyloid beta (1 to 42) aggregation (unknown origin) at 50 uM after 24 hrs by thioflavin T fluorescence assay relative to untreated control Homo sapiens 70.94 %
Inhibition of self-mediated amyloid beta (1 to 42) aggregation (unknown origin) at 20 uM after 48 hrs by thioflavin T fluorescence assay relative to control Homo sapiens 37.77 %
Inhibition of Cu2+-induced amyloid beta (1 to 42) (unknown origin) aggregation assessed as reduction of H2O2 production at 800 nM after 30 mins by HRP/Amplex red assay Homo sapiens 75.0 %
Inhibition of Cu2+-induced amyloid beta (1 to 42) (unknown origin) aggregation at 50 uM after 24 hrs by thioflavin-T based fluorometric assay Homo sapiens 66.7 %
PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 440.7 nM
PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 391.7 nM
PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 475.1 nM
PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 586.2 nM
PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 345.3 nM
Inhibition of recombinant human Amyloid beta (1 to 42) self-induced aggregation at 5 uM after 48 hrs by thioflavin T-based fluorescence assay Homo sapiens 5.0 %
Inhibition of self-induced recombinant human Amyloid beta (1 to 42) aggregation at 50 uM after 24 hrs by thioflavin T-based fluorescence assay Homo sapiens 20.2 %
Inhibition of Cu2+-induced recombinant human Amyloid beta (1 to 42) aggregation at 50 uM after 24 hrs by thioflavin T-based fluorescence assay None 64.4 %
Inhibition of Cu2+-amyloid beta (1 to 40) catalyzed generation of hydroxyl radical assessed as 7-hrdroxy-CCA formation at 2 equiv preincubated for 1 hr followed by CCA addition measured over 60 mins by fluorescence assay None 87.7 %
Inhibition of Cu2+-amyloid beta (1 to 42 residues)-induced increase in H2O2 production at 800 nM after 30 mins by HRP/Amplex red assay None 68.0 %
Inhibition of Serratia marcescens IMP1 expressed in Escherichia coli BL21(DE3) at 50 uM using chromacef as substrate preincubated for 10 mins followed by substrate addition measured after 20 mins by HTS assay relative to control Serratia marcescens 60.0 %
Inhibition of Pseudomonas aeruginosa VIM2 expressed in Escherichia coli BL21(DE3) at 50 uM using chromacef as substrate preincubated for 10 mins followed by substrate addition measured after 20 mins by HTS assay relative to control Pseudomonas aeruginosa 60.0 %
Inhibition of bacterial MBP-fused NDM1 expressed in Escherichia coli BL21(DE3) at 50 uM using chromacef as substrate preincubated for 10 mins followed by substrate addition measured after 20 mins by HTS assay relative to control Bacteria 60.0 %
Metal chelating activity assessed as inhibition of Cu2+-induced amyloid beta (1 to 42 residues) aggregation at 50 uM after 24 hrs by thioflavin-T fluorescence assay (Rvb = 142%) None 47.7 %
Inhibition of amyloid beta (1 to 42) (unknown origin) self-induced aggregation at 5 uM after 48 hrs by thioflavin-T fluorescence assay relative to control Homo sapiens 1.9 %
Inhibition of amyloid beta (1 to 42) (unknown origin) self-induced aggregation at 5 uM after 48 hrs in presence of melatonin by thioflavin-T fluorescence assay relative to control Homo sapiens 22.5 %
Inhibition of HFIP-pretreated amyloid beta (1 to 42) (unknown origin) self-induced aggregation at 10 uM after 48 hrs by thioflavin T-based fluorometric assay relative to control Homo sapiens 25.72 %
Inhibition of Cu2+ - induced amyloid beta (1 to 42) (unknown origin) aggregation at 50 uM after 24 hrs by thioflavin T-based fluorometric assay relative to control None 61.4 %
Inhibition of Zn2+ - induced amyloid beta (1 to 42) (unknown origin) aggregation at 50 uM after 24 hrs by thioflavin T-based fluorometric assay relative to control None 55.3 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 1.25 %
Inhibition of Cu2+-induced HFIP pretreated human amyloid beta (1 to 42) aggregation at 40 uM measured after 24 hrs by ThT-based fluorescence assay relative to control None 38.8 %
Inhibition of Cu2+ induced aggregation of recombinant human amyloid beta (1 to 42) at 50 uM after 24 hrs by thioflavin-T based fluorescence assay None 87.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -4.07 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 4.018 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 1.26 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.04 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.04 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 1.26 %
Inhibition of HFIP-pretreated amyloid beta (1 to 42) (unknown origin) self-aggregation at 25 uM after 24 hrs by thioflavin-T fluorescence assay relative to control Homo sapiens 62.36 %
Inhibition of Cu2+-induced HFIP-pretreated amyloid beta (1 to 42) (unknown origin) aggregation at 25 uM measured after 24 hrs by thioflavin-T fluorescence assay relative to control None 40.14 %
Inhibition of AChE (unknown origin)-induced amyloid beta (1 to 42) aggregation at 1 to 5 uM measured after 24 hrs by ThT flourescence assay Homo sapiens 11.5 %
Inhibition of Cu2+ induced amyloid beta (1 to 42 residues) (unknown origin) aggregation by measuring reduction in fluorescence intensity at 20 uM after 24 hrs by thioflavin-T fluorescence method relative to control None 38.9 %

Related Entries

Cross References

Resources Reference
ChEBI 74460
ChEMBL CHEMBL497
DrugBank DB04815
DrugCentral 681
FDA SRS 7BHQ856EJ5
PDB CQL
PubChem 2788
SureChEMBL SCHEMBL3967
ZINC ZINC000006409735
CONTENTS