<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:39:04 UTC</creation_date>
  <update_date>2026-08-25 16:54:17 UTC</update_date>
  <accession/>
  <common_name>Clioquinol</common_name>
  <class>SmallMolecule</class>
  <description>Clioquinol (C9H5ClINO) is an organic compound with an average molecular weight of 305.50 g/mol. Clioquinol belongs to the haloquinolines, a subclass of quinolines and derivatives within the organic compounds. Biologically, it serves as an iron chelator (PMC13006651) and acts as an inhibitor of the Kappa-type opioid receptor (OPRK1). Regarding its health effects, it has a therapeutic effect on breast cancer (PMC9368267).

The compound is found in or released from 37 recorded sources across multiple sectors. These include healthcare, pharmaceuticals, and veterinary products, where it is used in antiinfectives, antiprotozoals, gynecologicals, medicated dressings, and antiseptics and disinfectants. It is also associated with food, food processing, and cookware, specifically in food preservation and the fermentation processes for beer and the preparation of wine or sparkling wine. Other recorded sources include drinking water and water supply, building and construction materials such as roofs, floors, ceilings, fencing, and tents or canopies, as well as household cleaning and consumer products including soap detergents, perfumes within detergents and soaps, bleaching agents, cigar cigarettes, and non electric simulated smoking devices. Additionally, it is found in electrical and electronic equipment, including communication cables or conductors, antennas, electric hearing aids, auxiliary devices, and conductors or conductive bodies characterised by the conductive materials. Recorded exposure routes for clioquinol include oral, cutaneous, topical, auricular, and vaginal.</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C9H5ClINO</chemical_formula>
  <average_molecular_weight>305.5</average_molecular_weight>
  <monisotopic_moleculate_weight>304.910434914</monisotopic_moleculate_weight>
  <iupac_name>5-chloro-7-iodoquinolin-8-ol</iupac_name>
  <traditional_iupac>clioquinol</traditional_iupac>
  <cas_registry_number>130-26-7</cas_registry_number>
  <smiles>OC1=C(I)C=C(Cl)C2=C1N=CC=C2</smiles>
  <inchi>InChI=1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H</inchi>
  <inchikey>QCDFBFJGMNKBDO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Quinolines and derivatives</class>
    <sub_class>Haloquinolines</sub_class>
    <direct_parent>Chloroquinolines</direct_parent>
    <alternate_parents>
      <alternative_parent>8-hydroxyquinolines</alternative_parent>
      <alternative_parent>Aryl chlorides</alternative_parent>
      <alternative_parent>Aryl iodides</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>O-iodophenols</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Organoiodides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridines and derivatives</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>2-iodophenol</substituent>
      <substituent>8-hydroxyquinoline</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Aryl chloride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Aryl iodide</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Chloroquinoline</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organochloride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organoiodide</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>monohydroxyquinoline</descriptor>
      <descriptor>organochlorine compound</descriptor>
      <descriptor>organoiodine compound</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Clioquinol Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143906</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>3.36</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.64e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-chloro-7-iodoquinolin-8-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>305.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>304.910434914</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC1=C(I)C=C(Cl)C2=C1N=CC=C2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H5ClINO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QCDFBFJGMNKBDO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>33.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>60.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3bb381dad0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB04815</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>2788</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>2686</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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      <target_id>BE0000632</target_id>
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  </targets>
</compound>
