Clioquinol (CED0005794)

Record Information
Version1.0
Creation Date2016-05-22 03:39:04 UTC
Update Date2026-08-25 16:54:17 UTC
Accession NumberCHEM016637
Identification
Common NameClioquinol
ClassSmall Molecule
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.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
5-Chlor-7-jod-8-hydroxy-chinolinChEBI
5-Chloro-7-iodo-8-hydroxyquinolineChEBI
5-Chloro-7-iodo-8-quinolinolChEBI
5-Chloro-8-hydroxy-7-iodoquinolineChEBI
7-Iodo-5-chloro-8-hydroxyquinolineChEBI
7-Iodo-5-chloroxineChEBI
ChloroiodoquinChEBI
ClioquinolumChEBI
IodochlorhydroxyquinolineChEBI
IodochlorohydroxyquinChEBI
IodochloroxyquinolineChEBI
5 Chloro 7 iodo 8 quinolinolMeSH
ChinoformMeSH
ChloroiodoquineMeSH
Entero septolMeSH
Entero vioformMeSH
Entero-septolMeSH
Entero-vioformMeSH
EnteroSeptolMeSH
EnteroVioformMeSH
EnteroquinolMeSH
IodochlorhydroxyquinMeSH
VioformMeSH
Chemical FormulaC9H5ClINO
Average Molecular Mass305.500 g/mol
Monoisotopic Mass304.910 g/mol
CAS Registry Number130-26-7
IUPAC Name5-chloro-7-iodoquinolin-8-ol
Traditional Nameclioquinol
SMILESOC1=C(I)C=C(Cl)C2=C1N=CC=C2
InChI IdentifierInChI=1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
InChI KeyQCDFBFJGMNKBDO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chloroquinolines. Chloroquinolines are compounds containing a quinoline moiety, which carries one or more chlorine atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassHaloquinolines
Direct ParentChloroquinolines
Alternative Parents
Substituents
  • Chloroquinoline
  • 8-hydroxyquinoline
  • 2-iodophenol
  • Aryl chloride
  • Aryl halide
  • Aryl iodide
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organoiodide
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.26 g/LALOGPS
logP3.66ALOGPS
logP3.36ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)7.34ChemAxon
pKa (Strongest Basic)3.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.12 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity60.13 m³·mol⁻¹ChemAxon
Polarizability22.63 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0ufr-2279000000-6cf0bdc100cf284a8ce0Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-4931100000-28d4a47f77706f412213Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2901000000-22ecce16d52e911c9ef0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0009000000-892c7c5731408fbcc799Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0009000000-f8fbc9c4d6bbacbe91f9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6r-2089000000-8aabd74206b87576ca6eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-03cd6c1f1cfd97367fe5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-03cd6c1f1cfd97367fe5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ufr-4229000000-d5b666aba90b83aef86eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0009000000-232031ac93f8eb591f40Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0009000000-232031ac93f8eb591f40Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fb9-0292000000-09fcf691ca3683ac33bbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-08a7a28f0c28f4bd6f5aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-08a7a28f0c28f4bd6f5aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-3093000000-9d35d1f1c3845a4a56b4Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
914.0Log mg/kg[510:1600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
breast cancerhas_therapeutic_effect_onNot AvailablePMC9368267
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
312Antiseptics and disinfectantsHealthcare, pharmaceuticals & veterinary productsNot Available
313Medicated dressingsHealthcare, pharmaceuticals & veterinary productsNot Available
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
385AntiprotozoalsHealthcare, pharmaceuticals & veterinary productsNot Available
395AntiinfectivesHealthcare, pharmaceuticals & veterinary productsNot Available
495CeilingsBuilding & ConstructionNot Available
496FencingBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
526LoudspeakersElectrical & Electronic EquipmentNot Available
528MicrophonesElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
577Watch ChainsHousehold itemsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
589Life BuoysMarine, shipping & aquacultureNot Available
590Lifeboat EquipmentMarine, shipping & aquacultureNot Available
591LifeboatsMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
624Merry Go RoundsRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
635ButtonsTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
649Pins ClothesTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
654Sleeve LinksTextiles, leather & furnishingsNot Available
656Snap FastenersTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
663Sanitary EquipmentWastewater, sanitation & biosolidsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Metallo-beta-lactamase type 2 structureClick to view 3D structureMetallo-beta-lactamase type 2C7C422Klebsiella pneumoniaePredicted (SEA)0.0778492
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)56.9078
Click to view 3D structureCatechol O-methyltransferaseP22734Rattus norvegicusPredicted (SEA)0.233548
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)2.72472
Matrix metalloproteinase-14 structureClick to view 3D structureMatrix metalloproteinase-14P50281HumansPredicted (SEA)22.6541
Click to view 3D structureNonstructural protein 1Q194T2Influenza A virusPredicted (SEA)1.94623
Polyunsaturated fatty acid lipoxygenase ALOX12 structureClick to view 3D structurePolyunsaturated fatty acid lipoxygenase ALOX12P18054HumansPredicted (SEA)0.544945
Click to view 3D structureATP-dependent molecular chaperone HSP82C4YTQ8Candida albicans (strain WO-1) (Yeast)Predicted (SEA)4.35956
3',5'-cyclic-AMP phosphodiesterase 4D structureClick to view 3D structure3',5'-cyclic-AMP phosphodiesterase 4DQ08499HumansPredicted (SEA)16.7376
Click to view 3D structureBotulinum neurotoxin type AP0DPI0Clostridium botulinumPredicted (SEA)1.08989
Click to view 3D structureVacuolar aminopeptidase 1P14904Saccharomyces cerevisiae S288cPredicted (SEA)0.155698
Tyrosine-protein kinase Lck structureClick to view 3D structureTyrosine-protein kinase LckP06239HumansPredicted (SEA)380.683
Tyrosine-protein kinase Fyn structureClick to view 3D structureTyrosine-protein kinase FynP06241HumansPredicted (SEA)249.351
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)408.319
Mitogen-activated protein kinase 14 structureClick to view 3D structureMitogen-activated protein kinase 14Q16539HumansPredicted (SEA)241.333
Replicase polyprotein 1ab structureClick to view 3D structureReplicase polyprotein 1abP0DTD1SARS-CoV-2Predicted (SEA)59.399
Mitogen-activated protein kinase 1 structureClick to view 3D structureMitogen-activated protein kinase 1P28482HumansPredicted (SEA)248.183
Receptor tyrosine-protein kinase erbB-2 structureClick to view 3D structureReceptor tyrosine-protein kinase erbB-2P04626HumansPredicted (SEA)264.921
C-C chemokine receptor type 1 structureClick to view 3D structureC-C chemokine receptor type 1P32246HumansPredicted (SEA)4.98235
Amyloid-beta precursor protein structureClick to view 3D structureAmyloid-beta precursor proteinP05067HumansPredicted (SEA)51.0691
C-C chemokine receptor type 8 structureClick to view 3D structureC-C chemokine receptor type 8P51685HumansPredicted (SEA)1.24559
Mitogen-activated protein kinase 3 structureClick to view 3D structureMitogen-activated protein kinase 3P27361HumansPredicted (SEA)113.816
Photoreceptor-specific nuclear receptor structureClick to view 3D structurePhotoreceptor-specific nuclear receptorQ9Y5X4HumansPredicted (SEA)7.00643
Click to view 3D structureCarbonic anhydrase 15Q99N23Mus musculusPredicted (SEA)37.9904
Induced myeloid leukemia cell differentiation protein Mcl-1 structureClick to view 3D structureInduced myeloid leukemia cell differentiation protein Mcl-1Q07820HumansPredicted (SEA)90.4608
Concentrations
Not Available
External Links
DrugBank IDDB04815
HMDB IDHMDB0250327
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkClioquinol
Chemspider ID2686
ChEBI ID74460
PubChem Compound ID2788
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15074181
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15651505
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16087879
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=185949
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20651355
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21080020
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21199452
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21247386
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21426304
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21899946
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22248233
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22269164
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22627294
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=226725
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23044228
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23360710
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23627708