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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:29 UTC
HMDB IDHMDB0015373
Secondary Accession Numbers
  • HMDB15373
Metabolite Identification
Common NameChloroxine
DescriptionChloroxine is only found in individuals that have used or taken this drug. It is a synthetic antibacterial compound. Chloroxine is a compound used in some shampoos for the treatment of dandruff and seborrheic dermatitis of the scalp.Although the mechanism of action is not understood, chloroxine may slow down mitotic activity in the epidermis, thereby reducing excessive scaling associated with dandruff or seborrheic dermatitis of the scalp. Chloroxine induces SOS-DNA repair in E. coli, so chloroxine may be genotoxic to bacteria.
Structure
Data?1582753289
Synonyms
ValueSource
5,7-Dichlor-8-hydroxychinolinChEBI
5,7-Dichloro-8-hydroxyquinolineChEBI
5,7-Dichloro-8-oxyquinolineChEBI
5,7-Dichloro-8-quinolinolChEBI
5,7-DichlorooxineChEBI
5,7-DichloroxineChEBI
CHQChEBI
CapitrolKegg
ChloroxyquinolineHMDB
ChlorquinolHMDB
DichlorohydroxyquinolineHMDB
DichloroquinolinolHMDB
DichloroxinHMDB
DikhloroskinHMDB
Chloroxine hydrofluorideHMDB
DichloroquineHMDB
QuixalinHMDB
Chemical FormulaC9H5Cl2NO
Average Molecular Weight214.048
Monoisotopic Molecular Weight212.974819201
IUPAC Name5,7-dichloroquinolin-8-ol
Traditional Namechloroxine
CAS Registry Number773-76-2
SMILES
OC1=C(Cl)C=C(Cl)C2=C1N=CC=C2
InChI Identifier
InChI=1S/C9H5Cl2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
InChI KeyWDFKMLRRRCGAKS-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
  • 8-hydroxyquinoline
  • Chloroquinoline
  • Aryl chloride
  • Aryl halide
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point179.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.14 g/LNot Available
LogP3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP3.44ALOGPS
logP3.04ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.95ChemAxon
pKa (Strongest Basic)3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.12 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity51.57 m³·mol⁻¹ChemAxon
Polarizability19.32 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-1980000000-94c636ec42678fc3c467Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9380000000-a7e39a43858fab0dabfcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03xr-2790000000-123a4bb6fd1928cb1de5Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03xr-0390000000-37c6d6830bd09ef8b180Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03xr-2790000000-123a4bb6fd1928cb1de5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-d09114ffba76032f2260Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090000000-bec2467dddf8623c1212Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-2890000000-a3b154170895ae54e4d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-c4d6ff48d02a3a7ef424Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0090000000-c4d6ff48d02a3a7ef424Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-4490000000-2ef1669e8253d1294d4eSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01243 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01243 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01243
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2621
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChloroxine
METLIN IDNot Available
PubChem Compound2722
PDB IDNot Available
ChEBI ID59477
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Malaveille C, Brun G, Bartsch H: Genotoxicity of ochratoxin A and structurally related compounds in Escherichia coli strains: studies on their mode of action. IARC Sci Publ. 1991;(115):261-6. [PubMed:1820340 ]
  2. Malaveille C, Brun G, Bartsch H: Structure-activity studies in E. coli strains on ochratoxin A (OTA) and its analogues implicate a genotoxic free radical and a cytotoxic thiol derivative as reactive metabolites. Mutat Res. 1994 May 1;307(1):141-7. [PubMed:7513790 ]