Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:52 UTC |
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Update Date | 2022-03-07 02:51:58 UTC |
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HMDB ID | HMDB0015373 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Chloroxine |
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Description | Chloroxine 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. |
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Structure | OC1=C(Cl)C=C(Cl)C2=C1N=CC=C2 InChI=1S/C9H5Cl2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H |
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Synonyms | Value | Source |
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5,7-Dichlor-8-hydroxychinolin | ChEBI | 5,7-Dichloro-8-hydroxyquinoline | ChEBI | 5,7-Dichloro-8-oxyquinoline | ChEBI | 5,7-Dichloro-8-quinolinol | ChEBI | 5,7-Dichlorooxine | ChEBI | 5,7-Dichloroxine | ChEBI | CHQ | ChEBI | Capitrol | Kegg | Chloroxyquinoline | HMDB | Chlorquinol | HMDB | Dichlorohydroxyquinoline | HMDB | Dichloroquinolinol | HMDB | Dichloroxin | HMDB | Dikhloroskin | HMDB | Chloroxine hydrofluoride | HMDB | Dichloroquine | HMDB | Quixalin | HMDB |
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Chemical Formula | C9H5Cl2NO |
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Average Molecular Weight | 214.048 |
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Monoisotopic Molecular Weight | 212.974819201 |
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IUPAC Name | 5,7-dichloroquinolin-8-ol |
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Traditional Name | chloroxine |
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CAS Registry Number | 773-76-2 |
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SMILES | OC1=C(Cl)C=C(Cl)C2=C1N=CC=C2 |
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InChI Identifier | InChI=1S/C9H5Cl2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H |
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InChI Key | WDFKMLRRRCGAKS-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Quinolines and derivatives |
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Sub Class | Haloquinolines |
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Direct Parent | Chloroquinolines |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 179.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.14 g/L | Not Available | LogP | 3 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Chloroxine GC-MS (Non-derivatized) - 70eV, Positive | splash10-03di-1980000000-94c636ec42678fc3c467 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Chloroxine GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9380000000-a7e39a43858fab0dabfc | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Chloroxine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Chloroxine LC-ESI-qTof , Positive-QTOF | splash10-03xr-2790000000-123a4bb6fd1928cb1de5 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chloroxine , positive-QTOF | splash10-03xr-0390000000-37c6d6830bd09ef8b180 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chloroxine , positive-QTOF | splash10-03xr-2790000000-123a4bb6fd1928cb1de5 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chloroxine 10V, Positive-QTOF | splash10-03di-0090000000-d09114ffba76032f2260 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chloroxine 20V, Positive-QTOF | splash10-03di-0090000000-bec2467dddf8623c1212 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chloroxine 40V, Positive-QTOF | splash10-03dr-2890000000-a3b154170895ae54e4d7 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chloroxine 10V, Negative-QTOF | splash10-03di-0090000000-c4d6ff48d02a3a7ef424 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chloroxine 20V, Negative-QTOF | splash10-03di-0090000000-c4d6ff48d02a3a7ef424 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chloroxine 40V, Negative-QTOF | splash10-03di-4490000000-2ef1669e8253d1294d4e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chloroxine 10V, Positive-QTOF | splash10-03di-0090000000-80be7fa7d812c7b6db6c | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chloroxine 20V, Positive-QTOF | splash10-03di-0090000000-80be7fa7d812c7b6db6c | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chloroxine 40V, Positive-QTOF | splash10-0udr-0910000000-9bcfcb79997e6162aaa9 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chloroxine 10V, Negative-QTOF | splash10-03di-0090000000-5728a180bb940eedd66b | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chloroxine 20V, Negative-QTOF | splash10-03di-0090000000-5728a180bb940eedd66b | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chloroxine 40V, Negative-QTOF | splash10-001i-3930000000-f6cbc4acf91ef397b9d0 | 2021-10-11 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB01243 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB01243 | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB01243 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 2621 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Chloroxine |
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METLIN ID | Not Available |
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PubChem Compound | 2722 |
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PDB ID | Not Available |
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ChEBI ID | 59477 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - 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 ]
- 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 ]
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