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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 15:16:50 UTC |
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Update Date | 2022-03-07 02:51:47 UTC |
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HMDB ID | HMDB0014931 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Haloprogin |
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Description | Haloprogin is used as a topical ointment or cream in the treatment of Tinea infections. Tinea infections are superficial fungal infections caused by three species of fungi collectively known as dermatophytes (Trichophyton, Microsporum and Epidermophyton). Commonly these infections are named for the body part affected, including tinea corporis (general skin), tinea cruris (groin), and tinea pedis (feet). Haloprogin is a halogenated phenolic ether administered topically for dermotaphytic infections. The mechanism of action is unknown, but it is thought to be via inhibition of oxygen uptake and disruption of yeast membrane structure and function. |
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Structure | ClC1=CC(Cl)=C(Cl)C=C1OCC#CI InChI=1S/C9H4Cl3IO/c10-6-4-8(12)9(5-7(6)11)14-3-1-2-13/h4-5H,3H2 |
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Synonyms | Value | Source |
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Halotex | Kegg | Théraplix brand OF haloprogin | HMDB | Mycilan | HMDB | Westwood squibb brand OF haloprogin | HMDB | 3-Iodo-2-propynyl 2,4,5-trichlorophenyl ether | HMDB |
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Chemical Formula | C9H4Cl3IO |
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Average Molecular Weight | 361.391 |
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Monoisotopic Molecular Weight | 359.837241291 |
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IUPAC Name | 1,2,4-trichloro-5-[(3-iodoprop-2-yn-1-yl)oxy]benzene |
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Traditional Name | haloprogin |
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CAS Registry Number | 777-11-7 |
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SMILES | ClC1=CC(Cl)=C(Cl)C=C1OCC#CI |
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InChI Identifier | InChI=1S/C9H4Cl3IO/c10-6-4-8(12)9(5-7(6)11)14-3-1-2-13/h4-5H,3H2 |
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InChI Key | CTETYYAZBPJBHE-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenol ethers |
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Sub Class | Not Available |
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Direct Parent | Phenol ethers |
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Alternative Parents | |
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Substituents | - Phenoxy compound
- Phenol ether
- Alkyl aryl ether
- Chlorobenzene
- Halobenzene
- Aryl chloride
- Aryl halide
- Monocyclic benzene moiety
- Ether
- Haloacetylene or derivatives
- Organohalogen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Organochloride
- Organoiodide
- Organooxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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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 | 113.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.006 g/L | Not Available | LogP | 5.3 | 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 IndicesUnderivatized |
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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 - Haloprogin GC-MS (Non-derivatized) - 70eV, Positive | splash10-0nvi-2937000000-e0fbc50dec2df8a7392c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Haloprogin 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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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Haloprogin 10V, Positive-QTOF | splash10-03di-0009000000-205241bf6f19269ac44f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Haloprogin 20V, Positive-QTOF | splash10-03di-0009000000-685736b870ca3a5b7396 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Haloprogin 40V, Positive-QTOF | splash10-01q9-0904000000-0fa7f51cc65c247bc53e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Haloprogin 10V, Negative-QTOF | splash10-0a4i-0009000000-613da8314566eab0ea09 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Haloprogin 20V, Negative-QTOF | splash10-0a4i-0009000000-5526c9d6e567956ca1c8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Haloprogin 40V, Negative-QTOF | splash10-0a6r-0639000000-48169dabf0e58c7b946c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Haloprogin 10V, Positive-QTOF | splash10-03di-0009000000-13123a05c84264f3a263 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Haloprogin 20V, Positive-QTOF | splash10-03di-0029000000-82363b16547174d03783 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Haloprogin 40V, Positive-QTOF | splash10-06w9-4296000000-43a5c95da82f2b836304 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Haloprogin 10V, Negative-QTOF | splash10-0a4i-0009000000-c2d55deaed82c6582a92 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Haloprogin 20V, Negative-QTOF | splash10-0a4i-0009000000-c2d55deaed82c6582a92 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Haloprogin 40V, Negative-QTOF | splash10-0a4i-2249000000-3d6d4d91ac564a883d2b | 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 DB00793 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00793 | | 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 | DB00793 |
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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 | 3440 |
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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 | Haloprogin |
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METLIN ID | Not Available |
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PubChem Compound | 3561 |
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PDB ID | Not Available |
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ChEBI ID | 353862 |
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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 | - Harrison EF, Zygmunt WA: Haloprogin: mode of action studies in Candida albicans. Can J Microbiol. 1974 Sep;20(9):1241-5. [PubMed:4608935 ]
- Harrison EF, Zwadyk P Jr, Bequette RJ, Hamlow EE, Tavormina PA, Zygmunt WA: Haloprogin: a topical antifungal agent. Appl Microbiol. 1970 May;19(5):746-50. [PubMed:5422306 ]
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