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 02:51:44 UTC |
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HMDB ID | HMDB0014777 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Butoconazole |
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Description | Butoconazole is only found in individuals that have used or taken this drug. It is an imidazole antifungal used in gynecology.The exact mechanism of the antifungal action of butoconazole is unknown, however, it is presumed to function as other imidazole derivatives via inhibition of steroid synthesis. Imidazoles generally inhibit the conversion of lanosterol to ergosterol via the inhibition of the enzyme cytochrome P450 14α-demethylase, resulting in a change in fungal cell membrane lipid composition. This structural change alters cell permeability and, ultimately, results in the osmotic disruption or growth inhibition of the fungal cell. |
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Structure | ClC1=CC=C(CCC(CN2C=CN=C2)SC2=C(Cl)C=CC=C2Cl)C=C1 InChI=1S/C19H17Cl3N2S/c20-15-7-4-14(5-8-15)6-9-16(12-24-11-10-23-13-24)25-19-17(21)2-1-3-18(19)22/h1-5,7-8,10-11,13,16H,6,9,12H2 |
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Synonyms | Value | Source |
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1-[4-(4-Chloro-phenyl)-2-(2,6-dichloro-phenylsulfanyl)-butyl]-1H-imidazole | ChEBI | Butoconazol | ChEBI | Butoconazolum | ChEBI | Gynofort | Kegg | 1-[4-(4-Chloro-phenyl)-2-(2,6-dichloro-phenylsulphanyl)-butyl]-1H-imidazole | Generator | Butoconazole nitrate | HMDB | Bayer brand 1 OF butoconazole nitrate | HMDB | Mycelex-3 | HMDB | 1-(4-(4-Chlorophenyl)-2-(2,6-dichlorophenylthio)-N-butyl)-1H-imidazole | HMDB | Bayer brand 2 OF butoconazole nitrate | HMDB | Gynomyk | HMDB | Ther-RX brand OF butoconazole nitrate | HMDB | Femstal | HMDB | Aventis brand OF butoconazole nitrate | HMDB | Femstat | HMDB | Gynazole-1 | HMDB | Syntex brand OF butoconazole nitrate | HMDB | Will brand OF butoconazole nitrate | HMDB |
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Chemical Formula | C19H17Cl3N2S |
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Average Molecular Weight | 411.776 |
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Monoisotopic Molecular Weight | 410.017802365 |
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IUPAC Name | 1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl]-1H-imidazole |
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Traditional Name | butoconazole |
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CAS Registry Number | 64872-77-1 |
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SMILES | ClC1=CC=C(CCC(CN2C=CN=C2)SC2=C(Cl)C=CC=C2Cl)C=C1 |
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InChI Identifier | InChI=1S/C19H17Cl3N2S/c20-15-7-4-14(5-8-15)6-9-16(12-24-11-10-23-13-24)25-19-17(21)2-1-3-18(19)22/h1-5,7-8,10-11,13,16H,6,9,12H2 |
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InChI Key | SWLMUYACZKCSHZ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Phenylbutylamines |
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Direct Parent | Phenylbutylamines |
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Alternative Parents | |
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Substituents | - Phenylbutylamine
- Aryl thioether
- 1,3-dichlorobenzene
- Thiophenol ether
- Chlorobenzene
- Alkylarylthioether
- Halobenzene
- Aryl chloride
- Aryl halide
- N-substituted imidazole
- Azole
- Heteroaromatic compound
- Imidazole
- Azacycle
- Organoheterocyclic compound
- Sulfenyl compound
- Thioether
- Hydrocarbon derivative
- Organopnictogen compound
- Organic nitrogen compound
- Organosulfur compound
- Organohalogen compound
- Organochloride
- Organonitrogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic 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 | 159 °C (decomposition) | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.00082 g/L | Not Available | LogP | 6.7 | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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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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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Butoconazole GC-MS (Non-derivatized) - 70eV, Positive | splash10-0059-6921000000-df9fbb2ed1919d5db32d | 2017-08-28 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Butoconazole GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Butoconazole 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 - Butoconazole 10V, Positive-QTOF | splash10-03e9-0291800000-175d20ae946894d63ff0 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Butoconazole 20V, Positive-QTOF | splash10-02di-6966500000-99152c227089dc60fc64 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Butoconazole 40V, Positive-QTOF | splash10-016r-6900000000-33b44a1350666f009c48 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Butoconazole 10V, Negative-QTOF | splash10-0a4i-1110900000-66f5c95ad320950db5ee | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Butoconazole 20V, Negative-QTOF | splash10-014i-9330100000-d4e9c87c57f1a3ccac9d | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Butoconazole 40V, Negative-QTOF | splash10-016u-7900000000-e6e65ee82f67ecda0db0 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Butoconazole 10V, Positive-QTOF | splash10-03ec-0045900000-1fac55efca4ba6eccc60 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Butoconazole 20V, Positive-QTOF | splash10-03di-0212900000-f208005b553e381d5f6e | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Butoconazole 40V, Positive-QTOF | splash10-05r0-0903000000-5bc7d62d0a3041507d6a | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Butoconazole 10V, Negative-QTOF | splash10-0a4i-0200900000-432e3f6045e38ec2662a | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Butoconazole 20V, Negative-QTOF | splash10-069r-9520300000-1f132112bc9ce64d1aa1 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Butoconazole 40V, Negative-QTOF | splash10-001i-9100000000-a40b7e0b888e3f9f6938 | 2021-10-11 | Wishart Lab | View Spectrum |
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