Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2021-09-10 20:50:29 UTC |
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Update Date | 2021-09-26 22:50:43 UTC |
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HMDB ID | HMDB0243587 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | (2S,4S)-Ketoconazole |
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Description | 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group. Based on a literature review very few articles have been published on 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine. This compound has been identified in human blood as reported by (PMID: 31557052 ). (2s,4s)-ketoconazole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (2S,4S)-Ketoconazole is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. |
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Structure | CC(=O)N1CCN(CC1)C1=CC=C(OCC2COC(CN3C=CN=C3)(O2)C2=CC=C(Cl)C=C2Cl)C=C1 InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3 |
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Synonyms | Value | Source |
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Janssen brand OF ketoconazole | MeSH | Ketoconazole janssen brand | MeSH | Nizoral | MeSH |
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Chemical Formula | C26H28Cl2N4O4 |
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Average Molecular Weight | 531.431 |
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Monoisotopic Molecular Weight | 530.148760818 |
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IUPAC Name | 1-[4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one |
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Traditional Name | ketoconazole |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)N1CCN(CC1)C1=CC=C(OCC2COC(CN3C=CN=C3)(O2)C2=CC=C(Cl)C=C2Cl)C=C1 |
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InChI Identifier | InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3 |
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InChI Key | XMAYWYJOQHXEEK-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Diazinanes |
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Sub Class | Piperazines |
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Direct Parent | Phenylpiperazines |
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Alternative Parents | |
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Substituents | - Phenylpiperazine
- N-arylpiperazine
- Aminophenyl ether
- 1,3-dichlorobenzene
- Phenol ether
- Tertiary aliphatic/aromatic amine
- Phenoxy compound
- Dialkylarylamine
- Aniline or substituted anilines
- Alkyl aryl ether
- Ketal
- Halobenzene
- Chlorobenzene
- Monocyclic benzene moiety
- Aryl chloride
- Aryl halide
- N-substituted imidazole
- Benzenoid
- Meta-dioxolane
- Heteroaromatic compound
- Tertiary carboxylic acid amide
- Imidazole
- Azole
- Acetamide
- Carboxamide group
- Amino acid or derivatives
- Tertiary amine
- Acetal
- Oxacycle
- Azacycle
- Carboxylic acid derivative
- Ether
- Organooxygen compound
- Carbonyl group
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Amine
- Organonitrogen compound
- Organochloride
- Organopnictogen compound
- Organohalogen 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 | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | 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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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 10V, Positive-QTOF | splash10-001i-0031490000-58a475e5974da2dfdc18 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 20V, Positive-QTOF | splash10-0ik9-5395740000-08c010ea5c947e1a62f5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 40V, Positive-QTOF | splash10-014i-9520100000-76672a88c60da8324f81 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 10V, Negative-QTOF | splash10-00or-2090150000-e4d86d7a4af384399254 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 20V, Negative-QTOF | splash10-014i-9240000000-92849351dd004ec26239 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 40V, Negative-QTOF | splash10-00or-5940000000-e2a0f55e6d356bbc9c0e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 10V, Positive-QTOF | splash10-001i-0000090000-081787cba0594aced901 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 20V, Positive-QTOF | splash10-001i-0011980000-f9fa0eaf2d1b6889e098 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 40V, Positive-QTOF | splash10-066v-3140900000-ae27808322ff5c503bcf | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 10V, Negative-QTOF | splash10-004i-0010390000-0eb582e7b11176ec640c | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 20V, Negative-QTOF | splash10-014i-9030210000-9ea18251d96dd5cc657e | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 40V, Negative-QTOF | splash10-00o0-4930100000-6819285e7904a4b66c66 | 2021-10-12 | Wishart Lab | View Spectrum |
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