Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2021-09-11 21:48:36 UTC |
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Update Date | 2022-11-23 22:29:21 UTC |
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HMDB ID | HMDB0259292 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | Troglitazone |
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Description | Troglitazone, also known as rezulin, belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. Troglitazone is a drug which is used for the treatment of type ii diabetes mellitus. it is used alone or in combination with a sulfonylurea, metformin, or insulin as an adjunct to diet and exercise. Based on a literature review very few articles have been published on Troglitazone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Troglitazone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Troglitazone 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 | CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)NC4=O)C=C3)O2)C(C)=C1O InChI=1S/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,9-12H2,1-4H3,(H,25,27,28) |
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Synonyms | Value | Source |
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Rezulin | ChEBI | Romglizone | ChEBI | Troglitazona | ChEBI | Troglitazonum | ChEBI | Prelay | MeSH | Warner-lambert brand OF troglitazone | MeSH | Parke davis brand OF troglitazone | MeSH |
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Chemical Formula | C24H27NO5S |
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Average Molecular Weight | 441.54 |
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Monoisotopic Molecular Weight | 441.160993669 |
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IUPAC Name | 5-({4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)methoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione |
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Traditional Name | troglitazone |
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CAS Registry Number | Not Available |
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SMILES | CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)NC4=O)C=C3)O2)C(C)=C1O |
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InChI Identifier | InChI=1S/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,9-12H2,1-4H3,(H,25,27,28) |
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InChI Key | GXPHKUHSUJUWKP-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzopyrans |
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Sub Class | 1-benzopyrans |
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Direct Parent | 1-benzopyrans |
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Alternative Parents | |
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Substituents | - 1-benzopyran
- Phenoxy compound
- Phenol ether
- Alkyl aryl ether
- Thiazolidinedione
- Monocyclic benzene moiety
- Benzenoid
- Dicarboximide
- Thiazolidine
- Carbonic acid derivative
- Thiocarbamic acid derivative
- Carboxylic acid derivative
- Ether
- Oxacycle
- Azacycle
- Organonitrogen compound
- Organic oxide
- Organopnictogen compound
- Organic nitrogen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Carbonyl group
- 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 | 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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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troglitazone,2TMS,isomer #1 | CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C | 3787.1 | Semi standard non polar | 33892256 | troglitazone,2TMS,isomer #1 | CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C | 3580.1 | Standard non polar | 33892256 | troglitazone,2TMS,isomer #1 | CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C | 4173.1 | Standard polar | 33892256 | troglitazone,2TBDMS,isomer #1 | CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C(C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C(C)(C)C | 4226.5 | Semi standard non polar | 33892256 | troglitazone,2TBDMS,isomer #1 | CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C(C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C(C)(C)C | 3959.0 | Standard non polar | 33892256 | troglitazone,2TBDMS,isomer #1 | CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C(C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C(C)(C)C | 4270.1 | Standard polar | 33892256 |
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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 - Troglitazone GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a6r-1889600000-e7d440741c30fa701997 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Troglitazone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Troglitazone GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Troglitazone GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Troglitazone GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Troglitazone GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | 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 - Troglitazone 60V, Negative-QTOF | splash10-0f6t-1900000000-b41d1d9b00383779a8be | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Troglitazone 45V, Negative-QTOF | splash10-0f6t-0900000000-ab7c5539034df635ac14 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Troglitazone 75V, Negative-QTOF | splash10-0fr2-1900000000-1a1e22916ed5413720eb | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Troglitazone 90V, Negative-QTOF | splash10-014j-2900000000-52697cbd413c9fbe49f8 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Troglitazone 30V, Negative-QTOF | splash10-0005-1507900000-4f7d34b5dc4e0c481b68 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Troglitazone 15V, Negative-QTOF | splash10-0006-0000900000-8c86a1f2bb9af73c4ae9 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Troglitazone 60V, Positive-QTOF | splash10-014i-1900000000-c7a1ca757fec1b1a4e5e | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Troglitazone 75V, Positive-QTOF | splash10-014i-3900000000-c72fbe14217a1770ef4d | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Troglitazone 10V, Positive-QTOF | splash10-0006-0430900000-ceb18bd79d0f6da79e7d | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Troglitazone 20V, Positive-QTOF | splash10-014i-0912100000-c1ddd0b2276cc0642c28 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Troglitazone 40V, Positive-QTOF | splash10-0bt9-0910000000-70eed845667711a7ff74 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Troglitazone 10V, Negative-QTOF | splash10-0006-0133900000-d4c360adbc610d5363cf | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Troglitazone 20V, Negative-QTOF | splash10-0v4l-4759300000-7eda5e5df7869dbcd569 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Troglitazone 40V, Negative-QTOF | splash10-0006-9700000000-bbf919843d75c50ea813 | 2016-08-03 | Wishart Lab | View Spectrum |
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