Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-07-04 19:02:38 UTC |
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Update Date | 2021-09-14 14:58:38 UTC |
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HMDB ID | HMDB0060836 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | N-Desmethyl-O-hydroxy rosiglitazone |
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Description | N-Desmethyl-O-hydroxy rosiglitazone is a metabolite of rosiglitazone. Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approximately $2.5bn in 2006, but declined after reports of adverse effects. (Wikipedia) |
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Structure | OC1=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=CC=C1 InChI=1S/C17H17N3O4S/c21-13-2-1-7-18-15(13)19-8-9-24-12-5-3-11(4-6-12)10-14-16(22)20-17(23)25-14/h1-7,14,21H,8-10H2,(H,18,19)(H,20,22,23) |
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Synonyms | Not Available |
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Chemical Formula | C17H17N3O4S |
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Average Molecular Weight | 359.4 |
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Monoisotopic Molecular Weight | 359.093976737 |
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IUPAC Name | 5-[(4-{2-[(3-hydroxypyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione |
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Traditional Name | 5-[(4-{2-[(3-hydroxypyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione |
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CAS Registry Number | Not Available |
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SMILES | OC1=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=CC=C1 |
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InChI Identifier | InChI=1S/C17H17N3O4S/c21-13-2-1-7-18-15(13)19-8-9-24-12-5-3-11(4-6-12)10-14-16(22)20-17(23)25-14/h1-7,14,21H,8-10H2,(H,18,19)(H,20,22,23) |
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InChI Key | GWVBGLUFILBNNY-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
- Aminopyridine
- Hydroxypyridine
- Thiazolidinedione
- Secondary aliphatic/aromatic amine
- Monocyclic benzene moiety
- Imidolactam
- Pyridine
- Dicarboximide
- Heteroaromatic compound
- Thiazolidine
- Amino acid or derivatives
- Carbonic acid derivative
- Thiocarbamic acid derivative
- Carboxylic acid derivative
- Ether
- Azacycle
- Organoheterocyclic compound
- Secondary amine
- Amine
- Hydrocarbon derivative
- Organic nitrogen compound
- Carbonyl group
- Organic oxide
- Organic oxygen compound
- Organonitrogen compound
- Organooxygen compound
- Organopnictogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic 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 | |
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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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N-Desmethyl-O-hydroxy rosiglitazone,1TMS,isomer #1 | C[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)NC2=O)C=C1 | 3704.5 | Semi standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,1TMS,isomer #2 | C[Si](C)(C)N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=NC=CC=C1O | 3605.3 | Semi standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,1TMS,isomer #3 | C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCNC3=NC=CC=C3O)C=C2)C1=O | 3528.6 | Semi standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #1 | C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C | 3608.1 | Semi standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #1 | C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C | 3296.2 | Standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #1 | C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C | 4755.9 | Standard polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #2 | C[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1 | 3523.8 | Semi standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #2 | C[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1 | 3213.7 | Standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #2 | C[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1 | 4442.0 | Standard polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #3 | C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C)C=C2)C1=O | 3371.8 | Semi standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #3 | C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C)C=C2)C1=O | 3295.4 | Standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #3 | C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C)C=C2)C1=O | 4402.1 | Standard polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)[Si](C)(C)C | 3407.8 | Semi standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)[Si](C)(C)C | 3287.2 | Standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)[Si](C)(C)C | 4021.4 | Standard polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)NC2=O)C=C1 | 3956.8 | Semi standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=NC=CC=C1O | 3864.2 | Semi standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCNC3=NC=CC=C3O)C=C2)C1=O | 3803.8 | Semi standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C(C)(C)C | 4020.9 | Semi standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C(C)(C)C | 3649.6 | Standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C(C)(C)C | 4757.9 | Standard polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1 | 3960.7 | Semi standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1 | 3625.7 | Standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1 | 4458.4 | Standard polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C(C)(C)C)C=C2)C1=O | 3860.1 | Semi standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C(C)(C)C)C=C2)C1=O | 3688.0 | Standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C(C)(C)C)C=C2)C1=O | 4373.8 | Standard polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)[Si](C)(C)C(C)(C)C | 4022.2 | Semi standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)[Si](C)(C)C(C)(C)C | 3845.8 | Standard non polar | 33892256 | N-Desmethyl-O-hydroxy rosiglitazone,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)[Si](C)(C)C(C)(C)C | 4135.4 | 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 - N-Desmethyl-O-hydroxy rosiglitazone GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-1961000000-bdb89099b5ab84dcf743 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone GC-MS (1 TMS) - 70eV, Positive | splash10-00di-2955100000-bde6b78fb75b701962ad | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 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 - N-Desmethyl-O-hydroxy rosiglitazone 10V, Positive-QTOF | splash10-03di-0219000000-ab50299314a212f098be | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 20V, Positive-QTOF | splash10-000i-0974000000-2a33994dcccc3756ef03 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 40V, Positive-QTOF | splash10-01p9-3920000000-113ee2a6bfbed1aca6d5 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 10V, Negative-QTOF | splash10-0a4i-0549000000-36b7007e3a7548658c8c | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 20V, Negative-QTOF | splash10-0pbl-4591000000-9fddd5ced0e5ddb88dd5 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 40V, Negative-QTOF | splash10-0006-9400000000-571bdbdbd29573e6abf8 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 10V, Negative-QTOF | splash10-05fr-1098000000-7fbb6159e0a3d11a1b95 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 20V, Negative-QTOF | splash10-0006-9121000000-cac1b8fa1563e2c426d6 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 40V, Negative-QTOF | splash10-0006-9200000000-2572c44b8781aa19bef1 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 10V, Positive-QTOF | splash10-03di-0009000000-82b3876182bcc2781eaf | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 20V, Positive-QTOF | splash10-03dr-0977000000-a22398adddc85a82a31e | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 40V, Positive-QTOF | splash10-00sa-2900000000-4b8e0a5a07e1cc80c35d | 2021-10-12 | Wishart Lab | View Spectrum |
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