Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-06-15 17:46:37 UTC |
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Update Date | 2021-09-14 15:48:17 UTC |
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HMDB ID | HMDB0060599 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Lamivudine sulfoxide |
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Description | Lamivudine sulfoxide belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others. Lamivudine sulfoxide is an extremely weak basic (essentially neutral) compound (based on its pKa). lamivudine sulfoxide can be biosynthesized from lamivudine through its interaction with the enzyme sulfotransferase 1A1. In humans, lamivudine sulfoxide is involved in lamivudine metabolism pathway. Nitazoxanide, also known by the brand names Alinia and Annita (and by Daxon, Dexidex, Kidonax, Mitafar, Pacovanton, and Paramix in Mexico, by Nitax, Zox, Nitazox, Niazid and Toza in Bangladesh) is a synthetic nitrothiazolyl-salicylamide derivative and an antiprotozoal agent. It is poorly soluble in ethanol and practically insoluble in water. Lamivudine sulfoxide is a metabolite of nitazoxanide. Nitazoxanide is a light yellow crystalline powder. |
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Structure | NC1=NC(=O)N(C=C1)[C@H]1CS(=O)[C@@H](CO)O1 InChI=1S/C8H11N3O4S/c9-5-1-2-11(8(13)10-5)6-4-16(14)7(3-12)15-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+,16?/m1/s1 |
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Synonyms | Value | Source |
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Lamivudine sulphoxide | Generator |
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Chemical Formula | C8H11N3O4S |
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Average Molecular Weight | 245.256 |
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Monoisotopic Molecular Weight | 245.047026545 |
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IUPAC Name | 4-amino-1-[(2S,5R)-2-(hydroxymethyl)-3-oxo-1,3λ⁴-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one |
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Traditional Name | 4-amino-1-[(2S,5R)-2-(hydroxymethyl)-3-oxo-1,3λ⁴-oxathiolan-5-yl]pyrimidin-2-one |
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CAS Registry Number | Not Available |
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SMILES | NC1=NC(=O)N(C=C1)[C@H]1CS(=O)[C@@H](CO)O1 |
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InChI Identifier | InChI=1S/C8H11N3O4S/c9-5-1-2-11(8(13)10-5)6-4-16(14)7(3-12)15-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+,16?/m1/s1 |
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InChI Key | LJMQAXFNQNADRZ-FYZWQCAOSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Nucleoside and nucleotide analogues |
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Sub Class | Not Available |
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Direct Parent | Nucleoside and nucleotide analogues |
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Alternative Parents | |
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Substituents | - Aminopyrimidine
- Pyrimidone
- Hydropyrimidine
- Pyrimidine
- Imidolactam
- Monothioacetal
- Oxathiolane
- Heteroaromatic compound
- Sulfoxide
- Oxacycle
- Azacycle
- Sulfinyl compound
- Organoheterocyclic compound
- Hydrocarbon derivative
- Primary amine
- Primary alcohol
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Alcohol
- Amine
- Organic nitrogen 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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Lamivudine sulfoxide,1TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)CS1=O | 2452.8 | Semi standard non polar | 33892256 | Lamivudine sulfoxide,1TMS,isomer #2 | C[Si](C)(C)NC1=NC(=O)N([C@H]2CS(=O)[C@@H](CO)O2)C=C1 | 2513.9 | Semi standard non polar | 33892256 | Lamivudine sulfoxide,2TMS,isomer #1 | C[Si](C)(C)NC1=NC(=O)N([C@H]2CS(=O)[C@@H](CO[Si](C)(C)C)O2)C=C1 | 2522.5 | Semi standard non polar | 33892256 | Lamivudine sulfoxide,2TMS,isomer #1 | C[Si](C)(C)NC1=NC(=O)N([C@H]2CS(=O)[C@@H](CO[Si](C)(C)C)O2)C=C1 | 2706.4 | Standard non polar | 33892256 | Lamivudine sulfoxide,2TMS,isomer #1 | C[Si](C)(C)NC1=NC(=O)N([C@H]2CS(=O)[C@@H](CO[Si](C)(C)C)O2)C=C1 | 3461.2 | Standard polar | 33892256 | Lamivudine sulfoxide,2TMS,isomer #2 | C[Si](C)(C)N(C1=NC(=O)N([C@H]2CS(=O)[C@@H](CO)O2)C=C1)[Si](C)(C)C | 2466.0 | Semi standard non polar | 33892256 | Lamivudine sulfoxide,2TMS,isomer #2 | C[Si](C)(C)N(C1=NC(=O)N([C@H]2CS(=O)[C@@H](CO)O2)C=C1)[Si](C)(C)C | 2792.7 | Standard non polar | 33892256 | Lamivudine sulfoxide,2TMS,isomer #2 | C[Si](C)(C)N(C1=NC(=O)N([C@H]2CS(=O)[C@@H](CO)O2)C=C1)[Si](C)(C)C | 3377.5 | Standard polar | 33892256 | Lamivudine sulfoxide,3TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)CS1=O | 2487.1 | Semi standard non polar | 33892256 | Lamivudine sulfoxide,3TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)CS1=O | 2794.4 | Standard non polar | 33892256 | Lamivudine sulfoxide,3TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)CS1=O | 3023.4 | Standard polar | 33892256 | Lamivudine sulfoxide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)CS1=O | 2725.9 | Semi standard non polar | 33892256 | Lamivudine sulfoxide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@H]2CS(=O)[C@@H](CO)O2)C=C1 | 2779.7 | Semi standard non polar | 33892256 | Lamivudine sulfoxide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@H]2CS(=O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C=C1 | 2994.8 | Semi standard non polar | 33892256 | Lamivudine sulfoxide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@H]2CS(=O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C=C1 | 3185.1 | Standard non polar | 33892256 | Lamivudine sulfoxide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@H]2CS(=O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C=C1 | 3467.5 | Standard polar | 33892256 | Lamivudine sulfoxide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=NC(=O)N([C@H]2CS(=O)[C@@H](CO)O2)C=C1)[Si](C)(C)C(C)(C)C | 2936.0 | Semi standard non polar | 33892256 | Lamivudine sulfoxide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=NC(=O)N([C@H]2CS(=O)[C@@H](CO)O2)C=C1)[Si](C)(C)C(C)(C)C | 3282.1 | Standard non polar | 33892256 | Lamivudine sulfoxide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=NC(=O)N([C@H]2CS(=O)[C@@H](CO)O2)C=C1)[Si](C)(C)C(C)(C)C | 3339.4 | Standard polar | 33892256 | Lamivudine sulfoxide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)CS1=O | 3151.9 | Semi standard non polar | 33892256 | Lamivudine sulfoxide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)CS1=O | 3454.8 | Standard non polar | 33892256 | Lamivudine sulfoxide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)CS1=O | 3211.3 | 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 - Lamivudine sulfoxide GC-MS (Non-derivatized) - 70eV, Positive | splash10-03di-8910000000-0a97c81e597d46d13cec | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lamivudine sulfoxide GC-MS (1 TMS) - 70eV, Positive | splash10-0jbi-6900000000-73ae3c3a3bc573a6595d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lamivudine sulfoxide 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 - Lamivudine sulfoxide 10V, Positive-QTOF | splash10-03di-0910000000-63f9bb8a8fb1f78ab9f3 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lamivudine sulfoxide 20V, Positive-QTOF | splash10-03di-3900000000-04a8a42440e410019507 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lamivudine sulfoxide 40V, Positive-QTOF | splash10-03di-9700000000-c7cc0fb6f0db073b654f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lamivudine sulfoxide 10V, Negative-QTOF | splash10-0007-1970000000-742b32f84394a407678f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lamivudine sulfoxide 20V, Negative-QTOF | splash10-0006-4900000000-01d178cf401a4d93caf6 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lamivudine sulfoxide 40V, Negative-QTOF | splash10-0007-9000000000-15e4d8cb62057a01e18e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lamivudine sulfoxide 10V, Positive-QTOF | splash10-03di-0900000000-61fe3ac4032a2baf1b89 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lamivudine sulfoxide 20V, Positive-QTOF | splash10-03di-2900000000-230b224d4d0dd71d0a49 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lamivudine sulfoxide 40V, Positive-QTOF | splash10-02t9-9200000000-a6bfc3e9e9eb515dc639 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lamivudine sulfoxide 10V, Negative-QTOF | splash10-000l-0950000000-48771aeea64e340f2989 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lamivudine sulfoxide 20V, Negative-QTOF | splash10-0gvx-4900000000-3064775e4cd9496d7836 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lamivudine sulfoxide 40V, Negative-QTOF | splash10-0006-9400000000-82532a473432d6e507e3 | 2021-10-12 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
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