Record Information |
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Version | 1.0 |
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Created at | 2022-02-14 20:40:09 UTC |
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Updated at | 2022-03-10 22:17:40 UTC |
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NP-MRD ID | NP0044257 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 5-Methylthioribose |
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Description | 5-Methylthioribose belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. 5-Methylthioribose is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Methylthioribose exists in all living organisms, ranging from bacteria to humans. In humans, 5-methylthioribose is involved in the metabolic disorder called hypermethioninemia. Outside of the human body, 5-Methylthioribose has been detected, but not quantified in, several different foods, such as alaska wild rhubarbs, common verbena, greenthread tea, pasta, and irish moss. This could make 5-methylthioribose a potential biomarker for the consumption of these foods. 5-Methylthioribose is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | CSC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O InChI=1S/C6H12O4S/c1-11-2-3-4(7)5(8)6(9)10-3/h3-9H,2H2,1H3/t3-,4-,5-,6-/m1/s1 |
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Synonyms | Value | Source |
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S-Methyl-5-thio-D-ribose | Kegg | 5-Deoxy-5-(methylthio)ribose | HMDB | 5-Methylthio-D-ribose | HMDB | S(5)-Methyl-5-thio-D-ribose | HMDB | S5-Methyl-5-thio-D-ribose | HMDB | 5-Methylthioribose | HMDB | 5-S-Methyl-5-thio-D-ribose | HMDB | 5-S-Methyl-5-thio-beta-D-ribofuranose | HMDB | 5-S-Methyl-5-thio-β-D-ribofuranose | HMDB | S-Methyl-5-thio-D-ribofuranose | HMDB |
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Chemical Formula | C6H12O4S |
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Average Mass | 180.2220 Da |
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Monoisotopic Mass | 180.04563 Da |
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IUPAC Name | (2R,3R,4S,5S)-5-[(methylsulfanyl)methyl]oxolane-2,3,4-triol |
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Traditional Name | 5-methylthio-D-ribose |
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CAS Registry Number | 624740-12-1 |
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SMILES | CSC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C6H12O4S/c1-11-2-3-4(7)5(8)6(9)10-3/h3-9H,2H2,1H3/t3-,4-,5-,6-/m1/s1 |
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InChI Key | OLVVOVIFTBSBBH-KVTDHHQDSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Pentoses |
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Alternative Parents | |
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Substituents | - Pentose monosaccharide
- Tetrahydrofuran
- Secondary alcohol
- Hemiacetal
- 1,2-diol
- Oxacycle
- Organoheterocyclic compound
- Dialkylthioether
- Sulfenyl compound
- Thioether
- Polyol
- Hydrocarbon derivative
- Organosulfur compound
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental 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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Predicted Properties | |
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General References | - Della Ragione F, Carteni-Farina M, Gragnaniello V, Schettino MI, Zappia V: Purification and characterization of 5'-deoxy-5'-methylthioadenosine phosphorylase from human placenta. J Biol Chem. 1986 Sep 15;261(26):12324-9. [PubMed:3091600 ]
- Carteni-Farina M, della Ragione F, Cacciapuoti G, Porcelli M, Zappia V: Transport and metabolism of 5'-methylthioadenosine in human erythrocytes. Biochim Biophys Acta. 1983 Jan 19;727(2):221-9. doi: 10.1016/0005-2736(83)90407-8. [PubMed:6838867 ]
- Gianotti AJ, Tower PA, Sheley JH, Conte PA, Spiro C, Ferro AJ, Fitchen JH, Riscoe MK: Selective killing of Klebsiella pneumoniae by 5-trifluoromethylthioribose. Chemotherapeutic exploitation of the enzyme 5-methylthioribose kinase. J Biol Chem. 1990 Jan 15;265(2):831-7. [PubMed:2153115 ]
- Schroeder HR, Barnes CJ, Bohinski RC, Mallette MF: Biological production of 5-methylthioribose. Can J Microbiol. 1973 Nov;19(11):1347-54. doi: 10.1139/m73-217. [PubMed:4203512 ]
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