Record Information |
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Version | 1.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2024-04-19 10:03:48 UTC |
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NP-MRD ID | NP0001433 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Xanthosine |
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Description | Xanthosine, also known as xanthine riboside, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Xanthosine is a nucleoside derived from xanthine and ribose. Xanthosine exists in all living species, ranging from bacteria to plants to humans. In plants xanthosine is the biosynthetic precursor to 7-methylxanthosine which is produced by the action of the enzyme known as 7-methylxanthosine synthase. 7-Methylxanthosine in turn is the precursor to theobromine (the active alkaloid in chocolate), which in turn is the precursor to caffeine, the active alkaloid in coffee and tea. Within humans, xanthosine participates in a number of enzymatic reactions. In particular, xanthosine can be biosynthesized from xanthylic acid; which is catalyzed by the enzyme cytosolic purine 5'-nucleotidase. In addition, xanthosine can be converted into xanthine and ribose 1-phosphate; which is mediated by the enzyme purine nucleoside phosphorylase. Xanthosine monophosphate (XMP) is an intermediate in purine metabolism, formed from IMP (inosine monophosphate). |
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Structure | OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2O InChI=1S/C10H12N4O6/c15-1-3-5(16)6(17)9(20-3)14-2-11-4-7(14)12-10(19)13-8(4)18/h2-3,5-6,9,15-17H,1H2,(H2,12,13,18,19)/t3-,5-,6-,9-/m1/s1 |
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Synonyms | Value | Source |
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9-beta-D-Ribofuranosyl-3,9-dihydro-1H-purine-2,6-dione | ChEBI | 9-beta-D-Ribofuranosylxanthine | ChEBI | Xanthine 9-beta-D-ribofuranoside | ChEBI | Xanthine riboside | ChEBI | 9-b-D-Ribofuranosyl-3,9-dihydro-1H-purine-2,6-dione | Generator | 9-Β-D-ribofuranosyl-3,9-dihydro-1H-purine-2,6-dione | Generator | 9-b-D-Ribofuranosylxanthine | Generator | 9-Β-D-ribofuranosylxanthine | Generator | Xanthine 9-b-D-ribofuranoside | Generator | Xanthine 9-β-D-ribofuranoside | Generator | 3,9-Dihydro-9-b-D-ribofuranosyl-1H-purine-2,6-dione | HMDB | 3,9-Dihydro-9-beta-delta-ribofuranosyl-1H-purine-2,6-dione | HMDB | 3,9-Dihydro-9-D-ribofuranosyl-1H-purine-2,6-dione | HMDB | 3,9-Dihydro-9-delta-ribofuranosyl-1H-purine-2,6-dione | HMDB | 9-beta-delta-Ribofuranosylxanthine | HMDB | 9-D-Ribofuranosylxanthine | HMDB | 9-delta-Ribofuranosylxanthine | HMDB | 9 beta-D-Ribofuranosylxanthine | HMDB |
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Chemical Formula | C10H12N4O6 |
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Average Mass | 284.2255 Da |
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Monoisotopic Mass | 284.07568 Da |
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IUPAC Name | 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purine-2,6-diol |
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Traditional Name | 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purine-2,6-diol |
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CAS Registry Number | 146-80-5 |
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SMILES | OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2O |
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InChI Identifier | InChI=1S/C10H12N4O6/c15-1-3-5(16)6(17)9(20-3)14-2-11-4-7(14)12-10(19)13-8(4)18/h2-3,5-6,9,15-17H,1H2,(H2,12,13,18,19)/t3-,5-,6-,9-/m1/s1 |
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InChI Key | UBORTCNDUKBEOP-UUOKFMHZSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-09 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-09 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-09 | View Spectrum | 1D NMR | [1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-09 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600.133705802 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Purine nucleosides |
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Sub Class | Not Available |
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Direct Parent | Purine nucleosides |
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Alternative Parents | |
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Substituents | - Purine nucleoside
- Glycosyl compound
- N-glycosyl compound
- Xanthine
- 6-oxopurine
- Purinone
- Pentose monosaccharide
- Purine
- Imidazopyrimidine
- Alkaloid or derivatives
- Pyrimidone
- Pyrimidine
- Monosaccharide
- N-substituted imidazole
- Imidazole
- Heteroaromatic compound
- Tetrahydrofuran
- Azole
- Vinylogous amide
- Lactam
- Urea
- Secondary alcohol
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Alcohol
- Primary alcohol
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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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 | - Marti R, Nishigaki Y, Hirano M: Elevated plasma deoxyuridine in patients with thymidine phosphorylase deficiency. Biochem Biophys Res Commun. 2003 Mar 28;303(1):14-8. [PubMed:12646159 ]
- Dudley E, Lemiere F, Van Dongen W, Tuytten R, El-Sharkawi S, Brenton AG, Esmans EL, Newton RP: Analysis of urinary nucleosides. IV. Identification of urinary purine nucleosides by liquid chromatography/electrospray mass spectrometry. Rapid Commun Mass Spectrom. 2004;18(22):2730-8. [PubMed:15499664 ]
- Liebich HM, Di Stefano C, Wixforth A, Schmid HR: Quantitation of urinary nucleosides by high-performance liquid chromatography. J Chromatogr A. 1997 Feb 28;763(1-2):193-7. [PubMed:9129323 ]
- Khalil PN, Erb N, Khalil MN, Escherich G, Janka-Schaub GE: Validation and application of a high-performance liquid chromatographic-based assay for determination of the inosine 5'-monophosphate dehydrogenase activity in erythrocytes. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Sep 14;842(1):1-7. Epub 2006 May 24. [PubMed:16725387 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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