Record Information |
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Version | 1.0 |
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Created at | 2020-04-17 18:42:25 UTC |
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Updated at | 2020-12-07 19:11:05 UTC |
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CannabisDB ID | CDB004842 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Xanthosine exists in all living species, ranging from bacteria to humans. Within humans, xanthosine participates in a number of enzymatic reactions. In particular, xanthosine can be biosynthesized from xanthylic acid through the action of 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. A purine nucleoside in which xanthine is attached to ribofuranose via a beta-N(9)-glycosidic bond. In humans, xanthosine is involved in the metabolic disorder called the lesch-nyhan syndrome (lns) pathway. Xanthosine is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | |
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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 Molecular Weight | 284.23 |
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Monoisotopic Molecular Weight | 284.0757 |
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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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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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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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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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Spectra |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | Xanthosine, non-derivatized, GC-MS Spectrum | splash10-0032-0963000000-08e48347b76242e521e6 | Spectrum | GC-MS | Xanthosine, non-derivatized, GC-MS Spectrum | splash10-0032-0963000000-08e48347b76242e521e6 | Spectrum | Predicted GC-MS | Xanthosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05fu-9250000000-9694fd3e1c7370e27866 | Spectrum | Predicted GC-MS | Xanthosine, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0059-2110049000-cbeec0d3159947f31d5f | Spectrum | Predicted GC-MS | Xanthosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Xanthosine, TMS_3_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0udi-0900000000-e3e76f5bf26f34680c35 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0udi-7900000000-6e1f70509da5adf99678 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0a4r-9500000000-3cce63949eec45fa9204 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0udi-0910000000-b2c7e01e9105bba310aa | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0udi-0910000000-e6e1d21c0d22b3ad2821 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0910000000-b2c7e01e9105bba310aa | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0910000000-e6e1d21c0d22b3ad2821 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0uk9-8900000000-b0f93d77cf447ada9ed9 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-1900000000-19c92745c311f6435fd3 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0udi-2910000000-6f97748a645ffb972e67 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 0V, Positive | splash10-03di-0900000000-a999e0e022115ec9ec7a | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0910000000-63959f162289e268a620 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0zg0-8900000000-f8aa72afbf821cfb2cf2 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-4900000000-943b0d3fbe3cd8345d54 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-06rl-9400000000-3072bed88bbdca66de69 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0udi-0900000000-f3b10c4bf03522fbd1ff | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0940000000-f59c82b81d81cd9c6b68 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-0udi-0900000000-e0cf07456bb1d35aec56 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-6189db27589e05c3f039 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0940000000-2394018b58d040767e06 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-fec1dd4fe1f5f7e56482 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f79-1900000000-850759ea222062877fa9 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0f8c-1590000000-4fdccf755ee2b8b75ac6 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0f6x-6910000000-308e886a8ecec5d8cd09 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9500000000-af861bef2f6b2f10296c | 2016-09-12 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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Pathways |
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Pathways | Name | SMPDB/Pathwhiz | KEGG | Purine Metabolism | | | Adenosine Deaminase Deficiency | | Not Available | Adenylosuccinate Lyase Deficiency | | Not Available | Gout or Kelley-Seegmiller Syndrome | | Not Available | Lesch-Nyhan Syndrome (LNS) | | Not Available |
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Protein Targets |
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Enzymes | |
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Transporters | Not Available |
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Metal Bindings | |
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Receptors | Not Available |
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Transcriptional Factors | Not Available |
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Concentrations Data |
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| Not Available |
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External Links |
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HMDB ID | HMDB0000299 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB001604 |
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KNApSAcK ID | C00007222 |
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Chemspider ID | 58484 |
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KEGG Compound ID | C01762 |
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BioCyc ID | XANTHOSINE |
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BiGG ID | 38352 |
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Wikipedia Link | Xanthosine |
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METLIN ID | 3408 |
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PubChem Compound | 64959 |
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PDB ID | Not Available |
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ChEBI ID | 18107 |
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References |
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General References | Not Available |
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