Structure via PubChem · Public domain (PubChem)
xanthosine
Sign in to saveAlso known as 9-beta-D-ribofuranosyl-3,9-dihydro-1H-purine-2,6-dione, xanthine 9-beta-D-ribofuranoside, 9-beta-D-Ribofuranosylxanthine, Xanthine riboside, 9-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-3H-purine-2,6-dione, 9-[(2R,3R,4R,5R)-3,4-dihydroxy-5-methylol-tetrahydrofuran-2-yl]-3H-purine-2,6-quinone, 9-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-2,6-dione, 3,9-Dihydro-9-delta-ribofuranosyl-1H-purine-2,6-dione
Xanthosine is a nucleoside derived from xanthine and ribose. It is the biosynthetic precursor to 7-methylxanthosine by the action of 7-methylxanthosine synthase. 7-Methylxanthosine in turn is the precursor to theobromine (active alkaloid in chocolate), which in turn is the precursor to caffeine, the alkaloid in coffee and tea.
Chemical data
- Formula
- C10H12N4O6
- Molecular weight
- 284.23 g/mol
- IUPAC name
- 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-2,6-dione
- SMILES
- C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)NC(=O)NC2=O
- InChIKey
- UBORTCNDUKBEOP-UUOKFMHZSA-N
- XLogP
- -2.4
- Polar surface area
- 146 Ų
- H-bond donors
- 5
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- alkaloid
- Mass
- 284.076
Show 6 more facts
- chemical formula
- C₁₀H₁₂N₄O₆
- canonical SMILES
- C1=NC2=C(N1C3C(C(C(O3)CO)O)O)NC(=O)NC2=O
- isomeric SMILES
- C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)NC(=O)NC2=O
- found in taxon
- Escherichia coli
- Commons category
- Xanthosine
- subject has role
- primary metabolite
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Xanthosine is a nucleoside derived from xanthine and ribose. It is the biosynthetic precursor to 7-methylxanthosine by the action of 7-methylxanthosine synthase. 7-Methylxanthosine in turn is the precursor to theobromine (active alkaloid in chocolate), which in turn is the precursor to caffeine, the alkaloid in coffee and tea.
==See also== Xanthosine monophosphate Xanthosine diphosphate Xanthosine triphosphate
Excerpted from Wikipedia’s “xanthosine” article, available under the CC BY-SA 4.0 licence.