Xanthosine

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.

Xanthosine
Names
IUPAC name
Xanthosine
Systematic IUPAC name
9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,9-dihydro-1H-purine-2,6-dione
Other names
Xanthine riboside; 9-β-D-Ribofuranosylxanthine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.164
UNII
  • 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 N
    Key: UBORTCNDUKBEOP-UUOKFMHZSA-N N
  • InChI=1/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
    Key: UBORTCNDUKBEOP-UUOKFMHZBM
  • C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)NC(=O)NC2=O
  • O=C3Nc1c(ncn1[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO)C(=O)N3
Properties
C10H12N4O6
Molar mass 284.228 g·mol−1
Melting point Decomposes when heated
Sparingly soluble in cold water; freely soluble in hot water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references
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