Xanthosine

Xanthosine^[1]

Names
IUPAC name 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-2,6-dione
Other names Xanthine riboside; 9-beta-D-Ribofuranosylxanthine
Identifiers
CAS Number	146-80-5
3D model (Jmol)	Interactive image Interactive image
ChEMBL	ChEMBL402439
ChemSpider	58484
ECHA InfoCard	100.005.164
PubChem	64959
InChI 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 Key: UBORTCNDUKBEOP-UUOKFMHZSA-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
SMILES 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
Chemical formula	C10H12N4O6
Molar mass	284.23 g·mol^−1
Melting point	Decomposes when heated
Solubility in water	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).
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Infobox 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.^[2]

See also

• Xanthosine monophosphate
• Xanthosine diphosphate
• Xanthosine triphosphate

References

1. Merck Index, 11th Edition, 9974
2. Ashihara, Hiroshi; Yokota, Takao; Crozier, Alan (2013). "Biosynthesis and catabolism of purine alkaloids". Advances in Botanical Research. 68: 111–138. doi:10.1016/B978-0-12-408061-4.00004-3.