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Xanthosine

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Xanthosine^[1]
Names

IUPAC name Xanthosine^[2]
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
CAS Number	146-80-5^Y
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL402439^N
ChemSpider	58484^N
ECHA InfoCard	100.005.164
PubChem CID	64959
UNII	BM66HT53C3^Y
CompTox Dashboard(EPA)	DTXSID90861829
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^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
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	284.228 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 theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Xanthosine is anucleoside derived fromxanthine andribose. It is thebiosynthetic precursor to 7-methylxanthosine by the action of7-methylxanthosine synthase. 7-Methylxanthosine in turn is the precursor totheobromine (active alkaloid in chocolate), which in turn is the precursor tocaffeine, the alkaloid in coffee and tea.^[3]

^Merck Index, 11th Edition,9974
^International Union of Pure and Applied Chemistry (2014).Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013.The Royal Society of Chemistry. p. 1421.doi:10.1039/9781849733069.ISBN 978-0-85404-182-4.
^Ashihara, Hiroshi; Yokota, Takao; Crozier, Alan (2013).Biosynthesis and catabolism of purine alkaloids. Advances in Botanical Research. Vol. 68. pp. 111–138.doi:10.1016/B978-0-12-408061-4.00004-3.ISBN 978-0-12-408061-4.

Nucleic acid constituents

Ribonucleoside	Adenosine Guanosine 5-Methyluridine Uridine 5-Methylcytidine Cytidine Pseudouridine Inosine N⁶-Methyladenosine Xanthosine Wybutosine
Deoxyribonucleoside	Deoxyadenosine Deoxyguanosine Thymidine Deoxyuridine Deoxycytidine Deoxyinosine Deoxyxanthosine

Nucleotide
(Nucleoside monophosphate)

Ribonucleotide	AMP GMP m⁵UMP UMP CMP IMP XMP
Deoxyribonucleotide	dAMP dGMP dTMP dUMP dCMP dIMP dXMP
Cyclic nucleotide	cAMP cGMP c-di-GMP c-di-AMP cADPR cGAMP