Xanthosine - Misplaced Pages

Xanthosine
Names

IUPAC name Xanthosine
Systematic IUPAC name 9--3,9-dihydro-1H-purine-2,6-dione
Other names Xanthine riboside; 9-β-D-Ribofuranosylxanthine
Identifiers
CAS Number	146-80-5
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL402439
ChemSpider	58484
ECHA InfoCard	100.005.164
PubChem CID	64959
UNII	BM66HT53C3
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/s1Key: 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/s1Key: UBORTCNDUKBEOP-UUOKFMHZBM
SMILES C1=NC2=C(N13(((O3)CO)O)O)NC(=O)NC2=O O=C3Nc1c(ncn12O((O)2O)CO)C(=O)N3
Properties
Chemical formula	C₁₀H₁₂N₄O₆
Molar mass	284.228 g·mol
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 , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

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.

References

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

Nucleobase

Nucleoside

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

Nucleotide
(Nucleoside monophosphate)

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

Nucleoside diphosphate

ADP GDP mUDP UDP CDP Xanthosine diphosphate
dADP dGDP dTDP dUDP dCDP

Nucleoside triphosphate

ATP GTP mUTP UTP CTP ITP XTP
dATP dGTP dTTP dUTP dCTP dITP dXTP

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References