Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:35:40 UTC
Update Date2024-04-30 19:31:51 UTC
Metabolite IDMMDBc0000338
Metabolite Identification
Common NameXanthosine
DescriptionXanthosine, also known as xanthine riboside, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Xanthosine is a nucleoside derived from xanthine and ribose. Xanthosine exists in all living species, ranging from bacteria to plants to humans. In plants xanthosine is the biosynthetic precursor to 7-methylxanthosine which is produced by the action of the enzyme known as 7-methylxanthosine synthase. 7-Methylxanthosine in turn is the precursor to theobromine (the active alkaloid in chocolate), which in turn is the precursor to caffeine, the active alkaloid in coffee and tea. Within humans, xanthosine participates in a number of enzymatic reactions. In particular, xanthosine can be biosynthesized from xanthylic acid; which is catalyzed by the enzyme cytosolic purine 5'-nucleotidase. In addition, xanthosine can be converted into xanthine and ribose 1-phosphate; which is mediated by the enzyme purine nucleoside phosphorylase. Xanthosine monophosphate (XMP) is an intermediate in purine metabolism, formed from IMP (inosine monophosphate).
Structure
Synonyms
ValueSource
9-beta-D-Ribofuranosyl-3,9-dihydro-1H-purine-2,6-dioneChEBI
9-beta-D-RibofuranosylxanthineChEBI
Xanthine 9-beta-D-ribofuranosideChEBI
Xanthine ribosideChEBI
9-b-D-Ribofuranosyl-3,9-dihydro-1H-purine-2,6-dioneGenerator
9-Β-D-ribofuranosyl-3,9-dihydro-1H-purine-2,6-dioneGenerator
9-b-D-RibofuranosylxanthineGenerator
9-Β-D-ribofuranosylxanthineGenerator
Xanthine 9-b-D-ribofuranosideGenerator
Xanthine 9-β-D-ribofuranosideGenerator
3,9-Dihydro-9-b-D-ribofuranosyl-1H-purine-2,6-dioneHMDB
3,9-Dihydro-9-beta-delta-ribofuranosyl-1H-purine-2,6-dioneHMDB
3,9-Dihydro-9-D-ribofuranosyl-1H-purine-2,6-dioneHMDB
3,9-Dihydro-9-delta-ribofuranosyl-1H-purine-2,6-dioneHMDB
9-beta-delta-RibofuranosylxanthineHMDB
9-D-RibofuranosylxanthineHMDB
9-delta-RibofuranosylxanthineHMDB
9 beta-D-RibofuranosylxanthineHMDB
Molecular FormulaC10H12N4O6
Average Mass284.2255
Monoisotopic Mass284.075684136
IUPAC Name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purine-2,6-diol
Traditional Name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purine-2,6-diol
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2O
InChI Identifier
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
InChI KeyUBORTCNDUKBEOP-UUOKFMHZSA-N