FComEx: Xanthosine (PC000052)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:45 UTC

Update date

2017-01-19 02:36:11 UTC

FoodComEx ID

PC000052

FoodDB Record

FDB001604

Chemical Information

Name

Xanthosine

Description

Biological Source: Production by guanine-free mutants of bacteria e.g. Bacillus subtilis, Aerobacter aerogenesand is also reported from seeds of Trifolium alexandrinum Physical Description: Prismatic cryst. (H2O) (Chemnetbase) The deamination product of guanosine; Xanthosine monophosphate is an intermediate in purine metabolism, formed from IMP, and forming GMP.; Xanthylic acid can be used in quantitative measurements of the Inosine monophosphate dehydrogenase enzyme activities in purine metabolism, as recommended to ensure optimal thiopurine therapy for children with acute lymphoblastic leukaemia (ALL). (PMID: 16725387). Xanthosine is found in many foods, some of which are calabash, rambutan, apricot, and pecan nut.

CAS Number

146-80-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
β-D-Ribofuranoside, xanthine-9	biospider
1H-Purine-2,6-dione, 3, 9-dihydro-9-β-D-ribofuranosyl-	biospider
1H-Purine-2,6-dione, 3,9-dihydro-9-beta-D-ribofuranosyl-	biospider
3,9-Dihydro-9-b-D-ribofuranosyl-1H-purine-2,6-dione	biospider
3,9-Dihydro-9-beta-delta-ribofuranosyl-1H-purine-2,6-dione	biospider
3,9-Dihydro-9-D-ribofuranosyl-1H-purine-2,6-dione	biospider
3,9-Dihydro-9-delta-ribofuranosyl-1H-purine-2,6-dione	biospider
9-β-D-Ribofuranosylxanthine	biospider
9-b-D-Ribofuranosylxanthine	biospider
9-beta-D-ribofuranosyl-3,9-dihydro-1H-purine-2,6-dione	biospider
9-beta-D-Ribofuranosylxanthine	biospider
9-beta-delta-Ribofuranosylxanthine	biospider
9-D-Ribofuranosylxanthine	biospider
9-delta-Ribofuranosylxanthine	biospider
beta-D-Ribofuranoside, xanthine-9	biospider
Xanthine riboside	biospider

Chemical Formula

C10H12N4O6

IUPAC name

9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purine-2,6-diol

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)

InChI Key

UBORTCNDUKBEOP-UHFFFAOYSA-N

Isomeric SMILES

OCC1OC(C(O)C1O)N1C=NC2=C1N=C(O)N=C2O

Average Molecular Weight

284.2255

Monoisotopic Molecular Weight

284.075684136

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents