AFCDB: Xanthosine (FDB001604)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:02 UTC

Update date

2019-11-26 02:56:36 UTC

Primary ID

FDB001604

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	27.8 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.2	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	11.33	ChemAxon
pKa (Strongest Basic)	0.078	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.4 m³·mol⁻¹	ChemAxon
Polarizability	25.52 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

Classification

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

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
Xanthine
6-oxopurine
Purinone
Pentose monosaccharide
Purine
Imidazopyrimidine
Alkaloid or derivatives
Pyrimidone
Pyrimidine
Monosaccharide
N-substituted imidazole
Imidazole
Heteroaromatic compound
Tetrahydrofuran
Azole
Vinylogous amide
Lactam
Urea
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a nucleoside (XANTHOSINE )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	0
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0940000000-68452b15ecf92f55bc31	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-ae801ed00992f79b70da	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f79-2900000000-c426dbd88b86eaab5916	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f8c-1590000000-280418101f13bd239fe6	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6x-6910000000-263ac1943def8fa46bc3	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9800000000-263ab0fee77b0b93930c	2015-05-27	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

18107

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00299

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

38352

KNApSAcK ID

C00007222

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Xanthosine (FDB001604)

Structure for FDB001604 (Xanthosine)