Xanthosine
Basic information
- CAS
146-80-5- Standard SMILES
O=c1[nH]c(=O)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2[nH]1- InChIKey
UBORTCNDUKBEOP-UUOKFMHZSA-N- Molecular formula
- C10H12N4O6
- Average molar mass
- 284.23 g/mol
- Monoisotopic mass
- 284.07568412
Overview
Xanthosine is a purine nucleoside in which xanthine is attached to ribofuranose via a beta-N9-glycosidic bond. It has a role as a mouse metabolite, an Escherichia coli metabolite and a human metabolite. It is a purines D-ribonucleoside and a member of xanthosines.
Names & identifiers
- Preferred name
- Xanthosine
- IUPAC
- 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-2,6-dione
- English name
- XANTHOSINE
- Molecular formula
- C10H12N4O6
- Molecular weight
- 284.23
Names & synonyms
xanthosine146-80-5Xanthine riboside9 beta-D-ribofuranosylxanthineBM66HT53C39-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-2,6-dione1H-Purine-2,6-dione, 3,9-dihydro-9-beta-D-ribofuranosyl-CHEBI:18107DTXSID90861829NSC-189309-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-3H-purine-2,6-dione9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-9H-purine-2,6-diol
Show more names
1g1-Benzyl-3,3-difluoropiperidin-4-one9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purine-2,6-diol1-(Tetrahydrofuran-3-yl)piperazine4-broMo-1-ethyl-5-nitro-1H-pyrazolelithiuM trihydroxy(4-Methylpyridin-2-yl)borate2,4-dichloro-6,8-dihydro-5H-thiopyrano[3,4-d]pyriMidineTert-butyl 3-broMo-7,8-dihydro-[1,2,4]triazolo[4,3-c]pyriMidine-6(5H)-carboxylateXrXao
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purine-2,6-diolRefChem:195180DTXCID1014748557-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl)-3H-purine-2,6-dione205-679-99-beta-D-RibofuranosylxanthineXanthosine-13C5MFCD00005726
Database identifiers
- CAS
146-80-5- PubChem CID
- 64959
- DTXSID
DTXSID90861829- ChEMBL
CHEMBL402439- ChEBI
CHEBI:18107- UNII
- BM66HT53C3
- EC Number
- 205-679-9
- Nikkaji
- J9.367J
Properties
Computed structural properties
- XLogP
- -2.4
- Topological polar surface area
- 146 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 2
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 434
Experimental & physicochemical properties
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
Physical DescriptionSolid
Collision Cross Section
158 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
158.3 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
172.8 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
161.36 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
162.4 Ų [M-2H+Na]-
Physicochemical properties
- Melting point
- 174 · 174~176℃
- Density
- 2.25 · 2.25±0.1 g/cm3(Predicted)
- refractive index
- -52 ° · -52 ° (C=8, 0.3mol/L NaOH)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
- solubility
- Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
- form
- Solid
- pka
- 1 · pK1:<2.5(+1);pK2:5.67(0);pK3:12.00(-1) (25°C)
- color
- White to Off-White
- Merck
- 14 · 14,10065
- Stability
- Hygroscopic
- 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
- InChIKey
- UBORTCNDUKBEOP-UUOKFMHZSA-N
- SMILES
- O[C@H]1[C@@H](O)[C@H](N(C=N2)C3=C2C(NC(N3)=O)=O)O[C@@H]1CO
- CAS DataBase Reference
- 146 · 146-80-5(CAS DataBase Reference)
- FDA UNII
- 66 HT53C3 · BM66HT53C3
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 21 · NA.21
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302+H332-H314
- Precautionary statements
- 501 · P501-P260-P270-P271-P264-P280-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- HS Code
- 29349990 · 29349990
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationXanthosine: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- wgk
- 3
- hs_code
- 29349990
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302+H332-H314
- Precautionary statements
- P501-P260-P270-P271-P264-P280-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405
Chemistry & industry
Pharmacology
Tissue LocationsPlacenta
Cellular LocationsCytoplasm
Metabolite PathwaysAdenine phosphoribosyltransferase deficiency (APRT)
Applications
UsesXanthosine-13C5, is the labeled analogue of Xanthosine (X742100), the deamination product of Guanosine. It is also a potential biomarker for detecting radiation exposure.
UsesThe deamination product of Guanosine. Potential biomarker for detecting radiation exposure. XANTHOSINE is used in the amplification of DNA isothermal strand displacement.
Additional notes
DefinitionChEBI: A purine nucleoside in which xanthine is attached to ribofuranose via a beta-N9-glycosidic bond.
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