9-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,3,6,9-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 179596
• Molecular Formular: C10H12N4O6
• Molecular Mass: 284.22548
• Monoisotopic Mass: 284.07568412
• SMILES: [nH]1c(=O)[nH]c2c(c1=O)ncn2[C@H]1C([C@H]([C@H](O1)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cnc2c1[nH]c(=O)[nH]c2=O
• 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/s1
• InChIKey: UBORTCNDUKBEOP-ACJOCUEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,3,6,9-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: 9-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-dihydropurine-2,6-dione
• Synonyms: 3,9-Dihydro-9-β-D-ribofuranosyl-1H-purine-2,6-dione Dihydrate; Xanthine Riboside Dihydrate; 9-β-D-Ribofuranosylxanthine Dihydrate; NSC 18930 Dihydrate; Xanthine-9 β-D-Ribofuranoside Dihydrate; Xanthosine Dihydrate

Database IDs

• CAS Number: 5968-90-1
• PubChem SID: 164235506
• PubChem CID: 44282993

CALCULATED PROPERTIES

• Acid pKa: 9.026443
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -1.8064616
• LogD (pH = 7.4): -1.8163598
• Log P: -1.8063322
• Molar Refractivity: 62.2085 cm^3
• Polarizability: 23.752626 Å^3
• Polar Surface Area: 145.94 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: >235°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - X742100

The deamination product of Guanosine. Potential biomarker for detecting radiation exposure. Used in the amplification of DNA isothermal strand displacement.

REFERENCES

• Magasanik, B, et al.: J. Bio. Chem., 206, 83 (1954).