2-amino-9-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-hydroxy-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 170629
• Molecular Formular: C10H13N5O6
• Molecular Mass: 299.24012
• Monoisotopic Mass: 299.08658316
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1O)c(=O)[nH]c(n2)N)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1c(O)nc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C10H13N5O6/c11-9-13-6-3(7(19)14-9)12-10(20)15(6)8-5(18)4(17)2(1-16)21-8/h2,4-5,8,16-18H,1H2,(H,12,20)(H3,11,13,14,19)/t2-,4?,5+,8-/m1/s1
• InChIKey: FPGSEBKFEJEOSA-UKPFUCPKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-hydroxy-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-hydroxy-1H-purin-6-one
• Synonyms: 2-Amino-9-β-D-ribofuranosyl-purine-6,8(1H,9H)-dione; 8-OHG; 8-Oxo-7,8-dihydroguanosine; 8-Oxoguanosine; NSC 90393; 8-Hydroxy Guanosine

Database IDs

• CAS Number: 3868-31-3
• PubChem SID: 164226539
• PubChem CID: 71749063

CALCULATED PROPERTIES

• Acid pKa: 10.084022
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -2.325589
• LogD (pH = 7.4): -2.3263319
• Log P: -2.3255336
• Molar Refractivity: 66.0753 cm^3
• Polarizability: 25.036772 Å^3
• Polar Surface Area: 175.45 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Hot Water
• Apperance: Off-White Solid
• Melting Point: 232-235°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H942770

It is a representative metabolite derived by the oxidation of Guanosine (G) and is regarded as a marker of oxidative stress in the cells.

REFERENCES

• Lin, T.-S. et al.: J. Med. Chem., 28, 1194 (1985)
• Risom, L., et al.: Mutat. Res., 592, 119 (1985)
• Knaapen, A., et al.: Mutagenesis, 21, 225 (1985)