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

• ChemBase ID: 170432
• Molecular Formular: C10H13N5O5
• Molecular Mass: 283.24072
• Monoisotopic Mass: 283.09166854
• SMILES: C1C([C@H](O[C@H]1n1c2c(nc1O)c(=O)[nH]c(n2)N)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](CC1O)n1c(O)nc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C10H13N5O5/c11-9-13-7-6(8(18)14-9)12-10(19)15(7)5-1-3(17)4(2-16)20-5/h3-5,16-17H,1-2H2,(H,12,19)(H3,11,13,14,18)/t3?,4-,5-/m1/s1
• InChIKey: HCAJQHYUCKICQH-YZNZAMEGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-8-hydroxy-9-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-8-hydroxy-9-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• Synonyms: 8-Oxo-dG; 8-Oxo-7,8-dihydrodeoxyguanosine; 8-Hydroxydeoxyguanosine; 7,8-Dihydro-8-oxo-2'-deoxyguanosine; 8-Hydroxy-2'-deoxyguanosine; 8-Hydroxy-2’-deoxyguanosine; 2'-Deoxy-7,8-dihydro-8-oxo-guanosine; 8-Oxo-7,8-dihydro-2'-deoxyguanosine; 8-Oxo-2'-deoxyguanosine

Database IDs

• CAS Number: 88847-89-6
• PubChem SID: 164226342
• PubChem CID: 9882223

CALCULATED PROPERTIES

• Acid pKa: 10.08777
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.424954
• LogD (pH = 7.4): -1.425686
• Log P: -1.4248954
• Molar Refractivity: 64.5646 cm^3
• Polarizability: 24.32116 Å^3
• Polar Surface Area: 155.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Crystalline Solid; White to Off-White Solid
• Melting Point: 205-210°C (dec.); 217-220°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H935500

A marker compound indicative of DNA damage associated with mutagenesis and carcinogenesis. Can induce differentiation of Friend murine erythroleukemia cells in vitro.

Toronto Research Chemicals - O850250

A marker compound indicative of DNA damage associated with mutagenesis and carcinogenesis. Can induce differentiation of Friend murine erythroleukemia cells in vitro.

REFERENCES

• Lin, T-S. et al.: J. Med Chem., 28, 1194*1198 (1985)
• Ueda, T., et al.: Chem. Pharm. Bull., 26, 2122 (1978)
• Jiang, F., et al.: Nature, 183, 382 (1978)