2-amino-8-hydroxy-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro(2-13C,1-15N)-1H-purin-6-one

• ChemBase ID: 176005
• Molecular Formular: C10H13N5O5
• Molecular Mass: 286.22019263
• Monoisotopic Mass: 286.08909317
• SMILES: [15nH]1[13c](nc2c(c1=O)nc(n2[C@H]1C[C@H]([C@H](O1)CO)O)O)[15NH2]
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1c(O)nc2c1n[13c]([15NH2])[15nH]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/i9+1,11+1,14+1
• InChIKey: HCAJQHYUCKICQH-XWVHDTTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-8-hydroxy-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro(2-^1^3C,1-^1^5N)-1H-purin-6-one
• IUPAC Traditional name: 2-amino-8-hydroxy-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl](2-^1^3C,1-^1^5N)-1H-purin-6-one
• Synonyms: 8-Oxo-dG-13C,15N2; 8-Oxo-2'-deoxyguanosine-13C,15N2; 8-Hydroxy-2’-deoxyguanosine-13C,15N2; 8-Oxo-7,8-dihydrodeoxyguanosine-13C,15N2; 2'-Deoxy-7,8-dihydro-8-oxo-guanosine-13C,15N2; 8-Oxo-7,8-dihydro-2'-deoxyguanosine-13C,15N2

Database IDs

• PubChem SID: 164231915
• PubChem CID: 71751372

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
• Apperance: White Solid
• Melting Point: 195-200°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - O850252

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

REFERENCES

• Ueda, T., et al.: Chem. Pharm. Bull., 26, 2122 (1978)
• Jiang, F., et al.: Nature, 183, 382 (1978)