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

• ChemBase ID: 175242
• Molecular Formular: C10H12N6O7
• Molecular Mass: 328.23828
• Monoisotopic Mass: 328.07674675
• SMILES: [nH]1c(nc2c(c1=O)nc(n2[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)[N+](=O)[O-])N
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1c(nc2c1nc(N)[nH]c2=O)[N+](=O)[O-]
• InChI: InChI=1S/C10H12N6O7/c11-9-13-6-3(7(20)14-9)12-10(16(21)22)15(6)8-5(19)4(18)2(1-17)23-8/h2,4-5,8,17-19H,1H2,(H3,11,13,14,20)/t2-,4-,5-,8-/m1/s1
• InChIKey: KGUOMRFOXYDMAH-UMMCILCDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-nitro-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 8-nitroguanosine
• Synonyms: 8-Nitroguanosine

Database IDs

• CAS Number: 337536-53-5
• PubChem SID: 164231152
• PubChem CID: 16727417

CALCULATED PROPERTIES

• Acid pKa: 10.0601015
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -2.081998
• LogD (pH = 7.4): -2.082825
• Log P: -2.081984
• Molar Refractivity: 71.4191 cm^3
• Polarizability: 26.463879 Å^3
• Polar Surface Area: 201.04 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N496050

A highly reactive redox-active nucleic acid derivative that is is formed in cellular RNA as biomarker of exposure to reactive nitrogen species. Recent studies suggest that it might contribute to the pathogenesis of inflammation-associated carcinogenesis.

REFERENCES

• Sawa, T. et al.: Biochem. Biophys. Res. Comm., 311, 300 (2003)
• Masuda, M. et al.: Chem.-Biol. Inter., 139, 187 (2003)
• Kaneko, K. et al.: Cancer Lett., 262, 239 (2003)