2-amino-8-nitro-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 175240
• Molecular Formular: C5H4N6O3
• Molecular Mass: 196.12366
• Monoisotopic Mass: 196.03448802
• SMILES: [nH]1c(nc2c(c1=O)nc([nH]2)[N+](=O)[O-])N
• Canonical SMILES: [O-][N+](=O)c1[nH]c2c(n1)c(=O)[nH]c(n2)N
• InChI: InChI=1S/C5H4N6O3/c6-4-8-2-1(3(12)10-4)7-5(9-2)11(13)14/h(H4,6,7,8,9,10,12)
• InChIKey: IYHJRKNFFYAOGE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-8-nitro-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-8-nitro-1,9-dihydropurin-6-one
• Synonyms: 2-Amino-1,9-dihydro-8-nitro-6H-purin-6-one; 2-Amino-1,7-dihydro-8-nitro-6H-purin-6-one; 8-Nitroguanine

Database IDs

• CAS Number: 168701-80-2
• PubChem SID: 164231150
• PubChem CID: 4112249

CALCULATED PROPERTIES

• Acid pKa: 0.1609579
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.4307532
• LogD (pH = 7.4): -1.4339907
• Log P: -1.0233444
• Molar Refractivity: 44.8228 cm^3
• Polarizability: 15.23597 Å^3
• Polar Surface Area: 141.98 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Yellow to Brown Solid
• Melting Point: >260°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N496010

8-Nitroguanine as a potential biomarker for progression of malignant fibrous histiocytoma, a model of inflammation-related cancer.

REFERENCES

• Surh, Y., et al.: Mutat. Res., 480, 243 (2001)
• Balkwill, F., et al.: Lancet, 357, 539 (2001)
• Kawanishi, S., et al.: Biol. Chem., 387, 365 (2001)
• Hoki, Y., et al.: Cancer Sci., 98, 163 (2001)