(6,7,8-13C3)-3H,10H-pyrimido[1,2-a]purin-10-one

• ChemBase ID: 177217
• Molecular Formular: C8H5N5O
• Molecular Mass: 190.13616451
• Monoisotopic Mass: 190.05947432
• SMILES: n12c(nc3c(c1=O)nc[nH]3)n[13cH][13cH][13cH]2
• Canonical SMILES: O=c1c2nc[nH]c2nc2n1[13cH][13cH][13cH]n2
• InChI: InChI=1S/C8H5N5O/c14-7-5-6(11-4-10-5)12-8-9-2-1-3-13(7)8/h1-4H,(H,10,11)/i1+1,2+1,3+1
• InChIKey: ZREGNVKUSNORFO-VMIGTVKRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6,7,8-^1^3C₃)-3H,10H-pyrimido[1,2-a]purin-10-one
• IUPAC Traditional name: (6,7,8-^1^3C₃)-3H-pyrimido[1,2-a]purin-10-one
• Synonyms: Pyrimido[1,2-a]purin-10(3H)-one-13C3; M1G-13C3; Pyrimido[1,2-a]purin-10(1H)-one-13C3

Database IDs

• PubChem SID: 164233127
• PubChem CID: 71751900

CALCULATED PROPERTIES

• Acid pKa: 10.096015
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.41978827
• LogD (pH = 7.4): -0.4204933
• Log P: -0.4197063
• Molar Refractivity: 50.0389 cm^3
• Polarizability: 17.183456 Å^3
• Polar Surface Area: 73.71 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: >179°C (Dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P997402

Labelled M1G. M1G is a secondary DNA damage product arising from primary reactive oxygen species (ROS) damage to membrane lipids or deoxyribose. It is a guanine adduct formed by reaction of malondialdehyde with DNA.

REFERENCES

• Ham, A., et al.: Chem. Res. Toxicol., 13, 1243 (2000)
• Sharma, R., et al.: Clin. Cancer Res., 7, 1452 (2000)
• Jeong, Y., et al.: Chem. Res. Toxicol., 18, 51 (2000)