3-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl](6,7,8-13C3)-3H,10H-pyrimido[1,2-a]purin-10-one

• ChemBase ID: 165918
• Molecular Formular: C13H13N5O4
• Molecular Mass: 306.25138451
• Monoisotopic Mass: 306.10681844
• SMILES: n12c(nc3c(c1=O)ncn3[C@H]1C[C@H]([C@H](O1)CO)O)n[13cH][13cH][13cH]2
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1cnc2c1nc1n[13cH][13cH][13cH]n1c2=O
• InChI: InChI=1S/C13H13N5O4/c19-5-8-7(20)4-9(22-8)18-6-15-10-11(18)16-13-14-2-1-3-17(13)12(10)21/h1-3,6-9,19-20H,4-5H2/t7-,8-,9-/m1/s1/i1+1,2+1,3+1
• InChIKey: QZDHOBJINVXQCJ-HJSIFLHTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl](6,7,8-^1^3C₃)-3H,10H-pyrimido[1,2-a]purin-10-one
• IUPAC Traditional name: 3-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl](6,7,8-^1^3C₃)pyrimido[1,2-a]purin-10-one
• Synonyms: M1G-DR-13C3; 3-(2-Deoxy-β-D-erythro-pentofuranosyl)pyrimido[1,2-a]purin-10(3H)-one-13C3

Database IDs

• PubChem SID: 162260051
• PubChem CID: 71315452

CALCULATED PROPERTIES

• Acid pKa: 13.886744
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -1.0790473
• LogD (pH = 7.4): -1.0790199
• Log P: -1.0790194
• Molar Refractivity: 75.1245 cm^3
• Polarizability: 27.6999 Å^3
• Polar Surface Area: 112.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Yellow Solid

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D232907

The major labelled DNA adduct of endogenous carcinogen malondialdehyde.

REFERENCES

• Marnett, L., et al.: Mutat. Res., 148, 25 (1985)
• Rouzer, C., et al.: Chem. Res. Toxicol., 10, 181 (1985)
• Marnett, L., et al.: Mutat. Res., 424, 83 (1985)
• Marnett, L., et al.: J. Clin. Invest., 111, 583 (1985)