1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl](7,8-13C2,2,7,8-2H3)-1H,4H,5H-imidazo[2,1-b]purin-4-one

• ChemBase ID: 168206
• Molecular Formular: C12H13N5O4
• Molecular Mass: 293.24802968
• Monoisotopic Mass: 293.1034636
• SMILES: [nH]1c2n(c3c(c1=O)ncn3[C@H]1C[C@H]([C@H](O1)CO)O)[13cH][13cH]n2
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1cnc2c1n1[13cH][13cH]nc1[nH]c2=O
• InChI: InChI=1S/C12H13N5O4/c18-4-7-6(19)3-8(21-7)17-5-14-9-10(20)15-12-13-1-2-16(12)11(9)17/h1-2,5-8,18-19H,3-4H2,(H,13,15,20)/t6-,7-,8-/m1/s1/i1+1,2+1
• InChIKey: DUHWHZGZQYBCAZ-XNTGKRBTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl](7,8-^1^3C₂,2,7,8-^2H₃)-1H,4H,5H-imidazo[2,1-b]purin-4-one
• IUPAC Traditional name: 1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl](7,8-^1^3C₂,2,7,8-^2H₃)-5H-imidazo[2,1-b]purin-4-one
• Synonyms: 1-(2-Deoxy-β-D-erythro-pentofuranosyl)-1H-imidazo[2,1-b]purin-4(5H)-one-d3; N2,3-Etheno-2'-deoxy Guanosine-d3

Database IDs

• PubChem SID: 162262338
• PubChem CID: 71316441

CALCULATED PROPERTIES

• Acid pKa: 9.82159
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.6340802
• LogD (pH = 7.4): -1.6356035
• Log P: -1.634
• Molar Refractivity: 79.8769 cm^3
• Polarizability: 26.49128 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E678002

A labelled etheno-substituted purine nucleoside derivative with fluorescent and biochemical properties. Etheno-DNA adducts are promutagenic lesions present in normal animal and human tissues that are believed to be important in the etiol. of cancer relate

REFERENCES

• Schlatter, J., et al.: Food Chem. Toxicol., 28, 205 (1990)
• Chen, H., et al.: Chem. Res. Toxicol., 12, 1119 (1990)
• Nair, J., et al.: Mutat. Res., 424, 59 (1990)