(2R,3R,5R)-2-(hydroxymethyl)-5-{3H-imidazo[2,1-f]purin-3-yl}oxolan-3-ol

• ChemBase ID: 168288
• Molecular Formular: C12H13N5O3
• Molecular Mass: 275.26332
• Monoisotopic Mass: 275.1018393
• SMILES: [C@H]1(C[C@@H](O[C@@H]1CO)n1c2ncn3c(c2nc1)ncc3)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1cnc2c1ncn1c2ncc1
• InChI: InChI=1S/C12H13N5O3/c18-4-8-7(19)3-9(20-8)17-6-14-10-11-13-1-2-16(11)5-15-12(10)17/h1-2,5-9,18-19H,3-4H2/t7-,8-,9-/m1/s1
• InChIKey: XQQIMTUYVDUWKJ-IWSPIJDZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,5R)-2-(hydroxymethyl)-5-{3H-imidazo[2,1-f]purin-3-yl}oxolan-3-ol
• IUPAC Traditional name: (2R,3R,5R)-2-(hydroxymethyl)-5-{imidazo[2,1-f]purin-3-yl}oxolan-3-ol
• Synonyms: 3-(2-Deoxy-β-D-erythro-pentofuranosyl)-3H-imidazo[2,1-i]purine; 1,N6-Etheno-2'-deoxyadenosine; 1,N6-Etheno-dA; 1,N6-Ethenodeoxyadenosine; Ethenodeoxyadenosine; N1,N6-Etheno-2'-deoxyadenosine; Etheno-2'-deoxy-β-D-adenosine

Database IDs

• CAS Number: 68498-25-9
• PubChem SID: 162262420
• PubChem CID: 71221844

CALCULATED PROPERTIES

• Acid pKa: 13.886744
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.5439609
• LogD (pH = 7.4): -1.4458379
• Log P: -1.4443976
• Molar Refractivity: 68.0811 cm^3
• Polarizability: 26.568136 Å^3
• Polar Surface Area: 97.7 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E890380

An etheno DNA-adduct of adenosine found in atherosclerotic lesions in aorta smooth muscle cells induced via lipid peroxidation. A biomarker for genotoxicity.

REFERENCES

• Nair, J. et al.: Mut. Res. Fund. Mol. Mech. Mutagen., 621, 95 (2007)
• Meerang, M. et al.: Free Rad. Biol. Med., 44, 1863 (2007)
• Brink, A. et al.: Mut. Res. Gen. Toxicol. Env. Mutagen., 678, 123 (2007)