(2R,3R,5R)-5-{2-amino-6-[2-hydroxy(2H4)ethoxy]-9H-purin-9-yl}-2-(hydroxymethyl)oxolan-3-ol

• ChemBase ID: 170548
• Molecular Formular: C12H17N5O5
• Molecular Mass: 311.29388
• Monoisotopic Mass: 311.12296867
• SMILES: n1c(nc2c(c1OCCO)ncn2[C@H]1C[C@H]([C@H](O1)CO)O)N
• Canonical SMILES: OCCOc1nc(N)nc2c1ncn2[C@@H]1O[C@@H]([C@@H](C1)O)CO
• InChI: InChI=1S/C12H17N5O5/c13-12-15-10-9(11(16-12)21-2-1-18)14-5-17(10)8-3-6(20)7(4-19)22-8/h5-8,18-20H,1-4H2,(H2,13,15,16)/t6-,7-,8-/m1/s1
• InChIKey: ITCDOLZXZOEIBY-BWZBUEFSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,5R)-5-{2-amino-6-[2-hydroxy(^2H₄)ethoxy]-9H-purin-9-yl}-2-(hydroxymethyl)oxolan-3-ol
• IUPAC Traditional name: (2R,3R,5R)-5-{2-amino-6-[2-hydroxy(^2H₄)ethoxy]purin-9-yl}-2-(hydroxymethyl)oxolan-3-ol
• Synonyms: 2'-Deoxy-6-O-(2-hydroxyethyl-d4)guanosine; OHEdG-d4; O6-(2-Hydroxyethyl-d4)-2'-deoxyguanosine

Database IDs

• PubChem SID: 164226458
• PubChem CID: 71749027

CALCULATED PROPERTIES

• Acid pKa: 13.858959
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -1.3593217
• LogD (pH = 7.4): -1.3593134
• Log P: -1.359313
• Molar Refractivity: 74.3864 cm^3
• Polarizability: 28.929129 Å^3
• Polar Surface Area: 148.77 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 164-166°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H942022

A labelled DNA adduct from N-nitrosodiethanolamine and related β-oxidized nitrosamines. It is produced by nitrosamine bident carcinogens.

REFERENCES

• Wilson, V., et al.: Cancer Res., 48, 2156 (1988)
• Gorelick, N., et al.: Mutat. Res., 288, 5 (1988)
• Niedernhofer, L., wt al.: Chem. Res. Toxicol., 10, 556 (1988)