2-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 172948
• Molecular Formular: C13H19N5O6
• Molecular Mass: 341.31986
• Monoisotopic Mass: 341.13353335
• SMILES: [C@@H]1([C@H]([C@@H](O[C@@H]1CO)n1cnc2c1nc([nH]c2=O)N)OCCOC)O
• Canonical SMILES: COCCO[C@@H]1[C@H](O)[C@H](O[C@H]1n1cnc2c1nc(N)[nH]c2=O)CO
• InChI: InChI=1S/C13H19N5O6/c1-22-2-3-23-9-8(20)6(4-19)24-12(9)18-5-15-7-10(18)16-13(14)17-11(7)21/h5-6,8-9,12,19-20H,2-4H2,1H3,(H3,14,16,17,21)/t6-,8-,9-,12-/m1/s1
• InChIKey: DLLBJSLIKOKFHE-WOUKDFQISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)oxolan-2-yl]-1H-purin-6-one
• Synonyms: 2'-O-(2-Methoxyethyl)guanosine

Database IDs

• CAS Number: 473278-54-5
• PubChem SID: 164228858
• PubChem CID: 11024293

CALCULATED PROPERTIES

• Acid pKa: 10.157276
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -2.110135
• LogD (pH = 7.4): -2.1107378
• Log P: -2.1100671
• Molar Refractivity: 80.4158 cm^3
• Polarizability: 30.584269 Å^3
• Polar Surface Area: 153.45 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M262525

A guanosine derivative as building blocks for cross-linking oligonucleotides.

REFERENCES

• Altmann, K., et al.: Bioorg. Med. Chem. Lett., 5, 431 (1995)