(2R,4R,5R)-2-(2-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 160459
• Molecular Formular: C10H13N5O4
• Molecular Mass: 267.24132
• Monoisotopic Mass: 267.09675392
• SMILES: n1c(nc2c(c1)ncn2[C@H]1C([C@H]([C@H](O1)CO)O)O)N
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cnc2c1nc(N)nc2
• InChI: InChI=1S/C10H13N5O4/c11-10-12-1-4-8(14-10)15(3-13-4)9-7(18)6(17)5(2-16)19-9/h1,3,5-7,9,16-18H,2H2,(H2,11,12,14)/t5-,6+,7?,9-/m1/s1
• InChIKey: JVOJULURLCZUDE-WJZMDOFJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5R)-2-(2-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,4R,5R)-2-(2-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 2-Amino-9-β-D-ribofuranosylpurine; NSC 36906; 2-Aminopurine Riboside

Database IDs

• CAS Number: 4546-54-7
• PubChem SID: 162254594
• PubChem CID: 46780354

CALCULATED PROPERTIES

• Acid pKa: 12.453977
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.100645
• LogD (pH = 7.4): -2.0079696
• Log P: -2.0066354
• Molar Refractivity: 62.8281 cm^3
• Polarizability: 24.544918 Å^3
• Polar Surface Area: 139.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; Methanol
• Apperance: Off-White Crystalline Solid
• Melting Point: 105-115°C

DETAILS

Toronto Research Chemicals - A628900

A probe of structural dynamicas and charge transfer in DNA .

REFERENCES

• Liu, Q., et al.: J. Mol. Biol., 267, 163 (1997)
• Lunn, F., et al.: J. Biol. Chem., 283, 2010 (1997)