(2S,5S)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol

• ChemBase ID: 165845
• Molecular Formular: C10H13N5O3
• Molecular Mass: 251.24192
• Monoisotopic Mass: 251.1018393
• SMILES: C1C([C@@H](O[C@@H]1n1c2c(nc1)c(ncn2)N)CO)O
• Canonical SMILES: OC[C@@H]1O[C@@H](CC1O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5?,6-,7-/m0/s1
• InChIKey: OLXZPDWKRNYJJZ-BYRXKDITSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5S)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• IUPAC Traditional name: (2S,5S)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• Synonyms: 9-(2-Deoxy-β-L-erythro-pentofuranosyl)-9H-purin-6-amine; 2'-Deoxy-β-L-adenosine

Database IDs

• CAS Number: 14365-45-8
• PubChem SID: 162259978
• PubChem CID: 59891165

CALCULATED PROPERTIES

• Acid pKa: 13.886734
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.3084735
• LogD (pH = 7.4): -1.1920375
• Log P: -1.1903259
• Molar Refractivity: 61.6849 cm^3
• Polarizability: 23.860369 Å^3
• Polar Surface Area: 119.31 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White Solid
• Melting Point: 186-187°C

DETAILS

Toronto Research Chemicals - D231625

A useful synthon for modified oligodeoxyribonucleotides.

REFERENCES

• Fujimori, S., et al.: Nucleoside & Nucleotide, 11(2-4), 341 (1992)