(2R,3S,5S)-2-(6-amino-9H-purin-9-yl)-5-(iodomethyl)oxolane-3,4-diol

• ChemBase ID: 171599
• Molecular Formular: C10H12IN5O3
• Molecular Mass: 377.13845
• Monoisotopic Mass: 376.99848727
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)c(ncn2)N)CI)O)O
• Canonical SMILES: IC[C@H]1O[C@H]([C@H](C1O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C10H12IN5O3/c11-1-4-6(17)7(18)10(19-4)16-3-15-5-8(12)13-2-14-9(5)16/h2-4,6-7,10,17-18H,1H2,(H2,12,13,14)/t4-,6?,7+,10-/m1/s1
• InChIKey: FUWWLIOFNXNKQR-HMEJCUHCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5S)-2-(6-amino-9H-purin-9-yl)-5-(iodomethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,5S)-2-(6-aminopurin-9-yl)-5-(iodomethyl)oxolane-3,4-diol
• Synonyms: 5'-Deoxy-5'-iodoadenosine; 5'-Iodo-5'-deoxyadenosine; 5'-Iodo-5'-deoxy Adenosine

Database IDs

• CAS Number: 4099-81-4
• PubChem SID: 164227509
• PubChem CID: 45039580

CALCULATED PROPERTIES

• Acid pKa: 12.472285
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.3916618
• LogD (pH = 7.4): -0.2781723
• Log P: -0.27650648
• Molar Refractivity: 74.6328 cm^3
• Polarizability: 29.072178 Å^3
• Polar Surface Area: 119.31 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 178-187°C

DETAILS

Toronto Research Chemicals - I705000

Important precursors for the synthesis of nucleotides, sugar nucleosides and as biologically active substances.

REFERENCES

• Jain, T.C., et al.: J. Org. Chem., 39, 20 (1974)