[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl acetate

• ChemBase ID: 159076
• Molecular Formular: C12H15N5O5
• Molecular Mass: 309.278
• Monoisotopic Mass: 309.10731861
• SMILES: n1cnc2c(c1N)ncn2[C@H]1[C@@H]([C@@H]([C@H](O1)COC(=O)C)O)O
• Canonical SMILES: CC(=O)OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C12H15N5O5/c1-5(18)21-2-6-8(19)9(20)12(22-6)17-4-16-7-10(13)14-3-15-11(7)17/h3-4,6,8-9,12,19-20H,2H2,1H3,(H2,13,14,15)/t6-,8-,9-,12-/m1/s1
• InChIKey: RMIAANGDAQJRIT-WOUKDFQISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl acetate
• Synonyms: Adenosine 5'-Acetate; 5'-Acetyladenosine; NSC 91775; 5'-O-Acetyl Adenosine

Database IDs

• CAS Number: 2140-25-2
• PubChem SID: 162253211
• PubChem CID: 11953391

CALCULATED PROPERTIES

• Acid pKa: 12.456749
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -1.7649919
• LogD (pH = 7.4): -1.6515044
• Log P: -1.6498384
• Molar Refractivity: 72.3471 cm^3
• Polarizability: 28.403112 Å^3
• Polar Surface Area: 145.61 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A168060

Adenosine derivative.

REFERENCES

• Bloch, A., et al.: J. Med. Chem., 10, 908 (1967)
• Wilson, D., et al.: Biochemistry, 32, 1689 (1967)
• Ferrero, M., et al.: Chem. Rev., 100, 4319 (1967)