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

• ChemBase ID: 178847
• Molecular Formular: C16H19N5O7
• Molecular Mass: 393.35136
• Monoisotopic Mass: 393.12844797
• SMILES: c1nc(c2c(n1)n(cn2)[C@@H]1[C@@H]([C@@H]([C@H](O1)COC(=O)C)OC(=O)C)OC(=O)C)N
• Canonical SMILES: CC(=O)O[C@@H]1[C@H](OC(=O)C)[C@H](O[C@@H]1n1cnc2c1ncnc2N)COC(=O)C
• InChI: InChI=1S/C16H19N5O7/c1-7(22)25-4-10-12(26-8(2)23)13(27-9(3)24)16(28-10)21-6-20-11-14(17)18-5-19-15(11)21/h5-6,10,12-13,16H,4H2,1-3H3,(H2,17,18,19)/t10-,12-,13-,16+/m1/s1
• InChIKey: GCVZNVTXNUTBFB-VSBTWAGUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R,5S)-3,4-bis(acetyloxy)-5-(6-amino-9H-purin-9-yl)oxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4R,5S)-3,4-bis(acetyloxy)-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl acetate
• Synonyms: 9-(2,3,5-Tri-O-acetyl-α-D-ribofuranosyl)-9H-purin-6-amine; 9-(2,3,5-Tri-O-acetyl-α-D-ribofuranosyl)adenine; 2,3,5-Tri-O-acetyl α-Adenosine

Database IDs

• CAS Number: 953089-09-3
• PubChem SID: 164234757
• PubChem CID: 40806590

CALCULATED PROPERTIES

• Acid pKa: 18.535484
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): -0.88270015
• LogD (pH = 7.4): -0.7692491
• Log P: -0.76758766
• Molar Refractivity: 90.6501 cm^3
• Polarizability: 36.117744 Å^3
• Polar Surface Area: 157.75 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T733805

An Adenosine (A280400) impurity.

REFERENCES

• Ciuffreda, P. et al.: Mag, Reson. Chem., 45, 781 (2007)
• Long, X., et al.: J. Pharmacol. Exper. Ther., 335, 781 (2007)
• Ham, M., et al.: J. Pharmacol. Exper. Ther., 335, 607 (2007)