(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol

• ChemBase ID: 173235
• Molecular Formular: C11H15N5O4
• Molecular Mass: 281.2679
• Monoisotopic Mass: 281.11240399
• SMILES: n1cnc2c(c1N)ncn2[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)OC
• Canonical SMILES: CO[C@@H]1[C@H](O)[C@H](O[C@H]1n1cnc2c1ncnc2N)CO
• InChI: InChI=1S/C11H15N5O4/c1-19-8-7(18)5(2-17)20-11(8)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
• InChIKey: FPUGCISOLXNPPC-IOSLPCCCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol
• IUPAC Traditional name: (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol
• Synonyms: 2'-O-Methyl-D-adenosine; 5-(6-Aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol; 2'-O-Methyl Adenosine

Database IDs

• CAS Number: 2140-79-6
• PubChem SID: 164229145
• PubChem CID: 102213

CALCULATED PROPERTIES

• Acid pKa: 12.992759
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -1.5629786
• LogD (pH = 7.4): -1.4495004
• Log P: -1.4478374
• Molar Refractivity: 67.9468 cm^3
• Polarizability: 26.43153 Å^3
• Polar Surface Area: 128.54 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 198-200°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M276150

Adenosine analog. Used for preparation of nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase.

REFERENCES

• Eldrup, A.B., et al.: J. Med. Chem., 47, 2283 (2004)
• Shim, J., et al.: Antiviral Res., 243 (2004)
• Wang, M., et al.: J. Biol. Chem., 278, 9489 (2004)