(2R,3S,5R)-2-[6-(benzylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 161386
• Molecular Formular: C17H19N5O4
• Molecular Mass: 357.36386
• Monoisotopic Mass: 357.14370411
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)c(ncn2)NCc1ccccc1)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1cnc2c1ncnc2NCc1ccccc1
• InChI: InChI=1S/C17H19N5O4/c23-7-11-13(24)14(25)17(26-11)22-9-21-12-15(19-8-20-16(12)22)18-6-10-4-2-1-3-5-10/h1-5,8-9,11,13-14,17,23-25H,6-7H2,(H,18,19,20)/t11-,13?,14+,17-/m1/s1
• InChIKey: MRPKNNSABYPGBF-OVHGWZCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-2-[6-(benzylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,5R)-2-[6-(benzylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 6-Benzylaminopurine Riboside; N-(Phenylmethyl)adenosine; 6-(Benzylamino)-9-β-D-ribofuranosylpurine; 6-Benzyladenosine; NSC 70423; N6-Benzyl Adenosine; N6-Benzyladenosine; 6-Benzylaminopurine Riboside

Database IDs

• CAS Number: 4294-16-0
• PubChem SID: 162255521
• PubChem CID: 71313763

CALCULATED PROPERTIES

• Acid pKa: 12.453924
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.14998783
• LogD (pH = 7.4): -0.06597662
• Log P: -0.06478667
• Molar Refractivity: 93.3016 cm^3
• Polarizability: 35.859524 Å^3
• Polar Surface Area: 125.55 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Methanol; Water
• Apperance: Off-White Powder; White Solid
• Melting Point: 146-148°C; 166-168°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B224615

A selective A1 adenosine receptor agonist.

Toronto Research Chemicals - B228050

A selective A1 adenosine receptor agonist.

REFERENCES

• Cappellacci, L., et al.: J. Med. Chem., 51, 4260 (2008)
• Fells, J., et al.: Bioorg. Med. Chem., 16, 6207 (2008)
• Van Roel, C., et al.: J. Med. Chem., 42, 8, 1393 (1999)