(2R,3S,5R)-2-(6-amino-8-bromo-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 162742
• Molecular Formular: C10H12BrN5O4
• Molecular Mass: 346.13738
• Monoisotopic Mass: 345.00726589
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1Br)c(ncn2)N)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1c(Br)nc2c1ncnc2N
• InChI: InChI=1S/C10H12BrN5O4/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,13,14)/t3-,5?,6+,9-/m1/s1
• InChIKey: VJUPMOPLUQHMLE-DTUHVUQASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-2-(6-amino-8-bromo-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,5R)-2-(6-amino-8-bromopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 6-Amino-8-bromopurine Riboside; NSC 79213; 8-Bromo Adenosine

Database IDs

• CAS Number: 2946-39-6
• PubChem SID: 162256877
• PubChem CID: 46783463

CALCULATED PROPERTIES

• Acid pKa: 12.452744
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.040446
• LogD (pH = 7.4): -1.0270739
• Log P: -1.0268967
• Molar Refractivity: 70.8204 cm^3
• Polarizability: 27.664213 Å^3
• Polar Surface Area: 139.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: >170°C (dec.)

Safety Information

• Storage Condition: Refrigerator

REFERENCES

• Dang, Q., et al.: J. Med. Chem., 52, 2880 (2009)
• Du, J., et al.: Biochem., 48, 2878 (2009)