2-amino-8-bromo-9-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 162893
• Molecular Formular: C10H12BrN5O5
• Molecular Mass: 362.13678
• Monoisotopic Mass: 361.00218051
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1Br)c(=O)[nH]c(n2)N)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1c(Br)nc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C10H12BrN5O5/c11-9-13-3-6(14-10(12)15-7(3)20)16(9)8-5(19)4(18)2(1-17)21-8/h2,4-5,8,17-19H,1H2,(H3,12,14,15,20)/t2-,4?,5+,8-/m1/s1
• InChIKey: ASUCSHXLTWZYBA-UKPFUCPKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-8-bromo-9-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-8-bromo-9-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• Synonyms: 2-Amino-8-bromo-6-hydroxypurine Riboside; NSC 174257; NSC 79211; 8-Bromoguanosine

Database IDs

• CAS Number: 4016-63-1
• PubChem SID: 162257028
• PubChem CID: 46783649

CALCULATED PROPERTIES

• Acid pKa: 10.114233
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.6421795
• LogD (pH = 7.4): -1.642893
• Log P: -1.6421511
• Molar Refractivity: 72.2459 cm^3
• Polarizability: 27.512737 Å^3
• Polar Surface Area: 155.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Hot Water; Methanol (Sparingly)
• Apperance: White Solid
• Melting Point: >210°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

REFERENCES

• Hu, H., et al.: Mol. Pharmacol., 69, 1542 (2006)
• Mallett, D., et al.: J. Pharm. Biomed. Anal., 49, 100 (2006)