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

• ChemBase ID: 162813
• Molecular Formular: C10H12BrN5O4
• Molecular Mass: 346.13738
• Monoisotopic Mass: 345.00726589
• SMILES: C1C([C@H](O[C@H]1n1c2c(nc1Br)c(=O)[nH]c(n2)N)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](CC1O)n1c(Br)nc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C10H12BrN5O4/c11-9-13-6-7(14-10(12)15-8(6)19)16(9)5-1-3(18)4(2-17)20-5/h3-5,17-18H,1-2H2,(H3,12,14,15,19)/t3?,4-,5-/m1/s1
• InChIKey: MKDXZFVCXWXGBQ-YZNZAMEGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-8-bromo-9-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-8-bromo-9-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• Synonyms: 8-Bromo-2'-deoxy-guanosine; 8-Bromo-2'-deoxyguanosine; NSC 105830; 8-Bromo-2'-deoxyguanosine

Database IDs

• CAS Number: 13389-03-2
• PubChem SID: 162256948
• PubChem CID: 46783430

CALCULATED PROPERTIES

• Acid pKa: 10.116888
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.74154204
• LogD (pH = 7.4): -0.7422499
• Log P: -0.741513
• Molar Refractivity: 70.7352 cm^3
• Polarizability: 26.78036 Å^3
• Polar Surface Area: 134.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Warm Water
• Apperance: White Solid
• Melting Point: >250°C dec.

Safety Information

• Storage Condition: -20°C Freezer

REFERENCES

• Chatgilialoglu, C., et al.: Chem. Res. Toxicol., 20, 1820 (2007)