2-amino-7-[(2S,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H,4H,5H-pyrrolo[3,2-d]pyrimidin-4-one

• ChemBase ID: 165473
• Molecular Formular: C11H14N4O5
• Molecular Mass: 282.25266
• Monoisotopic Mass: 282.09641957
• SMILES: [C@@H]1(C([C@H](O[C@H]1c1c2c([nH]c1)c(=O)[nH]c(n2)N)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)c1c[nH]c2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C11H14N4O5/c12-11-14-5-3(1-13-6(5)10(19)15-11)9-8(18)7(17)4(2-16)20-9/h1,4,7-9,13,16-18H,2H2,(H3,12,14,15,19)/t4-,7?,8+,9+/m1/s1
• InChIKey: RBYIXGAYDLAKCC-GLWRVUTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-7-[(2S,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H,4H,5H-pyrrolo[3,2-d]pyrimidin-4-one
• IUPAC Traditional name: 2-amino-7-[(2S,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H,5H-pyrrolo[3,2-d]pyrimidin-4-one
• Synonyms: 2-Amino-7-(β-D-ribofuranosyl[3,2-d]pyrimidin-4-one; 2-Amino-1,5-dihydro-7-β-D-ribofuranosyl-4H-pyrrolo[3,2-d]pyrimidin-4-one; 9-Deazaguanosine

Database IDs

• CAS Number: 102731-45-3
• PubChem SID: 162259606
• PubChem CID: 44325791

CALCULATED PROPERTIES

• Acid pKa: 11.003574
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -2.8228827
• LogD (pH = 7.4): -2.6323965
• Log P: -2.630039
• Molar Refractivity: 67.9808 cm^3
• Polarizability: 25.119558 Å^3
• Polar Surface Area: 153.19 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Beige Solid
• Melting Point: 259-264°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D201400

A guanosine analogue.

REFERENCES

• Girgis, N., et al.: J. Med. Chem., 33, 2750 (1990)
• Lin, C., et al.: Biochem., 33, 2703 (1990)