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

• ChemBase ID: 171805
• Molecular Formular: C10H13N5O5
• Molecular Mass: 283.24072
• Monoisotopic Mass: 283.09166854
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)c(nc(=O)[nH]2)N)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1cnc2c1[nH]c(=O)nc2N
• InChI: InChI=1S/C10H13N5O5/c11-7-4-8(14-10(19)13-7)15(2-12-4)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5?,6+,9-/m1/s1
• InChIKey: MIKUYHXYGGJMLM-DTUHVUQASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-amino-9-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,9-dihydro-2H-purin-2-one
• IUPAC Traditional name: 6-amino-9-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-2-one
• Synonyms: 1,2-Dihydro-2-oxo-adenosine Hydrate; Isoguanosine Hydrate

Database IDs

• CAS Number: 359436-55-8
• PubChem SID: 164227715
• PubChem CID: 59801633

CALCULATED PROPERTIES

• Acid pKa: 10.857788
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.8389428
• LogD (pH = 7.4): -2.8387556
• Log P: -2.8386073
• Molar Refractivity: 64.1877 cm^3
• Polarizability: 24.512907 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
• Apperance: Off-White Solid
• Melting Point: 237-241°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - I819500

A useful synthetic intermedate. A naturally occuring, biologically active isomer of guanosine. Reported to stimulate the accumulation of cyclic-AMP in the brain. It is an inhibitor of IMP pyrophosphorylase, and its 5’-di and -tri-phosphates inhibit gl

REFERENCES

• Divakar, K.J., et al.: J. Chem. Soc. Perkin Trans., 1, 771 (1991)
• Montsch, H.H., et al: Biochemistry, 14, 5593 (1991)
• Hagen, C.: Biochim. Biophys. Acta., 293, 105 (1991)
• Huang, M., et al.: J. Med. Chem., 15, 462 (1972)