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

• ChemBase ID: 169801
• Molecular Formular: C10H13N5O5
• Molecular Mass: 283.24072
• Monoisotopic Mass: 283.09166854
• SMILES: [C@H]1(C([C@@H](O[C@@H]1CO)n1c2nc([nH]c(=O)c2nc1)N)O)O
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cnc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)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: NYHBQMYGNKIUIF-ACJOCUEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• Synonyms: 2-Amino-1,9-dihydro-9-β-D-ribofuranosyl-6H-purin-6-one; DL-Guanosine; Guanine Ribonucleoside; 9-β-D-Ribofuranosylguanine; 2-Aminoinosine; NSC 19994; Vernine; Guanosine Hydrate

Database IDs

• CAS Number: 118-00-3
• PubChem SID: 162263933
• PubChem CID: 46780355

CALCULATED PROPERTIES

• Acid pKa: 10.155725
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.7063062
• LogD (pH = 7.4): -2.7068908
• Log P: -2.7062182
• Molar Refractivity: 64.6211 cm^3
• Polarizability: 24.328236 Å^3
• Polar Surface Area: 155.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: >230°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G837900

A constituent of nucleic acids.

REFERENCES

• Miles, et al.: Science, 142, 1458 (1963)
• Bugg, et al.: Biochem. Biophys. Res. Commun., 3, 436 (1963)