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

• ChemBase ID: 159703
• Molecular Formular: C13H17N5O6
• Molecular Mass: 339.30398
• Monoisotopic Mass: 339.11788329
• SMILES: C1(O)[C@@H](CO)O[C@H]([C@H]1O)n1c2nc([nH]c(=O)c2nc1OCC=C)N
• Canonical SMILES: C=CCOc1nc2c(n1[C@@H]1O[C@@H](C([C@@H]1O)O)CO)nc([nH]c2=O)N
• InChI: InChI=1S/C13H17N5O6/c1-2-3-23-13-15-6-9(16-12(14)17-10(6)22)18(13)11-8(21)7(20)5(4-19)24-11/h2,5,7-8,11,19-21H,1,3-4H2,(H3,14,16,17,22)/t5-,7?,8+,11-/m1/s1
• InChIKey: RQUVSNGNEJMOBE-DWVWSIQXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-(prop-2-en-1-yloxy)-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-(prop-2-en-1-yloxy)-1H-purin-6-one
• Synonyms: 8-(2-Propenyloxy)guanosine; 8-(Allyloxy)guanosine

Database IDs

• CAS Number: 126138-81-6
• PubChem SID: 162253838
• PubChem CID: 71313104

CALCULATED PROPERTIES

• Acid pKa: 10.104624
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -1.4484407
• LogD (pH = 7.4): -1.4491472
• Log P: -1.4483896
• Molar Refractivity: 79.7203 cm^3
• Polarizability: 30.256683 Å^3
• Polar Surface Area: 164.45 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Dimethylformamide
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - A561800

A guanosine derivative as an immunostimulant.

REFERENCES

• Reitz, A.B., et al.: J. Med. Chem., 37, 3561 (1994)