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

• ChemBase ID: 173752
• Molecular Formular: C11H15N5O5
• Molecular Mass: 297.2673
• Monoisotopic Mass: 297.10731861
• SMILES: [nH]1c(nc2c(c1=O)ncn2[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)OC)N
• Canonical SMILES: CO[C@@H]1[C@H](O)[C@H](O[C@H]1n1cnc2c1nc(N)[nH]c2=O)CO
• InChI: InChI=1S/C11H15N5O5/c1-20-7-6(18)4(2-17)21-10(7)16-3-13-5-8(16)14-11(12)15-9(5)19/h3-4,6-7,10,17-18H,2H2,1H3,(H3,12,14,15,19)/t4-,6-,7-,10-/m1/s1
• InChIKey: OVYNGSFVYRPRCG-KQYNXXCUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2'-O-methylguanosine
• Synonyms: O2’-Methylguanosine; 2'-O-Methyl Guanosine

Database IDs

• CAS Number: 2140-71-8
• PubChem SID: 164229662
• PubChem CID: 188959

CALCULATED PROPERTIES

• Acid pKa: 10.157278
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.0631769
• LogD (pH = 7.4): -2.0637617
• Log P: -2.0630918
• Molar Refractivity: 69.3723 cm^3
• Polarizability: 26.19804 Å^3
• Polar Surface Area: 144.22 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 227-231°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M311825

Guanosine analog. Used for preparation of nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase.

REFERENCES

• Eldrup, A.B., et al.: J. Med. Chem., 47, 2283 (2004)
• Shim, J., et al.: Antiviral Res., 243 (2004)
• Wang, M., et al.: J. Biol. Chem., 278, 9489 (2004)