(2R,3R,4S,5R)-2-(2-amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 173753
• Molecular Formular: C11H15N5O5
• Molecular Mass: 297.2673
• Monoisotopic Mass: 297.10731861
• SMILES: n1c(nc2c(c1OC)ncn2[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)N
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(N)nc2OC
• InChI: InChI=1S/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7-,10-/m1/s1
• InChIKey: IXOXBSCIXZEQEQ-KQYNXXCUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-(2-amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,4S,5R)-2-(2-amino-6-methoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 2-Amino-6-methoxy-9-β-D-ribofuranosyl-9H-purine; 2-Amino-6-methoxypurine Ribonucleoside; 6-Methoxy-9-β-D-ribofuranosyl-9H-purin-2-amine; NSC 66381; O-Methylguanosine; 6-O-Methyl Guanosine

Database IDs

• CAS Number: 7803-88-5
• PubChem SID: 164229663
• PubChem CID: 96312

CALCULATED PROPERTIES

• Acid pKa: 12.453927
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -1.5698577
• LogD (pH = 7.4): -1.5698531
• Log P: -1.5698491
• Molar Refractivity: 69.6048 cm^3
• Polarizability: 27.112698 Å^3
• Polar Surface Area: 148.77 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 121-125°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M311830

A guanine derivative that acts as modulators of GTPases and modulator-resistant enzymes; used in drug design and target validation.

REFERENCES

• Goth-Goldstein, R., et al.: Cancer Res., 40, 2623 (1980)
• Nakabeppu, Y., et al.: J. Biol. Chem., 259, 13723 (1980)
• Modrich, P., et al.: Science, 266, 1959 (1980)