(3R,4S,5R,6R)-6-(hydroxymethyl)-4-methoxyoxane-2,3,5-triol

• ChemBase ID: 173739
• Molecular Formular: C7H14O6
• Molecular Mass: 194.18246
• Monoisotopic Mass: 194.07903817
• SMILES: [C@@H]1([C@@H]([C@@H](C(O[C@H]1CO)O)O)OC)O
• Canonical SMILES: OC[C@@H]1OC(O)[C@H]([C@H]([C@@H]1O)OC)O
• InChI: InChI=1S/C7H14O6/c1-12-6-4(9)3(2-8)13-7(11)5(6)10/h3-11H,2H2,1H3/t3-,4-,5-,6+,7?/m1/s1
• InChIKey: SCBBSJMAPKXHAH-QTSLKERKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5R,6R)-6-(hydroxymethyl)-4-methoxyoxane-2,3,5-triol
• IUPAC Traditional name: (3R,4S,5R,6R)-6-(hydroxymethyl)-4-methoxyoxane-2,3,5-triol
• Synonyms: 3-O-Methylglucopyranose; 3-O-Methylglucose; NSC 61740; NSC 62383; 3-O-Methyl-D-glucopyranose

Database IDs

• CAS Number: 3370-81-8
• PubChem SID: 164229649
• PubChem CID: 96241

CALCULATED PROPERTIES

• Acid pKa: 11.3056965
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.2894135
• LogD (pH = 7.4): -2.2894666
• Log P: -2.2894127
• Molar Refractivity: 40.6746 cm^3
• Polarizability: 17.016506 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M309450

A methylated glucose; non-metabolizable hexose involved in the interference of glucose metabolism. It is used to study hexose translocation across the blood-brain interface via infusing into one internal carotid artery.

REFERENCES

• Himsworth, R.L. et al.: J. Physiol., 198, 467 (1968)
• Bidder, T.G. et al.: J. Neurochem., 15, 867 (1968)