(5S)-6-(hydroxymethyl)oxane-2,3,5-triol

• ChemBase ID: 165961
• Molecular Formular: C6H12O5
• Molecular Mass: 164.15648
• Monoisotopic Mass: 164.06847348
• SMILES: [C@@H]1(CC(C(OC1CO)O)O)O
• Canonical SMILES: OCC1OC(O)C(C[C@@H]1O)O
• InChI: InChI=1S/C6H12O5/c7-2-5-3(8)1-4(9)6(10)11-5/h3-10H,1-2H2/t3-,4?,5?,6?/m0/s1
• InChIKey: RJDIFQMDPPUATQ-ALMVMMGASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-6-(hydroxymethyl)oxane-2,3,5-triol
• IUPAC Traditional name: (5S)-6-(hydroxymethyl)oxane-2,3,5-triol
• Synonyms: 3-Deoxy-D-ribo-hexose; 3-Deoxyglucose; 3-Deoxy-D-glucose

Database IDs

• CAS Number: 2490-91-7
• PubChem SID: 162260094
• PubChem CID: 71315479

CALCULATED PROPERTIES

• Acid pKa: 11.4305525
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.242245
• LogD (pH = 7.4): -2.242285
• Log P: -2.2422445
• Molar Refractivity: 34.8263 cm^3
• Polarizability: 14.43744 Å^3
• Polar Surface Area: 90.15 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 129-131°C

DETAILS

Toronto Research Chemicals - D239040

Used for treating seizure and paroxysmal disorders.

REFERENCES

• Tetaud, E., et al.: Biochem. J., 317, 353 (1996)
• Manning, S., et al.: J. Biol. Chem., 277, 30942 (1996)
• Peier, A., et al.: Science, 296, 2046 (1996)