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

• ChemBase ID: 160668
• Molecular Formular: C6H12O5
• Molecular Mass: 164.15648
• Monoisotopic Mass: 164.06847348
• SMILES: [C@@H]1([C@@H](C(COC1CO)O)O)O
• Canonical SMILES: OCC1OCC([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C6H12O5/c7-1-4-6(10)5(9)3(8)2-11-4/h3-10H,1-2H2/t3?,4?,5-,6-/m1/s1
• InChIKey: MPCAJMNYNOGXPB-SXEFJBAOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R)-2-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (3S,4R)-2-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: 1-Deoxy-D-glucose; Polygalitol; 1,5-Anhydro-D-glucitol; 1,5-Anhydroglucitol; 1,5-Anhydrosorbitol; 1-Deoxy-D-glucopyranose; Aceritol; 1,5-Anhydro-D-glucitol; 1,5-Anhydromannitol; 2,6-Anhydro-D-mannitol; Styracit; Styracitol; 1,5-Anhydro-D-mannitol

Database IDs

• CAS Number: 154-58-5; 492-93-3
• PubChem SID: 162254803
• PubChem CID: 46780406

CALCULATED PROPERTIES

• Acid pKa: 12.66417
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.5683153
• LogD (pH = 7.4): -2.5683177
• Log P: -2.5683153
• Molar Refractivity: 34.8935 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; Methanol (Sparingly); Water
• Apperance: White Solid
• Melting Point: 142-143°C; 156-157°C

Safety Information

• Storage Condition: -20°C Freezer; -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A648000

This compound has been isolated from several plant and animal sources, discovered in human cerebrospinal fluid and blood plasma and found to be an inhibitor of several enzymes. Anhydroalditols are a class of reduced sugars which are present in many natur

Toronto Research Chemicals - A648980

A carbohydrate metabolism regulator that has been shown to inhibit gluconeogenesis from lactate plus pyruvate and from substrates that enter the gluconeogenic pathway as triose phosphate.

REFERENCES

• Yamanouchi, T. et al. Am. J. Physiol. 263, E268 (1992)
• Yoshioka, S. et al. Clin. Chem. 30, 188, (1992)
• Field, R.A. et al. Bioorg. Med. Chem. Lett. 1, 667 (1992)
• Cavallaro, C.L. and Schartz, J. J. Org. Chem. 61, 3863 (1996).
• Sinclair, H., et al.: Carbohydr. Res., 127, 146 (1984)
• Niwa, T., et al.: J. Chromatogr. Biomed. Appl., 613, 9 (1984)
• Harvey, D., et al.: J. Mass Spectrom., 32, 167 (1984)