(2R,3R,5R)-2,5-bis(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 160685
• Molecular Formular: C6H12O5
• Molecular Mass: 164.15648
• Monoisotopic Mass: 164.06847348
• SMILES: [C@@H]1(C([C@H](O[C@@H]1CO)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@@H]([C@H](C1O)O)CO
• InChI: InChI=1S/C6H12O5/c7-1-3-5(9)6(10)4(2-8)11-3/h3-10H,1-2H2/t3-,4-,5+,6?/m1/s1
• InChIKey: MCHWWJLLPNDHGL-VRPWFDPXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,5R)-2,5-bis(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,5R)-2,5-bis(hydroxymethyl)oxolane-3,4-diol
• Synonyms: NSC 129241; 2,5-Anhydro-D-mannitol

Database IDs

• CAS Number: 41107-82-8
• PubChem SID: 162254820
• PubChem CID: 59445981

CALCULATED PROPERTIES

• Acid pKa: 12.753447
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.5683153
• LogD (pH = 7.4): -2.5683172
• Log P: -2.5683153
• Molar Refractivity: 34.8935 cm^3
• Polarizability: 14.43744 Å^3
• Polar Surface Area: 90.15 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 100-101°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A649000

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

• Joet, T., et al.: Biochem. J., 381, 905 (2004)
• Girardin, E., et al.: J. Biol. Chem., 280, 38059 (2004)
• Nghiem, N., et al.: App. Biochem. Biotechnol., 141, 335 (2004)