(4R,5S)-2,6-bis(hydroxymethyl)oxane-2,3,4,5-tetrol

• ChemBase ID: 172531
• Molecular Formular: C7H14O7
• Molecular Mass: 210.18186
• Monoisotopic Mass: 210.07395279
• SMILES: C1([C@H]([C@@H](C(C(O1)(O)CO)O)O)O)CO
• Canonical SMILES: OCC1OC(O)(CO)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C7H14O7/c8-1-3-4(10)5(11)6(12)7(13,2-9)14-3/h3-6,8-13H,1-2H2/t3?,4-,5-,6?,7?/m1/s1
• InChIKey: HAIWUXASLYEWLM-AHCVODQZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5S)-2,6-bis(hydroxymethyl)oxane-2,3,4,5-tetrol
• IUPAC Traditional name: (4R,5S)-2,6-bis(hydroxymethyl)oxane-2,3,4,5-tetrol
• Synonyms: D-Manno-2-heptulose; (+)-Mannoheptulose; NSC 226836; D-Mannoheptulose

Database IDs

• CAS Number: 3615-44-9
• PubChem SID: 164228441
• PubChem CID: 46782101

CALCULATED PROPERTIES

• Acid pKa: 10.283604
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -3.3883414
• LogD (pH = 7.4): -3.388901
• Log P: -3.3883343
• Molar Refractivity: 42.3233 cm^3
• Polarizability: 17.671268 Å^3
• Polar Surface Area: 130.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 148-150°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M165100

Mannoheptulose occurs naturally in avocado fruit. It is used for normalizing insulin levels and reducing weight.

REFERENCES

• Lin, S., et al.: J. Biol. Chem., 265, 9670 (1990)
• Grimsby, J., et al.: Science, 301, 370 (1990)
• Matschinsky, F., et al.: Curr. Diabetes Rep., 5, 171 (1990)
• Matschinsky, F., et al.: Diabetes, 55, 1 (1990)