(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidine-2-sulfonic acid

• ChemBase ID: 175547
• Molecular Formular: C6H13NO7S
• Molecular Mass: 243.23492
• Monoisotopic Mass: 243.04127276
• SMILES: [C@@H]1([C@@H]([C@@H](C(N[C@H]1CO)S(=O)(=O)O)O)O)O
• Canonical SMILES: OC[C@@H]1NC([C@H]([C@H]([C@@H]1O)O)O)S(=O)(=O)O
• InChI: InChI=1S/C6H13NO7S/c8-1-2-3(9)4(10)5(11)6(7-2)15(12,13)14/h2-11H,1H2,(H,12,13,14)/t2-,3-,4+,5-,6?/m1/s1
• InChIKey: PLICPKOWHZITQE-GASJEMHNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidine-2-sulfonic acid
• IUPAC Traditional name: (3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidine-2-sulfonic acid
• Synonyms: (3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-piperidinesulfonic Acid; 5-Amino-5-deoxy-D-glucose-1-sulfonic Acid; Nojirimycin Bisulfite Adduct; Nojirimycin Sulfite Adduct; Nojirimycin-1-Sulfonic Acid

Database IDs

• CAS Number: 114417-84-4
• PubChem SID: 164231457
• PubChem CID: 451662

CALCULATED PROPERTIES

• Acid pKa: -3.9418468
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -5.655672
• LogD (pH = 7.4): -5.8374834
• Log P: -4.6825624
• Molar Refractivity: 46.3393 cm^3
• Polarizability: 20.102556 Å^3
• Polar Surface Area: 147.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 124-130°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N635000

An inhibitor of several glucosidases. Can be converted to Nojirimycin by treatment with Basic Resin.

REFERENCES

• Niwa, A., et al.: Agric. Biol. Chem., 34, 966 (1970)
• Reese, E.T., et al.: Carbohydr. Res., 18, 381 (1971)