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

• ChemBase ID: 172533
• Molecular Formular: C6H13NO6S
• Molecular Mass: 227.23552
• Monoisotopic Mass: 227.04635814
• SMILES: [C@@H]1([C@@H]([C@@H](C(N[C@H]1CO)S(=O)O)O)O)O
• Canonical SMILES: OC[C@@H]1NC(S(=O)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C6H13NO6S/c8-1-2-3(9)4(10)5(11)6(7-2)14(12)13/h2-11H,1H2,(H,12,13)/t2-,3-,4+,5+,6?/m1/s1
• InChIKey: WGYFMHXMHSNFFA-QTVWNMPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidine-2-sulfinic acid
• IUPAC Traditional name: (3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidine-2-sulfinic acid
• Synonyms: 5-Amino-5-deoxy-D-mannopyranose Hydrogensulfite; D-Mannojirimycin Bisulfite

Database IDs

• PubChem SID: 164228443
• PubChem CID: 71749897

CALCULATED PROPERTIES

• Acid pKa: -0.3527984
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -4.923538
• LogD (pH = 7.4): -5.5410304
• Log P: -4.841648
• Molar Refractivity: 44.8964 cm^3
• Polarizability: 19.43592 Å^3
• Polar Surface Area: 130.25 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 163-165°C

Safety Information

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

DETAILS

Toronto Research Chemicals - M165150

A potent inhibitor of alpha-mannosidase.

REFERENCES

• Hudlicky, T., et al.: J. Am. Chem. Soc., 116, 5099 (1994)