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

• ChemBase ID: 165859
• Molecular Formular: C6H14ClNO4
• Molecular Mass: 199.63266
• Monoisotopic Mass: 199.06113561
• SMILES: [C@H]1([C@@H](C(CNC1CO)O)O)O.Cl
• Canonical SMILES: OCC1NCC([C@H]([C@H]1O)O)O.Cl
• InChI: InChI=1S/C6H13NO4.ClH/c8-2-3-5(10)6(11)4(9)1-7-3;/h3-11H,1-2H2;1H/t3?,4?,5-,6+;/m0./s1
• InChIKey: ZJIHMALTJRDNQI-VSXNQDMQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R)-2-(hydroxymethyl)piperidine-3,4,5-triol hydrochloride
• IUPAC Traditional name: (3S,4R)-2-(hydroxymethyl)piperidine-3,4,5-triol hydrochloride
• Synonyms: (2R,3S,4R,5S)-2-Hydroxymethyl-3,4,5-piperidinetriol Hydrochloride; Migalastat Hydrochloride; 1-Deoxygalactostatin Hydrochloride; 1-Deoxygalactonojirimycin Hydrochloride; (2S,3S,4R,5S)-2-Hydroxymethyl-3,4,5-piperidinetriol Hydrochloride; 1-Deoxy-L-altronojirimycin Hydrochloride

Database IDs

• CAS Number: 75172-81-5; 355138-93-1
• PubChem SID: 162259992
• PubChem CID: 46780623

CALCULATED PROPERTIES

• Acid pKa: 12.906054
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -5.3671846
• LogD (pH = 7.4): -3.6328244
• Log P: -2.8857431
• Molar Refractivity: 36.5744 cm^3
• Polarizability: 15.1906805 Å^3
• Polar Surface Area: 92.95 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White to Tan Low Melting Solid; White Solid
• Melting Point: 244-246°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - D231750

α-Glycosidase inhibitor.

Toronto Research Chemicals - D236500

Proven to be an extremely potent and selective a-D-galactosidase inhibitor.

REFERENCES

• Jefferies, I., et al.: Bioorg. Med. Chem. Lett., 7, 1171 (1997)
• Hassan, A., et al.: Carbohydr. Res., 339, 1565 (1997)
• Paulsen, H., et al.: Chem. Ber., 113, 2601 (1980)