(3S,4R)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol hydrochloride

• ChemBase ID: 170544
• Molecular Formular: C8H18ClNO5
• Molecular Mass: 243.68522
• Monoisotopic Mass: 243.08735036
• SMILES: [C@H]1([C@@H](C(CN(C1CO)CCO)O)O)O.Cl
• Canonical SMILES: OCCN1CC(O)[C@H]([C@H](C1CO)O)O.Cl
• InChI: InChI=1S/C8H17NO5.ClH/c10-2-1-9-3-6(12)8(14)7(13)5(9)4-11;/h5-8,10-14H,1-4H2;1H/t5?,6?,7-,8+;/m0./s1
• InChIKey: QHWGCVIAMMMOPR-OODXIVFUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol hydrochloride
• IUPAC Traditional name: (3S,4R)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol hydrochloride
• Synonyms: (2S,3S,4R,5S)-1-(2-Hydroxyethyl)-2-(hydroxymethyl)-3,4,5-piperidinetriol Hydrochloride Salt; N-(2-Hydroxyethyl)-1-deoxy-L-altronojirimycin Hydrochloride Salt; (2R,3R,4S,5S)-1-(2-Hydroxyethyl)-2-(hydroxymethyl)-3,4,5-piperidinetriol Hydrochloride; N-(2-Hydroxyethyl)-1-deoxygalactonojirimycin Hydrochloride

Database IDs

• PubChem SID: 164226454
• PubChem CID: 71749025

CALCULATED PROPERTIES

• Acid pKa: 12.901322
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -5.2772155
• LogD (pH = 7.4): -3.6036737
• Log P: -3.1927972
• Molar Refractivity: 48.1614 cm^3
• Polarizability: 19.51395 Å^3
• Polar Surface Area: 104.39 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Semi-Solid; Off-White Solid

Safety Information

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

DETAILS

Toronto Research Chemicals - H942015

α-Glycosidase inhibitor.

Toronto Research Chemicals - H942000

α-Glycosidase inhibitor.

REFERENCES

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