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

• ChemBase ID: 174627
• Molecular Formular: C8H17NO5
• Molecular Mass: 207.22428
• Monoisotopic Mass: 207.11067265
• SMILES: [C@@H]1([C@@H](C(CN(C1CO)CCO)O)O)O
• Canonical SMILES: OCCN1CC(O)[C@H]([C@@H](C1CO)O)O
• InChI: InChI=1S/C8H17NO5/c10-2-1-9-3-6(12)8(14)7(13)5(9)4-11/h5-8,10-14H,1-4H2/t5?,6?,7-,8-/m1/s1
• InChIKey: IBAQFPQHRJAVAV-DWYQZRHDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
• IUPAC Traditional name: (3R,4R)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
• Synonyms: (2R,3R,4R,5S)-1-(2-Hydroxyethyl)-2-(hydroxymethyl)-3,4,5-piperidinetriol; [2R-(2α,3β,4α,5β)]-1-(2-Hydroxyethyl)-2-(hydroxymethyl)3,4,5-piperidinetrio; BAY 1099; BAY-m 1099; Diastabol; Glyset; N-(2-Hydroxyethyl)-1-deoxynojirimycin; N-(2-Hydroxyethyl)moranoline; Seibule; Miglitol

Database IDs

• CAS Number: 72432-03-2
• PubChem SID: 164230537
• PubChem CID: 71749029

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: Ethanol; Water
• Apperance: White Solid
• Melting Point: 145-147°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M344200

A potent α-glucosidase inhibitor. A new antidiabetic drug.

REFERENCES

• Lembcke, B., et al.: Digestion, 31, 120 (1985)
• Yoshikuni, Y., et al.: J. Pharmacobio-Dyn., 11, 356 (1985)