(3R,4R)-1-[2-hydroxy(2H4)ethyl]-2-(hydroxymethyl)piperidine-3,4,5-triol hydrochloride

• ChemBase ID: 174628
• 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-;/m1./s1
• InChIKey: QHWGCVIAMMMOPR-YSPZXBHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R)-1-[2-hydroxy(^2H₄)ethyl]-2-(hydroxymethyl)piperidine-3,4,5-triol hydrochloride
• IUPAC Traditional name: (3R,4R)-1-[2-hydroxy(^2H₄)ethyl]-2-(hydroxymethyl)piperidine-3,4,5-triol hydrochloride
• Synonyms: 2R,3R,4R,5S)-1-(2-Hydroxyethyl-d4)-2-(hydroxymethyl)-3,4,5-piperidinetriol Hydrochloride; [2R-(2α,3β,4α,5β)]-1-(2-Hydroxyethyl-d4)-2-(hydroxymethyl)-3,4,5-piperidinetrio Hydrochloride; BAY 1099-d4; BAY-m 1099-d4; Diastabol-d4; Glyset-d4; N-(2-Hydroxyethyl-d4)-1-deoxynojirimycin Hydrochloride; N-(2-Hydroxyethyl-4)moranoline Hydrochloride; Seibule-d4 Hydrochloride; Miglitol-d4 Hydrochloride

Database IDs

• PubChem SID: 164230538
• PubChem CID: 71750737

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

DETAILS

Toronto Research Chemicals - M344202

A labelled potent α-glucosidase inhibitor. Miglitol is a new antidiabetic drug.

REFERENCES

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