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

• ChemBase ID: 165997
• Molecular Formular: C6H13NO4
• Molecular Mass: 163.17172
• Monoisotopic Mass: 163.0844579
• SMILES: [C@@H]1([C@@H](C(CNC1CO)O)O)O
• Canonical SMILES: OCC1NCC([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C6H13NO4/c8-2-3-5(10)6(11)4(9)1-7-3/h3-11H,1-2H2/t3?,4?,5-,6-/m1/s1
• InChIKey: LXBIFEVIBLOUGU-SXEFJBAOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R)-2-(hydroxymethyl)piperidine-3,4,5-triol
• IUPAC Traditional name: (3R,4R)-2-(hydroxymethyl)piperidine-3,4,5-triol
• Synonyms: (2R,3R,4R,5S)-2-(Hydroxymethyl)-3,4,5-piperidinetriol; 5-Amino-1,5-dideoxy-D-glucopyranose; Duvoglustat; Moranolin; Moranoline; DNJ; Deoxynojirimycin

Database IDs

• CAS Number: 19130-96-2
• PubChem SID: 162260130
• PubChem CID: 46783361

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: White Solid
• Melting Point: 195-196°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D245000

Deoxynojirimycin inhibits mammalian glucosidase 1. As well, it inhibits intestinal and lysosmal alpha-glucosidases, beta-glucosidase from sweet almonds, pancreatic alpha-amylase and amyloglucosidase.

REFERENCES

• Eur. J. Biochem., 142, 85-90 (1984)
• Crit. Rev. Biochem., 16, 21-48 (1984)
• Biochem. Biochem. Acta. , 825, 95 (1984)
• Suhm, K., et al.: J. Biol. Chem., 267, 21671 (1992)