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

• ChemBase ID: 163243
• Molecular Formular: C10H21NO4
• Molecular Mass: 219.27804
• Monoisotopic Mass: 219.14705816
• SMILES: [C@H]1([C@@H](C(CN(C1CO)CCCC)O)O)O
• Canonical SMILES: CCCCN1CC(O)[C@H]([C@H](C1CO)O)O
• InChI: InChI=1S/C10H21NO4/c1-2-3-4-11-5-8(13)10(15)9(14)7(11)6-12/h7-10,12-15H,2-6H2,1H3/t7?,8?,9-,10+/m0/s1
• InChIKey: UQRORFVVSGFNRO-HORUIINNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R)-1-butyl-2-(hydroxymethyl)piperidine-3,4,5-triol
• IUPAC Traditional name: (3S,4R)-1-butyl-2-(hydroxymethyl)piperidine-3,4,5-triol
• Synonyms: (2R,3S,4R,5S)-1-Butyl-2-(hydroxymethyl)-3,4,5-piperidinetriol; NBDGJ; N-(n-Butyl)deoxygalactonojirimycin

Database IDs

• CAS Number: 141206-42-0
• PubChem SID: 162257378
• PubChem CID: 71314354

CALCULATED PROPERTIES

• Acid pKa: 12.902159
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -4.0550327
• LogD (pH = 7.4): -2.3039815
• Log P: -1.1787962
• Molar Refractivity: 55.7427 cm^3
• Polarizability: 22.479631 Å^3
• Polar Surface Area: 84.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 123-124°C

Safety Information

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

DETAILS

Toronto Research Chemicals - B690500

An extremely potent and selective a-D-galactosidase inhibitor. A selective inhibitior of GlcCer synthesis.

REFERENCES

• Paulsen, H., et al.: Chem. Ber., 113, 2601 (1980)
• Daniel, P.F., et al.: Proc. Int. Carbo. Symp., 13th, Ithaca, NY, Abstr. C43 (1980)
• Platt, F.M., et al.: J. Biol. Chem., 269, 27108 (1994)