(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidine-2-sulfonic acid

• ChemBase ID: 155717
• Molecular Formular: C6H13NO7S
• Molecular Mass: 243.23492
• Monoisotopic Mass: 243.04127276
• SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](N1)S(=O)(=O)O)O)O)O)O
• Canonical SMILES: OC[C@H]1N[C@H]([C@@H]([C@H]([C@@H]1O)O)O)S(=O)(=O)O
• InChI: InChI=1S/C6H13NO7S/c8-1-2-3(9)4(10)5(11)6(7-2)15(12,13)14/h2-11H,1H2,(H,12,13,14)/t2-,3-,4+,5-,6+/m1/s1
• InChIKey: PLICPKOWHZITQE-DVKNGEFBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidine-2-sulfonic acid
• IUPAC Traditional name: (2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidine-2-sulfonic acid
• Synonyms: Nojirimycin bisulfite microbial; 5-Amino-5-deoxyglucopyranose bisulfite; Nojirimycin 1-sulfonic acid

Database IDs

• CAS Number: 81703-56-2
• PubChem SID: 162249855; 24897840
• PubChem CID: 11128501

CALCULATED PROPERTIES

• Acid pKa: -3.9418468
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -5.655672
• LogD (pH = 7.4): -5.8374834
• Log P: -4.6825624
• Molar Refractivity: 46.3393 cm^3
• Polarizability: 20.102556 Å^3
• Polar Surface Area: 147.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Empirical Formula (Hill Notation): C6H13NO7S

DETAILS

Sigma Aldrich - N7779

Application
Inhibitor of β-glucosidase.
Inhibitor of β-glucosidases with about the same spectrum as parent nojirimycin, but 3- to 4-fold lower activity.1