(2R,3R,4R,5S,6R)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol

• ChemBase ID: 153929
• Molecular Formular: C7H15NO5
• Molecular Mass: 193.1977
• Monoisotopic Mass: 193.09502259
• SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@H](N1)CO)O)O)O)O
• Canonical SMILES: OC[C@H]1N[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C7H15NO5/c9-1-3-5(11)7(13)6(12)4(2-10)8-3/h3-13H,1-2H2/t3-,4-,5-,6+,7+/m1/s1
• InChIKey: CLVUFWXGNIFGNC-OVHBTUCOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol
• Synonyms: α-Homonojirimycin

Database IDs

• CAS Number: 119557-99-2
• PubChem SID: 162248068
• PubChem CID: 159496

CALCULATED PROPERTIES

• Acid pKa: 12.839471
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): -5.5904818
• LogD (pH = 7.4): -3.9289358
• Log P: -3.5160782
• Molar Refractivity: 42.5369 cm^3
• Polarizability: 17.7012 Å^3
• Polar Surface Area: 113.18 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C7H15NO5

DETAILS

Sigma Aldrich - 52388

Biochem/physiol Actions
α-Homonojirimycin is a potent inhibitor of a range of α-glucosidases, as well as an inhibitor of the glycoprotein processing enzyme glucosidase II.
Application
α-Homonojirimycin (HMJ) is used as an inhibitor of several carbohydrate degrading enzymes including α-glucosidases, glycoprotein processing enzyme glucosidase II and maltase.