(4S,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidin-2-one

• ChemBase ID: 172534
• Molecular Formular: C6H11NO5
• Molecular Mass: 177.15524
• Monoisotopic Mass: 177.06372246
• SMILES: [C@@H]1([C@@H](C(C(=O)NC1CO)O)O)O
• Canonical SMILES: OCC1NC(=O)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C6H11NO5/c8-1-2-3(9)4(10)5(11)6(12)7-2/h2-5,8-11H,1H2,(H,7,12)/t2?,3-,4+,5?/m1/s1
• InChIKey: AJJXPYDGVXIEHE-JOUZMPNTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidin-2-one
• IUPAC Traditional name: (4S,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidin-2-one
• Synonyms: D-Mannolactam; D-Mannonolactam; Nojirimycin B Lactam; (3S,4S,5R,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)-2-piperidinone; D-Manno-γ-lactam

Database IDs

• CAS Number: 62362-63-4
• PubChem SID: 164228444
• PubChem CID: 71749898

CALCULATED PROPERTIES

• Acid pKa: 10.985873
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -3.474435
• LogD (pH = 7.4): -3.4745347
• Log P: -3.474434
• Molar Refractivity: 36.7286 cm^3
• Polarizability: 15.020806 Å^3
• Polar Surface Area: 110.02 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 169-170°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M166000

A potent inhibitor of rat epididymal alpha-mannosidase and of apricot β-glucosidase.

REFERENCES

• Niwa, T., Tsuruoka, T. , et al.: J. Antibiot., 37, 1579 (1984)