(3S,4R)-3-hydroxy-4-{[(2S,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}piperidin-2-one

• ChemBase ID: 160540
• Molecular Formular: C10H17NO7
• Molecular Mass: 263.24448
• Monoisotopic Mass: 263.10050189
• SMILES: [C@@H]1([C@@H](C([C@@H](OC1)O[C@@H]1CCNC(=O)[C@H]1O)O)O)O
• Canonical SMILES: O[C@@H]1C(=O)NCC[C@H]1O[C@@H]1OC[C@H]([C@@H](C1O)O)O
• InChI: InChI=1S/C10H17NO7/c12-4-3-17-10(8(15)6(4)13)18-5-1-2-11-9(16)7(5)14/h4-8,10,12-15H,1-3H2,(H,11,16)/t4-,5-,6+,7+,8?,10+/m1/s1
• InChIKey: BHZMHPRIYUPDCT-NPTBQUCTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R)-3-hydroxy-4-{[(2S,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}piperidin-2-one
• IUPAC Traditional name: (3S,4R)-3-hydroxy-4-{[(2S,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}piperidin-2-one
• Synonyms: (3S,4R)-3-Hydroxy-4-(β-D-xylopyranosyloxy)-2-piperidinone; 5-Amino-3-O(-D-xylopyranosyl)-D-threo-pentano-1,5-lactam

Database IDs

• CAS Number: 284045-95-0
• PubChem SID: 162254675
• PubChem CID: 71313371

CALCULATED PROPERTIES

• Acid pKa: 11.908309
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -3.294305
• LogD (pH = 7.4): -3.2943182
• Log P: -3.2943048
• Molar Refractivity: 56.1198 cm^3
• Polarizability: 23.090034 Å^3
• Polar Surface Area: 128.48 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A632440

A xylobiose-derived lactam as nonbasic inhibitor of glycosidases.

REFERENCES

• Mega, T., et al.: J. Biochem., 94, 1637 (1981)
• Ermert, P., et al.: Helv. Chim. Acta, 74, 2043 (1981)
• Roeser, K., et al.: Biochim. Biophys Acta, 657, 321 (1981)