(3R,4R)-1-(12-aminododecyl)-2-(hydroxymethyl)piperidine-3,4,5-triol

• ChemBase ID: 160064
• Molecular Formular: C18H38N2O4
• Molecular Mass: 346.50532
• Monoisotopic Mass: 346.28315771
• SMILES: [C@@H]1([C@@H](C(CN(C1CO)CCCCCCCCCCCCN)O)O)O
• Canonical SMILES: NCCCCCCCCCCCCN1CC(O)[C@H]([C@@H](C1CO)O)O
• InChI: InChI=1S/C18H38N2O4/c19-11-9-7-5-3-1-2-4-6-8-10-12-20-13-16(22)18(24)17(23)15(20)14-21/h15-18,21-24H,1-14,19H2/t15?,16?,17-,18-/m1/s1
• InChIKey: XUKDCKJRAWVROB-OPQOLIRYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R)-1-(12-aminododecyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
• IUPAC Traditional name: (3R,4R)-1-(12-aminododecyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
• Synonyms: (2R,3R,4R,5S)-1-(6-Aminohexyl)-2-(hydroxymethyl)-3,4,5-piperidinetriol; N-(12-Aminododecyl)deoxynojirimycin

Database IDs

• CAS Number: 885484-41-3
• PubChem SID: 162254199
• PubChem CID: 46780261

CALCULATED PROPERTIES

• Acid pKa: 12.902996
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -4.9657373
• LogD (pH = 7.4): -2.7791264
• Log P: 0.8341927
• Molar Refractivity: 96.1369 cm^3
• Polarizability: 38.689434 Å^3
• Polar Surface Area: 110.18 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A608080

N-(12-Aminododecyl)deoxynojirimycin is used in the preparation of imino-alditols as glycosidase inhibitors.

REFERENCES

• Jefferies, I., et al.: Bioorg. Med. Chem. Lett., 7, 1171 (1997)
• Hassan, A., et al.: Carbohydr. Res., 339, 1565 (1997)
• Lundt, et al.: Bioorg. Med. Chem., 14, 1737 (1997)