(3R,4R)-2-(hydroxymethyl)-1-nonylpiperidine-3,4,5-triol

• ChemBase ID: 175559
• Molecular Formular: C15H31NO4
• Molecular Mass: 289.41094
• Monoisotopic Mass: 289.22530848
• SMILES: [C@@H]1([C@@H](C(CN(C1CO)CCCCCCCCC)O)O)O
• Canonical SMILES: CCCCCCCCCN1CC(O)[C@H]([C@@H](C1CO)O)O
• InChI: InChI=1S/C15H31NO4/c1-2-3-4-5-6-7-8-9-16-10-13(18)15(20)14(19)12(16)11-17/h12-15,17-20H,2-11H2,1H3/t12?,13?,14-,15-/m1/s1
• InChIKey: FTSCEGKYKXESFF-NEXFUWMNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R)-2-(hydroxymethyl)-1-nonylpiperidine-3,4,5-triol
• IUPAC Traditional name: (3R,4R)-2-(hydroxymethyl)-1-nonylpiperidine-3,4,5-triol
• Synonyms: (2R,3R,4R,5S)-2-(Hydroxymethyl)-1-nonyl-3,4,5-piperidinetriol; N-Nonyl-1-deoxynojirimycin; N-Nonyldeoxynojirimycin; NNDNJ; N-(n-Nonyl)deoxynojirimycin

Database IDs

• CAS Number: 81117-35-3
• PubChem SID: 164231469
• PubChem CID: 70864301

CALCULATED PROPERTIES

• Acid pKa: 12.902188
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.7318949
• LogD (pH = 7.4): 0.034929566
• Log P: 1.0440471
• Molar Refractivity: 78.7477 cm^3
• Polarizability: 31.646631 Å^3
• Polar Surface Area: 84.16 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 101-102°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N650300

An inhibitor of a-glucosidase 1 as well as being an inhibitor of HIV cytopathicity. A possible therapeutic agent for Gaucher disease.

REFERENCES

• Sawkar. A.R., et al.: PNAS, 99, 24, 15428 (2002)