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

• ChemBase ID: 173522
• Molecular Formular: C7H15NO4
• Molecular Mass: 177.1983
• Monoisotopic Mass: 177.10010797
• SMILES: [C@@H]1([C@@H](C(CN(C1CO)C)O)O)O
• Canonical SMILES: OCC1N(C)CC([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C7H15NO4/c1-8-2-5(10)7(12)6(11)4(8)3-9/h4-7,9-12H,2-3H2,1H3/t4?,5?,6-,7-/m1/s1
• InChIKey: AAKDPDFZMNYDLR-TVVDDFTJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R)-2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol
• IUPAC Traditional name: (3R,4R)-2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol
• Synonyms: N-Methylmoranolin; (2R,3R,4R,5S)-2-(Hydroxymethyl)-1-methyl-3,4,5-piperidinetriol; N-Methyldeoxynojirimycin

Database IDs

• CAS Number: 69567-10-8
• PubChem SID: 164229432
• PubChem CID: 71750282

CALCULATED PROPERTIES

• Acid pKa: 12.902485
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -4.7624073
• LogD (pH = 7.4): -3.035791
• Log P: -2.5026953
• Molar Refractivity: 41.8691 cm^3
• Polarizability: 17.006718 Å^3
• Polar Surface Area: 84.16 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White to Off-White
• Melting Point: 126-128°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M297000

Interfers with the normal processing of N-linked glycoproteins by inhibiting the action of glucosidases that remove glycosyl residues from Glc3Man9GlcNAc2 following the addition of this moiety to a nascent polypeptide.

REFERENCES

• FEBS Letts., 183, 29 (1985)
• Biochem. J., 226, 733 (1985)
• Biochem. J., 238, 335 (1985)
• Carbohydrate Res., 151, 21 (1985)
• Biochem. Cell Biol., 68, 1411 (1990)