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

• ChemBase ID: 71228
• Molecular Formular: C7H15NO4
• Molecular Mass: 177.1983
• Monoisotopic Mass: 177.10010797
• SMILES: N1([C@@H]([C@H]([C@@H]([C@H](C1)O)O)O)CO)C
• Canonical SMILES: OC[C@H]1N(C)C[C@@H]([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-XZBKPIIZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S)-2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4R,5S)-2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol
• Synonyms: (2R,3R,4R,5S)-2-(Hydroxymethyl)-1-methylpiperidine-3,4,5-triol; 1,5-Dideoxy-1,5-imino-1-methyl-D-sorbitol; N-Methyl-1-deoxynojirimycin

Database IDs

• CAS Number: 69567-10-8
• MDL Number: MFCD00133609
• Beilstein Number: 1524564
• PubChem SID: 24884758; 162103608; 24896690
• PubChem CID: 92381

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

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: mouse ... Gaa(14387), Glb1(12091), Treh(58866)rat ... Man2a1(25478), Si(497756)

Product Information

• Purity: ≥98%; ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C7H15NO4

DETAILS

Sigma Aldrich - M1777

Biochem/physiol Actions
Interferes with metabolism of N-linked glycoproteins by inhibition of glucosidase.

Sigma Aldrich - 66570

Other Notes
Inhibitor of glucosidase I1