(2R,3R,4R,5R)-2-(hydroxymethyl)piperidine-3,4,5-triol hydrochloride

• ChemBase ID: 18784
• Molecular Formular: C6H14ClNO4
• Molecular Mass: 199.63266
• Monoisotopic Mass: 199.06113561
• SMILES: C(O)[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN1)O.Cl
• Canonical SMILES: OC[C@H]1NC[C@H]([C@H]([C@@H]1O)O)O.Cl
• InChI: InChI=1S/C6H13NO4.ClH/c8-2-3-5(10)6(11)4(9)1-7-3;/h3-11H,1-2H2;1H/t3-,4-,5-,6-;/m1./s1
• InChIKey: ZJIHMALTJRDNQI-MVNLRXSJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5R)-2-(hydroxymethyl)piperidine-3,4,5-triol hydrochloride
• IUPAC Traditional name: deoxymannojirimycin hydrochloride
• Synonyms: 1,5-Dideoxy-1,5-imino-D-mannitol hydrochloride; 1-Deoxymannojirimycin hydrochloride; (+)-1-Deoxynojirimycin hydrochloride

Database IDs

• CAS Number: 73465-43-7
• MDL Number: MFCD00083611; MFCD00133247
• PubChem SID: 24894265; 160982091
• PubChem CID: 11390018

CALCULATED PROPERTIES

• Acid pKa: 12.906054
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -5.3671846
• LogD (pH = 7.4): -3.6328244
• Log P: -2.8857431
• Molar Refractivity: 36.5744 cm^3
• Polarizability: 15.1906805 Å^3
• Polar Surface Area: 92.95 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 197.5-198.7°C

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 97+%

DETAILS

Sigma Aldrich - D9160

Application
1-Deoxymannojirimycin (DMM) hydrochloride is an inhibitor of N-linked glycosylationan and has antiviral activity. Derivatives of deoxymannojirimycin may have anti-HIV activity. It has been used for treatment of T lymphocytes and to study it′s effect on allogeneic cytotoxic T lymphocytes (CTL)1. It is used for studies on Golgi-mediated glycoprotein processing.
Biochem/physiol Actions
1-Deoxymannojirimycin is an inhibitor of N-linked glycosylation. It is a mannosidase I inhibitor, alters cell-surface complex carbohydrate structure as assayed by PHA-L binding, and increases high mannose structures as indicated by the increased Con-A binding1.