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

• ChemBase ID: 2904
• Molecular Formular: C6H13NO4
• Molecular Mass: 163.17172
• Monoisotopic Mass: 163.0844579
• SMILES: OC[C@@H]1NC[C@@H](O)[C@H](O)[C@H]1O
• Canonical SMILES: OC[C@@H]1NC[C@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C6H13NO4/c8-2-3-5(10)6(11)4(9)1-7-3/h3-11H,1-2H2/t3-,4+,5-,6-/m0/s1
• InChIKey: LXBIFEVIBLOUGU-FSIIMWSLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R)-2-(hydroxymethyl)piperidine-3,4,5-triol
• IUPAC Traditional name: 1-deoxynojirimycin
• Synonyms: 1-Deoxy-Nojirimycin; 1-Deoxymannojirimycin; 1,5-Deoxy-1,5-imino-D-mannitol; 1,5-Dideoxy-1,5-imino-D-glucitol; DNJ; NOJ; DNM; 1-Deoxynojirimycin; 1,5-Dideoxy-1,5-Imino-D-Mannitol

Database IDs

• CAS Number: 19130-96-2
• PubChem SID: 160966351; 46507744; 46509136
• PubChem CID: 44387838

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -2.22
• LOG S: 0.5
• Solubility (Water): 5.11e+02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -1.80 [SANGSTER (1994)]

DETAILS

DrugBank - DB03206

• Drug Groups: experimental
• Description: An alpha-glucosidase inhibitor with antiviral action. Derivatives of deoxynojirimycin may have anti-HIV activity. [PubChem]
• Toxicity: ORL-RAT LD₅₀: > 5g/kg.

DrugBank - DB03955

• Drug Groups: experimental
• Description: An alpha-glucosidase inhibitor with antiviral action. Derivatives of deoxynojirimycin may have anti-HIV activity. [PubChem]