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

• ChemBase ID: 5907
• Molecular Formular: C15H31NO4
• Molecular Mass: 289.41094
• Monoisotopic Mass: 289.22530848
• SMILES: OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)CN1CCCCCCCCC
• Canonical SMILES: CCCCCCCCCN1C[C@H](O)[C@H]([C@@H]([C@H]1CO)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-LXTVHRRPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S)-2-(hydroxymethyl)-1-nonylpiperidine-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4R,5S)-2-(hydroxymethyl)-1-nonylpiperidine-3,4,5-triol
• Synonyms: (2R,3R,4R,5S)-2-(HYDROXYMETHYL)-1-NONYLPIPERIDINE-3,4,5-TRIOL; NN-DNJ

Database IDs

• CAS Number: 81117-35-3
• MDL Number: MFCD00905846
• PubChem SID: 99444754; 160969333
• PubChem CID: 501640

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 1.3
• LOG S: -1.48
• Solubility (Water): 9.58e+00 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C15H31NO4

DETAILS

DrugBank - DB08283

Drug information: experimental

Sigma Aldrich - N6414

Biochem/physiol Actions
NN-DNJ is a glucosidase inhibitor that acts as a pharmacologic chaperone. NN-DNJ also acts synergistically with proteostasis modulators such as celastrol and MG132 to stabilize mutant proteins in properly folded states. NN-DNJ stabilizes various proteins against misfolding, increasing proper trafficking from the endoplasmic reticulum. There is potential use in studying diseases marked by misfolded proteins and has shown antiviral activity.