(3S,4S,5R,6R)-6-acetamido-4,5-dihydroxypiperidine-3-carboxylic acid

• ChemBase ID: 155721
• Molecular Formular: C8H14N2O5
• Molecular Mass: 218.20716
• Monoisotopic Mass: 218.09027156
• SMILES: CC(=O)N[C@@H]1[C@H]([C@H]([C@H](CN1)C(=O)O)O)O
• Canonical SMILES: CC(=O)N[C@H]1NC[C@@H]([C@@H]([C@@H]1O)O)C(=O)O
• InChI: InChI=1S/C8H14N2O5/c1-3(11)10-7-6(13)5(12)4(2-9-7)8(14)15/h4-7,9,12-13H,2H2,1H3,(H,10,11)(H,14,15)/t4-,5-,6-,7+/m0/s1
• InChIKey: DQTKLICLJUKNCG-ZTYPAOSTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S,5R,6R)-6-acetamido-4,5-dihydroxypiperidine-3-carboxylic acid
• IUPAC Traditional name: (3S,4S,5R,6R)-6-acetamido-4,5-dihydroxypiperidine-3-carboxylic acid
• Synonyms: (3S, 4S, 5R, 6R)-6-(Acetylamino)-4,5-dihydroxy-3-piperidinecarboxylic acid; Siastatin B

Database IDs

• CAS Number: 54795-58-3
• MDL Number: MFCD01631253
• PubChem SID: 162249859; 24899775
• PubChem CID: 3042898

CALCULATED PROPERTIES

• Acid pKa: 3.184484
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -5.0675507
• LogD (pH = 7.4): -5.2640305
• Log P: -5.0689907
• Molar Refractivity: 47.6215 cm^3
• Polarizability: 19.455345 Å^3
• Polar Surface Area: 118.89 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble2.3 mL/vial (for a 10 mM solution)
• Apperance: lyophilized powder

Safety Information

• RTECS: TM6125400
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Packaging: vial of 23.0 μmol
• Biological Source: from microbial
• Empirical Formula (Hill Notation): C8H14N2O5

DETAILS

Sigma Aldrich - S8063

Application
Broad spectrum inhibitor of sialidase.
Biochem/physiol Actions
Streptomyces metabolite, a broad-spectrum inhibitor of neuraminidase (sialidase).1