N-[(3R,4R,5S,6R)-4,5-dihydroxy-2-(hydroxyimino)-6-(hydroxymethyl)oxan-3-yl]acetamide

• ChemBase ID: 158895
• Molecular Formular: C8H14N2O6
• Molecular Mass: 234.20656
• Monoisotopic Mass: 234.08518618
• SMILES: O1/C(=N/O)/[C@H]([C@H]([C@@H]([C@@H]1CO)O)O)NC(=O)C
• Canonical SMILES: OC[C@@H]1O/C(=N/O)/[C@H]([C@H]([C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C8H14N2O6/c1-3(12)9-5-7(14)6(13)4(2-11)16-8(5)10-15/h4-7,11,13-15H,2H2,1H3,(H,9,12)/b10-8+/t4-,5-,6-,7-/m1/s1
• InChIKey: NJBKCLCEXIDHDR-MXNBCVNWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5S,6R)-4,5-dihydroxy-2-(hydroxyimino)-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(3R,4R,5S,6R)-4,5-dihydroxy-2-(hydroxyimino)-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: 2-(Acetylamino)-2-deoxy-N-hydroxy-D-gluconimidic Acid δ-Lactone; LogNAc; 2-Acetamido-2-deoxy-D-gluconhydroximo-1,5-lactone DISCONTINUED

Database IDs

• CAS Number: 132152-76-2
• PubChem SID: 162253030
• PubChem CID: 6505019

CALCULATED PROPERTIES

• Acid pKa: 9.278837
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -3.0569673
• LogD (pH = 7.4): -3.0625725
• Log P: -3.0568953
• Molar Refractivity: 49.9707 cm^3
• Polarizability: 20.23232 Å^3
• Polar Surface Area: 131.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Foam

DETAILS

Toronto Research Chemicals - A155240

An intermediate in the synthesis of PugNAc (Cat. No. A15725), an inhibitor of glucosamidase.

REFERENCES

• Horsch, M., et al.: Eur. J. Biochem., 237, 476 (1996)
• Stubbs, K., et al.: J. Biol. Chem., 282, 21382 (1996)