N-[(3R,4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-2-oxooxolan-3-yl]acetamide

• ChemBase ID: 158884
• Molecular Formular: C8H13NO6
• Molecular Mass: 219.19192
• Monoisotopic Mass: 219.07428714
• SMILES: [C@@H]1(O)[C@H]([C@@H](CO)O)OC(=O)[C@@H]1NC(=O)C
• Canonical SMILES: OC[C@H]([C@@H]1OC(=O)[C@@H]([C@@H]1O)NC(=O)C)O
• InChI: InChI=1S/C8H13NO6/c1-3(11)9-5-6(13)7(4(12)2-10)15-8(5)14/h4-7,10,12-13H,2H2,1H3,(H,9,11)/t4?,5-,6-,7+/m1/s1
• InChIKey: JYOPKUOOYNIILV-BPDFOOOXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-2-oxooxolan-3-yl]acetamide
• IUPAC Traditional name: N-[(3R,4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-2-oxooxolan-3-yl]acetamide
• Synonyms: 2-(Acetylamino)-2-deoxy-D-galactonic Acid γ-Lactone; 2-Acetamido-2-deoxy-D-galactono-1,4-lactone

Database IDs

• CAS Number: 28876-38-2
• PubChem SID: 162253019
• PubChem CID: 53981505

CALCULATED PROPERTIES

• Acid pKa: 11.604101
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -3.0333087
• LogD (pH = 7.4): -3.0333326
• Log P: -3.0333083
• Molar Refractivity: 45.8801 cm^3
• Polarizability: 18.871698 Å^3
• Polar Surface Area: 116.09 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (partially); Water
• Apperance: White Solid
• Melting Point: 180-182°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A151850

Galactonic acid derivative as N-acetylglucosaminidase inhibitor.

REFERENCES

• Findlay, J., et al.: Biochem. J., 69 467 (1958)
• Walker, P. G., et al.: Biochem. J., 79, 288 (1958)