(2S,3R,4R,5R)-5-acetamido-3,4,6-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 158894
• Molecular Formular: C8H13NO7
• Molecular Mass: 235.19132
• Monoisotopic Mass: 235.06920176
• SMILES: [C@H]1([C@@H]([C@@H](C(O[C@H]1C(=O)O)O)NC(=O)C)O)O
• Canonical SMILES: CC(=O)N[C@@H]1C(O)O[C@H]([C@@H]([C@@H]1O)O)C(=O)O
• InChI: InChI=1S/C8H13NO7/c1-2(10)9-3-4(11)5(12)6(7(13)14)16-8(3)15/h3-6,8,11-12,15H,1H3,(H,9,10)(H,13,14)/t3-,4-,5-,6+,8?/m1/s1
• InChIKey: KSOXQRPSZKLEOR-YIDMHZNGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R,5R)-5-acetamido-3,4,6-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3R,4R,5R)-5-acetamido-3,4,6-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2-(Acetylamino)-2-deoxy-D-galacturonic Acid; 2-Acetamido-2-deoxy-D-galacturonic Acid

Database IDs

• CAS Number: 45171-33-3
• PubChem SID: 162253029
• PubChem CID: 71312730

CALCULATED PROPERTIES

• Acid pKa: 3.3725803
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -5.0140944
• LogD (pH = 7.4): -6.3100176
• Log P: -2.9002998
• Molar Refractivity: 46.8921 cm^3
• Polarizability: 19.432514 Å^3
• Polar Surface Area: 136.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A153500

A component of O-antigens of Pseudomonas aeruginosa.

REFERENCES

• Shaw, D., et al.: Eur. J. Biochem., 131, 633 (1983)
• Chart, H., et al.: J. Bacteriol., 158, 16 (1983)
• Szymanski, C., et al.: J. Biol. Chem., 278, 24509 (1983)