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

• ChemBase ID: 160098
• Molecular Formular: C6H12ClNO6
• Molecular Mass: 229.61558
• Monoisotopic Mass: 229.03531479
• SMILES: [C@H]1([C@@H]([C@@H](C(O[C@H]1C(=O)O)O)N)O)O.Cl
• Canonical SMILES: OC1O[C@@H](C(=O)O)[C@@H]([C@@H]([C@@H]1N)O)O.Cl
• InChI: InChI=1S/C6H11NO6.ClH/c7-1-2(8)3(9)4(5(10)11)13-6(1)12;/h1-4,6,8-9,12H,7H2,(H,10,11);1H/t1-,2-,3-,4+,6?;/m1./s1
• InChIKey: ADRQPIGNSYNVLW-OVRDBETASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R,5R)-5-amino-3,4,6-trihydroxyoxane-2-carboxylic acid hydrochloride
• IUPAC Traditional name: (2S,3R,4R,5R)-5-amino-3,4,6-trihydroxyoxane-2-carboxylic acid hydrochloride
• Synonyms: 2-Amino-2-deoxy-D-galacturonic Acid Hydrochloride; 2-Amino-2-deoxygalacturonic Acid Hydrochloride; D-Aminogalacturonic Acid Hydrochloride

Database IDs

• PubChem SID: 162254233
• PubChem CID: 71313224

CALCULATED PROPERTIES

• Acid pKa: 3.0938807
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -4.983328
• LogD (pH = 7.4): -5.037501
• Log P: -4.984006
• Molar Refractivity: 37.4483 cm^3
• Polarizability: 15.99048 Å^3
• Polar Surface Area: 133.24 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Beige Solid
• Melting Point: >135°C (dedc.)

Safety Information

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

DETAILS

Toronto Research Chemicals - A609690

2-Amino-2-deoxygalacturonic acid was a component of the lipopolysaccharide from P. aeruginosa NCTC 8505 and probably occurs in the region of polysaccharide responsible for O-antigenic specificity.

REFERENCES

• Wilkinson, S.G., et al.: Biochem. J., 149, 783 (1975)