(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(phenylamino)oxane-2-carboxylic acid

• ChemBase ID: 160706
• Molecular Formular: C12H15NO6
• Molecular Mass: 269.2506
• Monoisotopic Mass: 269.08993721
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1C(=O)O)Nc1ccccc1)O)O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Nc2ccccc2)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C12H15NO6/c14-7-8(15)10(12(17)18)19-11(9(7)16)13-6-4-2-1-3-5-6/h1-5,7-11,13-16H,(H,17,18)/t7-,8-,9+,10-,11+/m0/s1
• InChIKey: SPTXZDAXCOTKFR-QUARPLMYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(phenylamino)oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(phenylamino)oxane-2-carboxylic acid
• Synonyms: 1-Deoxy-1-(phenylamino)-β-D-glucopyranuronic Acid; Aniline β-D-Glucuronide

Database IDs

• CAS Number: 92117-30-1
• PubChem SID: 162254841
• PubChem CID: 10061605

CALCULATED PROPERTIES

• Acid pKa: 3.6966448
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -2.449712
• LogD (pH = 7.4): -3.954492
• Log P: -0.64766365
• Molar Refractivity: 63.7813 cm^3
• Polarizability: 25.020517 Å^3
• Polar Surface Area: 119.25 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A662500

A metabolite of Aniline. Arylamines are predominantly conjugated by constitutive enzyme forms in the liver.

REFERENCES

• Axelrod, J., et al.: J. Biol. Chem., 232 835 (1958)
• Lilienblum, W., et al.: Biochem. Pharmacol., 33, 2041 (1958)