(2S,3S,4S,5R)-3,4,5-trihydroxy-6-(6-oxo-1-phenyl-1,6-dihydropyridine-3-carbonyloxy)oxane-2-carboxylic acid

• ChemBase ID: 163713
• Molecular Formular: C18H17NO9
• Molecular Mass: 391.32888
• Monoisotopic Mass: 391.09033113
• SMILES: [C@@H]1([C@@H]([C@@H](C(O[C@H]1C(=O)O)OC(=O)c1cn(c(=O)cc1)c1ccccc1)O)O)O
• Canonical SMILES: OC(=O)[C@@H]1OC(OC(=O)c2ccc(=O)n(c2)c2ccccc2)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C18H17NO9/c20-11-7-6-9(8-19(11)10-4-2-1-3-5-10)17(26)28-18-14(23)12(21)13(22)15(27-18)16(24)25/h1-8,12-15,18,21-23H,(H,24,25)/t12-,13-,14+,15-,18?/m0/s1
• InChIKey: FJCGEWGRFLWJDE-ZBCYVVTKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(6-oxo-1-phenyl-1,6-dihydropyridine-3-carbonyloxy)oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(6-oxo-1-phenylpyridine-3-carbonyloxy)oxane-2-carboxylic acid
• Synonyms: 1-O-(5-Carboxy-N-phenyl-2-1H-pyridone)-D-glucuronic Acid (1:3 α:β mixture)

Database IDs

• PubChem SID: 162257848
• PubChem CID: 71314527

CALCULATED PROPERTIES

• Acid pKa: 3.2615705
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.6001751
• LogD (pH = 7.4): -3.8148785
• Log P: -0.38090995
• Molar Refractivity: 91.0174 cm^3
• Polarizability: 35.7688 Å^3
• Polar Surface Area: 153.83 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Hot Methanol; Water
• Apperance: Off-White Powder
• Melting Point: 156-168°C dec.

DETAILS

Toronto Research Chemicals - C181230

A metabolite of Pirfenidone, a new drug to treat patients with kidney disease who have diabetes.