(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic acid

• ChemBase ID: 174511
• Molecular Formular: C16H16O9
• Molecular Mass: 352.29284
• Monoisotopic Mass: 352.07943209
• SMILES: c1(ccc2c(c1)oc(=O)cc2C)O[C@H]1O[C@H]([C@@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@H](Oc2ccc3c(c2)oc(=O)cc3C)[C@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C16H16O9/c1-6-4-10(17)24-9-5-7(2-3-8(6)9)23-16-13(20)11(18)12(19)14(25-16)15(21)22/h2-5,11-14,16,18-20H,1H3,(H,21,22)/t11-,12+,13+,14-,16-/m0/s1
• InChIKey: ARQXEQLMMNGFDU-ADVQIIOHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[(4-methyl-2-oxochromen-7-yl)oxy]oxane-2-carboxylic acid
• Synonyms: 4-Methyl-2-oxo-2H-1-benzopyran-7-yl α-D-Galactopyranosiduronic Acid; 4-Methylumbelliferyl α-D-Galacturonic Acid

Database IDs

• CAS Number: 67968-37-0
• PubChem SID: 164230421
• PubChem CID: 71750690

CALCULATED PROPERTIES

• Acid pKa: 2.9729717
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.6557503
• LogD (pH = 7.4): -3.6463246
• Log P: -0.16860466
• Molar Refractivity: 79.8233 cm^3
• Polarizability: 31.865303 Å^3
• Polar Surface Area: 142.75 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

REFERENCES

• Courtin-Duchateau, M.C., et al.: Carbohydrate Res., 65, 23 (1978)