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

• ChemBase ID: 174520
• Molecular Formular: C16H16O9
• Molecular Mass: 352.29284
• Monoisotopic Mass: 352.07943209
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1C(=O)O)Oc1ccc2c(c1)oc(=O)cc2C)O)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-JHZZJYKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(4-methyl-2-oxochromen-7-yl)oxy]oxane-2-carboxylic acid
• Synonyms: 4-Methylumbelliferone β-D-Glucuronide; 4-Methyl-2-oxo-2H-1-benzopyran-7-yl β-D-Glucopyranosiduronic Acid; MUG; 4-Methylumbelliferyl β-D-Glucuronide; 4-Methylumbelliferyl-beta-D-glucuronide; 4-甲基-7-氧香豆素-β-D-葡萄糖苷酸

Database IDs

• CAS Number: 6160-80-1
• EC Number: 228-186-0
• MDL Number: MFCD00036772
• PubChem SID: 164230430
• PubChem CID: 91553

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

PROPERTIES

Physical Property

• Solubility: Water (with warming)
• Apperance: White Solid
• Melting Point: 134-139°C
• Optical Rotation: -106 (c=0.1 in water)

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Light Sensitive
• TSCA Listed: 是

Product Information

• Purity: 98%

DETAILS

Toronto Research Chemicals - M334550

A substrate for glucuronidase. Also used as a test for coliform bacteria in water.Fluorescence: max. Abs. 316nm; max. Em. 375nm; e x 10-3: 12

REFERENCES

• US Federal Register, 57, 24744 (1992)