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

• ChemBase ID: 133665
• Molecular Formular: C16H18O10
• Molecular Mass: 370.30812
• Monoisotopic Mass: 370.08999678
• SMILES: Cc1cc(=O)oc2c1ccc(c2)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)O)O)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.O
• InChI: InChI=1S/C16H16O9.H2O/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);1H2/t11-,12-,13+,14-,16+;/m0./s1
• InChIKey: URVSQZMOFUEQAW-YYHOVTOASA-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 hydrate
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(4-methyl-2-oxochromen-7-yl)oxy]oxane-2-carboxylic acid hydrate
• Synonyms: 4-Methylumbelliferyl-β-D-glucopyranosiduronic acid; MUG; 4-Methylumbelliferyl-β-D-glucuronide hydrate

Database IDs

• CAS Number: 881005-91-0
• EC Number: 228-186-0
• MDL Number: MFCD09039280
• PubChem SID: 162227942; 24885956; 24897034
• PubChem CID: 16218413

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: DMSO: soluble50 mg/mL, clear, colorless to very faintly yellow; pyridine: soluble0.1 M at 20 °C, clear, colorless
• Fluorescence: λex 365 nm; λem 445 nm in 0.1 M phosphate pH 6.5

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC); ≥99.0% (HPLC)
• Suitability: suitable for fluorescence
• Impurities: ≤0.005% Phosphorus (P); ≤0.1% free 4-Methylumbelliferone; ≤15% water
• Cation Traces: Al: ≤0.001%; Ca: ≤0.005%; Cu: ≤0.0005%; Fe: ≤0.0005%; K: ≤0.005%; Mg: ≤0.001%; Na: ≤0.005%; NH4+: ≤0.05%; Pb: ≤0.001%; Zn: ≤0.001%
• Antion Traces: chloride (Cl-): ≤0.05%
• Empirical Formula (Hill Notation): C16H16O9 · xH2O

DETAILS

Sigma Aldrich - 69602

Application
suitable as fluorogenic substrate for β-glucuronidase
Other Notes
Substrate for β-D-glucuronidase assay. Has been used in a method to measure liposome lysis by n-octylglucoside1

Sigma Aldrich - M9130

Application
Fluorescent substrate for β-glucuronidase. ≥98% (HPLC)