7-{[(2S,4R,5S)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-methyl-2H-chromen-2-one

• ChemBase ID: 174500
• Molecular Formular: C22H28O13
• Molecular Mass: 500.44992
• Monoisotopic Mass: 500.15299096
• SMILES: [C@@H]1([C@@H](C([C@@H](OC1CO)O[C@H]1[C@@H](C([C@@H](OC1CO)Oc1ccc2c(c1)oc(=O)cc2C)O)O)O)O)O
• Canonical SMILES: OCC1O[C@@H](Oc2ccc3c(c2)oc(=O)cc3C)C([C@H]([C@@H]1O[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O)O)O
• InChI: InChI=1S/C22H28O13/c1-8-4-14(25)32-11-5-9(2-3-10(8)11)31-21-19(30)17(28)20(13(7-24)34-21)35-22-18(29)16(27)15(26)12(6-23)33-22/h2-5,12-13,15-24,26-30H,6-7H2,1H3/t12?,13?,15-,16+,17-,18?,19?,20-,21-,22+/m1/s1
• InChIKey: PRTGXBPFDYMIJH-JWJKJFOQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-{[(2S,4R,5S)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-methyl-2H-chromen-2-one
• IUPAC Traditional name: 7-{[(2S,4R,5S)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-methylchromen-2-one
• Synonyms: 7-[(4-O-β-D-Glucopyranosyl-β-D-glucopyranosyl)oxy]-4-methyl-2H-1-benzopyran-2-one; 7-(β-Cellobiosyloxy)-4-methylcoumarin; 4-Methylumbelliferyl Cellobiopyranoside; 4-Methylumbelliferyl β-D-Cellobioside

Database IDs

• CAS Number: 72626-61-0
• PubChem SID: 164230410
• PubChem CID: 71750681

CALCULATED PROPERTIES

• Acid pKa: 11.934122
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -2.259715
• LogD (pH = 7.4): -2.2597275
• Log P: -2.2597148
• Molar Refractivity: 112.3692 cm^3
• Polarizability: 45.663193 Å^3
• Polar Surface Area: 204.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M334360

4-Methylumbelliferyl β-D-cellobioside is an enzyme ligand. 4-Methylumbelliferyl β-D-cellobioside is used as a substrate to measure (1,4)-β-Glucanase activity in sediments.

REFERENCES

• Boschker, H.T,S. et al.: Appl. Environ. Microbiol., 60, 3592 (1994)
• Malet, C. et al.: Biochemistry, 36, 13838 (1994)