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

• ChemBase ID: 174521
• Molecular Formular: C16H18O8
• Molecular Mass: 338.30932
• Monoisotopic Mass: 338.10016754
• SMILES: C1(C(C(C(C(O1)Oc1ccc2c(c1)oc(=O)cc2C)O)O)O)CO
• Canonical SMILES: OCC1OC(Oc2ccc3c(c2)oc(=O)cc3C)C(C(C1O)O)O
• InChI: InChI=1S/C16H18O8/c1-7-4-12(18)23-10-5-8(2-3-9(7)10)22-16-15(21)14(20)13(19)11(6-17)24-16/h2-5,11,13-17,19-21H,6H2,1H3
• InChIKey: YUDPTGPSBJVHCN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one
• IUPAC Traditional name: 4-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one
• Synonyms: 7-(β-D-mannopyranosyloxy)-4-methyl-2H-1-benzopyran-2-one; 4-Methylumbelliferyl-β-D-mannoside; 4-Methylumbelliferyl β-D-Mannopyranoside; 7-(α-L-Idopyranosyloxy)-4-methyl-2H-1-benzopyran-2-one; 4-Methylumbelliferyl α-L-Idopyranoside; 4-Methylumbelliferyl α-D-Mannopyranoside

Database IDs

• CAS Number: 28541-83-5; 67909-30-2; 66901-41-5
• PubChem SID: 164230431
• PubChem CID: 119835

CALCULATED PROPERTIES

• Acid pKa: 12.20014
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.4888793
• LogD (pH = 7.4): -0.48888606
• Log P: -0.4888792
• Molar Refractivity: 79.9559 cm^3
• Polarizability: 31.877827 Å^3
• Polar Surface Area: 125.68 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Hot Hater; Hot Water; Methanol; Water
• Apperance: Off-White Powder; White Solid
• Melting Point: 208-209°C; 221-223°C; 235-237°C

Safety Information

• Storage Condition: -20°C Freezer; -20°C Freezer, Under inert atmosphere
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - M334750

A substrate for mannosidase. Substrate inhibition was observed for all but the least reactive of these substrates.

Toronto Research Chemicals - M334745

A substrate for mannosidase.

Toronto Research Chemicals - M334600

4-Methylumbelliferyl α-L-Idopyranoside is a fluorogenic substrate in the assay of α-L-Iduronidase. It is useful for the detection of Hurlers syndrome.

REFERENCES

• McCarter, J., et al.: Biochem. J., 286, 721 (1992)
• Namchuk, M., et al.: Biochemistry, 34, 16194 (1992)
• Burmeister, W., et al.: J. Biol. Chem., 275, 39385 (1992)
• Matalon, R., et al.: Biochem. Biophys. Res. Commun., 47, 959 (1972)
• Zhao, K., et al.: J. Biol. Chem., 272, 22758 (1972)