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

• ChemBase ID: 174469
• Molecular Formular: C22H28O12
• Molecular Mass: 484.45052
• Monoisotopic Mass: 484.15807634
• SMILES: [C@H]1([C@@H](C([C@@H](OC1CO)Oc1ccc2c(c1)oc(=O)cc2C)O[C@H]1C([C@@H]([C@@H](C(O1)C)O)O)O)O)O
• Canonical SMILES: OCC1O[C@@H](Oc2ccc3c(c2)oc(=O)cc3C)C([C@H]([C@H]1O)O)O[C@@H]1OC(C)[C@H]([C@H](C1O)O)O
• InChI: InChI=1S/C22H28O12/c1-8-5-14(24)32-12-6-10(3-4-11(8)12)31-22-20(18(28)16(26)13(7-23)33-22)34-21-19(29)17(27)15(25)9(2)30-21/h3-6,9,13,15-23,25-29H,7H2,1-2H3/t9?,13?,15-,16+,17+,18+,19?,20?,21+,22-/m1/s1
• InChIKey: QVEUSHJADSGABK-WIJWQDJOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-{[(2S,4S,5R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,4S,5S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-methyl-2H-chromen-2-one
• IUPAC Traditional name: 7-{[(2S,4S,5R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,4S,5S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-methylchromen-2-one
• Synonyms: 7-[[2-O-(6-Deoxy-α-L-galactopyranosyl)-β-D-galactopyranosyl]oxy]-4-methyl-2H-1-benzopyran-2-one; Fuc1-α-2Gal-β-4Mu; 4-Methylumbelliferyl 2-O-(α-L-Fucopyranosyl)-β-D-galactopyranoside

Database IDs

• CAS Number: 225217-42-5
• PubChem SID: 164230379
• PubChem CID: 71750660

CALCULATED PROPERTIES

• Acid pKa: 12.10016
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -1.212805
• LogD (pH = 7.4): -1.2128135
• Log P: -1.2128049
• Molar Refractivity: 110.8255 cm^3
• Polarizability: 44.970135 Å^3
• Polar Surface Area: 184.6 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M333030

A synthetic chromogenic substrate for the assay of a-fucosidases.

REFERENCES

• For a related substrate, the p-nitrophenyl derivative see DiCioccio, R.A., et al.: Anal. Biochem., 11, 176 (1981)