Carboxyumbelliferyl β-D-galactopyranoside (CUG)

Key facts

CAS number

64664-99-9

Purity

>98%

Form

Solid

form

Molecular weight

368.29 Da

Molecular formula

C₁₆H₁₆O₁₀

PubChem

10133607

Nature

Synthetic

Solubility

Soluble in DMSO

Biochemical name

3-Carboxyumbelliferyl beta-D-galactopyranoside

Biological description

pH dependent blue fluorogenic β-galactosidase substrate that is well retained intracellularly for use in live cell analyses. Below the pKa (7.8), Abs. shifts to shorter wavelengths (325 to 340 nm) and fluorescence intensity decreases. These shifts may be used to measure compartmentalization of intracellular activity. Em = 445nm, ε = 32K is emission of fluorophore 3-carboxyumbelliferone released upon beta-galactosidase enzyme activity.

Canonical smiles

C1=CC2=C(C=C1OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C(=C2)C(=O)O

Isomeric smiles

C1=CC2=C(C=C1O[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)CO)O)O)O)OC(=O)C(=C2)C(=O)O

InChi

InChI=1S/C16H16O10/c17-5-10-11(18)12(19)13(20)16(26-10)24-7-2-1-6-3-8(14(21)22)15(23)25-9(6)4-7/h1-4,10-13,16-20H,5H2,(H,21,22)/t10-,11+,12+,13-,16-/m1/s1

InChiKey

HGMXXIAQZWTZLR-WUGLTUCPSA-N

IUPAC Name

2-oxo-7-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromene-3-carboxylic acid