Ligand tetrafluoro-1,4-benzoquinone

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Basic Ligand Information

Molecular Structure
Picture of tetrafluoro-1,4-benzoquinone (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6ClO2
tetrafluoro-1,4-benzoquinone
UGNWTBMOAKPKBL-UHFFFAOYSA-N
Synonyms:
2,3,5,6-tetrachloro-1,4-benzoquinone, chloranil, tetrachloro-1,4-benzoquinone, tetrachloro-p-benzoquinone, tetrachlorobenzoquinone

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
2,3,5,6-tetrachloro-1,4-benzoquinone + NADH + H+ = 2,3,5,6-tetrachlorohydroquinone + NAD+
-
show the reaction diagram
tetrachlorobenzoquinone + NADPH = tetrachlorohydroquinone + NADP+
-

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
2,3,5,6-tetrachlorohydroquinone + NAD+ = 2,3,5,6-tetrachloro-1,4-benzoquinone + NADH + H+
-

Substrate in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
2,3,5,6-tetrachloro-1,4-benzoquinone + NADH + H+ = 2,3,5,6-tetrachlorohydroquinone + NAD+
-
show the reaction diagram
tetrachlorobenzoquinone + NADPH = tetrachlorohydroquinone + NADP+
-

Product in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
pentachlorophenol + H2O2 = 2,3,5,6-tetrachloro-1,4-benzoquinone + HCl
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Inhibitor in Enzyme-catalyzed Reactions (6 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
inactivates the enzyme, feedback control
-
strong inhibition of succinate-phenazine methosulfate-(1,4-dichloroindophenol) oxidoreductase
-
i.e. TCBQ, inhibition of GSTA1-2 and GSTA1-1 by 70-80%, and GSTA2-2 by 25%, binds to cysteine residues of the enzyme, e.g. Cys17 of GSTA1-1, via a first reversible step to covalent binding, overview, Kitz-Wilson inactivation model
-

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (2 results)

COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
pH 6.5, 30°C, recombinant enzyme
129
-
substrate tetrafluoro-1,4-benzoquinone (constant D-glucose concentration, 20 mM), activity determined spectrophotometrically at 420 nm by measuring formation of H2O2 with a horse-radish peroxidase-coupled assay using 2,2'-azinobis(3-ethylbenzthiazolinesulfonic acid) as the chromogen, 30°C, pH 6.5
6.61
-

KM Value (6 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
pH 6.5, 30°C, recombinant enzyme
9.42
-
pH 6.5, substrate: D-glucose
substrate tetrafluoro-1,4-benzoquinone (constant D-glucose concentration, 20 mM), activity determined spectrophotometrically at 420 nm by measuring formation of H2O2 with a horse-radish peroxidase-coupled assay using 2,2'-azinobis(3-ethylbenzthiazolinesulfonic acid) as the chromogen, 30°C, pH 6.5
0.64
-
at 30°C with 25 mM glucose as susbtrate

Ki Value (1 result)

COMMENTARY
EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
LITERATURE
-
0.00045
-

IC50 Value (2 results)

COMMENTARY
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
LITERATURE
isoform PanK3, at pH 7.5 and 37°C
0.0059
-
fluorescence polarization assay
0.048
-

References & Links

Links to other databases for tetrafluoro-1,4-benzoquinone

ChEBI
PubChem
-
PubChem