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Ligand 2,6-dichlorophenolindophenol

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Basic Ligand Information

Molecular Structure
Picture of 2,6-dichlorophenolindophenol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
Molfile
C12H7ClNO2
2,6-dichlorophenolindophenol
FBWADIKARMIWNM-UHFFFAOYSA-N
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Synonyms:
2,6-dichloro-phenolindophenol, 2,6-dichloroindophenol, 2,6-dichlorophenol-indophenol, 2,6-dichlorophenolindolphenol, 2,6-dichlorophenol indophenol, DCPIP, dichlorophenol-indophenol, dichlorophenolindolphenol, dichlorophenolindophenol, dichlorophenol indophenol, dichlororphenol indophenol, dichlorphenolindophenol

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (15 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-sorbose + 2,6-dichlorophenolindophenol = 5-keto-D-fructose + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
L-sorbose + 2,6-dichlorophenolindophenol = L-sorbosone + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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4-pyridoxate + 2,6-dichloroindophenol = 5-formyl-3-hydroxy-2-methylpyridine-4-carboxylate + reduced 2,6-dichloroindophenol
show the reaction diagram
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isovaleryl-CoA + 2,6-dichlorophenolindophenol = ?
show the reaction diagram
-
4-cholesten-3-one + 2,6-dichlorophenol-indophenol = ? + reduced acceptor
show the reaction diagram
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beta-phenylethylamine + H2O + 2,6-dichlorophenol indophenol = phenylacetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (678 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
D-sorbitol + 2,6-dichlorophenolindophenol = L-sorbose + ?
show the reaction diagram
-
D-mannitol 1-phosphate + dichlorophenolindophenol = D-fructose 6-phosphate + reduced dichlorophenolindophenol
show the reaction diagram
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myo-inositol + 2,6-dichlorophenolindophenol = 2,4,6/3,5-pentahydroxycyclohexanone + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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2,6-dichloroindophenol + NADPH = ?
show the reaction diagram
-
geraniol + dichlorophenolindophenol = ?
show the reaction diagram
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2,6-dichloroindophenol + NADH + H+ = reduced 2,6-dichloroindophenol + NAD+
show the reaction diagram
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2,6-dichlorophenolindophenol + NADH = ?
show the reaction diagram
-
beta-D-glucose + 2,6-dichlorophenol-indophenol = ?
show the reaction diagram
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D-lactate + 2,6-dichlorophenolindophenol = pyruvate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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D-lactate + 2,6-dichlorophenolindophenol = pyruvate + ?
show the reaction diagram
-
methanol + 2,6-dichlorophenolindophenol = formaldehyde + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
L-sorbose + 2,6-dichloroindophenol = 5-dehydro-D-fructose + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
polyvinyl alcohol + 2,6-dichlorophenolindophenol = polyvinylketone + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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beta-D-glucose + 2,6-dichlorophenol indophenol = D-glucono-1,5-lactone + ?
show the reaction diagram
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veratryl alcohol + 2,6-dichlorophenol indophenol = veratrylaldehyde + red. 2,6-dichlorophenol indophenol
show the reaction diagram
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L-gulono-1,4-lactone + 2,6-dichlorophenolindophenol + O2 = L-ascorbic acid + ?
show the reaction diagram
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D-lactate + 2,6-dichlorophenol-indophenol = pyruvate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
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L-lactate + 2,6-dichlorophenol indophenol = pyruvate + reduced 2,6-dichlorophenol indophenol
show the reaction diagram
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choline + 2,6-dichlorophenolindophenol = betaine aldehyde + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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(R)-Pantolactone + 2,6-dichlorophenol-indophenol = 2-Dehydropantonolactone + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
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D-gluconate + 2,6-dichlorophenolindophenol = 2-oxogluconate + ?
show the reaction diagram
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D-glucose + 2,6-dichlorophenolindophenol = D-glucono-1,5-lactone + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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2-dehydro-D-gluconate + 2,6-dichlorophenolindophenol = 2,5-didehydro-D-gluconate + ?
show the reaction diagram
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4-pyridoxate + 2,6-dichloroindophenol = 5-formyl-3-hydroxy-2-methylpyridine-4-carboxylate + reduced 2,6-dichloroindophenol
show the reaction diagram
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4-phospho-D-erythronate + 2,6-dichloroindophenol = 3-hydroxy-4-phosphohydroxy-alpha-ketobutyrate + reduced 2,6-dichloroindophenol
show the reaction diagram
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2,6-dichloroindophenol + O2 = oxidized 2,6-dichloroindophenol + H2O
show the reaction diagram
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H2O + 2,6-dichlorophenolindophenol + hv = O2 + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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H2 + 2,6-dichlorophenolindophenol = H+ + ?
show the reaction diagram
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(S)-lactate + 2,6-dichlorophenolindophenol = pyruvate + ?
show the reaction diagram
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2,6-dichlorophenolindophenol + NADPH + O2 = ? + NO + NADP+
show the reaction diagram
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[methionine synthase]-cob(II)alamin + S-adenosyl-L-methionine + 2,6-dichlorophenolindophenol = [methionine synthase]methylcob(I)alamin + S-adenosylhomocysteine + ?
show the reaction diagram
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2,6-dichloroindophenol + NADPH + H+ = ?
show the reaction diagram
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nicotinate + H2O + 2,6-dichloroindophenol = 6-hydroxynicotinate + reduced 2,6-dichloroindophenol
show the reaction diagram
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xanthine + 2,6-dichlorophenolindophenol + H2O = urate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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6-hydroxynicotinate + H2O + 2,6-dichlorophenol indophenol = 2,6-dihydroxynicotinate + H2O2 + reduced 2,6-dichlorophenol indophenol
show the reaction diagram
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phenylacetyl-CoA + H2O + 2,6-dichlorophenolindophenol = phenylglyoxylyl-CoA + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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formate + 2,6-dichlorophenolindophenol = CO2 + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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(+)-pinoresinol + 2,6-dichlorophenolindophenol + phenazine methosulfate + H2O = (+)-6-hydroxypinoresinol + reduced 2,6-dichlorophenolindophenol + ?
show the reaction diagram
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NADH + 2,6-dichloroindophenol = NAD+ + reduced 2,6-dichloroindophenol
show the reaction diagram
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2,6-dichloroindophenol + NADH = reduced 2,6-dichloroindophenol + NAD+ + H+
show the reaction diagram
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2,6-dichlorophenolindophenol + NADPH = reduced 2,6-dichlorophenolindophenol + NADP+
show the reaction diagram
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pyruvate + CoA + dichlorophenol indophenol = acetyl-CoA + CO2 + ?
show the reaction diagram
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pyruvate + phosphate + 2,6-dichlorophenolindophenol + H2O = acetyl phosphate + CO2 + reduced 2,6-dichlorophenolindophenol + H2O2
show the reaction diagram
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arsenite + H2O + 2,6-dichlorophenolindophenol = arsenate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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arsenite + 2,6-dichlorophenol indophenol = arsenate + reduced 2,6-dichlorophenol indophenol
show the reaction diagram
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beta-cyclopiazonate + 2,6-dichlorophenolindophenol = alpha-cyclopiazonate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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(S)-dihydroorotate + 2,6-dichlorophenolindophenol = orotate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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butyryl-CoA + 2,6-dichlorophenolindophenol = ?
show the reaction diagram
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protoporphyrinogen-IX + 3 2,6-dichlorophenolindophenol = protoporphyrin-IX + 3 reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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glutaryl-CoA + 2,6-dichlorophenol indophenol = crotonoyl-CoA + CO2 + reduced 2,6-dichlorophenol indophenol
show the reaction diagram
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taurine + H2O + 2,6-dichlorophenol indophenol = sulfoacetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
show the reaction diagram
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glycine + 2,6-dichlorophenol-indophenol = HCN + CO2 + ?
show the reaction diagram
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sarcosine + H2O + 2,6-dichlorophenolindophenol = glycine + formaldehyde + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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sarcosine + 5,6,7,8-tetrahydrofolate + 2,6-dichlorophenolindophenol = ?
show the reaction diagram
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reduced electron-transferring flavoprotein + 2,6-dichloroindophenol = electron-transferring flavoprotein + reduced 2,6-dichloroindophenol
show the reaction diagram
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dimethylamine + H2O + 2,6-dichlorophenolindophenol = methylamine + formaldehyde + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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trimethylamine + H2O + 2,6-dichlorophenolindophenol = dimethylamine + formaldehyde + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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D-proline + 2,6-dichlorophenolindophenol = 1-pyrroline-2-carboxylate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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6-hydroxypseudooxynicotine + 2,6-dichlorophenolindophenol + H2O = 6-hydroxy-3-succinoylsemialdehyde-pyridine + methylamine + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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(S)-nicotine + 2,6-dichlorophenolindophenol + H2O = (S)-6-hydroxynicotine + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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NAD(P)H + 2,6-dichlorophenolindophenol = NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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NADPH + H+ + dichlorophenolindophenol = NADP+ + reduced dichlorophenolindophenol
show the reaction diagram
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2,6-dichloroindophenol + NADPH = ? + NADP+
show the reaction diagram
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2,6-dichloroindophenol + NADH = reduced 2,6-dichloroindophenol + NAD+
show the reaction diagram
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NADH + 2,6-dichlorophenol indophenol = NAD+ + ?
show the reaction diagram
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2,6-dichlorophenolindophenol + NADH + H+ = reduced 2,6-dichlorophenolindophenol + NAD+
show the reaction diagram
-
pyruvate + CoA + 2,6-dichlorophenolindophenol = acetyl-CoA + CO2 + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (11 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
D-xylose + 2,6-dichloroindophenol = D-xylono-1,5-lactone + 2,6-dichlorophenolindophenol
show the reaction diagram
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D-galactose + 2,6-dichlorophenolindophenol = 3-dehydro-D-galactose + 2,6-dichlorophenolindophenol
show the reaction diagram
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nicotinamide riboside + reduced 2,6-dichlorophenolindophenol = dihydronicotinamide riboside + 2,6-dichlorophenolindophenol
show the reaction diagram
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fumarate + reduced 2,6-dichlorophenolindophenol = succinate + 2,6-dichlorophenolindophenol
show the reaction diagram
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ferricyanide + reduced 2,6-dichlorophenolindophenol = ferrocyanide + 2,6-dichlorophenolindophenol
show the reaction diagram
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2,6-dichlorophenolindophenylacetate + H2O = 2,6-dichlorophenolindophenol + acetate
show the reaction diagram
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Enzyme Cofactor/Cosubstrate (19 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
can substitute for cytochrome c
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in vitro requirement, terminal acceptor
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electron acceptor
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acts in vitro as acceptor together with phenazine methosulfate
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acts in vitro as acceptor together with phenazine methosulfate
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activation
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required as electron acceptor, promotes barbiturate formation better than methylene blue
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in vitro 4000fold faster reaction than with the native acceptor
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Activator in Enzyme-catalyzed Reactions (8 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activation, enhances NADH-oxidation
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after addition of an artificial electron acceptor such as 2,6-dichloroindophenol, the nicotinate hydroxylase activity is significantly increased
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the rate of the overall process is higher than with oxygen
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enhances activity
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Inhibitor in Enzyme-catalyzed Reactions (16 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibition by excess substrate
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competitive inhibition
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inhibition of the dichlorophenolindophenol-specific enzyme at high concentrations
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formation of superoxide anion, in the presence of menadione
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substrate inhibition
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inhibition of O2 consumption
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0.05 mM, complete inhibition
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causes substrate inhibition at concentrations above 0.25 mM
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uncompetitive
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0.1 mM, weak inhibition
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (57 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
14.1
-
pH 7.6, 22°C
1.13
-
-
0.43
-
variant I22/S175
5.67
-
cosubstrate xanthine
4.8
-
-
1.5
-
-
50.2
-
-
330
-
pH 6.0, temperature not specified in the publication

KM Value (116 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0383
-
pH 7.6, 22°C
0.0368
-
-
1.6
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pH 8.8, 25°C
0.89
-
pH 6.5, 25°C
1
-
at 10 mM choline
0.21
-
-
0.0025
-
-
0.007
-
as electron acceptor under aerobic conditions
0.02
-
artificial electron acceptor
0.00016
-
-
0.0146
-
S175C mutant
0.33
-
-
0.115
-
in 50mM Tris/HCl, 150 mM KCl, 0.1% (v/v) Triton X-100, pH 8, at 30°C
0.015
-
with D-alanine
0.12
-
-
0.07
-
specific acceptor, cosubstrate: D-kynurenine
0.31
-
-
0.31
-
at pH 7.7 and 37°C
0.0034
-
wild type enzyme, at 25°C and pH 7.1 in 20 mM Tris-HCl
0.14
-
pH 8.0, 50°C
0.0125
-
-
0.0105
-
pH 6.0, temperature not specified in the publication
0.03
-
-
0.039
-
pH not specified in the publication, temperature not specified in the publication
0.0062
-
pH 7.0, 25°C
0.038
-
recombinant enzyme, pH and temperature not specified in the publication

Ki Value (3 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.078
-
-
0.1152
-
pH 7.0, 25°C
0.015
-
-

References & Links

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Links to other databases for 2,6-dichlorophenolindophenol

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EXTERNAL LINKS
ChEBI
PubChem
UniChem