Ligand 2,4-dinitrophenol

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Basic Ligand Information

Molecular Structure
Picture of 2,4-dinitrophenol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H4N2O5
2,4-dinitrophenol
VZTUIEROBZXUFA-INIZCTEOSA-N
Synonyms:
dinitrophenol, nitrophene

Roles as Enzyme Ligand

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2,4-dinitroanisole + H2O = methanol + 2,4-dinitrophenol
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2,4-dinitrophenol + NADH + H+ + O2 = 2-nitrohydroquinone + nitrite + NAD+ + H2O
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2,4-dinitrophenol + NADPH + O2 = ?
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UDP-glucose + 2,4-dinitrophenol = UDP + 2,4-dinitrophenylglucoside
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (48 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2,4-dinitrophenyl butyrate + H2O = 2,4-dinitrophenol + butyrate
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thymidine 3'-(2,4-dinitrophenyl)phosphate + H2O = thymidine 3'-phosphate + 2,4-dinitrophenol
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2,4-dinitrophenyl phosphate + H2O = 2,4-dinitrophenol + phosphate
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2,4-dinitrophenyl alpha-N-acetyl-D-glucosaminide + H2O = 2,4-dinitrophenol + alpha-N-acetyl-D-glucosamine
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2,4-dinitrophenyl diethyl phosphate + H2O = 2,4-dinitrophenol + diethyl phosphate
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2,4-dinitrophenyl alpha-D-galactoside + H2O = 2,4-dinitrophenol + alpha-D-galactose
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2,4-dinitrophenyl-beta-D-mannopyranoside + H2O = 2,4-dinitrophenol + alpha-D-mannose
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2,4-dinitrophenyl-alpha-N-acetyl-D-glucosaminide + H2O = 2,4-dinitrophenol + N-acetyl-D-glucosamine
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2,4-dinitrophenyl-N-acetyl-beta-D-glucosaminide + H2O = 2,4-dinitrophenol + N-acetyl-beta-D-glucosaminide
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2,4-dinitrophenyl-beta-D-Glc-(1-4)-beta-D-Glc-(1-3)-beta-D-Glc + H2O = 2,4-dinitrophenol + beta-D-Glc-(1-4)-beta-D-Glc-(1-3)-beta-D-Glc
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2,4-dinitrophenyl-beta-mannobioside + H2O = 2,4-dinitrophenol + beta-mannobiose
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2,4-dinitrophenyl 6-phospho-beta-D-glucoside + H2O = 2,4-dinitrophenol + D-glucose 6-phosphate
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2,4-dinitrophenyl cellobiose + H2O = 2,4-dinitrophenol + cellobiose
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2,4-dinitrophenyl beta-D-glucopyranoside + H2O = 2,4-dinitrophenol + D-glucopyranose
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2,4-dinitroanisole + H2O = methanol + 2,4-dinitrophenol
show the reaction diagram
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S-2,4-dinitrophenyl-L-Cys-Gly + H2O = 2,4-dinitrophenol + L-Cys-Gly
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7-amido-4-carboxymethylcoumarin-YVADAPK(Dnp)-OH + H2O = dinitrophenol + 7-amino-4-carbamoylmethylcoumarin-YVADAPK
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o-aminobenzoyl-LPETG-2,4-dinitrophenyl + H2O = o-aminobenzoyl-LPETG + 2,4-dinitrophenol
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1-chloro-2,4-dinitrobenzene + H2O = 2,4-dinitrophenol + chloride
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ATP + H2O + S-(2,4-dinitrobenzene)-glutathione[side1] = ADP + phosphate + glutathione[side 2] + 2,4-dinitrophenol
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Activator in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activity 101.6%
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activation
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a cellular metabolic poison that activates AMPK in numerous cell types, including skeletal muscle, mechanism, overview
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2,4-dinitrophenol increases the expression of HVP1, treatment with abscisic acid and 2,4-dinitrophenol increases Na+/H+ antiport activity and proton translocating activities by H+-PPase and H+-ATPase in tonoplast vesicles, and treatment with abscisic acid also increases the amount of V-PPase protein of tonoplast vesicles, overview
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stimulates, stimulation is prevented by 0.2-1.0 mM Ca2+
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Inhibitor in Enzyme-catalyzed Reactions (39 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
1 mM, complete inhibition
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competitive inhibition
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0.1 mM, 83% loss of activity
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1 mM, 40% residual activity
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50 microM, 41.7% residual AtraAOX2 activity
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1 mM, 86% inhibition
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0.1 mM, 80% inhibition of hydroxylamine reductase activity
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5 mM, 67% inhibition
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diminishes yield of phosphoribosyladenosine triphosphate by acting as parasite substrate
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16% inhibition at 1 mM
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weak
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brain enzyme, 0.25 mM: 50% inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (7 results)

Enzyme Kinetic Parameters

Ki Value (2 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0005
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0.25
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brain enzyme

References & Links

Links to other databases for 2,4-dinitrophenol

ChEBI
PubChem
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PubChem