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Ligand menadione

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Basic Ligand Information

Molecular Structure
Picture of menadione (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C11H8O2
menadione
MJVAVZPDRWSRRC-UHFFFAOYSA-N
Synonyms:
2-methyl-1,4-dihydronaphthoquinone, 2-methyl-1,4-naphthoquinone, 2-methylnaphthalene-1,4-dione, 2-methylnaphthoquinone, menadion, menaphthone, vitamin K3
Pathway Source
Pathways
MetaCyc
menaquinol-4 biosynthesis II

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
menadione + NADPH + H+ = ?
show the reaction diagram
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1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + menadione = 1-(beta-D-ribofuranosyl)nicotinamide + menadiol
show the reaction diagram
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protoporphyrinogen IX + 3 menadione = protoporphyrin IX + 3 menadiol
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (135 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
menadione + NADPH + H+ = ?
show the reaction diagram
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menadione + NADPH = ?
show the reaction diagram
-
menadione + NADPH = ?
show the reaction diagram
-
menadione + NADPH = ?
show the reaction diagram
-
menadione + NADPH = ? + NADP+
show the reaction diagram
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menadione + NADPH = ? + NADP+
show the reaction diagram
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menadione + NADPH = ?
show the reaction diagram
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menadione + NADP+ = ?
show the reaction diagram
-
menadione + NADPH + H+ = menadiol + NADP+
show the reaction diagram
-
menadione + NADPH = ?
show the reaction diagram
-
menadione + NADPH = ?
show the reaction diagram
-
pyridoxine + vitamin K3 = pyridoxal + ?
show the reaction diagram
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(S)-malate + vitamin K3 = oxaloacetate + reduced vitamin K3
show the reaction diagram
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D-glucose + menadione = D-glucono-1,5-lactone + menadiol
show the reaction diagram
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2-methyl-1,4-naphthoquinone + reduced coenzyme F420 = 2-methyl-1,4-naphthoquinol + oxidized coenzyme F420
show the reaction diagram
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ferrocytochrome c + menadione = ferricytochrome + oxidized menadione
show the reaction diagram
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menadione + NADPH + O2 = ? + NO + NADP+
show the reaction diagram
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[methionine synthase]-cob(II)alamin + S-adenosyl-L-methionine + menadione = [methionine synthase]methylcob(I)alamin + S-adenosylhomocysteine + ?
show the reaction diagram
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phenylacetyl-CoA + H2O + menadione = phenylglyoxylyl-CoA + menadiol
show the reaction diagram
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NADH + 2-methyl-1,4-naphthoquinone = NAD+ + 2-methyl-1,4-naphthoquinol
show the reaction diagram
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2-methyl-1,4-naphthoquinone + NADP+ = ? + NADPH + H+
show the reaction diagram
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menadione + NADPH = ?
show the reaction diagram
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succinate + menadione = fumarate + menadiol
show the reaction diagram
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protoporphyrinogen IX + 3 menadione = protoporphyrin IX + 3 menadiol
show the reaction diagram
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S-dihydroorotate + menadione = orotate + menadiol
show the reaction diagram
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menadione + NADPH + H+ = menadiol + NADP+
show the reaction diagram
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menadione + NADH + H+ = menadiol + NAD+
show the reaction diagram
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reduced electron-transferring-flavoprotein + menadione = electron-transferring-flavoprotein + menadiol
show the reaction diagram
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trans-4-hydroxy-L-proline + menadione = (3R,5S)-3-hydroxy-1-pyrroline-5-carboxylate + menadiol
show the reaction diagram
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5-methyltetrahydrofolate + menadione = 5,10-methylenetetrahydrofolate + reduced menadiol
show the reaction diagram
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(S)-nicotine + menadione + H2O = (S)-6-hydroxynicotine + menadiol
show the reaction diagram
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L-proline + menadione = (S)-1-pyrroline-5-carboxylate + menadiol
show the reaction diagram
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2-methyl-1,4-naphthoquinone + O2 + NADH + H+ = ?
show the reaction diagram
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NADPH + H+ + menadione = NADP+ + menadiol
show the reaction diagram
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menadione + NADPH + H+ = menadiol + NADP+
show the reaction diagram
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NADH + H+ + menadione = NAD+ + menadiol
show the reaction diagram
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menadione + NADH = reduced menadione + NAD+
show the reaction diagram
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nitrobenzene + menadione = N-hydroxyaniline + menadiol + H2O
show the reaction diagram
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nitrite + menadione + H2O = nitrate + menadiol
show the reaction diagram
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menadione + NADH + H+ = ? + NAD+
show the reaction diagram
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menadione + NADH = ? + NAD+
show the reaction diagram
-
menadione + NADPH = ?
show the reaction diagram
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S-adenosyl-L-methionine + menadione = ?
show the reaction diagram
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menadione + O2 + H+[side 1] = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (12 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
nicotinamide riboside + menadiol = dihydronicotinamide riboside + menadione
show the reaction diagram
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2-methylnaphthalene + H2O2 = 2-methylnaphthalene-1,4-dione + H2O
show the reaction diagram
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2-methyl-1,4-naphthoquinone + NAD(P)H = 2-methyl-1,4-dihydronaphthoquinone + NAD(P)+
show the reaction diagram
nitrate + 2-methyl-1,4-naphthoquinol = nitrite + 2-methyl-1,4-naphthoquinone + H2O
show the reaction diagram
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menadiol + oxidized dithiothreitol = menadione + dithiothreitol
show the reaction diagram
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menadiol + O2 + n H+[side 1] = menadione + H2O + n H+[side 2]
show the reaction diagram
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Enzyme Cofactor/Cosubstrate (3 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
triple cofactor requirement for FAD, quinone and phospholipid. Maximum rate when phosphatidylethanolamine is added to the enzyme before the quinone
-
little catalytic efficiency, N-terminally truncated protein
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Activator in Enzyme-catalyzed Reactions (13 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
the enzyme shows more than 4fold increased activity at 2.5 mM menadione
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1.0 mM, oxidative stress induces Pseudomonas putida FprA but not FprB
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inhibitory versus substrates vanillin and phenanthridine, activating versus substrate xanthine
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slight stimulation
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0.3 mM, increase in expression of azoR mRNA relative to the expression at zero time before stress is applied, at 10 min 25.5, at 20 min 13.3
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stimulates oxidation of ferrocytochrome c3 with adenylyl sulfate and FAD as electron mediator
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induces expression of heavy and light subunit
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Inhibitor in Enzyme-catalyzed Reactions (83 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.02 mM, time dependent inactivation
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competitive versus D-glucuronate
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0.125 mM: 62.1% inhibition
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39% residual activity at 0.05 mM
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34% residual activity at 0.05 mM
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32% residual actitivty at 0.05 mM
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microsomal-bound enzyme
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78% residual activity at 0.1 mM
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slight
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tested at 1.0 mM, 33% inhibition
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above 0.03 mM
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substrate inhibition of wild-type enzyme and mutant Q183A, no inhibition of mutant Q183E
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inhibits enzyme activity in yeast extracts
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85% inhibition at 0.2 mM
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inhibits nitrate reductase
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1 mM, 61% residual activity
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0.015 mM, 97% inhibition
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i.e. vitamin K3, shows a significantly stronger potency to inhibit isozyme PKM2 than to inhibit isozymes PKM1 and PKL
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PDHK2 activity is inhibited via reversible oxidation of Cys45 and Cys392 on PDHK2
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i.e. 2-methyl-1,4-naphthoquinone, oxidative stress caused by menadione inhibits MEKK1, which can be reversed by DTT and glutathione, inhibition is thus caused by a reversible Cys1238 oxidation mechanism followed by binding to glutathione, no inhibition of MEKK1 mutant C1238V
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more than 80% inhibition of pol gamma at 0.03 mM, does not affect other human DNA polymerase isozymes
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upon exposure of human cells, the amount of enzyme protein decreases rapidly
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1 h incubation at 0.02 mM leads to loss of the activity of thiosulfate sulfurtransferase by 33%. In addition, 3-mercaptosulfurtransferase and the level of sulfane sulfur and glutathione are decreased
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1 h incubation at 0.02 mM leads to loss of the activity of 3-mercaptosulfurtransferase by 20%. In addition, thiosulfate sulfurtransferase and the level of sulfane sulfur and glutathione are decreased
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inhibits Cdc25B irreversibly
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inhibition mechanism
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wild-type cells are not able to grow on menadione containing substrate, but the recombinant strain is able to survive at 0.1 mM menadione, induction of enzyme expression by superoxide generation
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3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (73 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.65
-
pH 7.4, 25°C
0.125
-
at pH 7.4 and 37°C
1.45
-
wild-type, pH 6.4, 37°C
1.61
-
variant I22/S175
1.67
-
with 2,6-dichlorophenolindophenol, pH 7.6, 30°C
18.3
-
-
0.281
-
pH 8.0, 37°C
25.3
-
of NADPH:acceptor oxidoreductase acitivity of the beta subunit of the enzyme
6.6
-
recombinant enzyme, pH 7.4, 25°C
85.4
-
pH 6.5, recombinant enzyme
0.058
-
pH 7.8, 37°C
1.45
-
-
3278
-
-
0.483
-
pH 7.6, 30°C
0.15
-
at 50°C, pH 6.5
0.44
-
at pH 7.5 and 30°C
0.077
-
pH 8.0, 25°C

KM Value (116 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.018
-
at pH 7.4 and 37°C
0.31
-
-
0.0076
-
-
0.25
-
-
0.05
-
pH 7.0, 30°C
3
-
-
0.184
-
-
0.00376
-
pH 8.0, 37°C
0.035
-
of NADPH: acceptor oxidoreductase activity of the beta subunit of the enzyme
0.0163
-
recombinant enzyme, pH 7.4, 25°C
0.49
-
-
0.0159
-
-
0.077
-
pH 7.8, 37°C
0.0053
-
-
0.275
-
-
0.009
-
temperature not specified in the publication, pH 8.0
0.0162
-
-
0.02
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at pH 7.5 and 30°C

Ki Value (14 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.306
-
at pH 7.5 and 25°C

IC50 Value (18 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.006
-
isozyme pol gamma, in 50 mM Tris-HCl (pH 7.5) containing 1 mM dithiothreitol, 50% (v/v) glycerol, and 0.1 mM EDTA, at 37°C

References & Links

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Links to other databases for menadione

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ChEBI
PubChem
ChEBI
PubChem