Ligand 5-hydroxy-1,4-naphthoquinone

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Basic Ligand Information

Molecular Structure
Picture of 5-hydroxy-1,4-naphthoquinone (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C10H6O3
5-hydroxy-1,4-naphthoquinone
WQBJZVZIHOSAIX-GUCLMQHLSA-N
Synonyms:
5-hydroxy-1,4-naphthohydroquinone, 5-hydroxynaphthalene-1,4-dione, 5-hydroxynaphthoquinone, juglone, juglone derivatives
Pathway Source
Pathways

Roles as Enzyme Ligand

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

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5-hydroxy-1,4-naphthoquinone + O2 = 3,5-dihydroxy-1,4-naphthoquinone + H2O
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (21 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5-hydroxy-1,4-naphthoquinone + O2 = 3,5-dihydroxy-1,4-naphthoquinone + H2O
show the reaction diagram
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5-hydroxy-1,4-naphthoquinone + NADP+ = ? + NADPH + H+
show the reaction diagram
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5-hydroxy-1,4-naphthoquinone + NADPH + H+ = 5-hydroxy-1,4-naphthoquinol + NADP+
show the reaction diagram
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NADH + H+ + juglone = NAD+ + ?
show the reaction diagram
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nitric oxide + juglone = ?
show the reaction diagram
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5-hydroxy-1,4-naphthoquinone + NADH = 5-hydroxy-1,4-naphthoquinol + NAD+
show the reaction diagram
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5-hydroxy-1,4-naphthoquinone + NADPH = ?
show the reaction diagram
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5-hydroxy-1,4-naphthoquinone + NAD(P)H = 5-hydroxy-1,4-naphthoquinol + NAD(P)+
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
NO + 5-hydroxy-1,4-naphthoquinol = N2O + H2O + 5-hydroxy-1,4-naphthoquinone
show the reaction diagram
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nitrate + 5-hydroxy-1,4-naphthoquinol = nitrite + 5-hydroxy-1,4-naphthoquinone + H2O
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (26 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
i.e. juglone
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0.001 mM juglone reduces activity to 50%
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0.001 mM juglone reduces activity to 50%
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microsomal-bound enzyme
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0.015 mM, 46.1% inhibition
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IC50: 0.25 mM
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poor inhibitory activity
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5-hydroxy-1,4-naphthoquinone, juglone, acts as a strong, time and concentration dependent inactivator of urease. The reactivation of juglone-modified urease shows the participation of reversible and irreversible contribution in the inactivation. In the presence of an excess of DTT, urease inactivated by juglone regains 70% of its activity. The reversible inactivation is attributed to oxidation of the essential urease thiols by reactive oxygen species (ROS) realizing during reduction of juglone to seminaphthoquinone. The irreversible contribution in the inhibition is assumed as an arylation of urease thiol groups by juglone
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3D Structure of Enzyme-Ligand-Complex (PDB) (24 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (14 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.19
-
pH 7.4, 25C
0.324
-
pH 7.6, 30C
5.5
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pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25C

KM Value (17 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0045
-
pH 7.4, 25C
0.14
-
-
0.141
-
pH and temperature not specified in the publication
0.29
-
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Ki Value (2 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.00015
-
pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25C
0.0000559
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mutant enzyme C69A

IC50 Value (5 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.001
-
-
0.001
-
pH 7.5, 12C
0.0096
-
pH 7.5, 30C
0.25
-
IC50: 0.25 mM
0.025
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pH 7.7, temperature not provided

References & Links

Links to other databases for 5-hydroxy-1,4-naphthoquinone

ChEBI
PubChem
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PubChem