Ligand plumbagin

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Basic Ligand Information

Molecular Structure
Picture of plumbagin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C11H8O3
plumbagin
VCMMXZQDRFWYSE-UHFFFAOYSA-N
Synonyms:
2-methyl-5-hydroxy-1,4-naphthoquinone, 5-Hydroxy-2-methyl-1,4-naphthoquinone, 5-hydroxy-2-methyl-1,4-naphtoquinone, 5-hydroxy-2-methyl-naphthalene-1,4-dione, 5-hydroxy-2-methylnaphthalene-1,4-dione, oxidized plumbagin
Pathway Source
Pathways

Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5-hydroxy-2-methyl-1,4-naphthoquinone + O2 = 3,5-dihydroxy-2-methyl-1,4-naphthoquinone + H2O
show the reaction diagram
-
2-methyl-5-hydroxy-1,4-naphthoquinone + NADP+ = ? + NADPH + H+
show the reaction diagram
-
nitric oxide + plumbagin = ?
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
fumarate + reduced plumbagin = succinate + oxidized plumbagin
show the reaction diagram
-
-
2 5-hydroxy-2-methyl-1,4-naphthoquinone + NADPH + H+ = 5-hydroxy-2-methyl-1,4-naphthoquinone + NADP+
show the reaction diagram
-
-
NO + 5-hydroxy-2-methyl-1,4-naphthoquinol = N2O + H2O + 5-hydroxy-2-methyl-1,4-naphthoquinone
show the reaction diagram
-
-

Enzyme Cofactor/Cosubstrate (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
a quinone analogue
-

Inhibitor in Enzyme-catalyzed Reactions (18 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
microsomal-bound enzyme
-
inhibition is only 50% even at 0.1 mM
-
inhibition of NOX4
-
poor inhibitory activity
-
leads to uPA inhibition and downregulation, inhibits adhesion, migration and invasion in HepG2 cells
-

3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (4 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE

KM Value (2 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0043
-
pH 7.4, 25°C
0.256
-
pH and temperature not specified in the publication

IC50 Value (9 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0021
-
pH 7.5, 30°C
0.7
-
IC50: 0.7 mM

References & Links

Links to other databases for plumbagin

ChEBI
PubChem
ChEBI
PubChem