Information on EC 1.14.13.116 - geranylhydroquinone 3''-hydroxylase

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The expected taxonomic range for this enzyme is: Lithospermum erythrorhizon

EC NUMBER
COMMENTARY hide
1.14.13.116
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RECOMMENDED NAME
GeneOntology No.
geranylhydroquinone 3''-hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
geranylhydroquinone + NADPH + H+ + O2 = 3''-hydroxygeranylhydroquinone + NADP+ + H2O
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
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shikonin biosynthesis
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Ubiquinone and other terpenoid-quinone biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
geranylhydroquinone,NADPH:oxygen oxidoreductase (3''-hydroxylating)
Contains cytochrome P-450.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Sieb. et Zucc.
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
geranylhydroquinone + NADPH + H+ + O2
3''-hydroxygeranylhydroquinone + NADP+ + H2O
show the reaction diagram
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
geranylhydroquinone + NADPH + H+ + O2
3''-hydroxygeranylhydroquinone + NADP+ + H2O
show the reaction diagram
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likely to be involved in shikonin and dihydroechinofuran biosynthesis
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?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
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required, could not be replaced by NADH, FAD or FMN. The optimal concentration of NADPH for this reaction is between 1 and 5 mM
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ancymidol
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1 mM, 38% inhibition
CO
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inhibitory effect of CO is reversed by illumination
cytochrome c
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0.01 mM, 96% inhibition
ketoconazole
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1 mM, 62% inhibition
Metyrapone
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1 mM, 14% inhibition
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P-450
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involved in activity
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0015
geranylhydroquinone
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pH 7.4, 30°C, microsomal fraction
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.4
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activity in K-phosphate buffer at pH 7.4 is only 40% of that observed in Tris-HCl buffer
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.7 - 8.3
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50% of maximal activiyt at pH 6.7 and pH 8.3. Tris-Cl buffer
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
addition of glycerol (20%, v/v) to the microsomal fraction before freezing results in the loss of 80% of the activity
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stable against freezing
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70°C, 1 month, microsomal protein retains 82% of the original activity
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