Information on EC 1.14.13.87 - licodione synthase

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The expected taxonomic range for this enzyme is: Glycyrrhiza echinata

EC NUMBER
COMMENTARY hide
1.14.13.87
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RECOMMENDED NAME
GeneOntology No.
licodione synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
liquiritigenin + NADPH + H+ + O2 = licodione + NADP+ + H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
echinatin biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
liquiritigenin,NADPH:oxygen oxidoreductase (licodione-forming)
A heme-thiolate protein (P-450). It probably forms 2-hydroxyliquiritigenin which spontaneously forms licodione. NADH can act instead of NADPH, but more slowly.
CAS REGISTRY NUMBER
COMMENTARY hide
157972-05-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2S)-liquiritigenin + NADH + H+ + O2
licodione + NAD+ + H2O
show the reaction diagram
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requires NAD(P)H and O2 for activity, the reaction mechanism is likely to be 2-hydroxylation of the flavanone molecule to yield 2-hydroxyliquiritigenin and the subsequent hemiacetal opening to give licodione, introduces one atom of oxygen into the substrate, NADH serves as hydride donor less effectively than NADPH
i.e. 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-propanedione
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?
(2S)-liquiritigenin + NADPH + H+ + O2
licodione + NADP+ + H2O
show the reaction diagram
(2S)-naringenin + NADPH + H+ + O2
2-hydroxynaringenin + NADP+ + H2O
show the reaction diagram
eriodictyol + NADPH + H+ + O2
luteolin + NADP+ + 2 H2O
show the reaction diagram
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product is formed after acid treatment
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?
additional information
?
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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
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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NAD(P)H
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requirement
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ancymidol
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0.001 mM: 33% inhibition, 0.01 mM: 68% inhibition, 0.1 mM: 81% inhibition
ketoconazole
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0.001 mM: 44% inhibition, 0.01 mM: 86% inhibition, 0.1 mM: 72% inhibition
Metyrapone
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0.001 mM: 23% inhibition, 0.01 mM: 57% inhibition, 0.1 mM: 74% inhibition
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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yeast extract induces LS activity
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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yeast extract-induced
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
CYP Ge-5/CYP93B1, expression in Sf9 insect cells and in Saccharomyces cerevisiae BJ2168