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Enzyme Nomenclature
Information on EC 1.14.13.87 - licodione synthase
Word Map on EC 1.14.13.87
- 1.14.13.87
-
2s-flavanone
- glycyrrhiza
- flavone
- echinatin
-
monooxygenase
- apigenin
- licorice
-
retrochalcone
- 7,4'-dihydroxyflavone
- isoflavone
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The expected taxonomic range for this enzyme is: Glycyrrhiza echinata
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EC NUMBER 
COMMENTARY 
1.14.13.87
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RECOMMENDED NAME
GeneOntology No.
licodione synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
liquiritigenin + NADPH + H+ + O2 = licodione + NADP+ + H2O
mechanism, stereoselectivity
liquiritigenin + NADPH + H+ + O2 = licodione + NADP+ + H2O
a heme-thiolate protein, P-450, it probably forms 2-hydroxyliquiritigenin which spontaneously forms licodione, NADH can act instead of NADPH, but more slowly, reaction mechanism
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liquiritigenin + NADPH + H+ + O2 = licodione + NADP+ + H2O
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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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.
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CAS REGISTRY NUMBER
COMMENTARY
157972-05-9
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2S)-liquiritigenin + NADH + H+ + O2
licodione + NAD+ + H2O
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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
-
?
eriodictyol + NADPH + H+ + O2
luteolin + NADP+ + 2 H2O
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product is formed after acid treatment
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?
(2S)-liquiritigenin + NADPH + H+ + O2
licodione + NADP+ + H2O
hydroxylation of liquiritigenin at C-2 and formation of licodione as a result of non-enzymatic hemiacetal opening, selectivity towards (2S)-flavanone
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-
?
(2S)-liquiritigenin + NADPH + H+ + O2
licodione + NADP+ + H2O
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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, NADPH serves as hydride donor more effectively than NADH
i.e. 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-propanedione
-
?
(2S)-naringenin + NADPH + H+ + O2
2-hydroxynaringenin + NADP+ + H2O
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the product is further converted into apigenin when treated with acid
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?
(2S)-naringenin + NADPH + H+ + O2
2-hydroxynaringenin + NADP+ + H2O
selectivity towards (2S)-flavanone
the product is further converted into apigenin when treated with HCl
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?
additional information
?
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involved in flavonoid biosynthesis, may play a role symbiotic plant-microbe interactions
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-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
involved in flavonoid biosynthesis, may play a role symbiotic plant-microbe interactions
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-
-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
cytochrome P450
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cytochrome P450-dependent, cytochrome P450 monooxygenase
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
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
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
recombinant enzyme, expressed in Sf9 insect cells or yeast cells
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
CYP Ge-5/CYP93B1, expression in Sf9 insect cells and in Saccharomyces cerevisiae BJ2168
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.87)
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