BRENDA - Enzyme Database show
show all sequences of 1.14.14.162

Licodione synthase, a cytochrome P450 monooxygenase catalyzing 2-hydroxylation of 5-deoxyflavanone, in cultured Glycyrrhiza echinata L. cells

Otani, K.; Takahashi, T.; Furuya, T.; Ayabe, S.; Plant Physiol. 105, 1427-1432 (1994)

Data extracted from this reference:

Activating Compound
Activating Compound
Commentary
Organism
Structure
additional information
yeast extract induces LS activity
Glycyrrhiza echinata
Inhibitors
Inhibitors
Commentary
Organism
Structure
Ancymidol
0.001 mM: 33% inhibition, 0.01 mM: 68% inhibition, 0.1 mM: 81% inhibition
Glycyrrhiza echinata
ketoconazole
0.001 mM: 44% inhibition, 0.01 mM: 86% inhibition, 0.1 mM: 72% inhibition
Glycyrrhiza echinata
Metyrapone
0.001 mM: 23% inhibition, 0.01 mM: 57% inhibition, 0.1 mM: 74% inhibition
Glycyrrhiza echinata
Localization
Localization
Commentary
Organism
GeneOntology No.
Textmining
microsome
-
Glycyrrhiza echinata
-
-
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
additional information
Glycyrrhiza echinata
involved in flavonoid biosynthesis, may play a role symbiotic plant-microbe interactions
?
-
-
-
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Glycyrrhiza echinata
-
-
-
Reaction
Reaction
Commentary
Organism
a flavanone + [reduced NADPH-hemoprotein reductase] + O2 = a 2-hydroxyflavanone + [oxidized NADPH-hemoprotein reductase] + 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
Glycyrrhiza echinata
Source Tissue
Source Tissue
Commentary
Organism
Textmining
cell suspension culture
yeast extract-induced
Glycyrrhiza echinata
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2
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
657025
Glycyrrhiza echinata
licodione + [oxidized NADPH-hemoprotein reductase] + H2O
i.e. 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-propanedione
-
-
?
(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2
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
657025
Glycyrrhiza echinata
licodione + [oxidized NADPH-hemoprotein reductase] + H2O
i.e. 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-propanedione
-
-
?
(2S)-naringenin + [reduced NADPH-hemoprotein reductase] + O2
-
657025
Glycyrrhiza echinata
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
the product is further converted into apigenin when treated with acid
-
-
?
additional information
involved in flavonoid biosynthesis, may play a role symbiotic plant-microbe interactions
657025
Glycyrrhiza echinata
?
-
-
-
-
Temperature Optimum [C]
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
25
-
assay at
Glycyrrhiza echinata
Cofactor
Cofactor
Commentary
Organism
Structure
cytochrome P450
cytochrome P450-dependent, cytochrome P450 monooxygenase
Glycyrrhiza echinata
Activating Compound (protein specific)
Activating Compound
Commentary
Organism
Structure
additional information
yeast extract induces LS activity
Glycyrrhiza echinata
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
cytochrome P450
cytochrome P450-dependent, cytochrome P450 monooxygenase
Glycyrrhiza echinata
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
Ancymidol
0.001 mM: 33% inhibition, 0.01 mM: 68% inhibition, 0.1 mM: 81% inhibition
Glycyrrhiza echinata
ketoconazole
0.001 mM: 44% inhibition, 0.01 mM: 86% inhibition, 0.1 mM: 72% inhibition
Glycyrrhiza echinata
Metyrapone
0.001 mM: 23% inhibition, 0.01 mM: 57% inhibition, 0.1 mM: 74% inhibition
Glycyrrhiza echinata
Localization (protein specific)
Localization
Commentary
Organism
GeneOntology No.
Textmining
microsome
-
Glycyrrhiza echinata
-
-
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
additional information
Glycyrrhiza echinata
involved in flavonoid biosynthesis, may play a role symbiotic plant-microbe interactions
?
-
-
-
Source Tissue (protein specific)
Source Tissue
Commentary
Organism
Textmining
cell suspension culture
yeast extract-induced
Glycyrrhiza echinata
-
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2
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
657025
Glycyrrhiza echinata
licodione + [oxidized NADPH-hemoprotein reductase] + H2O
i.e. 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-propanedione
-
-
?
(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2
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
657025
Glycyrrhiza echinata
licodione + [oxidized NADPH-hemoprotein reductase] + H2O
i.e. 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-propanedione
-
-
?
(2S)-naringenin + [reduced NADPH-hemoprotein reductase] + O2
-
657025
Glycyrrhiza echinata
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
the product is further converted into apigenin when treated with acid
-
-
?
additional information
involved in flavonoid biosynthesis, may play a role symbiotic plant-microbe interactions
657025
Glycyrrhiza echinata
?
-
-
-
-
Temperature Optimum [C] (protein specific)
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
25
-
assay at
Glycyrrhiza echinata
Other publictions for EC 1.14.14.162
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [C]
Temperature Range [C]
Temperature Stability [C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [C] (protein specific)
Temperature Range [C] (protein specific)
Temperature Stability [C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
748594
Vanegas
Indirect and direct routes to ...
Oryza sativa Japonica Group
Microb. Cell Fact.
17
107
2018
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1
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2
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4
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1
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1
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1
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2
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2
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748966
Du
CYP93G2 is a flavanone 2-hydr ...
Oryza sativa
Plant Physiol.
154
324-333
2010
-
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1
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2
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5
-
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2
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1
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1
1
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2
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2
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2
2
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655536
Akashi
Identification of a cytochrome ...
Glycyrrhiza echinata
FEBS Lett.
431
287-290
1998
-
-
1
-
-
-
-
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1
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1
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3
-
-
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1
-
-
-
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4
-
1
-
-
-
-
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1
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1
1
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-
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1
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1
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-
-
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4
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1
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-
657025
Otani
Licodione synthase, a cytochro ...
Glycyrrhiza echinata
Plant Physiol.
105
1427-1432
1994
1
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-
-
-
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3
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1
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1
-
1
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1
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1
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4
-
1
-
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-
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1
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1
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1
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-
-
-
3
-
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1
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1
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-
-
-
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1
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4
-
1
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-
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