BRENDA - Enzyme Database show
show all sequences of 1.14.14.126

CYP716A179 functions as a triterpene C-28 oxidase in tissue-cultured stolons of Glycyrrhiza uralensis

Tamura, K.; Seki, H.; Suzuki, H.; Kojoma, M.; Saito, K.; Muranaka, T.; Plant Cell Rep. 36, 437-445 (2017)

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
gene CYP716A179, DNA and amino acid sequence determination and analysis, phylogenetic analysis, quantitative real-time PCR enzyme analysis, recombinant expression in Saccharomyces cerevisiae results in production of oleanolic acid, ursolic acid, and betulinic acid from beta-amyrin, alpha-amyrin, and lupeol, respectively, galactose-inducible dual expression of Lotus japonicus CPR1 and CYP716A179
Glycyrrhiza uralensis
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
alpha-amyrin + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
Glycyrrhiza uralensis
overall reaction
ursolic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
?
alpha-amyrin + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
Glycyrrhiza uralensis 308-19
overall reaction
ursolic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
?
alpha-amyrin + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis
-
uvaol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
alpha-amyrin + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis 308-19
-
uvaol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
beta-amyrin + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
Glycyrrhiza uralensis
overall reaction
oleanolate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis
-
erythrodiol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis 308-19
-
erythrodiol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
betulin + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis
-
betulinic aldehyde + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
betulinic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis
-
betulinic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
erythrodiol + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis
-
oleanolic aldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
?
lupeol + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
Glycyrrhiza uralensis
-
betulin + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
?
lupeol + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
Glycyrrhiza uralensis
overall reaction
betulinic acid+ 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
?
oleanolic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis
-
oleanolate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
oleanolic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis 308-19
-
oleanolate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
urosolic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis
-
ursolic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
uvaol + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis
-
urosolic aldehyde + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Glycyrrhiza uralensis
A0A1L7NXK5
-
-
Glycyrrhiza uralensis 308-19
A0A1L7NXK5
-
-
Source Tissue
Source Tissue
Commentary
Organism
Textmining
leaf
-
Glycyrrhiza uralensis
-
additional information
transcript level of CYP716A179 in leaves is lower than that in intact roots
Glycyrrhiza uralensis
-
root
-
Glycyrrhiza uralensis
-
stolon
tissue-cultured stolons
Glycyrrhiza uralensis
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
alpha-amyrin + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
overall reaction
746060
Glycyrrhiza uralensis
ursolic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
-
?
alpha-amyrin + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
overall reaction
746060
Glycyrrhiza uralensis 308-19
ursolic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
-
?
alpha-amyrin + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis
uvaol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
alpha-amyrin + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis 308-19
uvaol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
beta-amyrin + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
overall reaction
746060
Glycyrrhiza uralensis
oleanolate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
-
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis
erythrodiol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis 308-19
erythrodiol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
betulin + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis
betulinic aldehyde + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
betulinic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis
betulinic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
erythrodiol + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis
oleanolic aldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
lupeol + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
-
746060
Glycyrrhiza uralensis
betulin + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
-
?
lupeol + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
overall reaction
746060
Glycyrrhiza uralensis
betulinic acid+ 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
-
?
additional information
the enzyme catalyzes a three-step oxidation reaction at the C-28 position of beta-amyrin, alpha-amyrin, and lupeol to produce oleanolic acid, ursolic acid, and betulinic acid, respectively
746060
Glycyrrhiza uralensis
?
-
-
-
-
additional information
the enzyme catalyzes a three-step oxidation reaction at the C-28 position of beta-amyrin, alpha-amyrin, and lupeol to produce oleanolic acid, ursolic acid, and betulinic acid, respectively
746060
Glycyrrhiza uralensis 308-19
?
-
-
-
-
oleanolic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis
oleanolate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
oleanolic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis 308-19
oleanolate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
urosolic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis
ursolic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
uvaol + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis
urosolic aldehyde + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
Cofactor
Cofactor
Commentary
Organism
Structure
cytochrome P450
-
Glycyrrhiza uralensis
NADPH-hemoprotein reductase
A flavoprotein containing both FMN and FAD. This enzyme catalyses the transfer of electrons from NADPH, an obligatory two-electron donor, to microsomal P-450 monooxygenases, EC 1.14.14._
Glycyrrhiza uralensis
Cloned(Commentary) (protein specific)
Commentary
Organism
gene CYP716A179, DNA and amino acid sequence determination and analysis, phylogenetic analysis, quantitative real-time PCR enzyme analysis, recombinant expression in Saccharomyces cerevisiae results in production of oleanolic acid, ursolic acid, and betulinic acid from beta-amyrin, alpha-amyrin, and lupeol, respectively, galactose-inducible dual expression of Lotus japonicus CPR1 and CYP716A179
Glycyrrhiza uralensis
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
cytochrome P450
-
Glycyrrhiza uralensis
NADPH-hemoprotein reductase
A flavoprotein containing both FMN and FAD. This enzyme catalyses the transfer of electrons from NADPH, an obligatory two-electron donor, to microsomal P-450 monooxygenases, EC 1.14.14._
Glycyrrhiza uralensis
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
alpha-amyrin + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
Glycyrrhiza uralensis
overall reaction
ursolic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
?
alpha-amyrin + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
Glycyrrhiza uralensis 308-19
overall reaction
ursolic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
?
alpha-amyrin + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis
-
uvaol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
alpha-amyrin + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis 308-19
-
uvaol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
beta-amyrin + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
Glycyrrhiza uralensis
overall reaction
oleanolate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis
-
erythrodiol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis 308-19
-
erythrodiol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
betulin + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis
-
betulinic aldehyde + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
betulinic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis
-
betulinic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
erythrodiol + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis
-
oleanolic aldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
?
lupeol + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
Glycyrrhiza uralensis
-
betulin + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
?
lupeol + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
Glycyrrhiza uralensis
overall reaction
betulinic acid+ 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
?
oleanolic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis
-
oleanolate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
oleanolic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis 308-19
-
oleanolate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
urosolic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis
-
ursolic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
uvaol + [reduced NADPH-hemoprotein reductase] + O2
Glycyrrhiza uralensis
-
urosolic aldehyde + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
Source Tissue (protein specific)
Source Tissue
Commentary
Organism
Textmining
leaf
-
Glycyrrhiza uralensis
-
additional information
transcript level of CYP716A179 in leaves is lower than that in intact roots
Glycyrrhiza uralensis
-
root
-
Glycyrrhiza uralensis
-
stolon
tissue-cultured stolons
Glycyrrhiza uralensis
-
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
alpha-amyrin + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
overall reaction
746060
Glycyrrhiza uralensis
ursolic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
-
?
alpha-amyrin + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
overall reaction
746060
Glycyrrhiza uralensis 308-19
ursolic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
-
?
alpha-amyrin + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis
uvaol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
alpha-amyrin + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis 308-19
uvaol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
beta-amyrin + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
overall reaction
746060
Glycyrrhiza uralensis
oleanolate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
-
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis
erythrodiol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis 308-19
erythrodiol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
betulin + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis
betulinic aldehyde + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
betulinic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis
betulinic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
erythrodiol + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis
oleanolic aldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
lupeol + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
-
746060
Glycyrrhiza uralensis
betulin + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
-
?
lupeol + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
overall reaction
746060
Glycyrrhiza uralensis
betulinic acid+ 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
-
?
additional information
the enzyme catalyzes a three-step oxidation reaction at the C-28 position of beta-amyrin, alpha-amyrin, and lupeol to produce oleanolic acid, ursolic acid, and betulinic acid, respectively
746060
Glycyrrhiza uralensis
?
-
-
-
-
additional information
the enzyme catalyzes a three-step oxidation reaction at the C-28 position of beta-amyrin, alpha-amyrin, and lupeol to produce oleanolic acid, ursolic acid, and betulinic acid, respectively
746060
Glycyrrhiza uralensis 308-19
?
-
-
-
-
oleanolic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis
oleanolate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
oleanolic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis 308-19
oleanolate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
urosolic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis
ursolic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
uvaol + [reduced NADPH-hemoprotein reductase] + O2
-
746060
Glycyrrhiza uralensis
urosolic aldehyde + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
Other publictions for EC 1.14.14.126
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)
744248
Zhan
Cytochrome P450 CYP716A254 ca ...
Anemone flaccida
Biochem. Biophys. Res. Commun.
495
1271-1277
2018
-
-
1
-
-
-
-
-
2
-
-
1
-
3
-
-
-
-
-
1
-
-
2
-
1
-
-
-
1
-
-
2
-
-
-
-
-
1
2
-
-
-
-
-
-
-
2
-
-
1
-
-
-
-
-
1
-
-
2
-
1
-
-
-
1
-
-
-
-
2
2
-
-
-
745002
Yasumoto
Functional characterization o ...
Solanum lycopersicum
Front. Plant Sci.
8
21
2017
-
-
1
-
-
-
-
-
-
-
-
6
-
2
-
-
-
-
-
4
-
-
6
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
6
-
-
-
-
-
6
-
-
6
-
-
-
-
-
-
-
-
-
-
2
4
-
-
-
745906
Misra
Two CYP716A subfamily cytochr ...
Ocimum basilicum
New Phytol.
214
706-720
2017
-
-
1
-
1
-
-
-
-
-
-
4
-
4
-
-
-
-
-
3
-
-
5
-
-
-
-
-
-
-
-
3
-
-
-
-
-
1
3
-
1
-
-
-
-
-
-
-
-
4
-
-
-
-
-
3
-
-
5
-
-
-
-
-
-
-
-
-
1
3
3
1
-
-
746004
Jo
beta-Amyrin synthase (EsBAS) ...
Eleutherococcus senticosus
Phytochemistry
135
53-63
2017
-
-
1
-
-
-
-
-
1
1
-
4
-
7
-
-
-
-
-
2
-
-
7
1
-
-
-
-
-
-
-
3
-
-
-
-
-
1
3
-
-
-
-
-
-
-
1
1
-
4
-
-
-
-
-
2
-
-
7
1
-
-
-
-
-
-
-
-
1
2
2
1
-
-
746048
Tamura
Cytochrome P450 monooxygenase ...
Platycodon grandiflorus
Plant Cell Physiol.
58
874-884
2017
-
-
1
-
-
-
-
-
-
-
-
4
-
5
-
-
-
-
-
4
-
-
11
-
1
-
-
-
-
-
-
2
-
-
-
-
-
2
4
-
-
-
-
-
-
-
-
-
-
4
-
-
-
-
-
8
-
-
11
-
2
-
-
-
-
-
-
-
-
2
3
-
-
-
746049
Han
Transcriptomic analysis of Ka ...
Kalopanax septemlobus
Plant Cell Physiol.
59
319-330
2017
-
-
1
-
-
-
-
-
2
1
-
1
-
7
-
-
-
-
-
-
-
-
1
-
1
-
-
-
-
-
-
3
-
-
-
-
-
1
3
-
-
-
-
-
-
-
2
1
-
1
-
-
-
-
-
-
-
-
1
-
1
-
-
-
-
-
-
-
-
2
2
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