Information on EC 1.14.13.52 - isoflavone 3'-hydroxylase

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Mark a special word or phrase in this record:
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)


The expected taxonomic range for this enzyme is: Papilionoideae

EC NUMBER
COMMENTARY
1.14.13.52
-
RECOMMENDED NAME
GeneOntology No.
isoflavone 3'-hydroxylase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
formononetin + NADPH + H+ + O2 = calycosin + NADP+ + H2O
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydroxylation
-
-
-
-
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
Isoflavonoid biosynthesis
-
-
isoflavonoid biosynthesis II
-
-
maackiain biosynthesis
-
-
rot-2'-enonate biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
formononetin,NADPH:oxygen oxidoreductase (3'-hydroxylating)
A heme-thiolate protein (P-450). Also acts on biochanin A and other isoflavones with a 4'-methoxy group. Involved in the biosynthesis of the pterocarpin phytoalexins medicarpin and maackiain.
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
isoflavone 3'-monooxygenase
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
110183-50-1
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
var. mongholicus
UniProt
Manually annotated by BRENDA team
strain ILC3279 resistant to Ascochyta rabiei and strain ILC susceptible to Ascochyta rabiei, elicitor-induced
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
-
calycosin-7-O-beta-D-glucoside pathway, calycosin and calycosin-7-O-beta-D-glucoside accumulate in whole plants, mainly leaves, in response to low temperature
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2'-hydroxyformononetin + NADPH + O2
2',3' dihydroxyformononetin + H2O
show the reaction diagram
-
39% of activity with biochanin A
-
-
?
biochanin A + NADPH + O2
pratensein + NADP+ + H2O
show the reaction diagram
-
-
-
-
ir
biochanin A + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
formononetin + NADPH + H+ + O2
calycosin + NADP+ + H2O
show the reaction diagram
Q2ENF7
-
-
-
?
formononetin + NADPH + H+ + O2
calycosin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
formononetin + NADPH + H+ + O2
calycosin + NADP+ + H2O
show the reaction diagram
Q2ENF7
calycosin concentration in different tissues, biosynthetic pathway leading to calycosin-7-O-beta-D-glucoside, overview
-
-
?
formononetin + NADPH + O2
3'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
ir
formononetin + NADPH + O2
3'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram
-
involved in the biosynthesis of the pterocarpin phytoalexin maackiain, cytochrome P450-dependent monooxygenase
-
-
ir
formononetin + NADPH + O2
calycosin + NADP+ + H2O
show the reaction diagram
-
50% of activity with biochanin A
-
-
?
genistein + NADPH + O2
?
show the reaction diagram
-
19% of activity with biochanin A
-
-
?
additional information
?
-
-
no substrates are genistein and daidzein, monohydroxylation of 4'-methoxyisoflavones
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
formononetin + NADPH + H+ + O2
calycosin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
formononetin + NADPH + H+ + O2
calycosin + NADP+ + H2O
show the reaction diagram
Q2ENF7
calycosin concentration in different tissues, biosynthetic pathway leading to calycosin-7-O-beta-D-glucoside, overview
-
-
?
formononetin + NADPH + O2
3'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram
-
involved in the biosynthesis of the pterocarpin phytoalexin maackiain, cytochrome P450-dependent monooxygenase
-
-
ir
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADH
-
8.5% of NADPH under same conditions
additional information
-
no cofactors are FAD and FMN
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
BAS110
-
-
CO
-
ratio CO:O2 of 9:1 leads to 88-96% inhibition
cytochrome c
-
0.01 mM reduces activity to 4%, 0.1 mM reduces activity to 1%
juglone
-
0.001 mM juglone reduces activity to 50%
tetcyclasis
-
-
Triadimefone
-
-
ketoconazol
-
-
additional information
-
no inhibition by 5 mM KCN and 1 mM EDTA
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADH
-
synergistic effect with NADPH, 150% of NADPH activity
additional information
-
cells susceptible to Ascochyta rabiei can be elicitor-induced to 500% activity
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.11
Biochanin A
-
pH 8.0, 2 mM NADPH
12.5
Biochanin A
-
-
0.05
formononetin
-
pH 8.0, 2 mM NADPH
11
formononetin
-
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.1
Biochanin A
-
pH 8.0, 2 mM NADPH
0.028
formononetin
-
pH 8.0, 2 mM NADPH
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
calycosin concentration in different tissues, overview
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.5
-
assay conditions
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
-
assay conditions
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
MRNA is found after arbuscular mycorrhizal colonization
Manually annotated by BRENDA team
-
low mRNA levels
Manually annotated by BRENDA team
additional information
-
calycosin concentration in different tissues, quantitative enzyme expression analysis, overview
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, 100 mM potassium phosphate, pH 7.5 containing 400 mM sucrose and 3.5 mM 2-mercaptoethanol, 24 h
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, quantitative tissue-dependent expression analysis, overview
-
PCR-amplification
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
gradual increase (1.8fold) of enzyme expression after low-temperature treatment (4 h 2C) of plants adapted to 16C, dramatic increase of expression in warm-treatment plants (16C to 25C or from 2C to 25C), maximum at h 4 during treatment, higher levels than at low-temperature induction, cold-induced mRNA accumulation is light dependent
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
-
Astragalus membranaceus var. mongholicus is a medicinal plant in traditional Chinese medicine, the enzyme products calycosin and calycosin-7-O-beta-D-glucoside are two major isoflavones related to the bioactivity of the herb