Information on EC 1.14.13.53 - 4'-methoxyisoflavone 2'-hydroxylase

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The enzyme appears in viruses and cellular organisms

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EC NUMBER
COMMENTARY hide
1.14.13.53
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RECOMMENDED NAME
GeneOntology No.
4'-methoxyisoflavone 2'-hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
formononetin + NADPH + H+ + O2 = 2'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydroxylation
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oxidation
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-
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redox reaction
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-
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
maackiain biosynthesis
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medicarpin biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
formononetin,NADPH:oxygen oxidoreductase (2'-hydroxylating)
A heme-thiolate protein (P-450). Acts on isoflavones with a 4'-methoxy group, such as formononetin and biochanin A. Involved in the biosynthesis of the pterocarpin phytoalexins medicarpin and maackiain. EC 1.14.13.89, isoflavone 2'-hydroxylase, is less specific and acts on other isoflavones as well as 4'-methoxyisoflavones.
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CAS REGISTRY NUMBER
COMMENTARY hide
110183-49-8
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Mervill cv. Harosoy 63, elicitor-induced
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Manually annotated by BRENDA team
elicitor-induced
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
biochanin A + NADPH + O2
2'-hydroxybiochanin A + NADP+ + H2O
show the reaction diagram
daidzein + NADPH + O2
2'-hydroxydaidzein + NADP+ + H2O
show the reaction diagram
formononetin + NADPH + O2
2'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram
genistein + NADPH + O2
2'-hydroxygenistein + NADP+ + H2O
show the reaction diagram
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
formononetin + NADPH + O2
2'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADH
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13.5% of NADPH under same conditions; can substitute for NADPH to a low degree only and shows a synergistic effect in the presence of NADPH
NADPH
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; best electron donor
additional information
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no cofactors are FAD and FMN
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mn2+
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cells treated with MnCl2 exhibit 5fold activity after 12 hours
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
BAS 110
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BAS 111
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CO
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ratio CO:O2 of 9:1 leads to 88-96% inhibition
cytochrome c
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0.01 mM cytochrome c reduces activity to 14%, 0.1 mM cytochrome c reduces activity to 4%
juglone
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0.001 mM juglone reduces activity to 50%
ketoconazol
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tetcyclasis
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Triadimefone
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additional information
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no inhibition by 5 mM KCN and 1 mM EDTA
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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cells susceptible to Ascochyta rabiei can be elicitor-induced to 500% activity
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
13
Biochanin A
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3.3
formononetin
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
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assay conditions
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
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assay conditions
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20�C, 100 mM potassium phosphate, pH 7.5 containing 400 mM sucrose and 3.5 mM 2-mercaptoethanol, 24 h
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Saccharomyces cerevisae
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expressed in Saccharomyces cerevisae overexpressing CYP81E1
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.53)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)