Information on EC 1.14.13.53 - 4'-methoxyisoflavone 2'-hydroxylase:
   PRINT
Please wait a moment until all data are loaded. This message will disappear when all data are loaded.
Mark a special word or phrase in this record:  
Select one or more organisms in this record:

The lowest common taxonomy group for this enzyme is: Papilionoideae

Show additional data Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)

Please login to have access to the AMENDA and FRENDA data

EC NUMBERCOMMENTARY
1.14.13.53-

RECOMMENDED NAMEGeneOntology No.
4'-methoxyisoflavone 2'-hydroxylaseGO:0047957

REACTIONREACTION DIAGRAMCOMMENTARYORGANISM UNIPROT ACCESSION NO.LITERATURE
formononetin + NADPH + H+ + O2 = 2'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram		-Cicer arietinum-285318
formononetin + NADPH + H+ + O2 = 2'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram		----

REACTION TYPEORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
hydroxylation----
oxidation----
redox reaction----
reduction----

PATHWAYKEGG LinkMetaCyc Link
maackiain biosynthesis-PWY-2464
medicarpin biosynthesis-PWY-2463

SYSTEMATIC NAMEIUBMB 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.

SYNONYMSORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
isoflavone 2'-hydroxylase----
isoflavone 2'-hydroxylaseCicer arietinum-ambiguous285318
isoflavone 2'-monooxygenase----
isoflavone 2'-monooxygenaseCicer arietinum-ambiguous285318

CAS REGISTRY NUMBERCOMMENTARY
110183-49-8-

ORGANISMCOMMENTARYLITERATURESEQUENCE CODESEQUENCE DB SOURCE
Cicer arietinum-285318--Manually annotated by BRENDA team
Cicer arietinumstrain ILC3279 resistant to Ascochyta rabiei and strain ILC susceptible to Ascochyta rabiei, elicitor-induced285319, 285320--Manually annotated by BRENDA team
Glycine maxMervill cv. Harosoy 63, elicitor-induced285325--Manually annotated by BRENDA team
Glycyrrhiza echinataelicitor-induced285323--Manually annotated by BRENDA team
Lotus japonicus-285324--Manually annotated by BRENDA team

GENERAL INFORMATIONORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

SUBSTRATEPRODUCT                      REACTION DIAGRAMORGANISM UNIPROT ACCESSION NO. COMMENTARY/
Substrate		 LITERATURE/
Substrate		 COMMENTARY/
Product		 LITERATURE/
Product		 Reversibility
r=reversible
ir=irreversible
?=not specified
biochanin A + NADPH + O22'-hydroxybiochanin A + NADP+ + H2O
show the reaction diagram		Cicer arietinum--285320---
biochanin A + NADPH + O22'-hydroxybiochanin A + NADP+ + H2O
show the reaction diagram		Cicer arietinum--285318--?
biochanin A + NADPH + O22'-hydroxybiochanin A + NADP+ + H2O
show the reaction diagram		Cicer arietinum--285318-285318ir
biochanin A + NADPH + O22'-hydroxybiochanin A + NADP+ + H2O
show the reaction diagram		Cicer arietinum--285319-285319ir
daidzein + NADPH + O22'-hydroxydaidzein + NADP+ + H2O
show the reaction diagram		Glycyrrhiza echinata--285323-285323ir
daidzein + NADPH + O22'-hydroxydaidzein + NADP+ + H2O
show the reaction diagram		Cicer arietinum-2.0% of the activity with biochanin A285318--?
formononetin + NADPH + O22'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram		Cicer arietinum--285318, 285319--ir
formononetin + NADPH + O22'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram		Lotus japonicus--285324--ir
formononetin + NADPH + O22'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram		Glycyrrhiza echinata--285323--ir
formononetin + NADPH + O22'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram		Cicer arietinum-involved in the biosynthesis of the pterocarpin phytoalexin medicarpin285320---
formononetin + NADPH + O22'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram		Cicer arietinum-involved in the biosynthesis of the pterocarpin phytoalexin medicarpin285318--ir
formononetin + NADPH + O22'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram		Cicer arietinum-cytochrome P450-dependent monooxygenase285320---
formononetin + NADPH + O22'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram		Cicer arietinum-cytochrome P450-dependent monooxygenase285318--ir
formononetin + NADPH + O22'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram		Glycyrrhiza echinata-cytochrome P450-dependent monooxygenase285323--ir
formononetin + NADPH + O22'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram		Cicer arietinum-78.1% of the activity with biochanin A285318--?
genistein + NADPH + O22'-hydroxygenistein + NADP+ + H2O
show the reaction diagram		Glycine max--285325-285325?
genistein + NADPH + O22'-hydroxygenistein + NADP+ + H2O
show the reaction diagram		Glycyrrhiza echinata--285323-285323ir
genistein + NADPH + O22'-hydroxygenistein + NADP+ + H2O
show the reaction diagram		Cicer arietinum-2.2% of the activity with biochanin A285318--?
additional information?-Cicer arietinum-monohydroxylation of 4'-methoxyisoflavones, no substrates are genistein and daidzein285318, 285320---
additional information?-Glycyrrhiza echinata-no substrates are 5,7,4'-trihydroxyflavone, 7,4'-dihydroxyflavone, trans-cinnamic acid and 4-coumaric acid285323---

NATURAL SUBSTRATESNATURAL PRODUCTSREACTION DIAGRAMORGANISM UNIPROT ACCESSION NO.COMMENTARY SUBSTRATELITERATURE
(Substrate)		COMMENTARY PRODUCTLITERATURE
(Product)
formononetin + NADPH + O22'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram		Cicer arietinum-involved in the biosynthesis of the pterocarpin phytoalexin medicarpin285320, 285318--
formononetin + NADPH + O22'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram		Cicer arietinum-cytochrome P450-dependent monooxygenase285320, 285318--
formononetin + NADPH + O22'-hydroxyformononetin + NADP+ + H2O
show the reaction diagram		Glycyrrhiza echinata-cytochrome P450-dependent monooxygenase285323--

COFACTORORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATUREIMAGE
NADHCicer arietinum-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 NADPH285318 2D-image
NADPHCicer arietinum-; best electron donor285318 2D-image
additional informationCicer arietinum-no cofactors are FAD and FMN285318-

METALS and IONS ORGANISM UNIPROT ACCESSION NO.COMMENTARY LITERATURE
Mn2+Cicer arietinum-cells treated with MnCl2 exhibit 5fold activity after 12 hours285320

INHIBITORSORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
BAS 110Cicer arietinum--285320 2D-image
BAS 111Cicer arietinum--285320 2D-image
COCicer arietinum-ratio CO:O2 of 9:1 leads to 88-96% inhibition285320 2D-image
cytochrome cCicer arietinum-0.01 mM cytochrome c reduces activity to 14%, 0.1 mM cytochrome c reduces activity to 4%285318 2D-image
jugloneCicer arietinum-0.001 mM juglone reduces activity to 50%285320 2D-image
tetcyclasisCicer arietinum--285320 2D-image
TriadimefoneCicer arietinum--285320 2D-image
ketoconazolCicer arietinum--285320 2D-image
additional informationCicer arietinum-no inhibition by 5 mM KCN and 1 mM EDTA285318-

ACTIVATING COMPOUNDORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
NADHCicer arietinum-135% of NADPH activity; synergistic effect with NADPH285318 2D-image
NADHGlycine max-synergistic effect with NADPH285325 2D-image
additional informationCicer arietinum-cells susceptible to Ascochyta rabiei can be elicitor-induced to 500% activity285318-

KM VALUE [mM]KM VALUE [mM] MaximumSUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
13-Biochanin ACicer arietinum--285320 2D-image
3.3-formononetinCicer arietinum--285320 2D-image

TURNOVER NUMBER [1/s] TURNOVER NUMBER MAXIMUM[1/s] SUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

kcat/KM VALUE [1/mMs-1]kcat/KM VALUE [1/mMs-1] MaximumSUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

Ki VALUE [mM]Ki VALUE [mM] MaximumINHIBITORORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

IC50 VALUE [mM]IC50 VALUE [mM] MaximumINHIBITORORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

SPECIFIC ACTIVITY [µmol/min/mg] SPECIFIC ACTIVITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

pH OPTIMUMpH MAXIMUMORGANISM UNIPROT ACCESSION NO. COMMENTARYLITERATURE
7.4-Cicer arietinum--285320
7.5-Cicer arietinum-assay conditions285318, 285319

pH RANGEpH RANGE MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

TEMPERATURE OPTIMUMTEMPERATURE OPTIMUM MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
25-Cicer arietinum-assay conditions285319
30-Cicer arietinum--285320

TEMPERATURE RANGE TEMPERATURE MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

pI VALUEpI VALUE MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

SOURCE TISSUE ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE SOURCE
cell cultureCicer arietinum-suspension285318Manually annotated by BRENDA team
cell suspension cultureCicer arietinum--285318, 285319Manually annotated by BRENDA team
cell suspension cultureGlycyrrhiza echinata--285323Manually annotated by BRENDA team
cell suspension cultureLotus japonicus--285324Manually annotated by BRENDA team
cell suspension cultureGlycine max--285325Manually annotated by BRENDA team

LOCALIZATION ORGANISM UNIPROT ACCESSION NO. COMMENTARY GeneOntology No. LITERATURE SOURCE
microsomeCicer arietinum---285318, 285319Manually annotated by BRENDA team
microsomeGlycyrrhiza echinata---285323Manually annotated by BRENDA team
microsomeLotus japonicus---285324Manually annotated by BRENDA team
microsomeGlycine max---285325Manually annotated by BRENDA team

PDBSCOPCATHORGANISM
No entries in this field

MOLECULAR WEIGHT MOLECULAR WEIGHT MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

SUBUNITS ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

POSTTRANSLATIONAL MODIFICATION ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

Crystallization/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

pH STABILITYpH STABILITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

TEMPERATURE STABILITYTEMPERATURE STABILITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARYLITERATURE
No entries in this field

GENERAL STABILITYORGANISM UNIPROT ACCESSION NO.LITERATURE
No entries in this field

ORGANIC SOLVENT ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

OXIDATION STABILITY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

STORAGE STABILITY ORGANISM UNIPROT ACCESSION NO. LITERATURE
-20°C, 100 mM potassium phosphate, pH 7.5 containing 400 mM sucrose and 3.5 mM 2-mercaptoethanol, 24 hCicer arietinum-285318

Purification/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

Cloned/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
expressed in Saccharomyces cerevisae overexpressing CYP81E1Glycyrrhiza echinata-285323
expressed in Saccharomyces cerevisaeLotus japonicus-285324

EXPRESSION ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

ENGINEERINGORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

Renatured/COMMENTARYORGANISM UNIPROT ACCESSION NO.LITERATURE
No entries in this field

APPLICATIONORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

REF. AUTHORS TITLE JOURNAL VOL. PAGES YEAR ORGANISMLINK TO PUBMEDSOURCE
285318Hinderer, W.; Flentje, U.; Barz, W.Microsomal isoflavone 2'- and 3'-hydroxylases from chickpea (Cicer arietinum L.) cell suspensions induced for pterocarpan phytoalexin formationFEBS Lett.214101-1061987Cicer arietinum-
285319Daniel, S.; Tiemann, K.; Wittkampf, U.; Bless, W.; Hinderer, W.; Barz, W.Elicitor-induced metabolic changes in cell cultures of chickpea (Cicer arietinum L.) cultivars resistant and susceptible to Ascochyta rabieiPlanta182270-2781990Cicer arietinum-
285320Clemens, S.; Hinderer, W; Wittkampf, U; Barz, W.Characterization of cytochrome P450-dependent isoflavone hydroxylases from chickpeaPhytochemistry32653-6571993Cicer arietinum-
285323Akashi, T.; Aoki, T.; Ayabe, S.I.CYP81E1, a cytochrome P450 cDNA of licorice (Glycyrrhiza echinata L.), encodes isoflavone 2'-hydroxylaseBiochem. Biophys. Res. Commun.25167-701998Glycyrrhiza echinata PubMed
285324Shimada, N.; Akashi, T.; Aoki, T.; Ayabe, S.i.Induction of isoflavonoid pathway in the model legume Lotus japonicus: molecular characterization of enzymes involved in phytoalexin biosynthesisPlant Sci.16037-472000Lotus japonicus PubMed
285325Kochs, G.; Grisebach, H.Enzymic synthesis of isoflavonesEur. J. Biochem.155311-3181986Glycine max PubMed

LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.53)
ExplorEnz
ExPASy
KEGG
MetaCyc
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)