Enzyme

A cytochrome P-450 (heme thiolate) protein found in plants. The reaction involves the migration of the 2-phenyl group of the flavanone to the 3-position of the isoflavanone. The 2-hydroxyl group is derived from the oxygen molecule. EC 4.2.1.105, 2-hydroxyisoflavanone dehydratase, acts on the products with loss of water and formation of genistein and daidzein, respectively.

IFS2

Enzyme

2-hydroxyisoflavanone synthase

Enzyme name

EC:1.14.14.87

Entry

Oxidoreductases;Acting on paired donors, with incorporation or reduction of molecular oxygen;With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor

Class

liquiritigenin, [reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating, aryl migration)

Sysname

(1) liquiritigenin + O2 + [reduced NADPH---hemoprotein reductase] = 2,4',7-trihydroxyisoflavanone + H2O + [oxidized NADPH---hemoprotein reductase] [RN:R07777];(2) (2S)-naringenin + O2 + [reduced NADPH---hemoprotein reductase] = 2,4',5,7-tetrahydroxyisoflavanone + H2O + [oxidized NADPH---hemoprotein reductase] [RN:R07778]

Reaction

2,4',7-trihydroxyisoflavanone [CPD:C15567];H2O [CPD:C00001];[oxidized NADPH---hemoprotein reductase] [CPD:C03161];2,4',5,7-tetrahydroxyisoflavanone [CPD:C12631]

Product

Species information

Mikania micrantha

Species name

Bittervine (Mikania micrantha) is a species of eudicot in the family Asteraceae (daisy family).

Species info

Gene sequence info

Mikania_micrantha.IFS2.fa

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>rna-gnl|WGS:SZYD|E3N88_mrna22216
MTIAFFKSKHAKSHLPPSPFSLPIIGHLHLLTPNPHQAFHRLSLRYGPIIRLFMGYEPCVVICSPKIAQEFLKTYENAYSDRPQNSATAYITYGSKDFAFAPYGPYWKFMKKIVMSQLLNGTTLDSLVQVRQDEINHFVKSISQKVGRAVNLNVELVKVANNLITRLLLGERCSEQAGQADDIRRMVSEINEAISSFNLSDNIWLFKNLDLQGFGKRVKDIHRRFDALIEKVIKEHEEAPSQEKDLLSILLHIAEYETMDIHLTKENIKAFILNIFVAATDNSAITPEWGLSELINHPNIMRKAIAEIDNVVGKDKLIQESDVQNLPYLQAIIKETLRLHPPIPLIPRKSKEDQTVAGYHIQANTNIFINTWALGRDPNHWENPLEFRPERFEEKQMDVRGQHFEFLPFGSGRRMCPGTSLGLKMVYTTFGAMIQCFEIGSIVLQMDQLE
>rna-gnl|WGS:SZYD|E3N88_mrna22217
MADFQPYFFHFLILLISTIFILAFFKSKNAKSHLPPSPFSIPIIGHLHLLTPNPHQAFHRLSLRYGPVFRLFMGCEPCVVTCSPKIAQEFLKTYENAYLDRPLNSATTYMTYGSKDFAFAPHGPHWKFMKKIVMSQLLNGTTIDSLHHVRQDEINHFVKSISQKVGKAVNLNAELVQVTNNLISRLLLGERCSEQAGQADDIRKMVFEITAEAGAFNLSDNIWLFKKLDLQWFGKRVKDIHRRFDALIEKIIKEHEESQSQEKDLLNILLRIAEDETMDIHLTRENIKAFILNIFVAGTDNSALAPEWGLSELINHPNIMRKAVAEIDNVVGKDRLIQESDVENLPYLQAIIKETLRLHPPVPLIPRKSTEDRTVAGYHIQANTSIFINTWALGRDPNYWENPLEFRPERFEEKPMDVRGQHFEFLPFGSGRRMCPGTSLGLKMVYATFGAMIQCFEWKAGEDGNLARVDMEEGCGFNLPKANPLVCVPVARLDPIPMHVFK
>rna-gnl|WGS:SZYD|E3N88_mrna22218
MGSFNLSDNIWLFKNLDLQWFGKRVKDIHRRFDALIEKIIKEHEEAQSQEKDLLSILLHIAEDETMDINLTRENIKAFILNIFVAGTDNSAIIAEWGLSELINHPNIMRKAVAEIDNVVGKDRLIQESDVQNLPYLRAIIKETLRLHPPVPLIPRKSTEDRTLAGLDLLYCKWISWSKCVNLFLSSSY
>rna-gnl|WGS:SZYD|E3N88_mrna22220
MDVRGQHFEFLPFGSGRRMCPGTSLGLKMVYTTFGAMIQCFEWKAGEDGNLATVDMDEGHGISLPKANHLICIGTRRHAVRTSTLSKSNQSPFVD
>rna-gnl|WGS:SZYD|E3N88_mrna22221
MADFQPYFFHFLILLISIAITLAFFKSKNAKSHLHPPSPFSLPIIGHLHLLTPTPHQAFHRLSLRYGPVFRLFMGSEPCVVTCSPKIAQEFLKTYENAYLDRPLNSATTYITYGSKDFAFAPHGPYWKFMRKMVMSQLLNGTTIDSMLQVRQDEINHFVKSISQKVGRAVYINAELVKVTNNLISRLLLGERCSEQAGQADDIRKMVFGITEAIGSFNLSDNIWLFKNLDLQGYGKRVKDFHRRFDALIEKIIKEHEESQSQEKDLLSMLLHIAEDEKMDIHLTRENIKAFILNIFVAGTDNSALTPEWGLSELINHPNIMRKAVAEIDNVVGKDRLIQESDIPNLPYLQAIIKETLRLHPPVPLIPRKSTEDRTVAGYHIQANTSIFINIWALGRDPNHWENPLEFRPERFEEKQMDVRGQHFEFLPFGSGRRMCPGTSLGLKMVYTTLGAMIQCFEWKAGEDGNLARVDMDEKRGFNLPKAKPLVCVPVARLDPIPMSIDH
>rna-gnl|WGS:SZYD|E3N88_mrna22227
MVDFQPYFFHFLILLISTIFILAFFKSKNAKSHLPPSPFSLPIIGHLHLLTPNPHQAFHRLSLRYGPITAEAGAFNLSDNIWLFKKLDLQWFGKRVKDIHRRFDALIEKIIKEHEESQSQEKDLLNILLRIAEDETMDIHLTRENIKAFILNIFVAGTDNSALAPEWGLSELINHPNIMRKAVAEIDNVVGKDRLIQESDVENLPYLQAIIKETLRLHPPVPLIPRKSTEDRTVAGYHIQANTSIYINTWALGRDPNHWENPLEFMPERFEEKPMDVRGQHFEFLPFGSGRRMCPGTSLGLKMVYATFGAMIQCFEWKAGEDGNLARVDMDEGCGFNLPKANPLVCVPVARLDPIPMHVFK
>rna-gnl|WGS:SZYD|E3N88_mrna22228
MADFQPYFFHFLILLISIAITLAFFKSKNAKSHLHPPSPFSLPIIGHLHLLTPTPHQAFHRLSLRYGPVFRLFMGSEPCVVTCSPKIAQEFLKTYENAYLDRPLNSATTYITYGSKDFAFAPHGPYWKFMRKMVMSQLLNGTTIDSMLQVRQDEINHFVKSISQKVGRAVYINAELVKVTNNLISRLLLGERCSEQAGQADDIRKMVFGITEAIGSFNLSDNIWLFKNLDLQGYGKRVKDFHRRFDALIEKIIKEHEESQSQEKDLLSMLLHIAEDETMDIHLTRENIKAFILNIFVAGTDNSALTPEWGLSELINHPNIMRKAVAEIDNVVGKDRLIQESDIPNLPYLQAIIKETLRLHPPVPLIPRKSTEDRTVAGYHIQANTSIFINIWALGRDPNHWENPLEFRPERFEEKQMDVRGQHFEFLPFGSGRRMCPGTSLGLKMVYTTLGAMIQCFEWKAGEDGNLTRVDMDEKRGFNLPKAKPLVCVPVARLDPIPMSIIDR
>rna-gnl|WGS:SZYD|E3N88_mrna22230
MRKAVAEIDNVVGKDRLIQESDMQNLPYLRAIIKETLRLHPPVPLIPRKSKEDQTVAGYHIQANTSIFINTWALGRDPNHWENPLEFMPERFEEKQMDVRGQHFEFLPFGSGRRMCPGISLGLKMLHATFGAMIQCFEWKAGEDGNLARVDMDEGLGLSLPKANHLVCVPVARLDPIPMSIDH
>rna-gnl|WGS:SZYD|E3N88_mrna32586
MNKVVEEIDQVVGKNKLLQESDIPNLPYLQNTVKETLRLHPAAPLLQKLPTEDCIVGGYHIPANTITFINLWSLGRDPTYWERPLEFRPERFEEKQIDVRGQNFHFLPFGSGKRMCPGVSLGLMFVYTILGSMIQCFTWKAGKYGNLTSVDMEEGTGIALTRANPLVCVPTTRLDLDPLGKQCSTCNNESDTYCGLVERLPSGLDGGRGVIRQLGRGGIRLVLGCLYFPCSASLNLWKHGCKLVAWVGAARGQGLGWSLIGLGLFWAGVWLIRWKPAVAAHFWHLVLLPWLLRCCWS
>rna-gnl|WGS:SZYD|E3N88_mrna32583
MVDFLSYFVLILTCVIPTIVIFKTYKSSRANAPLPPTPFRLPVIGNLHLLGPIIHQHFHKLSFKYGPVFRLFLGSTPCIVVSSAKVVEEIYRESENVFLRRPPIAANYNVTYGGKGFIFAPYGSYWKFVKKITMSQLLSGNTLDILLQVRRDEINHFIKNLSRKAKVGKSVEIEVMLGNVTSNMISRMVTGNKYAEEDDEVGDIMKIMADVDKLYGKLNLSDHIWFFKNIDLQGIEKTSMDIRKRFDALMDKILIEHEEAREQNIETRKVKDLLNILLEISEDDHMEIKLTRDNIKALILDIFLAGTDTSSKTIEWALAELINHPNIMKKAVEEIDQVVGKNRLLQESDIPNLPYLQSIVKETLRLHPVAPMIQRLSSEDCIVGGYHIPANTTTFINLWSLGRDPTYWERPLEFRPERFEDKQIDVRGQNFHFLPFGSGRRMCPGTTLGLMFVYTILGSMIQCFTWKAGKYGNLTSVDMEEGVAITLRRANPLVCAPTTRLDLDLLLS
>rna-gnl|WGS:SZYD|E3N88_mrna36190
MVDIYGYLILFFISVISVLFIRSFFLSSRSKLRLPPSPFALPIIGHLHLLAPIPHQALHNLSTRYGPVFQFFLGSVPCLAVSSPEMAKEFLRTYEASYLDRPRNATTVYLTYGSKDFMFAPYGPYWKLMKKLVMSDLLNGKTLDLLLPVRQDEVKQFINSLSQKAKLGKAVDVKDELLKLTNNVISRMLMSERCSEEENEASDMRKLVTEISKITGEFNLADYIWFLKNLDLQGYGKRVREIHPRFNKLIDRIISEHEDERRKRKGEDEAKDLLDILLKISEDDTMEMKVTKDNIKAFILNLFIAGTDTSALTIEWGLAELINHPGIMKKAVEEIDREVGKTRLVEESDIPNLPYLQAIVKETLRLHPTAPMIPRTSTEDCTVGGYHVPAKTTVFVNVWALGRDPENWDDPLKFNPERFELSQVDVRGQHFHMLPFGSGRRMCPGTSLAMQVVQVTLGVMVQCFEWKAGEDGVDMEEGPGITLPRANPLVCVPVARLDSTLF
>rna-gnl|WGS:SZYD|E3N88_mrna10990
MPYYQACYYTILICLISFLISKLYKSCHVKSHLPPCPFRLPVIGHLHLLSPHPHQAFHKLSIKHGPLFQLYLGSTPCVVVSSPETAKEILKTHETAFLDRPPNSIVDYFAYGGKGFIFAPYGPYWKFLKKIIMSELLNGKTLDSLIPVRHDEINRFIKHLSQKAKDGRFVELEGELMKLTSNVISRLFMSKRCSEEDDEIGNIAKIIAETGEIIGKFNLSDHIWFCKNLDLQGFGRISKDVHGRFDAVIEMIIRDHEKARMQDKGVKDLLNILLDISEDESMEMKLTRENIKAFIKDILAAGTDTSAISVEWALAELINHPNIMKKAVEEIDQVVGKNRLLNEKDIPNLPYLQAIVKESLRLHPTAPLILRSSTQDRNVGGYHIPANTTTLVNVWSLGRDPIHWDQPLKFKPERFEGKQWDVRGQHFHLLPFGTGRRMCPGTSLGLLTVHITLGAMIQCFEWKAGRYGNLSMVDMEEGIGITLPRANPLVCIPVARLDPIPFSI
>rna-gnl|WGS:SZYD|E3N88_mrna10991
MSDIHSYVLFFIIWLISTILIRALFKSTSAKPRLPPSPFALPIIGHLHLLAPIPHQAFHKLSLRYGPVFRILLGSVPSVVACSPEMAKEFLKTYENAYLDRPQNSAVAYLTYGSQDFSFAPYGSYWKFMKKIVMSQLLNGTTLDLLLPIRQDEINRFMKSLSQKAKIGKAVDLEGQLVRISNNVISRMLMSERCSENEDEAGEMKKLVKEIAEITGKFNLSDYIWIFKNLDLQGFGKRLKDIRRRFDELIERIIKEHEESRKQKSEKMDLLNILLDVAQDESMEIKLTRENIKSFILDIFAAGTDTSAITIEWALAELINHPNIMKKAVDEIDKVVGKNRLLQESDIPNLAYLQAIVKETLRLHSTGPMILRQSTEDCIVAGYHIPANTTIFINVWALGRDPNHWEDPLEFRPERFEQHNLDVRGQHFHMLPFGSGRRMCPGISLAMQVIHTTLGSMIQCFDWKAGEDGNLTSVNMEEGLGITLPRANHLICIPVARLDPIPV
>rna-gnl|WGS:SZYD|E3N88_mrna17336
MKQNHRLPPSPPSLPIIGHLHHLGPLVHQSLHDLSTRYGPLMHIRLGSVSCVVASTPDLAQDLLKANDLTFSYRKHTLAINHVTYGVGFAFAPYGPQKERVNMTEELLKLTNNVISQMMMSIRCSGTDSEADEAKVIVREVTKIFGEFNVSDFIWFCKNIDLQGFKKRYEEIRARYDALLEKIICEKEEMRKREQKGKDGKRKDFLDLLLDVFEDKEAQVNITRNNIKATILDFFVAGTDTTAVTTEWTLAELMNNPHVLEKARQEIDTVVGNKRLVNESDIPNMPYIQAIIKESLRLHPPIPLLIRKSNANINVRGYNIPSGSLLYVNIWSIGRNPQHWESPLEFKPDRFLEIGGSSLDFKGQNFKFLPFGTGRRSCPGVNLAMREAHVVVATLIQCFEWNHVDDKHGSLNMKERGGLTIPRAVDLVCLPSLRPNCPNIFP

Gene tree

Gene tree

Sheng jun & Dong yang Teams, Yunnan agriculture University