KEGG   ORTHOLOGY: K13225
Entry
K13225                      KO                                     
Symbol
BX4, CYP71C1, CYP71C6
Name
3-hydroxyindolin-2-one monooxygenase [EC:1.14.14.109]
Pathway
map00402  Benzoxazinoid biosynthesis
map00999  Biosynthesis of various plant secondary metabolites
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00952  Benzoxazinoid biosynthesis, indoleglycerol phosphate => DIMBOA-glucoside
Reaction
R07422  3-hydroxyindolin-2-one,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (2-hydroxy-2H-1,4-benzoxazin-3(4H)-one-forming)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00402 Benzoxazinoid biosynthesis
    K13225  BX4, CYP71C1, CYP71C6; 3-hydroxyindolin-2-one monooxygenase
   00999 Biosynthesis of various plant secondary metabolites
    K13225  BX4, CYP71C1, CYP71C6; 3-hydroxyindolin-2-one monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K13225  BX4, CYP71C1, CYP71C6; 3-hydroxyindolin-2-one monooxygenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.109  3-hydroxyindolin-2-one monooxygenase
     K13225  BX4, CYP71C1, CYP71C6; 3-hydroxyindolin-2-one monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP71 family
   K13225  BX4, CYP71C1, CYP71C6; 3-hydroxyindolin-2-one monooxygenase
Genes
ATS: 109753191
TAES: 123101969 123110086 123119085
TUA: 125555414
ZMA: 100382554
AG: BAB87817(CYP71C6v1) CAA57422(CYP71C1)
Reference
PMID:9235894 (CYP71C1)
  Authors
Frey M, Chomet P, Glawischnig E, Stettner C, Grun S, Winklmair A, Eisenreich W, Bacher A, Meeley RB, Briggs SP, Simcox K, Gierl A.
  Title
Analysis of a chemical plant defense mechanism in grasses.
  Journal
Science 277:696-9 (1997)
DOI:10.1126/science.277.5326.696
  Sequence
[ag:CAA57422]
Reference
PMID:7823905
  Authors
Frey M, Kliem R, Saedler H, Gierl A
  Title
Expression of a cytochrome P450 gene family in maize.
  Journal
Mol Gen Genet 246:100-9 (1995)
DOI:10.1007/BF00290138
  Sequence
[ag:CAA57422]
Reference
PMID:16260753
  Authors
Nomura T, Ishihara A, Yanagita RC, Endo TR, Iwamura H.
  Title
Three genomes differentially contribute to the biosynthesis of benzoxazinones in hexaploid wheat.
  Journal
Proc Natl Acad Sci U S A 102:16490-5 (2005)
DOI:10.1073/pnas.0505156102
Reference
PMID:11976964 (CYP71C6)
  Authors
Nomura T, Ishihara A, Imaishi H, Endo TR, Ohkawa H, Iwamura H
  Title
Molecular characterization and chromosomal localization of cytochrome P450 genes involved in the biosynthesis of cyclic hydroxamic acids in hexaploid wheat.
  Journal
Mol Genet Genomics 267:210-7 (2002)
DOI:10.1007/s00438-002-0653-x
  Sequence
[ag:BAB87817]
LinkDB

KEGG   ENZYME: 1.14.14.109
Entry
EC 1.14.14.109              Enzyme                                 
Name
3-hydroxyindolin-2-one monooxygenase;
BX4 (gene name);
CYP71C1 (gene name)
Class
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
Sysname
3-hydroxyindolin-2-one,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (2-hydroxy-2H-1,4-benzoxazin-3(4H)-one-forming)
Reaction(IUBMB)
3-hydroxyindolin-2-one + [reduced NADPH---hemoprotein reductase] + O2 = 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one [oxidized NADPH---hemoprotein reductase] + H2O [RN:R07422]
Reaction(KEGG)
R07422
Substrate
3-hydroxyindolin-2-one [CPD:C11130];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
2-hydroxy-2H-1,4-benzoxazin-3(4H)-one [oxidized NADPH---hemoprotein reductase];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme-thiolate) protein. The enzyme is involved in the biosynthesis of protective and allelophatic benzoxazinoids in some plants, most commonly from the family of Poaceae (grasses).
History
EC 1.14.14.109 created 2012 as EC 1.14.13.139, transferred 2018 to EC 1.14.14.109
Pathway
ec00402  Benzoxazinoid biosynthesis
ec00999  Biosynthesis of various plant secondary metabolites
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K13225  3-hydroxyindolin-2-one monooxygenase
Genes
ATS: 109753191
TAES: 123101969 123110086 123119085
TUA: 125555414
ZMA: 100382554
Reference
1  [PMID:10385992]
  Authors
Glawischnig E, Grun S, Frey M, Gierl A
  Title
Cytochrome P450 monooxygenases of DIBOA biosynthesis: specificity and conservation among grasses.
  Journal
Phytochemistry 50:925-30 (1999)
DOI:10.1016/S0031-9422(98)00318-5
Reference
2  [PMID:9235894]
  Authors
Frey M, Chomet P, Glawischnig E, Stettner C, Grun S, Winklmair A, Eisenreich W, Bacher A, Meeley RB, Briggs SP, Simcox K, Gierl A.
  Title
Analysis of a chemical plant defense mechanism in grasses.
  Journal
Science 277:696-9 (1997)
DOI:10.1126/science.277.5326.696
  Sequence
[ag:CAA57422]
Reference
3  [PMID:11393516]
  Authors
Spiteller P, Glawischnig E, Gierl A, Steglich W
  Title
Studies on the biosynthesis of 2-hydroxy-1,4-benzoxazin-3-one (HBOA) from 3-hydroxyindolin-2-one in Zea mays.
  Journal
Phytochemistry 57:373-6 (2001)
DOI:10.1016/S0031-9422(01)00037-1
  Sequence
[ag:CAA57422]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.109
IUBMB Enzyme Nomenclature: 1.14.14.109
ExPASy - ENZYME nomenclature database: 1.14.14.109
BRENDA, the Enzyme Database: 1.14.14.109
LinkDB

KEGG   REACTION: R07422
Entry
R07422                      Reaction                               
Name
3-hydroxyindolin-2-one,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (2-hydroxy-2H-1,4-benzoxazin-3(4H)-one-forming)
Definition
3-Hydroxyindolin-2-one + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> HBOA + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
C11130 + C03024 + C00007 <=> C15769 + C03161 + C00001
Reaction class
RC02044  C11130_C15769
Enzyme
1.14.14.109
Pathway
rn00402  Benzoxazinoid biosynthesis
rn00999  Biosynthesis of various plant secondary metabolites
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00952  Benzoxazinoid biosynthesis, indoleglycerol phosphate => DIMBOA-glucoside
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.109
     R07422  3-Hydroxyindolin-2-one + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> HBOA + [Oxidized NADPH---hemoprotein reductase] + H2O
Orthology
K13225  3-hydroxyindolin-2-one monooxygenase [EC:1.14.14.109]
Other DBs
RHEA: 31930
LinkDB

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