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Information on EC 1.14.14.82 - flavonoid 3'-monooxygenase and Organism(s) Arabidopsis thaliana and UniProt Accession Q9SD85

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IUBMB Comments
A cytochrome P-450 (heme-thiolate) protein found in plants. Acts on a number of flavonoids, including the flavanone naringenin and the flavone apigenin. Does not act on 4-coumarate or 4-coumaroyl-CoA.
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This record set is specific for:
Arabidopsis thaliana
UNIPROT: Q9SD85
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The taxonomic range for the selected organisms is: Arabidopsis thaliana
The enzyme appears in selected viruses and cellular organisms
Synonyms
csf3'h, cyp75b4, cyp75b, sf3'h1, cyp75b3, cyp75b1, flavonoid 3'-monooxygenase, flavonoid 3-hydroxylase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
flavonoid 3'-hydroxylase
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flavonoid 3'-hydroxylase
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flavonoid 3-hydroxylase
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-
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NADPH:flavonoid-3'-hydroxylase
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oxygenase, flavonoid 3'-mono-
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oxygenase, flavonoid 3-mono-
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additional information
the enzyme belongs to the vast and versatile cytochrome P450 protein family of enzymes
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
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oxidation
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reduction
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SYSTEMATIC NAME
IUBMB Comments
flavonoid,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
A cytochrome P-450 (heme-thiolate) protein found in plants. Acts on a number of flavonoids, including the flavanone naringenin and the flavone apigenin. Does not act on 4-coumarate or 4-coumaroyl-CoA.
CAS REGISTRY NUMBER
COMMENTARY hide
75991-44-5
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85340-98-3
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85340-98-3
oxygenase, flavonoid 3-mono-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
5-deoxyleucopelargonidin + [reduced NADPH-hemoprotein reductase] + O2
5-deoxyleucocyanidin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
apigenin + [reduced NADPH-hemoprotein reductase] + O2
luteolin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
dihydrokaempferol + [reduced NADPH-hemoprotein reductase] + O2
dihydroquercetin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
kaempferol + [reduced NADPH-hemoprotein reductase] + O2
quercetin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
leucopelargonidin + [reduced NADPH-hemoprotein reductase] + O2
leucocyanidin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
naringenin + [reduced NADPH-hemoprotein reductase] + O2
eriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
additional information
?
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the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
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?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
dihydrokaempferol + [reduced NADPH-hemoprotein reductase] + O2
dihydroquercetin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
naringenin + [reduced NADPH-hemoprotein reductase] + O2
eriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
additional information
?
-
the hydroxylation pattern of the B-ring of flavonoids is determined by the activity of the flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase, phylogenetic analysis of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, flavonoid biosynthesis pathways, overview
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-
?
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0074
5-deoxyleucopelargonidin
pH 7.3, 25°C
0.0064
apigenin
pH 7.3, 25°C
0.009
dihydrokaempferol
pH 7.3, 25°C
0.0019
kaempferol
pH 7.3, 25°C
0.0012
naringenin
pH 7.3, 25°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
12.3
5-deoxyleucopelargonidin
pH 7.3, 25°C
9.3
apigenin
pH 7.3, 25°C
12.7
dihydrokaempferol
pH 7.3, 25°C
5.8
kaempferol
pH 7.3, 25°C
2.1
naringenin
pH 7.3, 25°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1700
5-deoxyleucopelargonidin
pH 7.3, 25°C
1500
apigenin
pH 7.3, 25°C
1400
dihydrokaempferol
pH 7.3, 25°C
3100
kaempferol
pH 7.3, 25°C
1800
naringenin
pH 7.3, 25°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
senescing leaf, low expression level
Manually annotated by BRENDA team
high expression level
Manually annotated by BRENDA team
low expression level
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
mutation tt7 carrying an internal stop codon leads to the transparent testa phenotype due to lack of tannins in the seed coat
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
F3PH_ARATH
513
1
56787
Swiss-Prot
Mitochondrion (Reliability: 5)
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, detailed phylogenetic analysis and comparison of sequences of both enzymes indicate that F3',5'H is recruited from F3'H before the divergence of angiosperms and gymnosperms, overview
expression in Saccharomyces cerevisiae
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expression is induced by UV irradiation
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Seitz, C.; Eder, C.; Deiml, B.; Kellner, S.; Martens, S.; Forkmann, G.
Cloning, functional identification and sequence analysis of flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase cDNAs reveals independent evolution of flavonoid 3,5-hydroxylase in the Asteraceae family
Plant Mol. Biol.
61
365-381
2006
Allium cepa (Q6QHJ9), Arabidopsis thaliana (Q9SD85), Callistephus chinensis (Q9FPN5), Gentiana triflora (Q59I68), Gerbera hybrid cultivar (Q38L00), Glycine max (Q8W3Y5), Ipomoea nil (Q767R1), Matthiola incana (Q9FPN2), Osteospermum hybrid cultivar (Q304R0), Pelargonium x hortorum (Q9FPM9), Perilla frutescens (Q93XJ2), Petunia x hybrida (Q9SBQ9), Pilosella officinarum (Q0QLB3), Torenia hybrid cultivar (Q8S9C6)
Manually annotated by BRENDA team
Schoenbohm, C.; Martens, S.; Eder, C.; Forkmann, G.; Weisshaar, B.
Identification of the Arabidopsis thaliana flavonoid 3-hydroxylase gene and functional expression of the encoded P450 enzyme
Biol. Chem.
381
749-753
2000
Arabidopsis thaliana (Q9SD85)
Manually annotated by BRENDA team
Schwinn, K.; Miosic, S.; Davies, K.; Thill, J.; Gotame, T.P.; Stich, K.; Halbwirth, H.
The B-ring hydroxylation pattern of anthocyanins can be determined through activity of the flavonoid 3-hydroxylase on leucoanthocyanidins
Planta
240
1003-1010
2014
Arabidopsis thaliana (Q9SD85), Fragaria x ananassa, Tagetes erecta (C1J0N9)
Manually annotated by BRENDA team