Information on EC 1.14.13.21 - flavonoid 3'-monooxygenase

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The expected taxonomic range for this enzyme is: Magnoliophyta

EC NUMBER
COMMENTARY
1.14.13.21
-
RECOMMENDED NAME
GeneOntology No.
flavonoid 3'-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a flavonoid + NADPH + H+ + O2 = a 3'-hydroxyflavonoid + NADP+ + H2O
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
(+)-dihydrokaempferol 3',5'-hydroxylase
-
-
Biosynthesis of secondary metabolites
-
-
Flavone and flavonol biosynthesis
-
-
Flavonoid biosynthesis
-
-
flavonol biosynthesis
-
-
leucodelphinidin biosynthesis
-
-
leucopelargonidin and leucocyanidin biosynthesis
-
-
luteolin biosynthesis
-
-
Metabolic pathways
-
-
syringetin biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
flavonoid,NADPH:oxygen oxidoreductase (3'-hydroxylating)
Acts on a number of flavonoids, including naringenin and dihydrokaempferol. Does not act on 4-coumarate or 4-coumaroyl-CoA.
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
flavonoid 3'-hydroxylase
-
-
-
-
flavonoid 3-hydroxylase
-
-
-
-
NADPH:flavonoid-3'-hydroxylase
-
-
-
-
oxygenase, flavonoid 3'-mono-
-
-
-
-
oxygenase, flavonoid 3-mono-
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
75991-44-5
-
85340-98-3
oxygenase, flavonoid 3-mono-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
snapdragon
-
-
Manually annotated by BRENDA team
gene F3'H-1, two clones
SwissProt
Manually annotated by BRENDA team
line '01'
SwissProt
Manually annotated by BRENDA team
sweet orange
-
-
Manually annotated by BRENDA team
Columnea hybrida
-
-
-
Manually annotated by BRENDA team
different cultivars
-
-
Manually annotated by BRENDA team
gene F3'h1
SwissProt
Manually annotated by BRENDA team
i.e. Pharbitis nil, cv. japanese morning glory
SwissProt
Manually annotated by BRENDA team
gene MdF3'HI; gene MdF3'HI
UniProt
Manually annotated by BRENDA team
gene MdF3'HIIa; gene MdF3'HIIa
UniProt
Manually annotated by BRENDA team
gene MdF3'HIIb; gene MdF3'HIIb
UniProt
Manually annotated by BRENDA team
enzyme present only in lines of organism with wild-type allele b+
-
-
Manually annotated by BRENDA team
japonica rice lines T65, T65-Plw (purple leaves), Nipponbare, Zhonghua 11, Tainong 67
-
-
Manually annotated by BRENDA team
var. crispa
SwissProt
Manually annotated by BRENDA team
syn. Rechsteineria
-
-
Manually annotated by BRENDA team
F3'H1; i.e. Sorghum vulgare, 3 genes F3'H1, F3'H2, and F3'H3
SwissProt
Manually annotated by BRENDA team
F3'H2; i.e. Sorghum vulgare, 3 genes F3'H1, F3'H2, and F3'H3
SwissProt
Manually annotated by BRENDA team
F3'H3; i.e. Sorghum vulgare, 3 genes F3'H1, F3'H2, and F3'H3
SwissProt
Manually annotated by BRENDA team
cv. red cultivar Cabernet Sauvignon
-
-
Manually annotated by BRENDA team
cv. Shiraz
SwissProt
Manually annotated by BRENDA team
gene F3'h1; cv. Cabernet Sauvignon, gene F3'h1
SwissProt
Manually annotated by BRENDA team
gene F3'h2; cv. Cabernet Sauvignon, gene F3'h2
SwissProt
Manually annotated by BRENDA team
gene F3'h3; cv. Cabernet Sauvignon, gene F3'h3
SwissProt
Manually annotated by BRENDA team
gene F3'h4; cv. Cabernet Sauvignon, gene F3'h4
SwissProt
Manually annotated by BRENDA team
two copies of the gene encoding the competing F3H enzyme are present in the grape genome, the second is transcriptionally silent
-
-
Manually annotated by BRENDA team
Vitis vinifera PN40024
two copies of the gene encoding the competing F3H enzyme are present in the grape genome, the second is transcriptionally silent
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
-
duplication of F3'H genes in plants, overview
metabolism
-
role in anthocyanin regulation and flavone biosynthesis, interaction with chalcone synthase 1 as shown by yeast fusion experiment
metabolism
-
flavonoid 3',5'-hydroxylases and flavonoid 3'-hydroxylases competitively control the synthesis of delphinidin and cyanidin, the precursors of blue and red anthocyanins, anthocyanin profiling in strain PN40024, overview
metabolism
-
MdF3'H genes are coordinately expressed with other genes in the anthocyanin biosynthetic pathway in apple
metabolism
T1NXM4
the drastic decline of flavonoid 3'-hydroxylase expression occurring during fruit ripening in Fragaria ananassa is reflected by the anthocyanin composition, which shows a prevalence of pelargonidin in ripe fruits of Fragaria ananassa
metabolism
T1NXM1
the high expression of flavonoid 3'-hydroxylase during fruit ripening in Fragaria vesca is reflected by the anthocyanin composition, which shows a high content of cyanidin
metabolism
Vitis vinifera PN40024
-
flavonoid 3',5'-hydroxylases and flavonoid 3'-hydroxylases competitively control the synthesis of delphinidin and cyanidin, the precursors of blue and red anthocyanins, anthocyanin profiling in strain PN40024, overview
-
physiological function
A9ZMJ6
part of flavonoid biosynthetic pathway
physiological function
-
the enzyme introduces a hydroxyl group at 3' position of the B-ring of the flavonoid molecule leading to the formation of 3',4'-hydroxylated flavonoids
physiological function
-
enzyme expression is associated with anthocyanin accumulation in five different sweet potato cultivars tested
physiological function
-
loss of enzyme activity leads to accumulation of 3,5-di-O-(beta-glucopyranosyl)pelargonidin 6''-O-4,6'''-O-1-cyclic malate instead of 3,5-di-O-(beta-glucopyranosyl)cyanidin 6''-O-4,6'''-O-1-cyclic malate, the only difference between these two anthocyanins is a hydroxyl group present at the 3' position in the B-ring of aglycone. Loss of enzyme results in a color change in buds from purple to deep pink. Mutation is due to an active hAT type transposable element, designated Tdic101. The color change is attributed to Tdic101 insertion into the second intron of flavonoid 3'-hydroxylase
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
apiforol + + NADPH + H+ + O2
luteoforol + NADP+ + H2O
show the reaction diagram
F6KZD5
-
-
-
?
apigenin + NADPH + H+ + O2
luteolin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
apigenin + NADPH + O2
luteolin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
apigenin + NADPH + O2
luteolin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
apigenin + NADPH + O2
luteolin + NADP+ + H2O
show the reaction diagram
-
-
-
?
apigenin + NADPH + O2
luteolin + NADP+ + H2O
show the reaction diagram
Columnea hybrida
-
-
-
?
apigenin + NADPH + O2
luteolin + NADP+ + H2O
show the reaction diagram
Q93XJ2
-
-
-
?
apigenin + NADPH + O2
luteolin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
apigenin + NADPH + O2
luteolin + NADP+ + H2O
show the reaction diagram
T1NXM4
-
-
-
?
apigenin + NADPH + O2
luteolin + NADP+ + H2O
show the reaction diagram
T1NXM1
-
-
-
?
apigenin + NADPH + O2
luteolin + NADP+ + H2O
show the reaction diagram
Columnea hybrida Heklua
-
-
-
?
dihydrokaempferol + + NADPH + H+ + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
dihydrokaempferol + NADPH + H+ + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
dihydrokaempferol + NADPH + H+ + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
dihydrokaempferol + NADPH + H+ + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
C5IGQ3, C5IGQ4, C5IGQ5
-
-
-
?
dihydrokaempferol + NADPH + H+ + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
T1NXM4
-
-
-
?
dihydrokaempferol + NADPH + H+ + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
T1NXM1
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
ir
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q93XJ2
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
ir
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q6QHJ9
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q9SD85
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q59I68
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q8W3Y5
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q767R1
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q9FPM9
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q9SBQ9
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q9FPN2
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q8S9C6
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q0Z7U7, Q0Z7U8, Q0Z7U9
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q3C211, Q3C212, Q3C213, Q3C214
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
A1XBC6
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q2UYU6
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q9FPN5
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q304R0
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q38L00
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q0QLB3
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
no activity
-
-
-
dihydrokaempferol + O2 + 2-oxoglutarate
dihydroquercetin + succinate + CO2
show the reaction diagram
-
-
-
-
?
kaempferol + NADPH + H+ + O2
quercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
kaempferol + NADPH + H+ + O2
quercetin + NADP+ + H2O
show the reaction diagram
C5IGQ3, C5IGQ4, C5IGQ5
-
-
-
?
kaempferol + NADPH + H+ + O2
quercetin + NADP+ + H2O
show the reaction diagram
T1NXM4
-
-
-
?
kaempferol + NADPH + H+ + O2
quercetin + NADP+ + H2O
show the reaction diagram
T1NXM1
-
-
-
?
kaempferol + NADPH + O2
quercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
kaempferol + NADPH + O2
quercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
kaempferol + NADPH + O2
quercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
naringenin + NADPH + H+ + O2
eriodyctiol + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
naringenin + NADPH + H+ + O2
eriodyctiol + NADP+ + H2O
show the reaction diagram
-
preferred substrate of the wild-type enzyme
-
-
?
naringenin + NADPH + H+ + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
C5IGQ3, C5IGQ4, C5IGQ5
-
-
-
?
naringenin + NADPH + H+ + O2
eriodyctol + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
-
ir
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
-
ir
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q93XJ2
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
-
ir
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q6QHJ9
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q9SD85
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q59I68
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q8W3Y5
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q767R1
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q9FPM9
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q9SBQ9
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q9FPN2
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q8S9C6
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q0Z7U7, Q0Z7U8, Q0Z7U9
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q3C211, Q3C212, Q3C213, Q3C214
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
A1XBC6
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q2UYU6
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q9FPN5
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q304R0
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q38L00
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q0QLB3
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
T1NXM4
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
T1NXM1
-
-
-
?
naringenin + O2 + 2-oxoglutarate
eriodictyol + succinate + CO2
show the reaction diagram
-
-
-
-
?
kaempferol + NADPH + O2
quercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
not: 4-coumarate, 4-coumaroyl-CoA
-
-
-
additional information
?
-
-
not: prunin
-
-
-
additional information
?
-
-
enzyme is involved in the anthocyanin biosynthesis pathway, overview, the pleiotropic T locus and two recessive alleles differentially affect structure and expression of the enzyme
-
-
-
additional information
?
-
-
the enzyme is involved in the biosynthesis of anthocyanins responsible for e.g. the colour of flowers
-
-
-
additional information
?
-
-
the enzyme is involved in the biosynthesis of anthocyanins responsible for e.g. the colour of flowers, analysis of flower piment content
-
-
-
additional information
?
-
Q2UYU6
flavonoid biosynthetic pathway, enzyme regulation, overview
-
-
-
additional information
?
-
Q0Z7U7, Q0Z7U8, Q0Z7U9
the enzyme is involved in biosynthesis of anthocyanin pigments and 3-deoxyanthocyanidin phytoalexins in Sorghum, F3'H1 expression is involved in light-specific anthocyanin accumulation, differential regulation of F3'H genes/alleles responding to different external stimuli, overview
-
-
-
additional information
?
-
Q0Z7U7, Q0Z7U8, Q0Z7U9
the enzyme is involved in biosynthesis of anthocyanin pigments and 3-deoxyanthocyanidin phytoalexins in Sorghum, F3'H1 expression is involved in light-specific anthocyanin accumulation, differential regulation of F30H genes/alleles responding to different external stimuli, overview
-
-
-
additional information
?
-
Q0Z7U7, Q0Z7U8, Q0Z7U9
the enzyme is involved in biosynthesis of anthocyanin pigments and 3-deoxyanthocyanidin phytoalexins in Sorghum, F3'H2 expression is involved in pathogen-specific 3-deoxyanthocyanidin synthesis, differential regulation of F3'H genes/alleles responding to different external stimuli, overview
-
-
-
additional information
?
-
Q3C211, Q3C212, Q3C213, Q3C214
the enzyme is involved in the biosynthetic pathway of delphinidin-based anthocyanins, as well as of the flavonols quercetin and myricetin and procyanidin and prodelphinidin, correlation of enzyme expression pattern and flavonoid composition, flavonoid composition in organs of Vitis vinifera, flavonoid biosynthetic pathways, overview
-
-
-
additional information
?
-
-
the enzyme plays a role in the phenyl-propanoid pathway and the biosynthesis of cyanidin- and delphinidin-based anthocyanin pigments in the socalled red cultivars of grapevine, metabolic profiling and colour variations, overview, the enzyme is responsible for flavonoid accumulation in tissues
-
-
-
additional information
?
-
Q93XJ2
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
-
-
-
additional information
?
-
Q6QHJ9
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
-
-
-
additional information
?
-
Q9SD85
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
-
-
-
additional information
?
-
Q59I68
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
-
-
-
additional information
?
-
Q8W3Y5
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
-
-
-
additional information
?
-
Q767R1
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
-
-
-
additional information
?
-
Q9FPM9
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
-
-
-
additional information
?
-
Q9SBQ9
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
-
-
-
additional information
?
-
Q9FPN2
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
-
-
-
additional information
?
-
Q8S9C6
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
-
-
-
additional information
?
-
Q9FPN5
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
-
-
-
additional information
?
-
Q304R0
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
-
-
-
additional information
?
-
Q38L00
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
-
-
-
additional information
?
-
Q0QLB3
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
-
-
-
additional information
?
-
A1XBC6
transcription level of the F3'H genes is not the reason for the different seed colorations found in near-isogenic lines, blackseeded L1 and yellow-seeded L2, of Brassica napus
-
-
-
additional information
?
-
-
endogenous flavonoid 3'-hydroxylase competes with recombinantly expressed flavonoid 3',5'-hydroxylase, EC 1.14.13.88, in Chrysanthemum plants for the same substrates in the flavonoid biosynthetic pathway, overview
-
-
-
additional information
?
-
-
substrate specificity of F3'H and the F3'5'H, flavonoid 3',5'-hydroxylase, EC 1.14.13.88, evolutionary derived from F3'H, is determined near the N-terminal end and the functional difference between these two enzymes near the C-terminal end, relatively few amino acids exchanges are required for the evolutionary extension of 3'- to 3',5'-hydroxylation activity, overview
-
-
-
additional information
?
-
-
the enzyme is involved in several steps of the flavonoid synthesis pathway and in control of pigmentation in developing soybean, presence of a threshold mRNA level associated with pigmentation during development, overview
-
-
-
additional information
?
-
F6KZD5
enzyme has a role in the conversion of monohydroxylated to dihydroxylated compounds in the B-ring of flavonoids
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
apigenin + NADPH + H+ + O2
luteolin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
apigenin + NADPH + O2
luteolin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
apigenin + NADPH + O2
luteolin + NADP+ + H2O
show the reaction diagram
Columnea hybrida, Columnea hybrida Heklua
-
-
-
-
?
dihydrokaempferol + NADPH + H+ + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
dihydrokaempferol + NADPH + H+ + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
dihydrokaempferol + NADPH + H+ + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
C5IGQ3, C5IGQ4, C5IGQ5
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
ir
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q93XJ2
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
ir
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q6QHJ9
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q9SD85
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q59I68
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q8W3Y5
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q767R1
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q9FPM9
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q9SBQ9
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q9FPN2
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q8S9C6
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q0Z7U7, Q0Z7U8, Q0Z7U9
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q3C211, Q3C212, Q3C213, Q3C214
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
A1XBC6
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q2UYU6
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q9FPN5
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q304R0
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q38L00
-
-
-
?
dihydrokaempferol + NADPH + O2
dihydroquercetin + NADP+ + H2O
show the reaction diagram
Q0QLB3
-
-
-
?
dihydrokaempferol + O2 + 2-oxoglutarate
dihydroquercetin + succinate + CO2
show the reaction diagram
-
-
-
-
?
kaempferol + NADPH + H+ + O2
quercetin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
naringenin + NADPH + H+ + O2
eriodyctiol + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
naringenin + NADPH + H+ + O2
eriodyctiol + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
naringenin + NADPH + H+ + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
C5IGQ3, C5IGQ4, C5IGQ5
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
-
ir
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
-
ir
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q93XJ2
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
-
-
-
-
ir
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q6QHJ9
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q9SD85
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q59I68
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q8W3Y5
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q767R1
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q9FPM9
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q9SBQ9
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q9FPN2
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q8S9C6
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q0Z7U7, Q0Z7U8, Q0Z7U9
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q3C211, Q3C212, Q3C213, Q3C214
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
A1XBC6
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q2UYU6
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q9FPN5
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q304R0
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q38L00
-
-
-
?
naringenin + NADPH + O2
eriodictyol + NADP+ + H2O
show the reaction diagram
Q0QLB3
-
-
-
?
naringenin + O2 + 2-oxoglutarate
eriodictyol + succinate + CO2
show the reaction diagram
-
-
-
-
?
kaempferol + NADPH + H+ + O2
quercetin + NADP+ + H2O
show the reaction diagram
C5IGQ3, C5IGQ4, C5IGQ5
-
-
-
?
additional information
?
-
-
enzyme is involved in the anthocyanin biosynthesis pathway, overview, the pleiotropic T locus and two recessive alleles differentially affect structure and expression of the enzyme
-
-
-
additional information
?
-
-
the enzyme is involved in the biosynthesis of anthocyanins responsible for e.g. the colour of flowers
-
-
-
additional information
?
-
-
the enzyme is involved in the biosynthesis of anthocyanins responsible for e.g. the colour of flowers, analysis of flower piment content
-
-
-
additional information
?
-
Q2UYU6
flavonoid biosynthetic pathway, enzyme regulation, overview
-
-
-
additional information
?
-
Q0Z7U7, Q0Z7U8, Q0Z7U9
the enzyme is involved in biosynthesis of anthocyanin pigments and 3-deoxyanthocyanidin phytoalexins in Sorghum, F3'H1 expression is involved in light-specific anthocyanin accumulation, differential regulation of F3'H genes/alleles responding to different external stimuli, overview
-
-
-
additional information
?
-
Q0Z7U7, Q0Z7U8, Q0Z7U9
the enzyme is involved in biosynthesis of anthocyanin pigments and 3-deoxyanthocyanidin phytoalexins in Sorghum, F3'H1 expression is involved in light-specific anthocyanin accumulation, differential regulation of F30H genes/alleles responding to different external stimuli, overview
-
-
-
additional information
?
-
Q0Z7U7, Q0Z7U8, Q0Z7U9
the enzyme is involved in biosynthesis of anthocyanin pigments and 3-deoxyanthocyanidin phytoalexins in Sorghum, F3'H2 expression is involved in pathogen-specific 3-deoxyanthocyanidin synthesis, differential regulation of F3'H genes/alleles responding to different external stimuli, overview
-
-
-
additional information
?
-
Q3C211, Q3C212, Q3C213, Q3C214
the enzyme is involved in the biosynthetic pathway of delphinidin-based anthocyanins, as well as of the flavonols quercetin and myricetin and procyanidin and prodelphinidin, correlation of enzyme expression pattern and flavonoid composition, flavonoid composition in organs of Vitis vinifera, flavonoid biosynthetic pathways, overview
-
-
-
additional information
?
-
-
the enzyme plays a role in the phenyl-propanoid pathway and the biosynthesis of cyanidin- and delphinidin-based anthocyanin pigments in the socalled red cultivars of grapevine, metabolic profiling and colour variations, overview, the enzyme is responsible for flavonoid accumulation in tissues
-
-
-
additional information
?
-
Q93XJ2
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
-
-
-
additional information
?
-
Q6QHJ9
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
-
-
-
additional information
?
-
Q9SD85
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
-
-
-
additional information
?
-
Q59I68
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
-
-
-
additional information
?
-
Q8W3Y5
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
-
-
-
additional information
?
-
Q767R1
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
-
-
-
additional information
?
-
Q9FPM9
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
-
-
-
additional information
?
-
Q9SBQ9
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
-
-
-
additional information
?
-
Q9FPN2
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
-
-
-
additional information
?
-
Q8S9C6
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
-
-
-
additional information
?
-
Q9FPN5
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
-
-
-
additional information
?
-
Q304R0
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
-
-
-
additional information
?
-
Q38L00
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
-
-
-
additional information
?
-
Q0QLB3
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
-
-
-
additional information
?
-
A1XBC6
transcription level of the F3'H genes is not the reason for the different seed colorations found in near-isogenic lines, blackseeded L1 and yellow-seeded L2, of Brassica napus
-
-
-
additional information
?
-
-
endogenous flavonoid 3'-hydroxylase competes with recombinantly expressed flavonoid 3',5'-hydroxylase, EC 1.14.13.88, in Chrysanthemum plants for the same substrates in the flavonoid biosynthetic pathway, overview
-
-
-
additional information
?
-
-
substrate specificity of F3'H and the F3'5'H, flavonoid 3',5'-hydroxylase, EC 1.14.13.88, evolutionary derived from F3'H, is determined near the N-terminal end and the functional difference between these two enzymes near the C-terminal end, relatively few amino acids exchanges are required for the evolutionary extension of 3'- to 3',5'-hydroxylation activity, overview
-
-
-
additional information
?
-
-
the enzyme is involved in several steps of the flavonoid synthesis pathway and in control of pigmentation in developing soybean, presence of a threshold mRNA level associated with pigmentation during development, overview
-
-
-
additional information
?
-
F6KZD5
enzyme has a role in the conversion of monohydroxylated to dihydroxylated compounds in the B-ring of flavonoids
-
-
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
cytochrome
-
a cytochrome P450 enzyme
-
cytochrome P450
-
0.21 nmol per mg of protein
-
cytochrome P450
-
cytochrome P-450-dependent enzyme
-
cytochrome P450
-
-
-
cytochrome P450
-
-
-
NADH
-
much lower product yield than with NADPH
NADH
-
no activity
NADH
-
about 12% of the activity with NADPH
NADPH
Columnea hybrida
-
-
NADPH
-
-
NADPH
A1XBC6
-
NADPH
Q0Z7U7, Q0Z7U8, Q0Z7U9
-
NADPH
Q6QHJ9
-
NADPH
Q9SD85
-
NADPH
Q59I68
-
NADPH
Q93XJ2
-
NADPH
Q9SBQ9
-
NADPH
Q0QLB3
-
NADPH
C5IGQ3, C5IGQ4, C5IGQ5
dependent on; dependent on; dependent on
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
-
a cytochrome P450 enzyme
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
alpha,alpha'-dipyridyl
-
partial
CO
-
inhibition reduced by irradiation with 450 nm light during incubation
CO
-
inhibition reduced by irradiation with 450 nm light during incubation
cytochrome c
-
-
cytochrome c
-
-
cytochrome c
-
-
diethyldicarbonate
-
-
diethyldicarbonate
-
partial
diethyldicarbonate
-
-
EDTA
-
partial
FeCl3
-
-
ketoconazole
-
cytochrome P450 inhibitor
ketoconazole
-
-
N-ethylmaleimide
-
2 mM: partial inhibition
N-ethylmaleimide
-
-
N-ethylmaleimide
-
1 mM: activation
NADP+
-
-
NaN3
-
-
NaN3
-
partial
p-chloromercuribenzoate
-
partial
p-chloromercuribenzoate
-
partial
p-chloromercuribenzoate
-
-
p-chloromercuribenzoate
-
partial
Tetcyclacis
-
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
N-ethylmaleimide
-
1 mM: activation
additional information
-
transcriptional induction of the enzyme is temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 2fold higher in red berries versus green berries
-
additional information
Q0Z7U7, Q0Z7U8, Q0Z7U9
light-activated expression of F3'H1; pathogen-induced expression of F3'H2
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0001
apigenin
T1NXM4
pH 7.0, 25C
0.019
apigenin
Q93XJ2
-
0.021
apigenin
-
-
0.048
apigenin
T1NXM1
pH 7.0, 25C
0.004
dihydrokaempferol
-
-
0.02
dihydrokaempferol
Q93XJ2
-
0.003
kaempferol
-
-
0.00715
kaempferol
Columnea hybrida
-
-
0.0058
NADPH
Columnea hybrida
-
with kaempferol
0.0008
Naringenin
-
-
0.001
Naringenin
T1NXM4
pH 7.0, 25C
0.004
Naringenin
T1NXM1
pH 7.0, 25C
0.009
Naringenin
T1NXM4
pH 7.0, 25C
0.02
Naringenin
Q93XJ2
-
0.021
Naringenin
T1NXM1
pH 7.0, 25C
0.022
Naringenin
T1NXM1
pH 7.0, 25C
24
Naringenin
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.000003
-
recombinant wild-type F3'H
additional information
Columnea hybrida
-
-
additional information
-
activities of recombinant chimeric mutant enzymes, overview
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7
T1NXM1
-
7.2
-
naringenin
7.4 - 7.6
-
-
7.5
-
apigenin
7.5
Q6QHJ9
assay at
7.5
Q9SD85
assay at
7.5
Q9FPN5
assay at
7.5
Q59I68
assay at
7.5
-
assay at
7.5
Q767R1
assay at
7.5
Q9FPN2
assay at
7.5
Q304R0
assay at
7.5
Q9FPM9
assay at
7.5
Q93XJ2
assay at
7.5
Q9SBQ9
assay at
7.5
Q0QLB3
assay at
7.5
Q8S9C6
assay at
7.5
Q38L00
assay at
8.5
-
-
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.8 - 8.4
-
half-maximal activity at pH 6.8 and 8.4
additional information
-
sharp drop in activity on either side of the optimum of pH 8.5
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30 - 37
-
-
30
-
-
30
Q6QHJ9
assay at
30
Q9SD85
assay at
30
Q9FPN5
assay at
30
Q59I68
assay at
30
Q767R1
assay at
30
Q9FPN2
assay at
30
Q9FPM9
assay at
30
Q93XJ2
assay at
30
Q9SBQ9
assay at
30
Q0QLB3
assay at
30
Q8S9C6
assay at
30
T1NXM1
-
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
10 - 25
-
10C: 30% of maximal activity, 25C: optimum
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.1
A1XBC6
amino acid sequence calculation
9
-
calculatd
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
most active in developmental stages 2-5 of bud and flower formation
Manually annotated by BRENDA team
-
high level of F3'H expression
Manually annotated by BRENDA team
-
berry skin and flesh
Manually annotated by BRENDA team
Q2UYU6
regulation during fruit development, overview, berry skin, transcriptional regulation of the enzyme, onset of expression after flowering, low expression at the onset of ripening, high expression after veraison concomitant with the accumulation of 3'- and 3',5'-hydroxylated anthocyanins, overview
Manually annotated by BRENDA team
-
throughout the development of fruits, the transcriptional levels of MdF3'H genes along with other anthocyanin biosynthesis genes are higher in the red-skinned cv. Red Delicious than that in the yellow-skinned cv. Golden Delicious. Patterns of MdF3'H gene expression correspond to accumulation patterns of flavonoids in apple fruit
Manually annotated by BRENDA team
A9ZMJ6
low amount
Manually annotated by BRENDA team
-
apex, apical leaflet, reddish pigmented shoot tips
Manually annotated by BRENDA team
-
enzyme is constitutively expressed in all tested tissues including fibrous roots, thick roots, storage roots, stems and leaves
Manually annotated by BRENDA team
-
of flowers at early stage of development
Manually annotated by BRENDA team
-
of immature seed coat
Manually annotated by BRENDA team
-
enzyme is constitutively expressed in all tested tissues including fibrous roots, thick roots, storage roots, stems and leaves. During storage root formation, enzyme is expressed most abundantly in the storage roots
Manually annotated by BRENDA team
Q2UYU6
F3'H is expressed consistent with the accumulation of 3'-hydroxylated proanthocyanidins in this tissue
Manually annotated by BRENDA team
-
high level of F3'H expression
Manually annotated by BRENDA team
-
predominantly in hilum and funiculus of immature seed coat
Manually annotated by BRENDA team
-
high level of F3'H expression
Manually annotated by BRENDA team
-
enzyme is constitutively expressed in all tested tissues including fibrous roots, thick roots, storage roots, stems and leaves
Manually annotated by BRENDA team
-
high level of F3'H expression
Manually annotated by BRENDA team
additional information
-
tissue expression pattern of gene GmF3'H at different developmental stages
Manually annotated by BRENDA team
additional information
A1XBC6
F3'H-1 tissue expression analysis
Manually annotated by BRENDA team
additional information
Q0Z7U7, Q0Z7U8, Q0Z7U9
no expression of F3'H3 in mesocotyl
Manually annotated by BRENDA team
additional information
Q2UYU6
tissue- and development-specific expression, F3'H is expressed in grapes before flowering, when 3'-hydroxylated flavonols are made, and after flowering, when proanthocyanidins are synthesized, the expression of flavonoid hydroxylases in grape is correlated to the expression of cytochrome b5, overview
Manually annotated by BRENDA team
additional information
-
one F3'H gene copy is expressed in both vegetative and reproductive organs at comparable levels among cultivars, while the other is transcriptionally silent
Manually annotated by BRENDA team
additional information
-
enzyme is constitutively expressed in all tested tissues including fibrous roots, thick roots, storage roots, stems and leaves. During storage root formation, enzyme is expressed most abundantly in the storage roots
Manually annotated by BRENDA team
additional information
Vitis vinifera PN40024
-
one F3'H gene copy is expressed in both vegetative and reproductive organs at comparable levels among cultivars, while the other is transcriptionally silent
-
Manually annotated by BRENDA team
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
Q93XJ2
x * 57500, deduced from gene sequence
?
A1XBC6
x * 56620, amino acid sequence calculation
?
-
x * 57360, calculated
additional information
A1XBC6
the secondary structure is dominated by alpha-helices and random coils
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0
-
addition of 14 mM mercaptoethanol, 15% sucrose, half-life 250 min
439004
10
-
addition of 14 mM mercaptoethanol, 15% sucrose, half-life 180 min
439004
20
-
addition of 14 mM mercaptoethanol, 15% sucrose, half-life 60 min
439004
30
-
addition of 14 mM mercaptoethanol, 15% sucrose, half-life 24 min
439004
100
-
10 min, activity destroyed
439002
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
14 mM mercaptoethanol plus 15% sucrose stabilize, mercaptoethanol can be replaced by 1.4 mM dithiothreitol
-
sucrose or glycerol plus dithiothreitol stabilize during purification and storage at -70C
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70C, storage of microsomes in presence of 14 mM mercaptoethanol and 15% sucrose, stable for several weeks
-
-80C, microsomal preparations containing 10% sucrose, frozen in liquid nitrogen, stable
-
-70C, sucrose or glycerol plus dithiothreitol stabilize during purification and storage
-
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
Q6QHJ9
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
Q9SD85
gene F3'H-1, two clones, DNA and amio acid sequence determination and analysis, sequence comparison, expression analysis, alternative polyadenylation in the 3'-UTR is adopted by this gene to generate heterogeneous transcripts, phylogenetic tree, functional expression of His-tagged F3'H-1 in Escherichia coli
A1XBC6
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
Q9FPN5
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
Q59I68
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 of wild-type enzyme and chimeric mutants in yeast strain INVSc 1 microsomes
-
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
-
gene F3'h1, DNA, amino acid sequence, and promoter determination and analysis, the promoter region of the gene contains a putative G-box, two MYB-binding domains, and TA-repeats, the structure and number of the TA repeats is cultivar-dependent and highly polymorphic, the enzyme is encoded in the Tau locus involved in control of the pubescens and seed coat color, genetic structure and organization, dominant Tau and recessive tau allele of the locus produce tawny and gray pubescence, respectively, alleles at the locus are associated with chilling tolerance, overview
Q8W3Y5
gene GmF3'H, DNA and amino acid sequence determination and analysis of 19 different cultivars, linked to the pleiotropic T locus and 2 recessive alleles, determination of the tissue expression pattern of gene GmF3'H
-
sf3'h1 gene, the enzyme is encoded at the T locus, quantitative expression analysis in wild-type and mutant plants
-
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
Q767R1
gene F3'H, DNA and amino acid sequence determination and analysis of wild-type and mutant genes, genomic organization, overview
-
gene MdF3'HI, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree, functional ectopic expression in Arabidopsis thaliana tt7 mutant and in Nicotiana tabacum; gene MdF3'HIIa, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree, functional ectopic expression in Arabidopsis thaliana tt7 mutant and in Nicotiana tabacum; gene MdF3'HIIb, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree, functional ectopic expression in Arabidopsis thaliana tt7 mutant and in Nicotiana tabacum
C5IGQ3, C5IGQ4, C5IGQ5
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
Q9FPN2
cloning of coding sequence in over-expression vector, for complementation analysis Agrobacterium-mediated transformation of the plasmid into transparent testa Arabidopsis mutant tt7 (defective in flavonoid 3'-hydroxylase gene) leads to quercetin (3',4'-hydroxylated) accumulation, for yeast fusion enzyme interaction study PCR-amplification from cDNA, subcloned in pGADT7 fusion vector transformed in Saccharomyces cervisiae strains AH109 and Y187, pair-wise combination of fusion constructs by mating
-
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
Q304R0
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
Q9FPM9
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
Q93XJ2
predominantly expressed in red form of plant
Q93XJ2
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
Q9SBQ9
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
Q0QLB3
expression in Escherichia coli JM109
A9ZMJ6
gene F3'H1, DNA and amio acid sequence determination and analysis, phylogenetic tree; gene F3'H1, DNA and amio acid sequence determination and analysis, phylogenetic tree, overexpression of F3'H1 under control of the CaMV 35S promoter using the Agrobacterium tumefaciens transfection method; gene F3'H2, DNA and amino acid sequence determination and analysis, phylogenetic tree, overexpression of F3'H1 under control of the CaMV 35S promoter using the Agrobacterium tumefaciens transfection method
Q0Z7U7, Q0Z7U8, Q0Z7U9
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
Q8S9C6
DNA and amino acid sequence determination and analysis, genetic mapping, phylogenetic analysis, expression analysis and metabolic profiling, phenotypes
-
gene F3'H, DNA and amino acid sequence determination and analysis, phylogenetic tree, developmental expression analysis, comparison of red and white cultivar enzyme expression levels, functional ectopic expression in Petunia hybrida altering flower color and flavonoid composition, overview
Q2UYU6
gene F3'h1, DNA and amino acid sequence determination and analysis, genomic structure, expression pattern analysis; gene F3'h2, DNA and amino acid sequence determination and analysis, genomic structure, expression pattern analysis; gene F3'h3, DNA and amino acid sequence determination and analysis, genomic structure, expression pattern analysis; gene F3'h4, DNA and amino acid sequence determination and analysis, genomic structure, expression pattern analysis
Q3C211, Q3C212, Q3C213, Q3C214
two genes F3'H, DNA and amino acid sequence determination, genomic analysis and expression analysis in strain PN40024, phylogenetic tree, overview
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
enzyme is highly expressed in all stages of fruit ripening
T1NXM1
drastic decline in expression during fruit ripening
T1NXM4
ectopic expression of apple F3'H genes contributes to anthocyanin accumulation in the Arabidopsis thaliana transparent testa7-1 mutant tt7 grown under nitrogen stress, overview. Transgenic Arabidopsis tt7 seedlings xpressing apple F3'H regain red color pigmentation and significantly accumulate both 4'-hydroxylated pelargonidin and 3',4'-hydroxylated cyanidin
-
light induced expression
-
increase at stage of pigmentation initiation
A9ZMJ6
enzyme expression is under control of pericarp color1, P1
F6KZD5
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
T484F
-
site-directed mutagenesis, altered substrate specificity compared to the wild-type enzyme
T487A
-
site-directed mutagenesis, altered substrate specificity compared to the wild-type enzyme
T487S
-
site-directed mutagenesis, a conservative Thr to Ser exchange at position 487 conferred additional 5'-hydroxylation activity to recombinant Gerbera hybrida F3'H
additional information
-
recombinant expression of the flavonoid 3',5'-hydroxylase, EC 1.14.13.88, from Petunia sp. in Dendrathemum grandiflora plants leads to competition of the endogenous flavonoid 3'-hydroxylase with the recombinant enzyme for the same substrates in the flavonoid biosynthetic pathway leading to a change in flower petal colors, phenotype, overview
additional information
-
loss of enzyme activity leads to accumulation of 3,5-di-O-(beta-glucopyranosyl)pelargonidin 6''-O-4,6'''-O-1-cyclic malate instead of 3,5-di-O-(beta-glucopyranosyl)cyanidin 6''-O-4,6'''-O-1-cyclic malate, the only difference between these two anthocyanins is a hydroxyl grouppresent at the 3' position in the B-ring of aglycone. Loss of enzme results in a color change in buds from purple to deep pink. Mutation is due to an active hAT type transposable element, designated Tdic101. The color change is attributed to Tdic101 insertion into the second intron of flavonoid 3'-hydroxylase
additional information
-
generation of chimeric constructs consisting of cDNA fragments of Gerbera hybrida F3'H and Osteospermum hybrida F3'5'H, EC 1.14.13.88, overview
Y484F/T487S
-
site-directed mutagenesis, altered substrate specificity compared to the wild-type enzyme
additional information
-
downregulation of the F3'H gene expression by virus-induced gene silencing in soybean does not alter the tawny pubescence pigmentation proved to be unchanged in greenhouse-grown plants, but is reduced when the steady-state mRNA level of the F3'H gene is reduced to approximately 5% of that of greenhouse-grown plants, phenotypes, overview
additional information
-
an enzyme-deficient mutant line shows altered flower color, i.e. magenta flowers instead of bright blue due to accumulation of dihydrokaempherol instead of dihydroquercetin
additional information
-
an enzyme-deficient mutant line shows altered flower color, i.e. pink flowers instead of dark purple due to accumulation of dihydrokaempherol instead of dihydroquercetin
additional information
-
an enzyme-deficient mutant line shows altered flower color, i.e. fuchsia flowers instead of bright blue due to accumulation of dihydrokaempherol instead of dihydroquercetin
additional information
-
transformation of enzyme overexpressing vector into Arabidopsis mutant tt7 defective in flavonoid 3'-hydroxylase gene, introduction of genes into yeast fusion system to monitor interactions with other enzymes in the anthocyanin regulation and flavone biosynthesis
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
F6KZD5
enzyme expression is under control of pericarp color1, P1. The P1 controlled 3-deoxyanthocyanidin and C-glycosyl flavone defence compounds accumulate at significantly higher levels in Pr1 silks as compared to pr1 silks. By virtue of increased maysin synthesis in Pr1 plants, corn ear worm larvae fed on Pr1/P1 silks show slower growth as compared to pr1/P1 silks
additional information
Q2UYU6
understanding the regulation of flavonoid hydroxylases could be used to modify flavonoid composition of fruits