Information on EC 2.3.1.74 - naringenin-chalcone synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.3.1.74
-
RECOMMENDED NAME
GeneOntology No.
naringenin-chalcone synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
3 malonyl-CoA + 4-coumaroyl-CoA = 4 CoA + naringenin chalcone + 3 CO2
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
aromatic polyketides biosynthesis
-
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flavonoid biosynthesis
-
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flavonoid biosynthesis (in equisetum)
-
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naringenin biosynthesis (engineered)
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xanthohumol biosynthesis
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Flavonoid biosynthesis
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Metabolic pathways
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
malonyl-CoA:4-coumaroyl-CoA malonyltransferase (cyclizing)
In the presence of NADH and a reductase, 6'-deoxychalcone is produced.
CAS REGISTRY NUMBER
COMMENTARY hide
56803-04-4
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
animal
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
human adenovirus
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Manually annotated by BRENDA team
Juglans sp.
walnut, Juglans nigra * Juglans regia
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
plant
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1102061 A+, 1102180 A+, 1102219 A+, 1102226 A+, 1110632 A+, 1240228 A+, 1240248 A+, 1246779 A+, 1307387 A+, 1361498 A+, 1361501 A+, 1361509 A+, 1361536 A+, 1365674 A+, 1365676 A+, 1728254 A+, 1731715 A+, 1887053 A+, 1890619 A+, 1890685 A+, 1890703 A+, 1890708 A+, 1890718 A+, 1890745 A+, 1890747 A+, 1890750 A+, 1890751 A+, 2743391 A+, 2914333 A+, 2914338 A+, 2914339 A+, 347802 A+, 676286 A+, 718652 A+, 719618 A+, 722314 A+, 735386 A+, 798499 A+, 1007659 A++, 1102085 A++, 1102087 A++, 1102094 A++, 1102098 A++, 1102115 A++, 1102133 A++, 1102140 A++, 1102143 A++, 1102144 A++, 1102156 A++, 1102191 A++, 1102220 A++, 1102223 A++, 1102873 A++, 1240227 A++, 1890602 A++, 1890650 A++, 1890657 A++, 1890676 A++, 1890679 A++, 1890688 A++, 2296957 A++, 2914324 A++, 487480 A++, 487483 A++, 658423 A++, 661452 A++, 673581 A++, 675501 A++, 1013756 A++, 1102064 A++, 1102065 A++, 1102068 A++, 1102077 A++, 1102079 A++, 1102084 A++, 1102086 A++, 1102088 A++, 1102096 A++, 1102107 A++, 1102118 A++, 1102120 A++, 1102125 A++, 1102137 A++, 1102148 A++, 1102153 A++, 1102155 A++, 1102157 A++, 1102158 A++, 1102224 A++, 1102225 A++, 1102864 A++, 1250881 A++, 1252375 A++, 1259537 A++, 1259634 A++, 1334733 A++, 1361470 A++, 1361474 A++, 1361481 A++, 1361484 A++, 1361493 A++, 1361499 A++, 1365708 A++, 1379587 A++, 1493112 A++, 1631042 A++, 1674171 A++, 1714678 A++, 1844208 A++, 1876339 A++, 1883597 A++, 1887467 A++, 1890601 A++, 1890603 A++, 1890604 A++, 1890605 A++, 1890607 A++, 1890611 A++, 1890616 A++, 1890623 A++, 1890629 A++, 1890632 A++, 1890633 A++, 1890635 A++, 1890637 A++, 1890646 A++, 1890665 A++, 1890672 A++, 1890684 A++, 1890711 A++, 1890737 A++, 2296943 A++, 2296944 A++, 2296945 A++, 2296946 A++, 2296951 A++, 2296958 A++, 2296965 A++, 2510293 A++, 2914320 A++, 3744 A++, 390060 A++, 487463 A++, 487475 A++, 487476 A++, 656929 A++, 660170 A++, 663042 A++, 663103 A++, 673859 A++, 676378 A++, 684699 A++, 705626 A++, 706171 A++, 721123 A++, 722633 A++, 736980 A++, 1102216 A+++, 1102104 A++++
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Uniprot
Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
Silene sp.
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
spinach
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Manually annotated by BRENDA team
genotype alpine and prairie
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
Verbena sp.
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2 malonyl-CoA + acetyl-CoA
4-hydroxy-6-methyl-2-pyrone + 3 CoA + 2 CO2
show the reaction diagram
3 malonyl-CoA + 4-coumaroyl-CoA
4 CoA + naringenin chalcone + 3 CO2
show the reaction diagram
3 malonyl-CoA + 4-hydroxycinnamoyl-CoA
4 CoA + naringenin chalcone
show the reaction diagram
-
the enzyme catalyzes the condensation of 4-hydroxycinnamoyl-CoA and three malonyl-CoA molecules to form the chalcone derivative, naringenin chalcone, which is the first committed step in the phenylpropanoid pathway of plants, leading to the biosynthesis of flavonoids, isoflavonoids, and anthocyanins
-
-
?
3 malonyl-CoA + hexanoyl-CoA
4 CoA + ? + 3 CO2
show the reaction diagram
-
37% of the activity with 4-coumaroyl-CoA
-
-
?
4-coumaroyl-CoA + malonyl-CoA
4-coumaroyltriacetic acid lactone
show the reaction diagram
-
-
wild-type enzyme shows low 4-coumaroyltriacetic acid lactone-producing activity at pH 7.5, but an appreciable level at pH 10. Substitutions V196M, T197A, and V196M/T197A causes a shift toward neutrality of the optimum pH for 4-coumaroyltriacetic acid lactone-producing activity. Enhancement of the tetraketide producing activity upon V196M and V196M/T197A substitutions is most markedly observed when 4-coumaroyl-CoA is used as the starter substrate, and only slightly with benzoyl-, caffeoyl- and hexanoyl-CoA
-
?
4-coumaroyl-CoA + malonyl-CoA
naringenin chalcone + CoA + CO2
show the reaction diagram
5-hydroxyferulyl-CoA + malonyl-CoA
? + CoA + CO2
show the reaction diagram
-
-
-
?
benzoyl-CoA + methylmalonyl-CoA
4-hydroxy-3,5-dimethyl-6-phenyl-pyran-2-one + 4-hydroxy-3,5-dimethyl-6-(1-methyl-2-oxo-2-phenyl-ethyl)-pyran-2-one + CoA + CO2
show the reaction diagram
-
-
-
-
?
caffeoyl-CoA + 3 malonyl-CoA
eriodictyol + 4 CoA + 3 CO2
show the reaction diagram
cinnamoyl-CoA + malonyl-CoA
5,7-dihydroxyflavanone + CoA + CO2
show the reaction diagram
decanoyl-CoA + malonyl-CoA
1-(2,4,6-trihydroxyphenyl)-decan-1-one + CoA + CO2
show the reaction diagram
-
-
-
-
?
ferulyl-CoA + malonyl-CoA
homoeriodictyol + CoA + CO2
show the reaction diagram
hexanoyl-CoA + malonyl-CoA
phlorocaprophenone + CoA + CO2
show the reaction diagram
-
-
-
-
?
hexanoyl-CoA + methylmalonyl-CoA
4-hydroxy-3,5-dimethyl-6-pentyl-pyran-2-one + CoA + CO2
show the reaction diagram
-
-
-
-
?
isobutyryl-CoA + malonyl-CoA
?
show the reaction diagram
-
-
-
-
?
isovaleryl-CoA + malonyl-CoA
?
show the reaction diagram
-
-
-
-
?
malonyl CoA + 4-coumaroyl-CoA + NADH
6'-deoxychalcone + CoA + CO2 + NAD+
show the reaction diagram
malonyl-CoA + 3-coumaroyl-CoA
? + CO2 + CoA
show the reaction diagram
-
34.4% of the activity with 4-coumaroyl-CoA + malonyl-CoA
-
-
?
malonyl-CoA + 3-hydroxybenzoyl-CoA
? + CO2 + CoA
show the reaction diagram
-
21.8% of the activity with 4-coumaroyl-CoA + malonyl-CoA
-
-
?
malonyl-CoA + 4-coumaroyl-CoA
naringenin chalcone + CoA + CO2
show the reaction diagram
malonyl-CoA + 4-coumaroyl-CoA + NADPH
5'-deoxyflavanone + CoA + CO2 + NADP+
show the reaction diagram
malonyl-CoA + benzoyl-CoA
phlorobenzophenone + CO2 + CoA
show the reaction diagram
malonyl-CoA + butyryl-CoA
phlorobutyrophenone + CO2 + CoA
show the reaction diagram
-
-
-
?
malonyl-CoA + cinnamoyl-CoA
?
show the reaction diagram
62% of the activity with 4-coumaroyl-CoA
-
-
?
malonyl-CoA + dihydro-p-coumaroyl-CoA
?
show the reaction diagram
50% of the activity with 4-coumaroyl-CoA
-
-
?
malonyl-CoA + dihydrocinnamoyl-CoA
?
show the reaction diagram
23% of the activity with 4-coumaroyl-CoA
-
-
?
malonyl-CoA + hexanoyl-CoA
?
show the reaction diagram
37% of the activity with 4-coumaroyl-CoA
-
-
?
malonyl-CoA + hexanoyl-CoA
phlorocaprophenone + CO2 + CoA
show the reaction diagram
malonyl-CoA + isovaleryl-CoA
?
show the reaction diagram
malonyl-CoA + n-butyryl-CoA
1-(2,4,6-trihydroxyphenyl)-butan-1-one + CoA + CO2
show the reaction diagram
-
-
-
-
?
malonyl-CoA + n-butyryl-CoA
?
show the reaction diagram
43% of the activitry with 4-coumaroyl-CoA
-
-
?
malonyl-CoA + octanoyl-CoA
1-(2,4,6-trihydroxyphenyl)-octan-1-one + CoA + CO2
show the reaction diagram
-
poor substrate
-
-
?
malonyl-CoA + phenylacetyl-CoA
phlorobenzylketone + CoA + Co2
show the reaction diagram
-
-
i.e. 2,4,6-trihydroxyphenylbenzylketone
?
octanoyl-CoA + malonyl-CoA
1-(2,4,6-trihydroxyphenyl)-octan-1-one + CoA + CO2
show the reaction diagram
-
-
-
-
?
sinapyl-CoA + malonyl-CoA
? + CoA + CO2
show the reaction diagram
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
3 malonyl-CoA + 4-coumaroyl-CoA
4 CoA + naringenin chalcone + 3 CO2
show the reaction diagram
3 malonyl-CoA + 4-hydroxycinnamoyl-CoA
4 CoA + naringenin chalcone
show the reaction diagram
-
the enzyme catalyzes the condensation of 4-hydroxycinnamoyl-CoA and three malonyl-CoA molecules to form the chalcone derivative, naringenin chalcone, which is the first committed step in the phenylpropanoid pathway of plants, leading to the biosynthesis of flavonoids, isoflavonoids, and anthocyanins
-
-
?
4-coumaroyl-CoA + malonyl-CoA
naringenin chalcone + CoA + CO2
show the reaction diagram
caffeoyl-CoA + 3 malonyl-CoA
eriodictyol + 4 CoA + 3 CO2
show the reaction diagram
-
-
-
?
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
CaCl2
Juglans sp.
-
1 mM, 15% increase of activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-methylcyclopropene
-
2'-hydroxygenistein
-
-
2-mercaptoethanol
3'-Nucleotidase
-
i.e. EC 3.1.3.6 hydrolyzes the phosphate group in the 3'-position of adenosine, a part of the CoA thioester substrates
-
4-Coumaroyl-CoA
apigenin
Ca2+
-
10-20% decrease at 1 mM
cerulenin
Cu2+
-
50% decrease above 1 mM
Dalbergioidin
-
-
diethyl diphosphate
-
inhibition of wild-type enzyme is pH independent, inhibition of C164S mutant increases with increasing pH between pH 6.2 to pH 7.4
dithiothreitol
-
60% inhibition
eriodictyol
eriodictyol chalcone
-
-
ethylene glycol
-
-
iodoacetamide
iodoacetic acid
-
-
isoliquiritigenin
-
-
isovitexin 2''-O-arabinoside
-
50% inhibition at 0.062 mM
Kievitone
luteolin
malonyl-3'-dephospho-CoA
-
50% inhibition at 0.003 mM
malonyl-CoA
Mg2+
-
10-20% decrease at 1 mM
naringenin
naringenin chalcone
p-chloromercuribenzoate
-
50% inhibition at 2.5 mM
potassium ascorbate
-
-
Zn2+
-
50% decrease above 1 mM
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-mercaptoethanol
bovine serum albumin
-
chlorogenic acid
-
increases eriodictyol formation by 20%
cysteine
Juglans sp.
-
dependent on
dithiothreitol
-
4fold increase at 20 mM
Dowex
Juglans sp.
-
77% increase of activity
-
EDTA
Juglans sp.
-
50 mM, 9% increase of activity
N2
Juglans sp.
-
79% increase of activity
Polyethyleneglycol
Juglans sp.
-
activity strongly dependent on 1.5%
Polyvinylpyrrolidone
Juglans sp.
-
10% w/v essential
Sucrose
Juglans sp.
-
25% increase of activity
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0006 - 0.0409
4-Coumaroyl-CoA
0.0054 - 0.0068
benzoyl-CoA
0.00145 - 0.0077
caffeoyl-CoA
0.011
decanoyl-CoA
-
pH 8.0, 30C
0.001 - 0.0025
Feruloyl-CoA
0.0007 - 0.0245
Hexanoyl-CoA
0.0149
isobutyryl-CoA
-
-
0.008
isovaleryl-CoA
-
-
0.001 - 35
malonyl-CoA
0.017
NADPH
-
-
0.0122
Octanoyl-CoA
-
pH 8.0, 30C
0.048
p-Coumaroyl-CoA
-
37C, pH 7.2
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.007 - 0.042
4-Coumaroyl-CoA
0.0113 - 0.0156
benzoyl-CoA
0.044
decanoyl-CoA
Scutellaria baicalensis
-
pH 8.0, 30C
0.147
Hexanoyl-CoA
Scutellaria baicalensis
-
pH 8.0, 30C
0.066
Octanoyl-CoA
Scutellaria baicalensis
-
pH 8.0, 30C
additional information
additional information
Medicago sativa
-
-
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0004
apigenin
-
-
0.0207
Kievitone
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0085
-
-
0.00918
-
-
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6
-
caffeoyl-CoA
6.5
-
caffeoyl-CoA
6.5 - 7
-
caffeoyl-CoA
6.5
-
caffeoyl-CoA and feruloyl-CoA
7
-
substrate 4-coumaroyl-CoA
7.9
-
4-coumaroyl-CoA
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
35
Juglans sp.
-
-
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20 - 50
-
less than 50% of maximal activity above and below
20 - 60
-
50% activity at 20C, 50C and 60C
25 - 45
Juglans sp.
-
less than 40% of maximal activity above and below
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.79
sequence calculation
5.86
sequence calculation; sequence calculation
7.1
-
calculated
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
Juglans sp.
-
-
Manually annotated by BRENDA team
expression patterns is higher at 70 d after pollination in both the cultivars. Expression of the gene coincides with the onset of accumulation of isoflavonoids in the embryos. CHS7 is expressed at significantly greater level in RCAT Angora than in Harovinton; expression patterns is higher at 70 d after pollination in both the cultivars. Expression of the gene coincides with the onset of accumulation of isoflavonoids in the embryos. CHS8 is expressed at significantly greater level in RCAT Angora than in Harovinton
Manually annotated by BRENDA team
-
patterns of enzyme gene expression in different genotypes of shoots undergoing rhizogenesis are associated with observed flavonoids content, and a high frequency of rhizogenesis is accompanied with low flavonoid content in shoots
Manually annotated by BRENDA team
expression of CHSL1 only within the tapetum during the free and early vacuolated microspore stages in both wheat and triticale
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
a vacuole-distributed isozyme synthesized at late developmental stage
Manually annotated by BRENDA team
additional information
PDB
SCOP
CATH
ORGANISM
UNIPROT
Azotobacter vinelandii (strain DJ / ATCC BAA-1303)
Azotobacter vinelandii (strain DJ / ATCC BAA-1303)