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2.3.1.74: chalcone synthase

This is an abbreviated version!
For detailed information about chalcone synthase, go to the full flat file.

Word Map on EC 2.3.1.74

Reaction

3 malonyl-CoA +

4-coumaroyl-CoA
= 4 CoA +
naringenin chalcone
 + 3 CO2

Synonyms

6'-deoxychalcone synthase, anther-specific chalcone synthase-like enzyme, ASCL1, ASCL2, chalcone synthase, chalcone synthase 6, chalcone synthase 7, chalcone synthase C2-Idf-I, chalcone synthase C2-Idf-II, chalcone synthetase, CHS, CHS var 2, chs-1, CHS-7, CHS01, CHS02, CHS03, CHS04, CHS05, CHS06, CHS07, CHS08, CHS088, CHS09, Chs1, CHS10, CHS11, CHS12, CHS13, CHS14, Chs2, CHS2 chalcone synthase, CHS3, CHS4, CHS444, CHS5, CHS6, CHS7, CHS768, CHS_H1, Cs-COR126, DOCS, EC 2.3.1.120, flavanone synthase, flavanone synthetase, GmIRCHS, MdCHS2, More, naringenin-chalcone synthase, naringenin-chalcone synthase 6, PgCHS, PKS1, Q7Y1Y0, RinPKS1, RiPKS4, RiPKS5, synthase, flavanone, vsad1

ECTree

     2 Transferases
         2.3 Acyltransferases
             2.3.1 Transferring groups other than aminoacyl groups
                2.3.1.74 chalcone synthase

Substrates Products

Substrates Products on EC 2.3.1.74 - chalcone synthase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2RS)-methylmalonyl-CoA + n-hexanoyl-CoA
triketide lactone + 6-ethyl-4-hydroxy-3,5-dimethyl-2-pyrone
show the reaction diagram
-
-
-
?
2 malonyl-CoA + 2 stearoyl-CoA
6-heptadecyl-4-hydroxy-2H-pyran-2-one + 4-hydroxy-6-(2-oxononadecyl)-2H-pyran-2-one + 2 CoA + 2 CO2
show the reaction diagram
-
-
-
?
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 + benzoyl-CoA
4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
show the reaction diagram
-
-
-
?
3 malonyl-CoA + caffeoyl-CoA
?
show the reaction diagram
-
-
-
?
3 malonyl-CoA + cinnamoyl-CoA
4 CoA + pinocembrin chalcone + 3 CO2
show the reaction diagram
-
preferred substrate
-
-
?
3 malonyl-CoA + feruloyl-CoA
?
show the reaction diagram
-
-
-
?
3 malonyl-CoA + hexanoyl-CoA
4 CoA + ? + 3 CO2
show the reaction diagram
37% of the activity with 4-coumaroyl-CoA
-
-
?
3 malonyl-CoA + sinapoyl-CoA
?
show the reaction diagram
-
-
-
?
4-coumaroyl-CoA + (2RS)-methylmalonyl-CoA
1-(4-hydroxyphenyl)pent-1-en-3-one
show the reaction diagram
-
-
-
?
4-coumaroyl-CoA + 3 malonyl-CoA
4-coumaroyltriacetic acid lactone + 4 CoA + 3 CO2
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 + 3 malonyl-CoA
naringenin chalcone + 4 CoA + 3 CO2
show the reaction diagram
5-hydroxyferulyl-CoA + malonyl-CoA
? + CoA + CO2
show the reaction diagram
-
-
-
?
benzoyl-CoA + malonyl-CoA
?
show the reaction diagram
22% activity compared to 4-coumaroyl-CoA
-
-
?
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
caffeoyl-CoA + malonyl-CoA
?
show the reaction diagram
43% activity compared to 4-coumaroyl-CoA
-
-
?
cinnamoyl diketide-NAC + (2RS)-methylmalonyl-CoA
methylated triketide styrylpyrone + ?
show the reaction diagram
-
-
-
?
cinnamoyl-CoA + malonyl-CoA
5,7-dihydroxyflavanone + CoA + CO2
show the reaction diagram
cinnamoyl-CoA + malonyl-CoA
?
show the reaction diagram
81% activity compared to 4-coumaroyl-CoA
-
-
?
decanoyl-CoA + malonyl-CoA
1-(2,4,6-trihydroxyphenyl)-decan-1-one + CoA + CO2
show the reaction diagram
-
-
-
-
?
feruloyl-CoA + malonyl-CoA
?
show the reaction diagram
52% activity compared to 4-coumaroyl-CoA
-
-
?
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 + 4-fluorocinnamoyl-CoA
fluorinated chalcone + alpha-pyrone + 2 CoA
show the reaction diagram
-
-
-
?
malonyl-CoA + acetyl-CoA
4-hydroxy-6-methyl-2-pyrone + CoA + CO2
show the reaction diagram
the reaction is catalyzed by isoform ASCL2 only
-
-
?
malonyl-CoA + acetyl-CoA
?
show the reaction diagram
malonyl-CoA + benzoyl-CoA
bis-noryangonin + 4-coumaroyl triacetic acid lactone + CoA + CO2
show the reaction diagram
-
-
-
?
malonyl-CoA + benzoyl-CoA
phlorobenzophenone + CO2 + CoA
show the reaction diagram
malonyl-CoA + butyryl-CoA
?
show the reaction diagram
malonyl-CoA + butyryl-CoA
phlorobutyrophenone + CO2 + CoA
show the reaction diagram
-
-
-
?
malonyl-CoA + caffeoyl-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 + feruloyl-CoA
?
show the reaction diagram
-
-
-
?
malonyl-CoA + hexanoyl-CoA
4-hydroxy-6-pentyl-2H-pyran-2-one + CoA + CO2
show the reaction diagram
-
-
-
?
malonyl-CoA + hexanoyl-CoA
?
show the reaction diagram
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 + octanoyl-CoA
6-heptyl-4-hydroxy-2H-pyran-2-one + CoA + CO2
show the reaction diagram
-
-
-
?
malonyl-CoA + octanoyl-CoA
?
show the reaction diagram
malonyl-CoA + phenylacetyl-CoA
phlorobenzylketone + CoA + Co2
show the reaction diagram
-
-
i.e. 2,4,6-trihydroxyphenylbenzylketone
?
malonyl-CoA + sinapoyl-CoA
?
show the reaction diagram
-
-
-
?
methylmalonyl-CoA + benzoyl-CoA
triketide alpha-pyrone + tetraketide alpha-pyrone
show the reaction diagram
-
-
-
?
n-hexanoyl-CoA + butyryl-CoA
phlorobutyrophenone + phlorocaprophenone
show the reaction diagram
-
-
-
?
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
?
-