2.3.1.211: bisdemethoxycurcumin synthase
This is an abbreviated version!
For detailed information about bisdemethoxycurcumin synthase, go to the full flat file.
Word Map on EC 2.3.1.211
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2.3.1.211
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curcuminoids
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oryza
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polyketide
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sativa
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synthesis
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turmeric
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starter
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curcuma
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longa
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thioester
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diarylheptanoids
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gingerol
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4-coumaroyl-coas
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phenylpropanoids
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rhizome
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hepatoprotective
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erythrorhizon
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cinnamic
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diketide
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one-pot
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shoot
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ammonia-lyase
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4-coumarate
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plant-specific
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lithospermum
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4-coumarate:coa
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analysis
- 2.3.1.211
-
curcuminoids
- oryza
- polyketide
- sativa
- synthesis
- turmeric
-
starter
-
curcuma
- longa
- thioester
-
diarylheptanoids
- gingerol
- 4-coumaroyl-coas
-
phenylpropanoids
- rhizome
-
hepatoprotective
- erythrorhizon
-
cinnamic
-
diketide
-
one-pot
- shoot
-
ammonia-lyase
- 4-coumarate
-
plant-specific
-
lithospermum
-
4-coumarate:coa
- analysis
Reaction
2 4-coumaroyl-CoA
+
Synonyms
ClPKS10, curcumin synthase, curcuminoid synthase, CUS, Os07g0271500, OsCUS
ECTree
2.3.1.211 bisdemethoxycurcumin synthaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 2.3.1.211 - bisdemethoxycurcumin synthase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2 cinnamoyl-CoA + malonyl-CoA + H2O
3 CoA + dicinnamoylmethane + 2 CO2
-
-
-
-
?
2 feruloyl-CoA + malonyl-CoA + H2O
3 CoA + 4-hydroxy-6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2H-pyran-2-one + curcumin
very low activity
-
-
?
4-coumaroyl-CoA + 3-oxodecanoyl-CoA
(1E,4Z)-5-hydroxy-1-(4-hydroxyphenyl)dodeca-1,4-dien-3-one + CoA + CO2 + H2O
-
-
-
-
?
4-coumaroyl-CoA + 3-oxododecanoyl-CoA
(1E,4Z)-5-hydroxy-1-(4-hydroxyphenyl)tetradeca-1,4-dien-3-one + CoA + CO2 + H2O
-
-
-
-
?
4-coumaroyl-CoA + 3-oxooctanoyl-CoA
(1E,4Z)-5-hydroxy-1-(4-hydroxyphenyl)deca-1,4-dien-3-one + CoA + CO2 + H2O
-
-
-
-
?
4-coumaroyl-CoA + 3-oxotetradecanoyl-CoA
(1E,4Z)-5-hydroxy-1-(4-hydroxyphenyl)hexadeca-1,4-dien-3-one + CoA + CO2 + H2O
-
-
-
-
?
4-coumaroyl-CoA + cinnamoyl-CoA + malonyl-CoA + H2O
3 CoA + cinnamoyl-4-coumaroyl-methane + 2 CO2
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-
-
-
?
cinnamoyl-CoA + 2 malonyl-CoA + H2O
3 CoA + 4-hydroxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one + 2 CO2
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cinnamoyl-CoA reacts to form a triketide pyrone with a small amount of dicinnamoylmethane
-
?
cinnamoyl-CoA + 3-oxo-octanoate + H2O
CoA + cinnamoyl(hexanoyl)methane + ?
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-
-
?
cinnamoyl-CoA + 3-oxo-octanoyl-N-acetylcysteamine thioester + H2O
CoA + cinnamoyl(hexanoyl)methane + ?
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-
-
?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
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-
-
-
?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
-
-
-
-
?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
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a minor product is a triketide pyrone formed from one 4-coumaroyl-CoA and two malonyl-CoAs. No formation of 5-(4-hydroxyphenyl)-3-oxo-pent-4-enoic acid and 4-hydroxybenzalacetone
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?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
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curcuminoid synthase catalyzes the formation of diketide-CoA by condensing 4-coumaroyl-CoA and malonyl-CoA. The resulting diketide-CoA is hydrolyzed and converted to a beta-keto acid. Finally, curcuminoid synthase catalyzes a decarboxylative condensation of the beta-keto acid with another molecule of 4-coumaroyl-CoA, to synthesize curcuminoid
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-
?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
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the reaction proceeds in three steps via formation of 4-coumaroyldiketide-CoA and 4-coumaroyl beta-keto acid, overview
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-
?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
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-
-
?
2 feruloyl-CoA + malonyl-CoA + H2O
3 CoA + curcumin + 2 CO2
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the reaction proceeds in three steps via formation of feruloyldiketide-CoA and feruloyl beta-keto acid, overview
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-
?
additional information
?
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the curcuminoid synthase might also use feruloyl-CoA as substrate, via demethoxycurcumin, to curcumin, possible pathway overview
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-
?
additional information
?
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curcuminoid synthase activity shows a requirement for both 4-coumaroyl-CoA and feruloyl-CoA to be present in the activity assay in order for any product to be observed
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-
?
additional information
?
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enzyme substrate specificity, mass spectrometric product analysis, curcuminoid synthase prefers 4-coumaroyl-CoA 2fold to cinnamoyl-CoA, detailed overview. Curcuminoid synthase appears to be capable of the synthesis of not only diarylheptanoids but also gingerol analogues, because it synthesized cinnamoyl(hexanoyl)methane, a putative intermediate of gingerol, from cinnamoyl-CoA and 3-oxooctanoic acid, feruloyl-CoA is a poor substrate, no activity with 3-oxo-5-phenyl-pent-4-enoic acid and 3-oxooctanoic acid as substrates. Products of curcuminoid synthase from diketide intermediates, relaxed specificity for the second extender substrate, overview
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-
?
additional information
?
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enzyme substrate specificity, mass spectrometric product analysis, curcuminoid synthase prefers 4-coumaroyl-CoA 2fold to cinnamoyl-CoA, detailed overview. Curcuminoid synthase appears to be capable of the synthesis of not only diarylheptanoids but also gingerol analogues, because it synthesized cinnamoyl(hexanoyl)methane, a putative intermediate of gingerol, from cinnamoyl-CoA and 3-oxooctanoic acid, feruloyl-CoA is a poor substrate, no activity with 3-oxo-5-phenyl-pent-4-enoic acid and 3-oxooctanoic acid as substrates. Products of curcuminoid synthase from diketide intermediates, relaxed specificity for the second extender substrate, overview
-
-
?
additional information
?
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the enzyme is capable of synthesizing gingerol-related compounds by condensing 4-coumaroyl-CoA with 3-oxooctanoic acid (a beta-keto acid), or with 3-oxoocarboxyl-N-acetylcysteamine thioester, a diketide-CoA analogue, in vitro. The enzyme is inactive with 3-oxoacyl derivatives of chain lengths beow C8 and above C14, overview
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-
?
