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Information on EC 2.3.1.133 - shikimate O-hydroxycinnamoyltransferase
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EC Tree
2.3.1.133 shikimate O-hydroxycinnamoyltransferaseIUBMB Comments
Caffeoyl-CoA, feruloyl-CoA and sinapoyl-CoA can also act as donors, but more slowly.
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Word Map
- 2.3.1.133
- lignin
-
phenylpropanoids
-
chlorogenic
-
hydroxycinnamoyl-coas
-
quinic
- caffeoyl-coa
- monolignols
-
caffeoyl
-
4-coumarate-coa
- 4-coumarate
-
3\'-hydroxylase
- agriculture
-
syringyl
- cardunculus
-
autoactive
- industry
The enzyme appears in viruses and cellular organisms
Synonyms
hydroxycinnamoyltransferase, shikimate o-hydroxycinnamoyltransferase, hydroxycinnamoyl-coa:shikimate hydroxycinnamoyltransferase, hydroxycinnamoyl-coa shikimate/quinate hydroxycinnamoyltransferase, hct1806, hydroxycinnamoyl-coa:shikimate hydroxycinnamoyl transferase, oshct4, hct4918, hydroxycinnamoyl-coa:quinate hydroxycinnamoyltransferase, shikimate hydroxycinnamoyltransferase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
CST
HCT
HCT1
two cDNAs are isolated HCT1A and HCT1B which are nearly identical
HQT
HST
hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyltransferase
hydroxycinnamoyl-CoA:quinate hydroxycinnamoyltransferase
hydroxycinnamoyl-CoA:shikimate hydroxycinnamoyl transferase
-
-
-
-
hydroxycinnamoyl-CoA:shikimate O-hydroxycinnamoyl transferase
-
-
-
-
hydroxycinnamoyl-CoA:shikimate/quinate hydroxycinnamoyltransferase
-
-
-
-
hydroxycinnamoyl-coenzyme A shikimate/quinate hydroxycinnamoyltransferase
-
-
hydroxycinnamoyltransferase
hydroxycinnamoyltransferase, shikimate
-
-
-
-
p-coumaroyl shikimate transferase
p-coumaroyl-CoA:5-O-shikimate p-coumaroyl transferase
p-coumaroyl-CoA:shikimic acid p-coumaroyl transferase
-
-
-
-
p-hydroxycinnamoyl-CoA:shikimate-p-hydroxycinnamoyl transferase
-
-
-
-
shikimate hydroxycinnamoyltransferase
CST
-
-
-
-
HCT
-
-
-
-
HST
-
-
-
-
hydroxycinnamoyl-CoA:quinate hydroxycinnamoyltransferase
-
shikimate hydroxycinnamoyltransferase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
4-coumaroyl-CoA + shikimate = CoA + 4-coumaroylshikimate
quasi-independent bi-bi random mechanism
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4-coumaroyl-CoA + shikimate = CoA + 4-coumaroylshikimate
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Acyl group transfer
Acyl group transfer
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
KEGG
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SYSTEMATIC NAME
IUBMB Comments
4-coumaroyl-CoA:shikimate O-(hydroxycinnamoyl)transferase
Caffeoyl-CoA, feruloyl-CoA and sinapoyl-CoA can also act as donors, but more slowly.
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CAS REGISTRY NUMBER
COMMENTARY
73904-44-6
-
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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
4-coumaroyl-CoA + 3-hydroxybenzoate
CoA + 3-(4-coumaroyl)oxybenzoate
Coleus scutellarioides
-
-
-
?
4-coumaroyl-CoA + catechol
CoA + 1-(4-coumaroyl)catechol
low affinity substrate
-
-
?
4-coumaroyl-CoA + catechol
CoA + 1-O-(4-coumaroyl)catechol
-
-
-
?
4-coumaroyl-CoA + glycerol
CoA + 2-O-(4-coumaroyl)glycerol + 1-O-(4-coumaroyl)glycerol
-
-
-
-
?
4-coumaroyl-CoA + hydroquinone
CoA + 1-(4-coumaroyl)hydroquinone
low affinity substrate
-
-
?
4-coumaroyl-CoA + hydroquinone
CoA + 1-O-(4-coumaroyl)hydroquinone
-
-
-
?
4-coumaroyl-CoA + L-malate
CoA + 2-O-(4-coumaryl)-L-malate
-
-
-
?
caffeoyl-CoA + 3-hydroxyanthranilate
CoA + 3-caffeoyloxyanthranilate
Coleus scutellarioides
-
-
-
?
caffeoyl-CoA + 3-hydroxybenzoate
CoA + 3-caffeoyloxybenzoate
Coleus scutellarioides
-
-
-
?
caffeoyl-CoA + L-malate
CoA + 2-O-caffeoyl-L-malate
-
-
-
?
caffeoyl-CoA + quinate
CoA + 5-O-caffeoylquinate
reaction of EC 2.3.1.99
-
-
r
cinnamoyl-CoA + 3-hydroxyanthranilate
CoA + 3-cinnamoyloxyanthranilate
Coleus scutellarioides
-
-
-
?
cinnamoyl-CoA + 3-hydroxybenzoate
CoA + 3-cinnamoyloxybenzoate
Coleus scutellarioides
-
-
-
?
CoA + 5-O-caffeoylquinate
caffeoyl-CoA + quinate
reaction of EC 2.3.1.99
-
-
r
feruloyl-CoA + 3-hydroxyanthranilate
CoA + 3-feruloyloxyanthranilate
Coleus scutellarioides
-
-
-
?
feruloyl-CoA + 3-hydroxybenzoate
CoA + 3-feruloyloxybenzoate
Coleus scutellarioides
-
-
-
?
sinapoyl-CoA + 3-hydroxyanthranilate
CoA + 3-sinapoyloxyanthranilate
Coleus scutellarioides
-
-
-
r
4-coumaroyl-CoA + 2,3-dihydroxybenzoate
CoA + 3-O-(4-coumaroyl)oxy-2-hydroxybenzoate
-
-
-
?
4-coumaroyl-CoA + 2,3-dihydroxybenzoate
CoA + 3-O-(4-coumaroyl)oxy-2-hydroxybenzoate
low affinity substrate
-
-
?
4-coumaroyl-CoA + 3,4-dihydroxybenzoate
CoA + 3-O-(4-coumaroyl)oxy-4-hydroxybenzoate
i.e. protocatechuate
-
-
?
4-coumaroyl-CoA + 3,4-dihydroxybenzoate
CoA + 3-O-(4-coumaroyl)oxy-4-hydroxybenzoate
i.e. protocatechuate
-
-
?
4-coumaroyl-CoA + 3-aminobenzoate
CoA + 3-N-(4-coumaroyl)aminobenzoate
-
-
-
?
4-coumaroyl-CoA + 3-aminobenzoate
CoA + 3-N-(4-coumaroyl)aminobenzoate
low affinity substrate
-
-
?
4-coumaroyl-CoA + 3-hydroxyanthranilate
CoA + 3-(4-coumaroyl)oxyanthranilate
-
-
-
?
4-coumaroyl-CoA + 3-hydroxyanthranilate
CoA + 3-(4-coumaroyl)oxyanthranilate
Coleus scutellarioides
-
-
-
?
4-coumaroyl-CoA + 3-hydroxyanthranilate
CoA + 3-(4-coumaroyl)oxyanthranilate
-
-
-
?
4-coumaroyl-CoA + 3-hydroxybenzoate
CoA + 3-O-(4-coumaroyl)oxy-benzoate
-
-
-
?
4-coumaroyl-CoA + 3-hydroxybenzoate
CoA + 3-O-(4-coumaroyl)oxy-benzoate
low affinity substrate
-
-
?
4-coumaroyl-CoA + 5-hydroxyanthranilate
CoA + 5-(4-coumaroyl)oxyanthranilate
-
-
-
?
4-coumaroyl-CoA + 5-hydroxyanthranilate
CoA + 5-(4-coumaroyl)oxyanthranilate
low affinity substrate
-
-
?
4-coumaroyl-CoA + gentisate
CoA + 5-O-(4-coumaroyl)gentisate
-
-
-
?
4-coumaroyl-CoA + gentisate
CoA + 5-O-(4-coumaroyl)gentisate
low affinity substrate
-
-
?
4-coumaroyl-CoA + quinate
CoA + 4-coumaroylquinate
-
-
-
r
4-coumaroyl-CoA + quinate
CoA + 4-coumaroylquinate
-
preferred substrate is shikimate
-
-
?
4-coumaroyl-CoA + quinate
CoA + 4-coumaroylquinate
reaction products are detected when quinic acid is used as an acceptor, although the amount of product formed is less than 2% of that formed when shikimic acid serves as the acceptor
-
-
?
4-coumaroyl-CoA + quinate
CoA + 5-O-(4-coumaroyl)quinate
-
-
-
?
4-coumaroyl-CoA + quinate
CoA + 5-O-(4-coumaroyl)quinate
-
-
-
?
4-coumaroyl-CoA + quinate
CoA + 5-O-(4-coumaroyl)quinate
low activity towards quinate
-
-
?
4-coumaroyl-CoA + shikimate
CoA + 4-coumaroylshikimate
-
-
-
?
4-coumaroyl-CoA + shikimate
CoA + 4-coumaroylshikimate
-
-
-
?
4-coumaroyl-CoA + shikimate
CoA + 4-coumaroylshikimate
-
recombinant HCT shows substrate-specificity towards shikimic acid in contrast to hydroxycinnamoyl-CoA quinate transferase, HQT, EC 2.3.1.99
-
-
?
4-coumaroyl-CoA + shikimate
CoA + 4-coumaroylshikimate
-
preferred substrate is shikimate
-
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
-
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
biosynthetic pathway of hydroxycinnamic acid glucaric acid
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
-
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
-
-
r
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
hydroxycinnamic acid-shikimate ester biosynthesis
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
Coleus scutellarioides
-
-
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
Coleus scutellarioides
preferred substrate for HST with shikimate as acceptor substrate is 4-coumaroyl-CoA
-
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
-
product determination
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
shikimate cannot be replaced by quinate
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
-
r
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
enzyme appears to play a critical role in the phenylpropanoid pathway, both upstream and downstream of the 3-hydroxylation step
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
enzyme appears to play a critical role in the phenylpropanoid pathway, both upstream and downstream of the 3-hydroxylation step
-
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
-
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
best substrate
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
hydroxycinnamic acid-shikimate ester biosynthesis
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
best substrate
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
-
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
-
product determination
-
?
caffeoyl-CoA + quinate
CoA + caffeoylquinate
reaction products are detected when quinic acid is used as an acceptor, although the amount of product formed is less than 2% of that formed when shikimic acid serves as the acceptor
-
-
?
caffeoyl-CoA + shikimate
CoA + 5-caffeoylshikimate
-
-
-
?
caffeoyl-CoA + shikimate
CoA + 5-caffeoylshikimate
-
-
-
r
caffeoyl-CoA + shikimate
CoA + 5-O-caffeoylshikimate
-
the activity is 100fold lower than the activity with coumaroyl-CoA
-
-
?
caffeoyl-CoA + shikimate
CoA + 5-O-caffeoylshikimate
-
condensation at 52% the rate of the reaction with p-coumaroyl-CoA
-
-
?
caffeoyl-CoA + shikimate
CoA + 5-O-caffeoylshikimate
-
-
-
?
cinnamoyl-CoA + shikimate
CoA + 5-O-cinnamoylshikimate
Coleus scutellarioides
very low activity
-
-
r
feruloyl-CoA + shikimate
CoA + 5-O-feruloylshikimate
-
-
-
?
feruloyl-CoA + shikimate
CoA + 5-O-feruloylshikimate
-
condensation at 22% the rate of the reaction with p-coumaroyl-CoA
-
-
?
sinapoyl-CoA + shikimate
CoA + 5-O-sinapoylshikimate
Coleus scutellarioides
very low activity
-
-
r
sinapoyl-CoA + shikimate
CoA + 5-O-sinapoylshikimate
-
condensation at 29% the rate of the reaction with p-coumaroyl-CoA
-
-
?
additional information
?
-
-
no substrates are 1-hydroxycinnamoyl glucose
-
-
?
additional information
?
-
-
no substrate: cinnamoyl-CoA, L-malate, D(+)-malate, L(+)-tartrate, m-tartrate, citrate, glucose, UDP-glucose, myo-inositol, tyramine, agmatine
-
-
?
additional information
?
-
HCT has a preference for shikimic acid over quinic acid, substrate specifities of the HCT key enzyme, overview
-
-
?
additional information
?
-
-
HCT has a preference for shikimic acid over quinic acid, substrate specifities of the HCT key enzyme, overview
-
-
?
additional information
?
-
Coleus scutellarioides
substrate specificity of recombinant HST: no activity with quinate and anthranilate, and tyramine, tryptamine, serotonin, dopamine, DOPA, 2-phenethylamine, phenol, as acceptors
-
-
?
additional information
?
-
-
the enzyme is involved in the phenylpropanoid pathway and the biosynthesis of curcuminoids and in lignification, the enzyme activity is modulated in plants as a mechanism to control production of specific metabolites, overview
-
-
?
additional information
?
-
-
the enzyme is part of the monolignol pathway, enzymes of this pathway are individually downregulated resulting in compositional changes in lignin and wall-bound hydroxycinnamic acids, modelling, enzyme expression and metabolism, regulation, overview
-
-
?
additional information
?
-
no substrate: anthranilate, glucose, malate, tyramine, spermidine, spermine, putrescine, agmatine, benzyl alcohol
-
-
?
additional information
?
-
-
no substrate: anthranilate, glucose, malate, tyramine, spermidine, spermine, putrescine, agmatine, benzyl alcohol
-
-
?
additional information
?
-
-
OsHCT4 mediates the trans-esterification of glycerol as well as shikimic acid in the presence of hydroxycinnamoyl-CoA in vitro, reaction product structure determination by NMR
-
-
?
additional information
?
-
-
HCT mediates formation of hydroxycinnamoylquinnate or hydroxycinnamoylshikimate
-
-
?
additional information
?
-
-
in vitro recombinant PeHCT shows substrate-specificity towards shikimic acid
-
-
?
additional information
?
-
-
no substrate: cinnamoyl-CoA, L-malate, D(+)-malate, L(+)-tartrate, m-tartrate, citrate, glucose, UDP-glucose, myo-inositol, tyramine, agmatine
-
-
?
additional information
?
-
-
1-hydroxycinnamoyl glucose esters, gluconolactone, galactonate, glucuronate, ascorbate, malate, m-tartrate
-
-
?
additional information
?
-
no reaction products are detected when HCT1 and either hydroxycinnamoyl-CoA derivative are incubated with malic acid, Glc, or L-DOPA as acceptor
-
-
?
additional information
?
-
no reaction products are detected when HCT1 and either hydroxycinnamoyl-CoA derivative are incubated with malic acid, Glc, or L-DOPA as acceptor
-
-
?
additional information
?
-
no reaction products are detected when HCT1 and either hydroxycinnamoyl-CoA derivative are incubated with malic acid, Glc, or L-DOPA as acceptor
-
-
?
additional information
?
-
no reaction products are detected when shikimic acid, quinic acid, Glc, or L-DOPA is used as an acceptor
-
-
?
additional information
?
-
no reaction products are detected when shikimic acid, quinic acid, Glc, or L-DOPA is used as an acceptor
-
-
?
additional information
?
-
no reaction products are detected when shikimic acid, quinic acid, Glc, or L-DOPA is used as an acceptor
-
-
?
additional information
?
-
-
the enzyme is involved in the phenylpropanoid pathway and the biosynthesis of curcuminoids and in lignification, the enzyme activity is modulated in plants as a mechanism to control production of specific metabolites, overview
-
-
?
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NATURAL SUBSTRATE
NATURAL 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
4-coumaroyl-CoA + shikimate
CoA + 4-coumaroylshikimate
-
recombinant HCT shows substrate-specificity towards shikimic acid in contrast to hydroxycinnamoyl-CoA quinate transferase, HQT, EC 2.3.1.99
-
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
biosynthetic pathway of hydroxycinnamic acid glucaric acid
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
hydroxycinnamic acid-shikimate ester biosynthesis
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
Coleus scutellarioides
-
-
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
enzyme appears to play a critical role in the phenylpropanoid pathway, both upstream and downstream of the 3-hydroxylation step
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
enzyme appears to play a critical role in the phenylpropanoid pathway, both upstream and downstream of the 3-hydroxylation step
-
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
-
hydroxycinnamic acid-shikimate ester biosynthesis
-
?
additional information
?
-
-
the enzyme is involved in the phenylpropanoid pathway and the biosynthesis of curcuminoids and in lignification, the enzyme activity is modulated in plants as a mechanism to control production of specific metabolites, overview
-
-
?
additional information
?
-
-
the enzyme is part of the monolignol pathway, enzymes of this pathway are individually downregulated resulting in compositional changes in lignin and wall-bound hydroxycinnamic acids, modelling, enzyme expression and metabolism, regulation, overview
-
-
?
additional information
?
-
-
HCT mediates formation of hydroxycinnamoylquinnate or hydroxycinnamoylshikimate
-
-
?
additional information
?
-
-
the enzyme is involved in the phenylpropanoid pathway and the biosynthesis of curcuminoids and in lignification, the enzyme activity is modulated in plants as a mechanism to control production of specific metabolites, overview
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Ca2+
Mg2+
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
RNAi
-
HCT silencing is achieved by transformation of Pinus radiata callus cells with pHF5
-
additional information