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BRENDA support

Ligand trans-cinnamic acid

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Basic Ligand Information

Molecular Structure
Picture of trans-cinnamic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H8O2
trans-cinnamic acid
WBYWAXJHAXSJNI-VOTSOKGWSA-N
Synonyms:
(2E)-3-phenylacrylic acid, (2E)-3-phenylprop-2-enoate, (2E)-3-phenylprop-2-enoic acid, (E)-3-phenyl-2-propenoic acid, (E)-cinnamate, (E)-cinnamic acid, cinnamate, Cinnamic acid, perdeuterated cinnamic acid, trans-cinnamate


Show all pahtways known for Show all BRENDA pathways known for trans-cinnamic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
trans-cinnamate + NADPH + O2 = 2-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
trans-cinnamate + NH3 = L-phenylalanine
show the reaction diagram

In Vivo Product in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-phenylpropanoate + electron-transfer flavoprotein EtfA-EtfB = trans-cinnamate + reduced electron-transfer flavoprotein EtfA-EtfB
show the reaction diagram
-
(E)-cinnamoyl-CoA + (R)-phenyllactate = (E)-cinnamate + (R)-phenyllactoyl-CoA
show the reaction diagram
-
L-phenylalanine = (E)-cinnamate + NH3
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (45 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
trans-cinnamic acid + H2O2 + Br- + H+ = trans-1-bromo-2-phenylethylene + erythro-2-bromo-3-hydroxy-3-phenylpropionic acid + H2O
show the reaction diagram
-
Br- + H2O2 + trans-cinnamic acid = (+/-)-erythro-2-bromo-3-hydroxy-3-phenylpropionic acid + H2O
show the reaction diagram
-
cinnamic acid + H2O2 = ? + H2O
show the reaction diagram
-
cinnamate + O2 = ?
show the reaction diagram
-
cinnamic acid + NADH + H+ + O2 = cinnamic acid-2,3-dihydrodiol + NAD+
show the reaction diagram
-
trans-cinnamate + NADPH + O2 = 2-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
cinnamic acid + [reduced NADPH-hemoprotein reductase] + O2 = ?
show the reaction diagram
-
cinnamate + [reduced NADPH-hemoprotein reductase] + O2 = 4-coumarate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
trans-cinnamic acid + O2 = ?
show the reaction diagram
-
cinnamic acid + AH2 + O2 = ? + A + H2O
show the reaction diagram
-
cinnamic acid + NADH + H+ = 3-phenylpropanoic acid + NAD+
show the reaction diagram
-
S-adenosyl-L-methionine + cinnamic acid = S-adenosyl-L-homocysteine + methyl cinnamate
show the reaction diagram
-
UDP-glucose + cinnamic acid = UDP + cinnamoyl-beta-1-D-glucose
show the reaction diagram
-
UDP-alpha-D-glucose + cinnamate = UDP + 1-O-cinnamoyl-beta-D-glucose
show the reaction diagram
-
UDP-glucose + cinnamic acid = UDP + cinnamoyl beta-D-glucoside
show the reaction diagram
-
triolein + cinnamic acid = monocinnamoyl oleoyl glycerol + dicinnamoyl oleoyl glyerol + monocinnamoyl dioleoyl glycerol
show the reaction diagram
-
trans-cinnamate = styrene + CO2
show the reaction diagram
ATP + trans-cinnamic acid + CoA = AMP + diphosphate + trans-cinnamoyl-CoA
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (59 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
trans-cinnamaldehyde + acceptor = trans-cinnamic acid + reduced acceptor
show the reaction diagram
-
cinnamaldehyde + H2O + acceptor = cinnamic acid + reduced acceptor
show the reaction diagram
-
trans-cinnamaldehyde + NAD+ + H2O = trans-cinnamic acid + NADH
show the reaction diagram
-
cinnamaldehyde + NAD+ + H2O = cinnamate + NADH + H+
show the reaction diagram
-
cinnamaldehyde + NAD+ + H2O = cinnamic acid + NADH + 2 H+
show the reaction diagram
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cinnamaldehyde + NAD+ + H2O = cinnamate + NADH + 2 H+
show the reaction diagram
-
trans-cinnamaldehyde + NAD+ + H2O = cinnamic acid + NADH + H+
show the reaction diagram
-
trans-cinnamaldehyde + NAD+ + H2O = trans-cinnamic acid + NADH + 2 H+
show the reaction diagram
-
cinnamaldehyde + H2O + O2 = cinnamic acid + H2O2
show the reaction diagram
-
cinnamaldehyde + H2O + oxidized benzyl viologen = cinnamate + reduced benzyl viologen
show the reaction diagram
-
cinnamaldehyde + H2O + oxidized benzyl viologen = cinnamate + reduced benzyl viologen + H+
show the reaction diagram
-
Cinnamaldehyde + carbamoyl methyl viologen = Cinnamate + reduced carbamoyl methyl viologen
show the reaction diagram
-
3-phenylpropanoate + electron-transfer flavoprotein EtfA-EtfB = trans-cinnamate + reduced electron-transfer flavoprotein EtfA-EtfB
show the reaction diagram
-
cinnamic acid ethylester + H2O = cinnamic acid + ethanol
show the reaction diagram
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trans-cinnamoyl imidazole + H2O = trans-cinnamate + imidazole
show the reaction diagram
-
cinnamoylcholine + H2O = cinnamic acid + choline
show the reaction diagram
-
cinnamoyl-CoA + H2O = cinnamic acid + CoA
show the reaction diagram
-
cinnamoyl-L-phenyllactate + H2O = cinnamic acid + L-phenyllactate
show the reaction diagram
-
cinnamamide + H2O = cinnamic acid + NH3
show the reaction diagram
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N-cinnamoylglycine + H2O = cinnamate + glycine
show the reaction diagram
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cinnamonitrile + H2O = cinnamic acid + NH3
show the reaction diagram
-
L-phenylalanine = cinnamic acid + NH3
show the reaction diagram
-
L-phenylalanine = (E)-cinnamate + NH3
show the reaction diagram
-
L-phenylalanine = (E)-cinnamate + NH3
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
induces the expression of the hca operon, the plu2201 and plu2202 genes, and stlA expression
-
presence of cinnamic acid increases the total stilbene production in the grape cell cultures 2.3-3.5 times in comparison with that in the untreated cells. Cinnamic acid affects the total stilbene production via a marked increase in the content of trans-resveratrol diglucoside (up to 2.2 times), t-piceid (up to three times), trans-resveratrol (up to 5.1 times), trans-epsilon-viniferin (up to eight times), and trans-delta-viniferin (up to 9.2 times)
-

Inhibitor in Enzyme-catalyzed Reactions (54 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
IC50: 0.050 mM
-
competitive inhibition
-
0.5 mM, 55% inhibition
-
40.2% inhibition at 0.04 mM, competitively inhibits the enzyme by binding to the active site, have a protective effect against reactive oxygen species in cells, structure-function relationship, computational molecular docking, overview
-
moderate substrate inhibition
-
preincubation
-
2.5 mM, 28% inhibition
-
Ki: 5 mM
-
16.1% inhibition at 0.5 mM
-
95% residual activity at 0.5 mM
-
inhibits RuBPC activity by decreasing the levels of endogenous free and perchloric acid soluble conjugated spermine, as well as the PAs ((spermidine + spermine) /putrescine) ratio
-
competitive
-
enzyme activitiy of pectin lyase decreases significantly when 0.1 mg/l of cinnamlic acid is added
-
40% inhibition at 0.01 mM, 67% inhibition at 0.05 mM
-

3D Structure of Enzyme-Ligand-Complex (PDB) (24 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (35 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.005
-
reconstituted enzyme system consisting of benzoate 4-hydroxylase i.e. P450rm, cytochrome P450 reductase, NADPH and dilauroylphosphatidylcholine
3.8
-
pH 7.0, 25°C
1.04
-
pH 10, 30°C
41.2
-
pH 8.5, 30°C, recombinant enzyme
41.2
-
pH 8.5, 30°C, recombinant enzyme

KM Value (76 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.54
-
pH 3.5, 25°C
1.7
-
with reduced carbamoyl methyl viologen as cosubstrate
0.18
-
-
0.18
-
pH 7.0, 25°C
0.19
-
pH 8.5, 30°C, recombinant enzyme
0.19
-
pH 8.5, 30°C, recombinant enzyme

Ki Value (18 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
12.7
-
-
0.94
-
-
0.3497
-
pH 7.0, 30°C
2.48
-
pH 7.4, 37°C
5
-
-
0.00000821
-
pH and temperature not specified in the publication
0.008
-
pH 8.5, 55°C

IC50 Value (11 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
8.15
-
recombinant enzyme, pH 6.5, 50°C
0.05
-
IC50: 0.050 mM
0.05
-
IC50: 0.050 mM
0.0434
-
pH 7.0, temperature not specified in the publication
0.0209
0.2296
IC50 ketonase reaction 20.9 microM, pH 6.5, room temperatur, IC50 enolase reaction 229.6 microM, pH 6.2, room temperatur
0.015
-
pH 6.5, 37°C

References & Links

Links to other databases for trans-cinnamic acid

ChEBI
PubChem
ChEBI
PubChem