Ligand Cinnamic acid

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Basic Ligand Information

Molecular Structure
Picture of Cinnamic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H8O2
Cinnamic acid
DAEAPNUQQAICNR-RRKCRQDMSA-N
Synonyms:
cinnamate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
UDP-alpha-D-glucose + cinnamate = UDP + 1-O-cinnamoyl-beta-D-glucose
show the reaction diagram
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ATP + cinnamate + CoA = AMP + diphosphate + cinnamoyl-CoA
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (21 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cinnamate + O2 = ?
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cinnamic acid + NADH + O2 + H+ = cinnamic acid-2,3-dihydrodiol + NAD+
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cinnamic acid + [reduced NADPH-hemoprotein reductase] + O2 = ?
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cinnamate + [reduced NADPH-hemoprotein reductase] + O2 = 4-coumarate + [oxidized NADPH-hemoprotein reductase] + H2O
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cinnamic acid + AH2 + O2 = ? + A + H2O
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cinnamic acid + NADPH + ATP = 3-phenyl-2-propen-1-al + NADP+ + AMP + H2O
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cinnamic acid + NADH = 3-phenylpropanoic acid + NAD+
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S-adenosyl-L-methionine + cinnamic acid = S-adenosyl-L-homocysteine + methyl cinnamate
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UDP-glucose + cinnamic acid = UDP + cinnamoyl-beta-1-D-glucose
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UDP-alpha-D-glucose + cinnamate = UDP + 1-O-cinnamoyl-beta-D-glucose
show the reaction diagram
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UDP-glucose + cinnamic acid = UDP + cinnamoyl 3-O-beta-D-glucoside
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triolein + cinnamic acid = monocinnamoyl oleoyl glycerol + dicinnamoyl oleoyl glyerol + monocinnamoyl dioleoyl glycerol
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ATP + cinnamate + CoA = AMP + diphosphate + cinnamoyl-CoA
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (33 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cinnamaldehyde + H2O + acceptor = cinnamic acid + reduced acceptor
show the reaction diagram
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cinnamaldehyde + NAD+ + H2O = cinnamate + NADH + H+
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cinnamaldehyde + NAD+ + H2O = cinnamate + NADH + H+
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cinnamaldehyde + NAD+ + H2O = cinnamic acid + NADH + 2 H+
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cinnamaldehyde + NAD+ + H2O = cinnamate + NADH + 2 H+
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cinnamaldehyde + H2O + O2 = cinnamic acid + H2O2
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cinnamaldehyde + H2O + oxidized benzyl viologen = cinnamate + reduced benzyl viologen
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cinnamaldehyde + H2O + oxidized benzyl viologen = cinnamate + reduced benzyl viologen + H+
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Cinnamaldehyde + carbamoyl methyl viologen = Cinnamate + reduced carbamoyl methyl viologen
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cinnamaldehyde + H2O + 2,6-dichlorophenol-indophenol = cinnamate + reduced 2,6-dichlorophenol-indophenol
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cinnamic acid ethylester + H2O = cinnamic acid + ethanol
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cinnamoylcholine + H2O = cinnamic acid + choline
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cinnamoyl-CoA + H2O = cinnamic acid + CoA
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cinnamoyl-L-phenyllactate + H2O = cinnamic acid + L-phenyllactate
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cinnamamide + H2O = cinnamic acid + NH3
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N-cinnamoylglycine + H2O = cinnamate + glycine
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cinnamonitrile + H2O = cinnamic acid + NH3
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L-phenylalanine = cinnamic acid + NH3
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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
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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)
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Inhibitor in Enzyme-catalyzed Reactions (34 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
IC50: 0.050 mM
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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
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preincubation
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2.5 mM, 28% inhibition
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Ki: 5 mM
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95% residual activity at 0.5 mM
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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
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enzyme activitiy of pectin lyase decreases significantly when 0.1 mg/l of cinnamlic acid is added
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40% inhibition at 0.01 mM, 67% inhibition at 0.05 mM
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IC50 ketonase reaction 20.9 microM, pH 6.5, room temperatur, IC50 enolase reaction 229.6 microM, pH 6.2, room temperatur
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (16 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.005
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reconstituted enzyme system consisting of benzoate 4-hydroxylase i.e. P450rm, cytochrome P450 reductase, NADPH and dilauroylphosphatidylcholine

KM Value (43 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.7
-
with reduced carbamoyl methyl viologen as cosubstrate
0.18
-
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Ki Value (9 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
4
-
37C, pH 6.0
0.94
-
-
2.48
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pH 7.4, 37C
5
-
-
0.00000821
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pH and temperature not specified in the publication
0.008
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pH 8.5, 55C

IC50 Value (7 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.05
-
IC50: 0.050 mM
0.05
-
IC50: 0.050 mM
0.0434
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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, 37C

References & Links

Links to other databases for Cinnamic acid

ChEBI
PubChem
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PubChem