Ligand cinnamaldehyde

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Basic Ligand Information

Molecular Structure
Picture of cinnamaldehyde (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H8O
cinnamaldehyde
KJPRLNWUNMBNBZ-QPJJXVBHSA-N
Synonyms:
(2E)-3-phenylprop-2-enal, (E)-cinnamaldehyde, 3-phenyl-1-propanone, 3-phenyl-2-propen-1-al, 3-phenyl-2-propenal, 3-phenylprop-2-enal, 3-phenylpropenal, cinnamic aldehyde, cinnamyl aldehyde, cinnamylaldehyde, trans-2-cinnamaldehyde, trans-cinnamaldehyde

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
cinnamaldehyde + NADH + H+ = cinnamyl alcohol + NAD+
-
show the reaction diagram
cinnamaldehyde + CoA + NADP+ = cinnamoyl-CoA + NADPH + H+
-

In Vivo Product in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
cinnamyl alcohol + NAD(P)+ = cinnamyl aldehyde + NAD(P)H + H+
-
-
show the reaction diagram
cinnamyl alcohol + O2 = cinnamaldehyde + H2O2
-
-
show the reaction diagram
cinnamoyl-CoA + NADPH + H+ = cinnamaldehyde + CoA + NADP+
-

Substrate in Enzyme-catalyzed Reactions (52 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
trans-cinnamaldehyde + NADPH = (2E)-3-phenylprop-2-en-1-ol + NADP+
-
show the reaction diagram
cinnamaldehyde + NADPH + H+ = cinnamyl alcohol + NADP+
-
show the reaction diagram
trans-cinnamaldehyde + NADPH = ?
-
show the reaction diagram
trans-cinnamaldehyde + acceptor = trans-cinnamic acid + reduced acceptor
-
show the reaction diagram
cinnamaldehyde + H2O + acceptor = cinnamic acid + reduced acceptor
-
show the reaction diagram
cinnamaldehyde + CoA + NADP+ = cinnamoyl-CoA + NADPH + H+
-
show the reaction diagram
trans-cinnamaldehyde + NAD+ + H2O = trans-cinnamic acid + NADH
-
show the reaction diagram
cinnamaldehyde + NAD+ + H2O = cinnamic acid + NADH + 2 H+
-
show the reaction diagram
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
cinnamaldehyde + H2O + 2,6-dichlorophenol-indophenol = cinnamate + reduced 2,6-dichlorophenol-indophenol
-
show the reaction diagram
trans-cinnamaldehyde + NADPH + H+ = 3-phenylpropanal + NADP+
-
show the reaction diagram
trans-2-cinnamaldehyde + NAD(P)H = cinnamaldehyde + NAD(P)+
-
show the reaction diagram
cinnamaldehyde + NADPH = ?
-
show the reaction diagram
cinnamaldehyde + 1,4-dithiane-2,5-diol = (2R)-2-phenyl-2,5-dihydrothiophene-3-carbaldehyde
-
show the reaction diagram
cinnamaldehyde = (2S,3R)-5-phenylpent-4-ene-2,3-diol + CO2
-
show the reaction diagram
cinnamaldehyde + pyruvate = (3E,5E)-2-oxo-6-phenylhexa-3,5-dienoic acid + H2O
-
show the reaction diagram
cyanide + cinnamaldehyde = (2S)-2-hydroxy-4-phenyl-(E)-but-3-enenitrile
-

Product in Enzyme-catalyzed Reactions (32 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
cinnamyl alcohol + NADP+ = cinnamyl aldehyde + NADPH
-
-
show the reaction diagram
cinnamic alcohol + NADP+ = cinnamic aldehyde + NADPH
-
show the reaction diagram
cinnamyl alcohol + acceptor = cinnamyl aldehyde + reduced acceptor
-
show the reaction diagram
cinnamic acid + NADPH + ATP = 3-phenyl-2-propen-1-al + NADP+ + AMP + H2O
-
-
show the reaction diagram
cinnamyl alcohol + O2 = cinnamyl aldehyde + H2O2
-
show the reaction diagram
trans-2-cinnamaldehyde + NAD(P)H = cinnamaldehyde + NAD(P)+
-
-
show the reaction diagram
acetaldehyde + benzaldehyde = cinnamaldehyde
-

Inhibitor in Enzyme-catalyzed Reactions (11 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
substrate inhibition mediated by cinnamaldehyde concentrations far from the Km value of 0.46 mM, which does not allow for excessively increasing the starting cinnamaldehyde concentration, since the process yield may be greatly affected
-
noncompetitive, 0.980 mM
-
competitive inhibition
-
substrate inhibition at high concentrations
-
efficiently inhibits N-acylhomoserine lactone production by isoform RhlI, specifically target short-chain N-acylhomoserine lactone synthase RhlI. trans-Cinnamaldehyde reduces the quorum-sensing-regulated pyocyanin production up to 42%; molecular docking ananlysis, mainly interacts with substrate binding sites. trans-Cinnamaldehyde is locked deeply into the binding site and forms hydrophobic and Pi-Pi interactions with surrounding residues Phe27, Trp33 and Phe105 and one hydrogen bond with Arg30
-
about 60% inhibition at 0.1 mM
-
inhibit the phospholipase C signaling
-
0.010 mg/ml, complete inhibition
-

3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (27 results)

COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
wild type enzyme, in 0.1 M glycine-NaOH buffer (pH 10.5), at 65°C
2.1
-
pH 7.7, 60°C
55
-
mutant enzyme W95L,, in 0.1 M glycine-NaOH buffer (pH 10.5), at 65°C
0.21
-
mutant enzyme W95L/N249Y, in 0.1 M glycine-NaOH buffer (pH 10.5), at 65°C
18.9
-
pH 8.0, 30°C
14.4
-
pH 7.5, 50°C
55
-
in 30 mM Tris-HCl (pH 8.0)
107.9
-
pH 6.5, 40°C
18
-
isoform CAD2, at pH 6.3 and 30°C
9.05
-
isoform CAD6, at pH 6.3 and 30°C
0.311
-
isoform CAD7, at pH 6.3 and 30°C
0.188
-
pH 7.5, 37°C, recombinant enzyme
7.7
-
pH 6.0, 30°C, recombinant enzyme
1437
-
pH 6.5, 40°C
5.63
-
pH 7.0, 25°C
in 30 mM Tris-HCl (pH 8.0)
107.9
-
-
107.9
-
pH 6.1, 30°C
11.16
-
-
26
-
enzyme ALDH-2
2.5
-
enzyme ALDH-1
7.83
-
partially purified protein, pH 7.0, 30°C
436.5
-
pH 7.6, 35°C
0.58
-
app. Kcat, pH 7.3 and 25°C
1.1
-
value above, app. Kcat, pH 5.4 and 25°C
3.5
-
-
15.7
-

KM Value (43 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
wild type enzyme, in 0.1 M glycine-NaOH buffer (pH 10.5), at 65°C
0.009
-
pH 7.7, 60°C
0.03
-
mutant enzyme W95L/N249Y, in 0.1 M glycine-NaOH buffer (pH 10.5), at 65°C
0.23
-
mutant enzyme W95L,, in 0.1 M glycine-NaOH buffer (pH 10.5), at 65°C
0.09
-
-
0.0053
-
pH 8.0, 30°C
0.92
-
pH 7.5, 50°C
0.03
-
pH 7.5, 37°C, recombinant enzyme
0.005
-
pH 6.5, 40°C
pH 6.0, 30°C, recombinant enzyme
0.01425
-
isoform CAD7, at pH 6.3 and 30°C
0.01411
-
isoform CAD6, at pH 6.3 and 30°C
0.02825
-
isoform CAD2, at pH 6.3 and 30°C
0.0053
-
in 30 mM Tris-HCl (pH 8.0)
0.017
-
in 30 mM Tris-HCl (pH 8.0)
0.017
-
-
0.017
-
pH 7.0, 25°C
pH 6.1, 30°C
3.4
-
-
0.0015
-
enzyme ALDH-2
0.000035
-
-
0.00055
-
recombinant ALDH3A1
0.006
-
enzyme ALDH-1
0.0004
-
pH 7.5, 25°C
0.0053
-
isoform citral dehydrogenase II, at pH 9.5 and 35°C
1.25
-
isoform citral dehydrogenase I, at pH 9.5 and 35°C
0.83
-
pH 9.5, 35°C
0.86
-
partially purified protein, pH 7.0, 30°C
0.1039
-
with carbamoyl methyl viologen as cosubstrate
0.012
-
pH 7.6, 35°C
0.008
-
above value, app. Km value, pH 5.4 and 25°C
1
-
app. Km value, pH 7.3 and 25°C
0.516
-
-
0.075
-
in 100 mM phosphate buffer (pH 7.4), at 25°C
1.426
-

Ki Value (2 results)

COMMENTARY
EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
LITERATURE
pH 6.1, 30°C
3.5
-
Kis value, pH 7.6, 35°C
0.6
-

IC50 Value (2 results)

COMMENTARY
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
LITERATURE
-
0.85
-
1 h incubation with recombinant TrxR, in TE buffer, at 25°C
0.0713
-

References & Links

Links to other databases for cinnamaldehyde

ChEBI
PubChem
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PubChem