Ligand cinnamyl alcohol

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Basic Ligand Information

Molecular Structure
Picture of cinnamyl alcohol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H10O
cinnamyl alcohol
OOCCDEMITAIZTP-QPJJXVBHSA-N
Synonyms:
(2E)-3-phenylprop-2-en-1-ol, (E)-cinnamyl alcohol, 3-phenyl-2-propen-1-ol, 3-phenyl-2-propenol, cinnamic alcohol, cinnamylalcohol, trans-cinnamyl alcohol

Roles as Enzyme Ligand

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

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cinnamyl alcohol + NAD(P)+ = cinnamyl aldehyde + NAD(P)H + H+
show the reaction diagram
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cinnamyl alcohol + O2 = cinnamaldehyde + H2O2
show the reaction diagram
-
acetyl-CoA + cinnamyl alcohol = CoA + cinnamyl acetate
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

Substrate in Enzyme-catalyzed Reactions (40 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cinnamyl alcohol + NAD+ = ?
show the reaction diagram
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cinnamyl alcohol + glutathione + NAD+ = S-cinnamylglutathione + NADH
show the reaction diagram
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cinnamyl alcohol + NADP+ = cinnamyl aldehyde + NADPH
show the reaction diagram
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cinnamic alcohol + NADP+ = cinnamic aldehyde + NADPH
show the reaction diagram
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cinnamyl alcohol + acceptor = cinnamyl aldehyde + reduced acceptor
show the reaction diagram
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Br- + H2O2 + trans-cinnamyl alcohol = (+/-)-1,3-dihydroxy-2-bromo-3-phenylpropane + H2O
show the reaction diagram
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(2E)-3-phenylprop-2-en-1-ol + FADH2 + O2 = (3-phenyloxiran-2-yl)methanol + 1-phenylpropane-1,2,3-triol + FAD + H2O
show the reaction diagram
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cinnamyl alcohol + O2 = cinnamyl aldehyde + H2O2
show the reaction diagram
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benzoyl-CoA + cinnamyl alcohol = cinnamyl benzoate + CoA
show the reaction diagram
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acetyl-CoA + cinnamyl alcohol = CoA + cinnamyl acetate
show the reaction diagram
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3'-phosphoadenylylsulfate + cinnamyl alcohol = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
trans-cinnamaldehyde + NADPH = (2E)-3-phenylprop-2-en-1-ol + NADP+
show the reaction diagram
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cinnamaldehyde + NADPH + H+ = cinnamyl alcohol + NADP+
show the reaction diagram
-
-
cinnamaldehyde + NADH + H+ = cinnamyl alcohol + NAD+
show the reaction diagram
-
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cinnamyl 4-O-methyl-D-glucopyranuronate + H2O = cinnamyl alcohol + 4-O-methyl-D-glucopyranuronate
show the reaction diagram
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-

Inhibitor in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitive mechanism, substrate inhibition
-
strong competitive inhibitor of vanillyl-alcohol oxidation
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shows substrate inhibition at higher concentration
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compound from Rhodiola rosea extract, inhibits both MAO A and MAO B
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (23 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
47.2
-
pH 7.7, 22C, cosustrate: benzoyl-CoA
1480
-
pH 7.5, 30C

KM Value (31 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.04
-
pH 9.5, 35C
0.036
-
-
0.0978
-
pH 7.7, 22C, cosustrate: benzoyl-CoA
2.03
-
pH 7.5, 30C

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.037
-
pH 8.5, 55C

References & Links

Links to other databases for cinnamyl alcohol

ChEBI
PubChem
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PubChem