Ligand caffeic acid

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Basic Ligand Information

Molecular Structure
Picture of caffeic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H8O4
caffeic acid
QAIPRVGONGVQAS-DUXPYHPUSA-N
Synonyms:
(2E)-3,4-dihydroxycinnamate, (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate, (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid, 3,4-dihydroxy-trans-cinnamate, 3,4-dihydroxycinnamate, 3,4-dihydroxycinnamic acid, 3,4-dihydroxy cinnamic acid, caffeate, trans-3,4-dihydroxycinnamate, trans-caffeate


Show all pahtways known for Show all BRENDA pathways known for caffeic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3,4-dihydroxy-trans-cinnamate + O2 = 3-(2-carboxyethenyl)-cis,cis-muconate
show the reaction diagram
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S-adenosyl-L-methionine + caffeic acid = S-adenosyl-L-homocysteine + ferulic acid
show the reaction diagram
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UDP-glucose + caffeate = UDP + caffeoyl beta-D-glucoside
show the reaction diagram
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sucrose + caffeic acid = D-fructose + caffeoyl-beta-D-glucoside
show the reaction diagram
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3'-phosphoadenylyl sulfate + caffeic acid = adenosine 3',5'-bisphosphate + ?
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3,4-dihydroxyphenylpropanoyl-CoA + (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate = 3,4-dihydroxyphenylpropanoate + (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl-CoA
show the reaction diagram
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ATP + caffeate + CoA = AMP + diphosphate + caffeoyl-CoA
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In Vivo Product in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
methyl caffeate + H2O = caffeic acid + methanol
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (61 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3,4-dihydroxy-trans-cinnamate + O2 = 3-(2-carboxyethenyl)-cis,cis-muconate
show the reaction diagram
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caffeic acid + FADH2 + O2 = 3,4,5-trihydroxycinnamic acid + FAD + H2O
show the reaction diagram
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caffeic acid + NADPH + ATP = 3-(3,4-dihydroxyphenyl)-2-propen-1-al + NADP+ + AMP + H2O
show the reaction diagram
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N6-(2-isopentenyl)adenine + caffeic acid = adenine + 3-methylbut-2-enal + ?
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2 S-adenosyl-L-methionine + caffeic acid = 2 S-adenosyl-L-homocysteine + ferulic acid + isoferulic acid
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S-adenosyl-L-methionine + caffeic acid = S-adenosyl-L-homocysteine + ?
show the reaction diagram
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caffeic acid + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + ?
show the reaction diagram
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S-adenosyl-L-methionine + caffeic acid = S-adenosyl-L-homocysteine + ?
show the reaction diagram
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S-adenosyl-L-methionine + caffeic acid = ?
show the reaction diagram
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UDP-glucose + caffeic acid = ?
show the reaction diagram
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UDP-glucose + caffeic acid = UDP + ?
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UDP-glucose + caffeic acid = UDP + ?
show the reaction diagram
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UDPglucose + caffeic acid = UDP + 4-O-glucosyl-caffeic acid
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UDP-glucose + caffeate = UDP + 1-caffeoyl-beta-D-glucose
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sucrose + caffeic acid = D-fructose + caffeic acid-3-O-alpha-D-glucopyranoside
show the reaction diagram
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sucrose + caffeic acid = D-fructose + caffeoyl-beta-D-glucoside
show the reaction diagram
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UDP-glucose + caffeic acid = UDP + 7-O-beta-D-glucosyl-caffeic acid
show the reaction diagram
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3'-phosphoadenylylsulfate + caffeic acid = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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3,4-dihydroxyphenylpropanoyl-CoA + (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate = 3,4-dihydroxyphenylpropanoate + (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl-CoA
show the reaction diagram
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rutin + caffeic acid = quercetin + caffeic acid 3'-O-rutinoside
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caffeic acid + H2O = ?
show the reaction diagram
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caffeate = 3,4-dihydroxystyrene + CO2
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (35 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-coumaric acid + AH2 + O2 = caffeic acid + A + H2O
show the reaction diagram
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1-O-caffeoyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside = caffeate + cyanidin 3,5-di-O-beta-D-glucoside
show the reaction diagram
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caffeoylcholine = caffeic acid + choline
show the reaction diagram
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chlorogenic acid + H2O = caffeic acid + (1S,3R,4R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
show the reaction diagram
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L-DOPA = 3,4-dihydroxy-trans-cinnamate + NH3
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Activator in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
the total turnover number is almost 5fold higher than that obtained for the reference reaction
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effect of a range of diphenol treatments on the activation of latent red clover PPO tested. 91.9% activation
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presence of caffeic acid increases the total stilbene production by 1.8- to 1.9fold
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strong activation
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enzyme form CM3 is activated
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treatment of the cells with 100 and 500 microg/ml of caffeic acid increases gamma-GCS activities by 1.4- and 1.8fold compared to the control group, respectively. At the same doses of caffeic acid, the treated cells show increased levels of glutathione by 1.7- and 2.7fold compared to the control, respectively
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Inhibitor in Enzyme-catalyzed Reactions (83 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
mixed type of inhibition
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18% inhibition at 0.05 mM
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18% inhibition at 0.05 mM
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0.01 mM, 20-30% inhibition
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0.2 mM, 98% inhibition; 0.2 mM, 98% inhibition
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competitive with respect to 2-oxoglutarate and ascorbate
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in vitro N-acetylserotonin methyltransferase activity is significantly and competitively inhibited by caffeic acid, a substrate of the caffeic acid O-methyltransferase, 73% inhibition at 0.01 mM, 93% at 0.1 mM
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23% residual activity at 0.1 mM
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10 mM, complete inhibition
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38% residual activity at 1 mM
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isoenzyme DS-Co
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30% inhibition
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1 mM, 44% inhibition
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0.02 mg/ml caffeic acid decreases the activating phosphorylation of GSK-3beta
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inhibition of P-PST and M-PST
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noncompetitive inhibition
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noncompetitive
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93.8% inhibition at 0.5 mM
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80% residual activity at 0.5 mM
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slight inhibition
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enzyme activitiy of pectin lyase decreases significantly when 0.1 mg/l of caffic acid is added
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42% inhibition at 0.01 mM, 67% inhibition at 0.05 mM
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3D Structure of Enzyme-Ligand-Complex (PDB) (3 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (29 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
106
-
-
189
-
pH 5.0, 16°C
1450
-
-
0.3
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pH 6.5, recombinant enzyme
0.068
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pH 7.5, 37°C, in presence of 0.1 mM Co2+
0.62
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pH 7.5, temperature not specified in the publication

KM Value (118 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.043
-
-
0.014
-
pH 7.5, 38°C
0.001
-
second substrate caffeic acid
2.3
-
-
0.0015
-
-
0.7077
-
-
0.32
-
pH 7.0, 30°C
0.075
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pH 7.5, 40°C

Ki Value (12 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.00008
-
at 37°C in 0.1 M Na-K phosphate buffer (pH 7.4)
0.3
-
-
0.018
-
-
0.82
-
-
0.01084
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pH and temperature not specified in the publication

IC50 Value (37 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0137
-
pH and temperature not specified in the publication
0.0125
-
pH and temperature not specified in the publication
0.2
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at pH 4.5 and 23°C
2.54
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pH and temperature not specified in the publication
0.085
-
pH 7.4, 37°C
0.085
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at pH 7.8 and 37°C
0.0005
0.002
IC50 ketonase reaction 0.5 microM, pH 6.5, room temperatur, IC50 enolase reaction 2.0 microM, pH 6.2, room temperatur
0.0027
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pH 6.5, 37°C

References & Links

Links to other databases for caffeic acid

ChEBI
PubChem
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PubChem