Ligand chlorogenic acid

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Basic Ligand Information

Molecular Structure
Picture of chlorogenic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C16H18O9
chlorogenic acid
CWVRJTMFETXNAD-JUHZACGLSA-N
Synonyms:
(1S,3R,4R,5R)-3-(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylic acid, 3-O-caffeoylquinate, 3-[3-(3,4 dihydroxyphenyl)acryloyl] oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid, 3-[3-(3-4 dihydroxyphenyl)acryloyl] oxy-1,4,5 trihydroxycyclohexane-1-carboxylic acid, 5-caffeoylquinate, 5-O-caffeoylquinate, caffeoylquinate, chlorogenate, trans-5-O-(4-Caffeoyl)-D-quinate, trans-5-O-caffeoyl-D-quinate


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

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
chlorogenic acid + O2 = ?
show the reaction diagram
-
chlorogenic acid + H2O2 = ? + H2O
show the reaction diagram
-
chlorogenate + glucarate = quinate + 2-O-caffeoylglucarate
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
trans-5-O-(4-coumaroyl)-D-quinate + [reduced NADPH-hemoprotein reductase] + O2 = trans-5-O-caffeoyl-D-quinate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
caffeoyl-CoA + quinate = CoA + 5-caffeoylquinate
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (29 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
S-adenosyl-L-methionine + chlorogenic acid = S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
S-adenosyl-L-methionine + chlorogenic acid = ?
show the reaction diagram
-
chlorogenate + glucarate = quinate + 2-O-caffeoylglucarate
show the reaction diagram
-
3'-phosphoadenylylsulfate + chlorogenic acid = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-
3'-phosphoadenylylsulfate + chlorogenic acid = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-
chlorogenic acid + H2O = ?
show the reaction diagram
-
chlorogenic acid + H2O = ?
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
trans-5-O-(4-coumaroyl)-D-quinate + [reduced NADPH-hemoprotein reductase] + O2 = trans-5-O-caffeoyl-D-quinate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
effect of a range of diphenol treatments on the activation of latent red clover PPO tested. 33.1% activation
-
increases eriodictyol formation by 20%
-
PP2B but not PP1 is stimulated 4fold by 0.1 mM chlorogenic acid
-

Inhibitor in Enzyme-catalyzed Reactions (42 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
IC50: 0.881-0.948 mM
-
0.1 mM, 30% inhibition
-
0.1 mM, 9% loss of activity
-
tyrosinase inhibitors from Marrubium velutinum, phenolic acids
-
i.e. 5-O-caffeoylquinic acid
-
COMT from liver, using 2-hydroxyestradiol as substrate, in Tris-HCl buffer (10 mM, pH 7.4), at 37°C; COMT from liver, using 4-hydroxyestradiol as substrate, in Tris-HCl buffer (10 mM, pH 7.4), at 37°C; COMT from placenta, using 2-hydroxyestradiol as substrate, in Tris-HCl buffer (10 mM, pH 7.4), at 37°C; COMT from placenta, using 4-hydroxyestradiol as substrate, in Tris-HCl buffer (10 mM, pH 7.4), at 37°C
-
20% inhibition
-
mixed-type versus ATP, noncompetitive versus 1D-myo-inositol 1,4,5-trisphosphate, slight inhibition, IC50 is 0.0012 mM
-
inhibition of P-PST and M-PST
-
30.8% inhibition at 1 mM
-
noncompetitive inhibition
-
noncompetitive
-
highly potent HDAC inhibitor, 40% residual activity at 0.5 mM
-
27% inhibition at 0.01 mM, 68% inhibition at 0.05 mM
-

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

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (19 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
1650
-
-
29.3
-
pH 6.0, 37°C

KM Value (57 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
2.5
-
isozyme I
20
-
-
19
-
pH 4.0, 30°C
4.1
-
-
0.0183
-
pH 6.0, 37°C

Ki Value (5 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.5
-
-
0.000135
-
pH and temperature not specified in the publication
0.043
-
pH 8.5, 55°C

IC50 Value (19 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.881
0.948
IC50: 0.881-0.948 mM
0.0001
-
pH 7.4, 37°C
0.0012
-
mixed-type versus ATP, noncompetitive versus 1D-myo-inositol 1,4,5-trisphosphate, slight inhibition, IC50 is 0.0012 mM
0.093
-
69.6% inhibition at 0.1 mM
0.375
-
pH and temperature not specified in the publication

References & Links

Links to other databases for chlorogenic acid

ChEBI
PubChem
ChEBI
PubChem