print visible entries

print all entries

Ligand caffeic acid phenethyl ester

Basic Ligand Information

Molecular Structure

close all tables

open all tables

Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (1 result)

top print hide

Show Substrate (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.73

phenethyl caffeate + H2O = phenylethanol + caffeate

746338

-

Product in Enzyme-catalyzed Reactions (2 results)

top print hide

Show Product (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.42

2-phenylethyl alcohol + 5-chlorogenic acid = 2-phenylethyl caffeate + quinate

-

-

3.1.1.42

2-phenylethyl bromide + 5-chlorogenic acid = 2-phenylethyl caffeate + 5-bromo-quinate

-

-

3.1.1.42

2 entries

Inhibitor in Enzyme-catalyzed Reactions (9 results)

top print hide

Show Inhibitors (9 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.17.3.2

55.0% inhibition at 0.004 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

686866

-

2.1.1.6

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

705398

-

3.1.3.16

down-regulation of expression of PP2A catalytic subunit in cells treated with caffeic acid phenethyl ester at 48 h

680061

-

3.5.1.24

-

734840

-

3.5.1.24

71.8% inhibition of recombinant enzyme at 5 mM, 80% at 10 mM, 50% at 03125 mM

734840

-

3.5.1.24

99.7% inhibition at 5 mM

735132

-

3.5.1.88

CAPE, does not chelate HpPDF and does not disrupt the metal-dependent catalysis

756536

4e9a, 3D-view

3.5.1.88

CAPE, an active component of propolis, 75% inhibition at 0.01 mM, the competitive inhibitor blocks the substrate entrance, preventing substrate from approaching the active site, but CAPE does not have chelate interaction with HpPDF and does not disrupt the metal-dependent catalysis

733259

4e9a, 3D-view

3.5.1.24

3 entries

3.5.1.88

2 entries

3.5.4.4

reduces the enzyme activity in vivo, suppresses the induction of the enzyme by cisplatin in vivo

670954

-

3D Structure of Enzyme-Ligand-Complex (PDB) (7 results)

top print hide

Show 3D Structure of Enzyme-Ligand-Complex (PDB) (7 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.1.1.112

5hnt, 3D-view

1.1.1.188

5hnt, 3D-view

1.1.1.239

5hnt, 3D-view

1.1.1.357

5hnt, 3D-view

1.1.1.64

5hnt, 3D-view

1.3.1.20

5hnt, 3D-view

3.5.1.88

4e9a, 3D-view

Enzyme Kinetic Parameters

IC₅₀ Value (4 results)

top print hide

Show IC50 Value (4 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.17.3.2

0.00626

-

pH 8.0, 37°C, competitive versus xanthine

686866

1.17.3.2

0.1567

-

pH 8.0, 37°C, inhibition of hydroxylradical formation in the dimethyl-1-pyrroline-N-oxide spin-trapping assay

686866

3.5.1.88

0.00402

-

pH and temperature not specified in the publication

756536

3.5.1.88

0.00402

-

pH and temperature not specified in the publication

733259

1.17.3.2

2 entries

3.5.1.88

2 entries

References & Links

Literature References (9)

top print hide

Show Reference (9 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

670954

15986578

The activities of liver adenosine deaminase, xanthine oxidase, catalase, superoxide dismutase enzymes and the levels of malondialdehyde and nitric oxide after cisplatin toxicity in rats: protective effect of caffeic acid phenethyl ester

2005

Yilmaz, H.R.; Sogut, S.; Ozyurt, B.; Ozugurlu, F.; Sahin, S.; Isik, B.; Uz, E.; Ozyurt, H.

Toxicol. Ind. Health

21

67-73

680061

17852432

Protein phosphatase 2A (PP2A) has a potential role in CAPE-induced apoptosis of CCRF-CEM cells via effecting human telomerase reverse transcriptase activity

2007

Avci, C.B.; Sahin, F.; Gunduz, C.; Selvi, N.; Aydin, H.H.; Oktem, G.; Topcuoglu, N.; Saydam, G.

Hematology

12

519-525

686866

17964425

Structure-activity relationship of C6-C3 phenylpropanoids on xanthine oxidase-inhibiting and free radical-scavenging activities

2007

Chang, Y.C.; Lee, F.W.; Chen, C.S.; Huang, S.T.; Tsai, S.H.; Huang, S.H.; Lin, C.M.

Free Radic. Biol. Med.

43

1541-1551

705398

19095062

Inhibition of human catechol-O-methyltransferase (COMT)-mediated O-methylation of catechol estrogens by major polyphenolic components present in coffee

2009

Zhu, B.T.; Wang, P.; Nagai, M.; Wen, Y.; Bai, H.W.

J. Steroid Biochem. Mol. Biol.

113

65-74

733259

23611786

Caffeic acid phenethyl ester (CAPE), an active component of propolis, inhibits Helicobacter pylori peptide deformylase activity

2013

Cui, K.; Lu, W.; Zhu, L.; Shen, X.; Huang, J.

Biochem. Biophys. Res. Commun.

435

289-294

734840

25526498

Effect of bile salt hydrolase inhibitors on a bile salt hydrolase from Lactobacillus acidophilus

2014

Lin, J.; Negga, R.; Zeng, X.; Smith, K.

Pathogens

3

947-956

735132

24454844

Discovery of bile salt hydrolase inhibitors using an efficient high-throughput screening system

2014

Smith, K.; Zeng, X.; Lin, J.

PLoS ONE

9

e85344

746338

-

Biochemical characteristics of three feruloyl esterases with a broad substrate spectrum from Bacillus amyloliquefaciens H47

2017

Wang, X.; Bai, Y.; Cai, Y.; Zheng, X.

Process Biochem.

53

109-115

756536

25174923

Peptide deformylase a new target in antibacterial, antimalarial and anticancer drug discovery

2015

Sangshetti, J.; Khan, F.; Shinde, D.

Curr. Med. Chem.

22

214-236

Links to other databases for caffeic acid phenethyl ester

top print hide

Show Links (1 entry)

ChEBI

PubChem

-