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Ligand 1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose

Basic Ligand Information

Molecular Structure

Related pathways

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Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (2 results)

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Show Substrate (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.20

1,2,3,4,6-penta-O-galloyl-beta-D-glucose + H2O = gallate + digalloylglucose + trigalloylglucose + tetragalloylglucose

768963

-

3.1.1.20

1,2,3,4,6-pentagalloyl glucose + H2O = gallic acid + D-glucose

94255, 94249

-

3.1.1.20

2 entries

Product in Enzyme-catalyzed Reactions (1 result)

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Show Product (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.143

1-O-galloyl-beta-D-glucose + 1,2,3,6-tetra-O-galloyl-beta-D-glucose = D-glucose + 1,2,3,4,6-penta-O-galloyl-beta-D-glucose

486328, 486327

-

Inhibitor in Enzyme-catalyzed Reactions (14 results)

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Show Inhibitors (14 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.100

compound is transported across cancer cell membrane to further down-regulate FAS and activate caspase-3 in MDA-MB-231 cells. Compared with other FAS inhibitors, including catechin gallate and morin, 1,2,3,4,6-penta-O-galloyl-beta-D-glucose involves a higher reversible fast-binding inhibition with an irreversible slow-binding inhibition, i.e. saturation kinetics with a dissociation constant of 0.59 microM and a limiting rate constant of 0.16 per min. The major reacting site of PGG is on the beta-ketoacyl reduction domain of FAS. Compound exhibits different types of inhibitions against the three substrates in the FAS overall reaction

735600

-

1.1.1.100

minimal inhibitory concentration 0.125 mg/ml

685704

-

1.1.1.100

minimal inhibitory concentration 0.25 mg/ml

685704

-

1.1.1.100

mixed type of inhibition. IC50 value 0.9 microgramm per ml, Ki value 0.21 microgramm per ml

685704

-

1.1.1.100

4 entries

1.1.1.21

46.6% inhibition at 0.002 mM

696552

-

2.3.1.67

IC50: 0.026 mM

658920

-

2.3.1.85

compound is transported across cancer cell membrane to further down-regulate FAS and activate caspase-3 in MDA-MB-231 cells. Compared with other FAS inhibitors, including catechin gallate and morin, 1,2,3,4,6-penta-O-galloyl-beta-D-glucose involves a higher reversible fast-binding inhibition with an irreversible slow-binding inhibition, i.e. saturation kinetics with a dissociation constant of 0.59 microM and a limiting rate constant of 0.16 per min. The major reacting site of PGG is on the beta-ketoacyl reduction domain of FAS. Compound exhibits different types of inhibitions against the three substrates in the FAS overall reaction

735600

-

2.7.7.53

35.81% activity remaining

760256

-

3.2.1.1

mixed non-competitive inhibition, KEI: 0.0026 mM, KEIS: 0.0039 mM, tested in a concentration range of 0.04 to 0.5 mM, reduced inhibitory efficiency of the mutants W58L and Y151M with 92 and 97% remaining enzyme activity at 0.00235 mM inhibitor concentration, respectively, pH 6.0, 37°C

691113

-

3.2.1.143

about 25% inhibition at 10 microM in vitro

697031

-

3.4.21.26

IC50: 170 nM

650847

-

3.4.21.26

specific, noncompetitive, and strong inhibition

683100

-

3.4.21.26

2 entries

3.4.22.69

remarkable inhibitory activity against SARS-CoV-2 3CLpro. In molecular docking, 1,2,3,4,6-pentagalloylglucose strongly interacts with the substrate binding pocket of SARS-CoV-2 3CLpro, forming hydrogen bonds with catalytic residues C145 and H41

764084

-

3.4.22.B63

-

773046

-

Enzyme Kinetic Parameters

K_M Value (1 result)

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Show KM Value (1 entry)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.1.1.20

5.9

-

-

94255

K_i Value (2 results)

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Show KI Value (2 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.2.1.1

0.00235

-

pH 6.0, 37°C, the mutants Y151M and W58L exhibit reduced inhibitory efficiency with 92 and 97% remaining enzyme activity at 0.00235 mM inhibitor concentration, respectively, pH 6.0, 37°C

691113

3.4.21.26

0.0000272

-

-

683100

IC₅₀ Value (5 results)

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Show IC50 Value (5 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

2.3.1.67

0.026

-

IC50: 0.026 mM

658920

2.3.1.85

0.0016

-

37°C, pH not specified in the publication

735600

3.4.21.26

0.00017

-

IC50: 170 nM

650847

3.4.22.69

0.0037

-

pH not specified in the publication, temperature not specified in the publication

764084

3.4.22.69

0.0069

-

pH not specified in the publication, temperature not specified in the publication

764084

3.4.22.69

2 entries

References & Links

Literature References (18)

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Show Reference (18 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

94249

-

Hydrolizing pathway, substrate specificity and inhibition of tannin acyl hydrolase of Asp. oryzae No. 7

1972

Iibuchi, S.; Minoda, Y.; Yamada, K.

Agric. Biol. Chem.

36

1553-1562

94255

-

A gallotannin degrading esterase from leaves of pedunculate oak

1997

Niehaus, J.U.; Gross, G.G.

Phytochemistry

45

1555-1560

486327

2757399

Biosynthesis of gallotannins: beta-glucogallin-dependent formation of 1,2,3,4,6-pentagalloylglucose by enzymatic galloylation of 1,2,3,6-tetragalloylglucose

1989

Cammann, J.; Denzel, K.; Schilling, G.; Gross, G.

Arch. Biochem. Biophys.

273

58-63

486328

-

Purification of tetragalloylglucose 4-O-galloyltransferase and preparation of antibodies against this key enzyme in the biosynthesis of hydrolyzable tannins

2000

Grundhofer, P.; Gross, G.G.

Z. Naturforsch. C

55

582-587

650847

11310664

Prolyl endopeptidase inhibitors from the underground part of Rhodiola sachalinensis

2001

Fan, W.; Tezuka, Y.; Ni, K.M.; Kadota, S.

Chem. Pharm. Bull.

49

396-401

658920

15051936

Tea polyphenols inhibit acetyl-CoA:1-alkyl-sn-glycero-3-phosphocholine acetyltransferase (a key enzyme in platelet-activating factor biosynthesis) and platelet-activating factor-induced platelet aggregation

2004

Sugatani, J.; Fukazawa, N.; Ujihara, K.; Yoshinari, K.; Abe, I.; Noguchi, H.; Miwa, M.

Int. Arch. Allergy Immunol.

134

17-28

683100

17703733

Plant phenolics as prolyl endopeptidase inhibitors

2007

Lee, S.H.; Jun, M.; Choi, J.Y.; Yang, E.J.; Hur, J.M.; Bae, K.; Seong, Y.H.; Huh, T.L.; Song, K.S.

Arch. Pharm. Res.

30

827-833

685704

18208374

The antibacterial efficacy of aceraceous plant may be related to inhibition of bacterial beta-ketoacyl-ACP reductase (FabG)

2008

Zhang, F.; Luo, S.Y.; Ye, Y.B.; Zhao, W.H.; Sun, X.G.; Wang, Z.Q.; Li, R.; Sun, Y.H.; Tian, W.X.; Zhang, Y.X.

Biotechnol. Appl. Biochem.

51

73-78

691113

19038368

Evidence for pentagalloyl glucose binding to human salivary alpha-amylase through aromatic amino acid residues

2009

Gyemant, G.; Zajacz, A.; Becsi, B.; Ragunath, C.; Ramasubbu, N.; Erdodi, F.; Batta, G.; Kandra, L.

Biochim. Biophys. Acta

1794

291-296

696552

18670102

Inhibitory effect of the compounds isolated from Rhus verniciflua on aldose reductase and advanced glycation endproducts

2008

Lee, E.H.; Song, D.G.; Lee, J.Y.; Pan, C.H.; Um, B.H.; Jung, S.H.

Biol. Pharm. Bull.

31

1626-1630

697031

18806807

Mono-galloyl glucose derivatives are potent poly(ADP-ribose) glycohydrolase (PARG) inhibitors and partially reduce PARP-1-dependent cell death

2008

Formentini, L.; Arapistas, P.; Pittelli, M.; Jacomelli, M.; Pitozzi, V.; Menichetti, S.; Romani, A.; Giovannelli, L.; Moroni, F.; Chiarugi, A.

Br. J. Pharmacol.

155

1235-1249

735600

24508804

In vitro inhibition of fatty acid synthase by 1,2,3,4,6-penta-O-galloyl-beta-D-glucose plays a vital role in anti-tumour activity

2014

Zhao, W.; Wang, Y.; Hao, W.; Zhao, M.; Peng, S.

Biochem. Biophys. Res. Commun.

445

346-351

760256

28892605

Inhibitors of the diadenosine tetraphosphate phosphorylase Rv2613c of Mycobacterium tuberculosis

2017

Goetz, K.H.; Hacker, S.M.; Mayer, D.; Duerig, J.N.; Stenger, S.; Marx, A.

ACS Chem. Biol.

12

2682-2689

760256

28892605

Inhibitors of the diadenosine tetraphosphate phosphorylase Rv2613c of Mycobacterium tuberculosis

2017

Goetz, K.H.; Hacker, S.M.; Mayer, D.; Duerig, J.N.; Stenger, S.; Marx, A.

ACS Chem. Biol.

12

2682-2689

764084

33454058

The inhibitory effects of PGG and EGCG against the SARS-CoV-2 3C-like protease

2022

Chiou, W.; Chen, J.; Chen, Y.; Yang, J.; Hwang, L.; Lyu, Y.; Yang, H.; Huang, C.

Biochem. Biophys. Res. Commun.

591

130-136

764084

33454058

The inhibitory effects of PGG and EGCG against the SARS-CoV-2 3C-like protease

2022

Chiou, W.; Chen, J.; Chen, Y.; Yang, J.; Hwang, L.; Lyu, Y.; Yang, H.; Huang, C.

Biochem. Biophys. Res. Commun.

591

130-136

760256

2 entries

764084

2 entries

768963

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Partial purification and characterization of a thermostable mushroom tannase induced during solid state fermentation of Toxicodendron vernicifluum stem bark by Fomitella fraxinea

2019

Kim, M.; Kim, D.; Gebru, Y.; Kim, G.; Kim, D.; Kim, J.; Han, H.; Kim, M.

Biocatal. Agricult. Biotechnol.

20

101177

773046

35706070

Identification and prioritization of promising lead molecules from Syzygium aromaticum against Sortase C from Streptococcus pyogenes an in silico investigation

2023

Mangal, P.; Jha, R.K.; Jain, M.; Singh, A.K.; Muthukumaran, J.

J. Biomol. Struct. Dyn.

41

5418-5435

Links to other databases for 1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose

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