Ligand view of 1-O-galloyl-beta-D-glucose (95614 - GDVRUDXLQBVIKP-HQHREHCSSA-N)

C₁₃H₁₆O₁₀

1-O-galloyl-beta-D-glucose

GDVRUDXLQBVIKP-HQHREHCSSA-N

KEGG

Biosynthesis of phenylpropanoids, Biosynthesis of various plant secondary metabolites

MetaCyc

gallotannin biosynthesis, galloylated catechin biosynthesis, pentagalloylglucose biosynthesis

2.3.1.90

1-O-galloyl-beta-D-glucose + 1-O-galloyl-beta-D-glucose = 1,6-di-O-galloyl-beta-D-glucose + D-glucose

487706, 487705, 487707

-

2.4.1.136

2 entries

2.4.1.177

UDP-glucose + gallate = UDP + galloyl beta-D-glucoside

0

-

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

-

UDP-glucose + gallate = UDP + galloyl beta-D-glucoside

0

-

1.1.1.21

i.e. beta-glucogallin or BGG, a major component of the Emblica officinalis medicinal plant, and a stable, potent, and specific inhibitor of aldose reductase, noncompetitive inhibition through binding the active site of AKR1B1, occupying both the anionic and the specificity pockets

-

-

-

about 15% inhibition at 1 mM, 34.4% inhibition at 5 mM

-

-

-

2.3

-

486327

2.3.1.90

66.7

-

0.008

-

pH and temperature not specified in the publication

738833

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

94250

-

Studies on fungal tannase. Part I. Formation, purification and catalytic properties of tannase of Aspergillus flavus

1968

Yamada, H.; Adachi, O.; Watanabe, M.; Sato, N.

Agric. Biol. Chem.

32

1070-1078

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

487705

-

Enzymic synthesis of di-O-phenylcarboxyl-beta-D-glucose esters by an acyltransferase from oak leaves

1990

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

Z. Naturforsch. C

45

37-41

487706

-

Synthesis of mono-, di- and trigalloyl-beta-D-glucose by beta-glucogallin-dependent galloyltransferases from oak leaves

1983

Gross, G.G.

Z. Naturforsch. C

38

519-523

487707

-

Enzymatic synthesis of 1,6-digalloylglucose from beta-glucogallin by beta-glucogallin:beta-glucogallin 6-0-galloyltransferase from oak leaves

1987

Schmidt, S.W.; Denzel, K.; Schilling, G.; Gross, G.G.

Z. Naturforsch. C

42

87-92

488579

-

Partial purification and properties of UDP-glucose: vanillate 1-O-glucosyl transferase from oak leaves

1983

Gross, G.

Phytochemistry

22

2179-2182

488580

-

Synthesis of beta-glucogallin from UDP-glucose and gallic acid by an enzyme preparation from oak leaves

1982

Gross, G.

FEBS Lett.

148

67-70

655009

11330666

Inhibitory effects of ellagi- and gallotannins on rat intestinal alpha-glucosidase complexes

2001

Toda, M.; Kawabata, J.; Kasai, T.

Biosci. Biotechnol. Biochem.

65

542-547

738155

26491981

Inhibition of 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase from Mycobacterium tuberculosis: in silico screening and in vitro validation

2015

Nirmal, C.R.; Rao, R.; Hopper, W.

Eur. J. Med. Chem.

105

182-193

738833

24341381

Design of an amide N-glycoside derivative of beta-glucogallin: a stable, potent, and specific inhibitor of aldose reductase

2014

Li, L.; Chang, K.C.; Zhou, Y.; Shieh, B.; Ponder, J.; Abraham, A.D.; Ali, H.; Snow, A.; Petrash, J.M.; LaBarbera, D.V.

J. Med. Chem.

57

71-77

757257

31514687

Structural insights of metallo-beta-lactamase revealed an effective way of inhibition of enzyme by natural inhibitors

2019

Gangadharappa, B.S.; Sharath, R.; Revanasiddappa, P.D.; Chandramohan, V.; Balasubramaniam, M.; Vardhineni, T.P.

J. Biomol. Struct. Dyn.

38

3757-3771

Ligand 1-O-galloyl-beta-D-glucose

Basic Ligand Information

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

Substrate in Enzyme-catalyzed Reactions (5 results)

Product in Enzyme-catalyzed Reactions (3 results)

Inhibitor in Enzyme-catalyzed Reactions (4 results)

Enzyme Kinetic Parameters

K_M Value (4 results)

IC₅₀ Value (1 result)

References & Links

Literature References (14)

Links to other databases for 1-O-galloyl-beta-D-glucose

Ligand 1-O-galloyl-beta-D-glucose

Basic Ligand Information

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

Substrate in Enzyme-catalyzed Reactions (5 results)

Product in Enzyme-catalyzed Reactions (3 results)

Inhibitor in Enzyme-catalyzed Reactions (4 results)

Enzyme Kinetic Parameters

KM Value (4 results)

IC50 Value (1 result)

References & Links

Literature References (14)

Links to other databases for 1-O-galloyl-beta-D-glucose

K_M Value (4 results)

IC₅₀ Value (1 result)