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Ligand wogonin

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

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

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.2.1.167

wogonoside + H2O = wogonin + D-glucuronate

0

-

Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Substrate (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.253

UDP-D-glucuronate + 5,7-dihydroxy-8-methoxyflavone = UDP + 5,7-dihydroxy-8-methoxyflavone-7-O-beta-D-glucuronate

706115

-

2.4.1.81

2-nitrophenyl-beta-D-glucopyranoside + wogonin = 2-nitrophenol + 5-hydroxy-8-methoxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl beta-D-glucopyranoside

759388

-

2.4.1.81

UDP-glucose + wogonin = UDP + ?

759388

-

2.4.1.81

2 entries

Product in Enzyme-catalyzed Reactions (4 results)

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Show Product (4 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.2.1.167

5,7-dihydroxy-8-methoxyflavone-7-O-beta-D-glucuronate + H2O = 5,7-dihydroxy-8-methoxyflavone + D-glucuronate

0

-

3.2.1.167

wogonoside + H2O = wogonin + ?

0

-

3.2.1.167

wogonoside + H2O = wogonin + D-glucuronate

0

-

3.2.1.167

3 entries

3.2.1.31

wogonin 7-O-beta-D-glucuronide + H2O = wogonin + beta-D-glucuronate

0

-

Inhibitor in Enzyme-catalyzed Reactions (5 results)

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Show Inhibitors (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.3.1.20

inhibits enzyme expression at concentrations higher than 0.0025 mM; inhibits enzyme expression at concentrations higher than 0.0025 mM

687141

-

2.7.10.1

slight inhibitory effect on epidermal growth factor receptor tyrosine kinase

661031

-

3.1.1.1

-

750021

-

3.3.2.10

20.88% inhibition

753858

-

7.6.2.2

impairs the function of P-glycoprotein and increases cellular content of etoposide in HL-60 cells. Wogonin may be used to reduce the excretion of anticancer agents via P-glycoprotein and to increase the pharmacological action in cancer cells. Wogonin may play a role in overcoming multidrug resistance

710872

-

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

2.4.1.253

0.107

-

pH 7.5, 37°C

706115

IC₅₀ Value (2 results)

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Show IC50 Value (2 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

3.1.1.1

0.01216

-

pH 7.4, 37°C

750021

3.3.2.10

0.1

-

above, pH not specified in the publication, 37°C

753858

References & Links

Literature References (7)

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Show Reference (7 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

661031

15135307

Transinactivation of the epidermal growth factor receptor tyrosine kinase and focal adhesion kinase phosphorylation by dietary flavonoids: effect on invasive potential of human carcinoma cells

2004

Lee, L.T.; Huang, Y.T.; Hwang, J.J.; Lee, A.Y.; Ke, F.C.; Huang, C.J.; Kandaswami, C.; Lee, P.P.; Lee, M.T.

Biochem. Pharmacol.

67

2103-2114

687141

17266043

Reversal of inflammation-associated dihydrodiol dehydrogenases (AKR1C1 and AKR1C2) overexpression and drug resistance in nonsmall cell lung cancer cells by wogonin and chrysin

2007

Wang, H.W.; Lin, C.P.; Chiu, J.H.; Chow, K.C.; Kuo, K.T.; Lin, C.S.; Wang, L.S.

Int. J. Cancer

120

2019-2027

706115

10724177

Purification and characterization of UDP-glucuronate: baicalein 7-O-glucuronosyltransferase from Scutellaria baicalensis Georgi. cell suspension cultures

2000

Nagashima, S.; Hirotani, M.; Yoshikawa, T.

Phytochemistry

53

533-538

710872

19723047

Inhibition of P-glycoprotein by wogonin is involved with the potentiation of etoposide-induced apoptosis in cancer cells

2009

Lee, E.; Enomoto, R.; Koshiba, C.; Hirano, H.

Ann. N. Y. Acad. Sci.

1171

132-136

750021

29421708

Characterization and structure-activity relationship studies of flavonoids as inhibitors against human carboxylesterase 2

2018

Weng, Z.M.; Ge, G.B.; Dou, T.Y.; Wang, P.; Liu, P.K.; Tian, X.H.; Qiao, N.; Yu, Y.; Zou, L.W.; Zhou, Q.; Zhang, W.D.; Hou, J.

Bioorg. Chem.

77

320-329

753858

30980876

Phytochemical constituents from Scutellaria baicalensis in soluble epoxide hydrolase inhibition kinetics and interaction mechanism merged with simulations

2019

Liu, Z.B.; Sun, C.P.; Xu, J.X.; Morisseau, C.; Hammock, B.D.; Qiu, F.

Int. J. Biol. Macromol.

133

1187-1193

759388

30821967

Identification and characterization of two new 1-O-acyl-glucose-ester forming glucosyltransferases from Erigeron breviscapus

2019

Yang, Y.; Liu, M.; Zhang, W.; Cao, Y.; Li, C.; Wang, W.

J. Agric. Food Chem.

67

2848-2855

Links to other databases for wogonin

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Show Links (1 entry)

ChEBI

PubChem