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Ligand emodin

Basic Ligand Information

Molecular Structure

Related pathways

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Roles as Enzyme Ligand

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

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Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.283

S-adenosyl-L-methionine + emodin = S-adenosyl-L-homocysteine + questin

721439, 777868, 778430

7WH9, 3D-view

Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Substrate (5 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.283

S-adenosyl-L-methionine + emodin = S-adenosyl-L-homocysteine + questin

721439, 755826, 777868, 778430

7WH9, 3D-view

2.1.1.88

S-adenosyl-L-methionine + emodin = S-adenosyl-L-homocysteine + questin

755826

-

2.1.1.B75

2 S-adenosyl-L-methionine + emodin = 2 S-adenosyl-L-homocysteine + O-methylemodin

755826

-

2.4.1.181

UDP-alpha-D-glucose + emodin = UDP + 7,8-dihydroxy-3-methyl-9,10-dioxo-9,10-dihydroanthracen-1-yl beta-D-glucopyranoside

488809

-

2.8.2.1

3'-phosphoadenylyl sulfate + emodin = adenosine 3',5'-bisphosphate + emodin O-sulfate

761964

-

Activator in Enzyme-catalyzed Reactions (6 results)

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Show Activating Compound (6 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.14.18.1

anthraquinone

689442

-

1.14.18.1

anthraquinone, slightly activates tyrosinase

689442

-

1.14.18.1

isolated from Radix polygoni multiflori, a herb used effectively to prevent graying and to treat skin depigmentation diseases in traditional Chinese medicine. Shows significant melanogenesis stimulation activities

688041

-

1.14.18.1

shows mild activating effects on tyrosinase. Isolated from Radix polygoni multiflori, a herb used effectively to prevent graying and treat skin depigmentation diseases in traditional Chinese medicine

688041

-

1.14.18.1

4 entries

3.4.21.73

i.e. emodin, an active compound of aloe. Emodin increases the fibrinolytic activity of fibroblast cells in a dose-dependent manner, linked to increased uPA activity and uPA gene up-regulation. Emodin also induces up-regulation of uPA inhibitor PAI-1. Up-regulations are independent of emodin's effect on nuclear factor kappaB. The effect on the uPA system may be via generation of reactive oxygen species

701373

-

3.4.22.1

i.e. 1,3,8-trihydroxy-6-methylanthraquinone, emodin at apoptosis-inducing concentrations causes expression and activation of cathepsin B protein

701315

-

Inhibitor in Enzyme-catalyzed Reactions (23 results)

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Show Inhibitors (23 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.146

-

711632, 740917

-

1.1.1.21

-

685456

-

1.14.18.1

anthraquinone, isolated from the root of Polygonum cuspidatum

689441

-

1.6.5.5

i.e. an anthraquinone, inhibits the enzymatic activity of NADPH-quinone reductase by binding to the active site. Emodin acts as a competitive inhibitor with respect to 2, 6-dichlorophenolindophenol, and emodin shows cytotoxicity against rat hepatocytes

765859

-

2.4.1.17

inhibits tizoxanide glucuronidation activities in the human liver and even more in intestinal microsomes; inhibits tizoxanide glucuronidation activities in the human liver and even more in intestinal microsomes

777105

-

2.7.10.2

i.e. 6-methyl-1,3,8-trihydroxyanthraquinone, Lck inhibitor

662172

-

2.7.10.2

inhibition of p56lck and c-Src

661540

-

2.7.11.1

-

672431

3BQC, 3D-view

2.7.11.1

-

672431

3C13, 3D-view

2.7.11.1

-

672431

3PZH, 3D-view

2.7.11.1

-

672431

3Q9W, 3D-view

2.7.11.1

-

672431

3Q9X, 3D-view

2.7.11.1

a CKII-specific inhibitor

664864

3BQC, 3D-view

2.7.11.1

a CKII-specific inhibitor

664864

3C13, 3D-view

2.7.11.1

a CKII-specific inhibitor

664864

3PZH, 3D-view

2.7.11.1

a CKII-specific inhibitor

664864

3Q9W, 3D-view

2.7.11.1

a CKII-specific inhibitor

664864

3Q9X, 3D-view

2.7.10.2

2 entries

2.7.11.1

10 entries

2.7.11.18

IC50: 0.008 mM

640629

-

3.1.26.13

i.e. frangula-emodin

708108

-

3.2.1.18

-

702681

-

3.4.15.1

45.79% inhibition at 1.63 ng/ml

700690

-

3.4.17.23

1,3,8-trihydroxy-6-methylanthraquinone (emodin) blocks interaction between the SARS corona virus spike protein and its receptor angiotensin-converting enzyme 2, 94.12% inhibition at 0.05 mM

677603

-

3.5.1.5

0.5 mM, 30°C, pH 6.8, 46.9% inhibition

752937

-

3D Structure of Enzyme-Ligand-Complex (PDB) (22 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (22 entries)

EC NUMBER

ENZYME 3D STRUCTURE

2.1.1.283

7WH9, 3D-view

2.7.1.37

1F0Q, 3D-view

2.7.11.1

3BQC, 3D-view

2.7.11.1

3C13, 3D-view

2.7.11.1

3PZH, 3D-view

2.7.11.1

3Q9W, 3D-view

2.7.11.1

3Q9X, 3D-view

2.7.11.1

3BQC, 3D-view

2.7.11.1

3C13, 3D-view

2.7.11.1

3PZH, 3D-view

2.7.11.1

3Q9W, 3D-view

2.7.11.1

3Q9X, 3D-view

2.7.11.1

3BQC, 3D-view

2.7.11.1

3C13, 3D-view

2.7.11.1

3PZH, 3D-view

2.7.11.1

3Q9W, 3D-view

2.7.11.1

3Q9X, 3D-view

2.7.11.1

3BQC, 3D-view

2.7.11.1

3C13, 3D-view

2.7.11.1

3PZH, 3D-view

2.7.11.1

3Q9W, 3D-view

2.7.11.1

3Q9X, 3D-view

2.7.11.1

20 entries

Enzyme Kinetic Parameters

K_M Value (2 results)

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Show KM Value (2 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.1.1.283

0.00034

-

pH 8.0, 30°C

721439

2.4.1.181

0.01

-

isoform I

488809

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

1.1.1.21

0.0159

-

pH 7.0, 37°C

685456

2.7.11.1

0.00185

-

-

672431

IC₅₀ Value (11 results)

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Show IC50 Value (11 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.1.1.146

0.000086

-

pH 7.4, 37°C

711632

1.1.1.146

0.000186

-

pH 7.4, 37°C

711632

1.1.1.146

2 entries

1.6.5.5

0.061

-

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

765859

2.4.1.17

0.00772

-

intestinal microsome, pH 7.4, 37°C

777105

2.4.1.17

0.0165

-

liver microsome, pH 7.4, 37°C

777105

2.4.1.17

2 entries

2.7.11.1

0.002

-

-

672431

2.7.11.18

0.008

-

IC50: 0.008 mM

640629

3.1.26.13

0.075

-

-

708108

3.2.1.18

0.11

-

in 50 mM Tris-HCl pH 7.5, at 25°C

702681

3.2.1.18

0.76

-

in 50 mM Tris-HCl pH 7.5, at 25°C

702681

3.2.1.18

2 entries

3.4.17.23

0.2

-

-

677603

References & Links

Literature References (29)

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Show Reference (29 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

488809

-

Purification and some properties of five anthraquinone-specific glucosyltransferases from Cinchona succirubra cell suspension culture

1987

Khouri, H.E.; Ibrahim, R.K.

Phytochemistry

26

2531-2535

640629

1466788

Inhibition of myosin light chain kinase, cAMP-dependent protein kinase, protein kinase C and of plant Ca(2+)-dependent protein kinase by anthraquinones

1992

Jinsart, W.; Ternai, B.; Polya, G.M.

Biol. Chem. Hoppe-Seyler

373

903-910

661540

15032721

Plant-derived protein tyrosine kinase inhibitors as anticancer agents

2004

Hollosy, F.; Keri, G.

Curr. Med. Chem. Anticancer Agents

4

173-197

662172

14534291

Tyrosine kinase p56lck regulates cell motility and nuclear factor kappaB-mediated secretion of urokinase type plasminogen activator through tyrosine phosphorylation of IkappaBalpha following hypoxia/reoxygenation

2003

Mahabeleshwar, G.H.; Kundu, G.C.

J. Biol. Chem.

278

52598-52612

664864

16520553

Phospholipase D is activated and phosphorylated by casein kinase-II in human U87 astroglioma cells

2006

Ahn, B.H.; Min, G.; Bae, Y.S.; Min do, S.

Exp. Mol. Med.

38

55-62

672431

17931986

Too much of a good thing: The role of protein kinase CK2 in tumorigenesis and prospects for therapeutic inhibition of CK2

2008

Duncan, J.S.; Litchfield, D.W.

Biochim. Biophys. Acta

1784

33-47

677603

16730806

Emodin blocks the SARS coronavirus spike protein and angiotensin-converting enzyme 2 interaction

2007

Ho, T.Y.; Wu, S.L.; Chen, J.C.; Li, C.C.; Hsiang, C.Y.

Antiviral Res.

74

92-101

685456

17978503

Anthraquinones from the seeds of Cassia tora with inhibitory activity on protein glycation and aldose reductase

2007

Jang, D.S.; Lee, G.Y.; Kim, Y.S.; Lee, Y.M.; Kim, C.S.; Yoo, J.L.; Kim, J.S.

Biol. Pharm. Bull.

30

2207-2210

688041

18343911

Effects of radix polygoni multiflori components on tyrosinase activity and melanogenesis

2008

Guan, S.; Su, W.; Wang, N.; Li, P.; Wang, Y.

J. Enzyme Inhib. Med. Chem.

23

252-255

689441

18338768

Anthraquinones from Polygonum cuspidatum as tyrosinase inhibitors for dermal use

2008

Leu, Y.L.; Hwang, T.L.; Hu, J.W.; Fang, J.Y.

Phytother. Res.

22

552-556

689442

18389468

A potent tyrosinase activator from Radix Polygoni multiflori and its melanogenesis stimulatory effect in B16 melanoma cells

2008

Guan, S.; Su, W.; Wang, N.; Li, P.; Wang, Y.

Phytother. Res.

22

660-663

700690

18803227

Inhibitory activities of Cassia tora and its anthraquinone constituents on angiotensin-converting enzyme

2009

Hyun, S.K.; Lee, H.; Kang, S.S.; Chung, H.Y.; Choi, J.S.

Phytother. Res.

23

178-184

701315

18789614

Participation of cathepsin B in emodin-induced apoptosis in HK-2 cells

2008

Wang, C.; Jiang, Z.; Yao, J.; Wu, X.; Sun, L.; Liu, C.; Duan, W.; Yan, M.; Sun, L.; Liu, J.; Zhang, L.

Toxicol. Lett.

181

196-204

701373

18328790

Emodin upregulates urokinase plasminogen activator, plasminogen activator inhibitor-1 and promotes wound healing in human fibroblasts

2008

Radha, K.S.; Madhyastha, H.K.; Nakajima, Y.; Omura, S.; Maruyama, M.

Vascul. Pharmacol.

48

184-190

702681

20097567

Potent inhibitor scaffold against Trypanosoma cruzi trans-sialidase

2010

Arioka, S.; Sakagami, M.; Uematsu, R.; Yamaguchi, H.; Togame, H.; Takemoto, H.; Hinou, H.; Nishimura, S.

Bioorg. Med. Chem.

18

1633-1640

708108

-

Synthesis of phenacyl derivatives of frangula-emodin and their HIV-1 RNase H activity

2009

Kharlamova, T.

Chem. Nat. Compd.

45

500-502

711632

20718744

Emodin, a natural product, selectively inhibits 11beta-hydroxysteroid dehydrogenase type 1 and ameliorates metabolic disorder in diet-induced obese mice

2010

Feng, Y.; Huang, S.L.; Dou, W.; Zhang, S.; Chen, J.H.; Shen, Y.; Shen, J.H.; Leng, Y.

Br. J. Pharmacol.

161

113-126

721439

1444712

Emodin O-methyltransferase from Aspergillus terreus

1992

Chen, Z.G.; Fujii, I.; Ebizuka, Y.; Sankawa, U.

Arch. Microbiol.

158

29-34

740917

25066675

Endocrine disruptors and other inhibitors of 11beta-hydroxysteroid dehydrogenase 1 and 2: Tissue-specific consequences of enzyme inhibition

2016

Vitku, J.; Starka, L.; Bicikova, M.; Hill, M.; Heracek, J.; Sosvorova, L.; Hampl, R.

J. Steroid Biochem. Mol. Biol.

155

207-216

752937

31054431

Natural urease inhibitors from Aloe vera resin and Lycium shawii and their structural-activity relationship and molecular docking study

2019

Rehman, N.U.; Khan, A.; Al-Harrasi, A.; Khiat, M.; Hussain, H.; Wadood, A.; Riaz, M.

Bioorg. Chem.

88

102955

752937

31054431

Natural urease inhibitors from Aloe vera resin and Lycium shawii and their structural-activity relationship and molecular docking study

2019

Rehman, N.U.; Khan, A.; Al-Harrasi, A.; Khiat, M.; Hussain, H.; Wadood, A.; Riaz, M.

Bioorg. Chem.

88

102955

755826

29043664

Substrate scope of O-methyltransferase from Streptomyces peucetius for biosynthesis of diverse natural products methoxides

2018

Parajuli, P.; Pandey, R.P.; Nguyen, T.H.T.; Dhakal, D.; Sohng, J.K.

Appl. Biochem. Biotechnol.

184

1404-1420

755826

29043664

Substrate scope of O-methyltransferase from Streptomyces peucetius for biosynthesis of diverse natural products methoxides

2018

Parajuli, P.; Pandey, R.P.; Nguyen, T.H.T.; Dhakal, D.; Sohng, J.K.

Appl. Biochem. Biotechnol.

184

1404-1420

761964

33239367

Combinatorial biosynthesis of sulfated benzenediol lactones with a phenolic sulfotransferase from Fusarium graminearum PH-1

2020

Xie, L.; Xiao, D.; Wang, X.; Wang, C.; Bai, J.; Yue, Q.; Yue, H.; Li, Y.; Molnar, I.; Xu, Y.; Zhang, L.

mSphere

5

e00949

761964

33239367

Combinatorial biosynthesis of sulfated benzenediol lactones with a phenolic sulfotransferase from Fusarium graminearum PH-1

2020

Xie, L.; Xiao, D.; Wang, X.; Wang, C.; Bai, J.; Yue, Q.; Yue, H.; Li, Y.; Molnar, I.; Xu, Y.; Zhang, L.

mSphere

5

e00949

752937

2 entries

755826

2 entries

761964

2 entries

765859

33122156

Emodin inhibited NADPH-quinone reductase competitively and induced cytotoxicity in rat primary hepatocytes

2020

Shukla, V.; Asthana, S.; Yadav, S.; Rajput, V.S.; Tripathi, A.

Toxicon

188

117-121

777105

38889874

Glucuronidation of tizoxanide, an active metabolite of nitazoxanide, in liver and small intestine Species differences in humans, monkeys, dogs, rats, and mice and responsible UDP-glucuronosyltransferase isoforms in humans

2024

Hanioka, N.; Isobe, T.; Saito, K.; Nagaoka, K.; Mori, Y.; Jinno, H.; Ohkawara, S.; Tanaka-Kagawa, T.

Comp. Biochem. Physiol. C Toxicol. Pharmacol.

283

109962

777868

35475366

Characterization and structural analysis of emodin-O-methyltransferase from Aspergillus terreus

2022

Xue, Y.; Liang, Y.; Zhang, W.; Geng, C.; Feng, D.; Huang, X.; Dong, S.; Zhang, Y.; Sun, J.; Qi, F.; Lu, X.

J. Agric. Food Chem.

70

5728-5737

778430

36328293

Microbial production of the plant-derived fungicide physcion

2022

Qi, F.; Zhang, W.; Xue, Y.; Geng, C.; Jin, Z.; Li, J.; Guo, Q.; Huang, X.; Lu, X.

Metab. Eng.

74

130-138

Links to other databases for emodin

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Show Links (1 entry)