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Ligand demethoxycurcumin

Basic Ligand Information

Molecular Structure

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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

2.4.1.17

UDP-D-glucuronate + demethoxy-curcumin = UDP + demethoxy-curcumin phenolic beta-D-monoglucuronide

694249

-

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

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Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.217

(4-coumaroyl)acetyl-CoA + feruloyl-CoA + H2O = demethoxycurcumin + CO2 + 2 CoA

0

-

2.3.1.219

(4-coumaroyl)acetyl-CoA + feruloyl-CoA + H2O = demethoxycurcumin + CO2 + CoA

0

-

2.3.1.219

4-coumaroyl-CoA + feruloylacetyl-CoA = demethoxycurcumin + CO2 + CoA

0

-

2.3.1.219

2 entries

Substrate in Enzyme-catalyzed Reactions (1 result)

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Show Substrate (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.17

UDP-D-glucuronate + demethoxy-curcumin = UDP + demethoxy-curcumin phenolic beta-D-monoglucuronide

694249

-

Product in Enzyme-catalyzed Reactions (3 results)

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Show Product (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.217

(4-coumaroyl)acetyl-CoA + feruloyl-CoA + H2O = demethoxycurcumin + CO2 + 2 CoA

0

-

2.3.1.219

(4-coumaroyl)acetyl-CoA + feruloyl-CoA + H2O = demethoxycurcumin + CO2 + CoA

0

-

2.3.1.219

4-coumaroyl-CoA + feruloylacetyl-CoA = demethoxycurcumin + CO2 + CoA

0

-

2.3.1.219

2 entries

Inhibitor in Enzyme-catalyzed Reactions (7 results)

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Show Inhibitors (7 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.21

i.e. 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione, extracted from Curcuma longa roots, IC50: 0.0159 mM

667349

-

1.3.1.22

complete inhibition at 0.3 mM

740941, 743212

-

1.8.1.9

-

711342

-

1.8.1.B1

inhibits in the micromolar concentration range

765654

-

3.4.21.59

-

754037

-

3.4.22.69

docking score -7.02 kcal/mol, forms hydrogen bonds with residue His163

765113

-

5.3.2.1

-

703331

-

Enzyme Kinetic Parameters

IC₅₀ Value (2 results)

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Show IC50 Value (2 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.1.1.21

0.0159

-

i.e. 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione, extracted from Curcuma longa roots, IC50: 0.0159 mM

667349

1.3.1.22

0.0225

-

at pH 7.4 and 37°C

740941, 743212

References & Links

Literature References (9)

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Show Reference (9 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

667349

16528793

Curcumin analogs as potent aldose reductase inhibitors

2006

Du, Z.Y.; Bao, Y.D.; Liu, Z.; Qiao, W.; Ma, L.; Huang, Z.S.; Gu, L.Q.; Chan, A.S.

Arch. Pharm.

339

123-128

694249

17628876

Glucuronidation of curcuminoids by human microsomal and recombinant UDP-glucuronosyltransferases

2007

Hoehle, S.I.; Pfeiffer, E.; Metzler, M.

Mol. Nutr. Food Res.

51

932-938

703331

19275614

Macrophage migration inhibitory factor (MIF) tautomerase inhibitors as potential novel anti-inflammatory agents: current developments

2009

Garai, J.; Lorand, T.

Curr. Med. Chem.

16

1091-1114

711342

20461157

Curcuminoids as inhibitors of thioredoxin reductase: a receptor based pharmacophore study with distance mapping of the active site

2009

Singh, D.V.; Misra, K.

Bioinformation

4

187-192

740941

-

Anti-androgenic curcumin analogues as steroid 5-alpha reductase inhibitors

2017

Srivilai, J.; Rabgay, K.; Khorana, N.; Waranuch, N.; Nuengchamnong, N.; Wisuitiprot, W.; Chuprajob, T.; Changtam, C.; Suksamrarn, A.; Chavasiri, W.; Sornkaew, N.; Ingkaninan, K.

Med. Chem. Res.

26

1550-1556

743212

-

Anti-androgenic curcumin analogues as steroid 5-alpha reductase inhibitors

2017

Srivilai, J.; Rabgay, K.; Khorana, N.; Waranuch, N.; Nuengchamnong, N.; Wisuitiprot, W.; Chuprajob, T.; Changtam, C.; Suksamrarn, A.; Chavasiri, W.; Sornkaew, N.; Ingkaninan, K.

Med. Chem. Res.

26

1550-1556

754037

30415460

An integrated molecular modeling approach for the tryptase monomer-curcuminoid recognition analysis conformational and bioenergetic features

2018

Wongrattanakamon, P.; Ampasavate, C.; Sirithunyalug, B.; Jiranusornkul, S.

J. Bioenerg. Biomembr.

50

447-459

765113

32896226

In-silico screening of plant-derived antivirals against main protease, 3CLpro and endoribonuclease, NSP15 proteins of SARS-CoV-2

2022

Sharma, A.; Goyal, S.; Yadav, A.; Kumar, P.; Gupta, L.

J. Biomol. Struct. Dyn.

40

86-100

765654

31329647

Effect of curcuminoids and curcumin derivate products on thioredoxin-glutathione reductase from Taenia crassiceps cysticerci. Evidence suggesting a curcumin oxidation product as a suitable inhibitor

2019

Guevara-Flores, A.; Martinez-Gonzalez, J.J.; Herrera-Juarez, A.M.; Rendon, J.L.; Gonzalez-Andrade, M.; Torres Duran, P.V.; Enriquez-Habib, R.G.; Del Arenal Mena, I.P.

PLoS ONE

14

e0220098

Links to other databases for demethoxycurcumin

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Show Links (1 entry)

ChEBI

PubChem