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Ligand isoferulic acid

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (4 results)

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Show Substrate (4 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.121

UDPglucose + 3-hydroxy-4-methoxy cinnamic acid = UDP + 3-hydroxy-4-methoxycinnamoyl-beta-1-D-glucose

488524

-

2.4.1.177

UDP-glucose + isoferulic acid = UDP + isoferuloyl beta-D-glucose

637801

-

2.4.1.35

UDP-glucose + isoferulic acid = UDP + isoferuloyl beta-D-glucoside

657831

-

6.2.1.12

ATP + isoferulate + CoA = AMP + diphosphate + isoferuloyl-CoA

612, 608, 611, 745004, 616

-

Product in Enzyme-catalyzed Reactions (4 results)

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Show Product (4 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.336

2 S-adenosyl-L-methionine + caffeic acid = 2 S-adenosyl-L-homocysteine + ferulic acid + isoferulic acid

-

-

3.1.1.49

isoferuloylcholine + H2O = isoferulic acid + choline

-

-

3.1.1.73

methyl 3-hydroxy-4-methoxycinnamate + H2O = 3-hydroxy-4-methoxycinnamic acid + methanol

-

-

3.1.1.73

methyl 3-hydroxy-4-methoxycinnamate + H2O = methanol + 3-hydroxy-4-methoxycinnamic acid

-

-

3.1.1.73

2 entries

Inhibitor in Enzyme-catalyzed Reactions (5 results)

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Show Inhibitors (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.14.18.1

tyrosinase inhibitors from Marrubium cylleneum, phenolic acids

685515

-

1.14.18.1

77.8% inhibition at 0.33 mM

713205

-

1.14.18.1

2 entries

1.17.3.2

competitively inhibits the enzyme by binding to the active site, have a protective effect against reactive oxygen species in cells, structure-function relationship, computational molecular docking, overview

686866

-

2.7.4.2

2.5 mM, 64% inhibition

645179

-

3.2.1.20

-

709294

-

Enzyme Kinetic Parameters

K_M Value (3 results)

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Show KM Value (3 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

6.2.1.12

0.026

-

-

611

6.2.1.12

0.1

-

3,4-dimethoxycinnamate, , isoenzyme 1

608

6.2.1.12

0.15

-

isoenzyme 2

608

6.2.1.12

3 entries

K_i Value (1 result)

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Show KI Value (1 entry)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.7.4.2

3.85

-

pH 7.4, 37°C

645179

IC₅₀ Value (4 results)

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Show IC50 Value (4 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.14.18.1

0.1149

-

in 0.1 M phosphate buffer (pH 7.0), at 37°C

713205

1.17.3.2

0.1432

-

pH 8.0, 37°C, versus xanthine

686866

3.2.1.20

0.45

-

substrate sucrose

709294

3.2.1.20

0.76

-

substrate maltose

709294

3.2.1.20

2 entries

References & Links

Literature References (13)

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Show Reference (13 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

608

240682

Isoenzymes of p-coumarate:CoA ligase from cell suspension cultures of Glycine max

1975

Knobloch, K.H.; Hahlbrock, K.

Eur. J. Biochem.

52

311-320

611

921295

4-Coumarate:CoA ligase from cell suspension cultures of Petroselinum hortense Hoffm.

1977

Knobloch, K.H.; Hahlbrock, K.

Arch. Biochem. Biophys.

184

237-248

612

-

Multiple forms of hydroxycinnamate:CoA ligase in etiolated pea seedlings

1977

Wallis, P.J.; Rhodes, M.J.C.

Phytochemistry

16

1891-1894

616

-

Distribution and roles of p-hydroxycinnamate:CoA ligase in lignin biosynthesis

1982

Kutsuki, H.; Shimada, M.; Higuchi, T.

Phytochemistry

21

267-271

488524

1719957

Enzymic synthesis of 1-O-(indol-3-ylacetyl)-beta-D-glucose. Purification of the enzyme from Zea mays, and preparation of antibodies to the enzyme

1991

Kowalczyk, S.; Bandurski, R.S.

Biochem. J.

279

509-514

637801

16667674

Phenylpropanoid metabolism in suspension cultures of Vanilla planifolia Andr. III. Conversion of 4-methoxycinnamic acids into 4-hydroxybenzoic acids

1990

Funk, C.; Brodelius, P.E.

Plant Physiol.

94

102-108

645179

226078

Inhibition of rat liver mevalonate pyrophosphate decarboxylase and mevalonate phosphate kinase by phenyl and phenolic compounds

1979

Shama Bhat, C.; Ramasarma, T.

Biochem. J.

181

143-151

657831

12741958

Regioselectivity of glucosylation of caffeic acid by a UDP-glucose:glucosyltransferase is maintained in planta

2003

Lim, E.K.; Higgins, G.S.; Li, Y.; Bowles, D.J.

Biochem. J.

373

987-992

685515

17287127

Identification of tyrosinase inhibitors from Marrubium velutinum and Marrubium cylleneum

2007

Karioti, A.; Protopappa, A.; Megoulas, N.; Skaltsa, H.

Bioorg. Med. Chem.

15

2708-2714

686866

17964425

Structure-activity relationship of C6-C3 phenylpropanoids on xanthine oxidase-inhibiting and free radical-scavenging activities

2007

Chang, Y.C.; Lee, F.W.; Chen, C.S.; Huang, S.T.; Tsai, S.H.; Huang, S.H.; Lin, C.M.

Free Radic. Biol. Med.

43

1541-1551

709294

19772492

A series of cinnamic acid derivatives and their inhibitory activity on intestinal alpha-glucosidase

2009

Adisakwattana, S.; Chantarasinlapin, P.; Thammarat, H.; Yibchok-Anun, S.

J. Enzyme Inhib. Med. Chem.

24

1194-1200

713205

21284262

Tyrosinase inhibitory activities of cinnamic acid analogues

2010

Takahashi, T.; Miyazawa, M.

Pharmazie

65

913-918

745004

28144249

Cloning, functional characterization and site-directed mutagenesis of 4-coumarate coenzyme A ligase (4CL) involved in coumarin biosynthesis in Peucedanum praeruptorum Dunn

2017

Liu, T.; Yao, R.; Zhao, Y.; Xu, S.; Huang, C.; Luo, J.; Kong, L.

Front. Plant Sci.

8

4-4

Links to other databases for isoferulic acid

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Show Links (1 entry)

ChEBI

PubChem

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