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Ligand 3,4-dimethoxybenzoic acid

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

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

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Show Natural Substrate (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.82

veratrate + NADH + H+ + O2 = isovanillate + NAD+ + H2O + formaldehyde

744457

-

1.14.13.82

veratric acid + NAD(P)H + H+ + O2 = isovanillic acid + NAD(P)+ + H2O + formaldehyde

674280

-

1.14.13.82

veratric acid + NAD(P)H + H+ + O2 = vanillic acid + NAD(P)+ + H2O + formaldehyde

674280

-

1.14.13.82

3 entries

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

3.5.5.1

4,5-dimethoxybenzonitrile + 2 H2O = 4,5-dimethoxybenzoic acid + NH3

0

-

Substrate in Enzyme-catalyzed Reactions (11 results)

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Show Substrate (11 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.10.3.2

veratric acid + O2 = ?

675042

-

1.11.1.13

veratric acid + H2O2 = ? + 2 H2O

765837

-

1.14.13.82

3,4-dimethoxybenzoate + O2 + NADH + H+ = isovanillate + NAD+ + H2O + formaldehyde

639289

-

1.14.13.82

veratrate + NADH + H+ + O2 = isovanillate + NAD+ + H2O + formaldehyde

744457

-

1.14.13.82

veratric acid + NAD(P)H + H+ + O2 = isovanillic acid + NAD(P)+ + H2O + formaldehyde

674280

-

1.14.13.82

veratric acid + NAD(P)H + H+ + O2 = vanillic acid + NAD(P)+ + H2O + formaldehyde

674280

-

1.14.99.15

3,4-dimethoxybenzoate + NADH + O2 = 4-hydroxy-3-methoxybenzoate + NAD+ + H2O + formaldehyde

438344, 438352

-

1.14.99.15

veratrate + AH2 + O2 = ?

727349

-

1.14.13.82

4 entries

1.14.99.15

2 entries

1.2.3.9

veratric acid + ? = veratraldehyde + ?

288400

-

2.1.1.382

3,4-dimethoxybenzoate + a [Co(I) methoxylated-aromatic-compound-specific corrinoid protein] = a [methyl-Co(III) methoxylated-aromatic-compound-specific corrinoid protein] + ?

764041

-

2.4.1.136

UDPglucose + veratrate = UDP + 1-O-veratroyl-beta-D-glucose

488579

-

Product in Enzyme-catalyzed Reactions (18 results)

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Show Product (18 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.3.7

veratraldehyde + O2 = veratric acid + H2O2

0

-

1.11.1.13

veratryl alcohol + H2O2 = 3,4-dimethoxybenzoic acid + 2 H2O

0

-

1.11.1.14

veratryl alcohol + H2O2 = 3,4-dimethoxybenzoic acid + 2 H2O

0

-

1.11.1.16

veratryl alcohol + H2O2 = 3,4-dimethoxybenzoic acid + 2 H2O

0

-

1.11.2.1

veratryl alcohol + H2O2 = 3,4-dimethoxybenzaldehyde + 3,4-dimethoxybenzoic acid + H2O

0

-

1.11.2.1

veratraldehyde + H2O2 = veratric acid + H2O

0

-

1.11.2.1

2 entries

1.17.3.2

3,4-dimethoxybenzaldehyde + H2O + O2 = 3,4-dimethoxybenzoate + H2O2

0

-

1.2.1.29

3,4-dimethoxybenzaldehyde + NAD+ + H2O = 3,4-dimethoxybenzoic acid + NADH + H+

0

-

1.2.1.3

3,4-dimethoxybenzaldehyde + NAD+ + H2O = 3,4-dimethoxybenzoate + NADH

0

-

1.2.1.3

3,4-dimethoxybenzaldehyde + NAD+ + H2O = 3,4-dimethoxybenzoic acid + NADH + H+

0

-

1.2.1.3

2 entries

1.2.1.67

veratraldehyde + NAD+ + H2O = veratrate + NADH + H+

0

-

1.2.3.1

3,4-dimethoxybenzaldehyde + H2O + O2 = 3,4-dimethoxybenzoate + H2O2

0

-

1.2.3.1

veratraldehyde + H2O + O2 = veratranoate + H2O2

0

-

1.2.3.1

veratraldehyde + H2O + O2 = veratric acid + H2O2

0

-

1.2.3.1

3 entries

1.2.3.9

veratraldehyde + O2 + H2O = veratric acid + H2O2

0

-

2.1.1.25

S-adenosyl-L-methionine + 4-hydroxy-3-methoxybenzoic acid = S-adenosyl-L-homocysteine + 3,4-dimethoxybenzoic acid

0

-

3.1.1.20

1-O-veratroyl-beta-D-glucose + H2O = 3,4-dimethoxybenzoic acid + beta-D-glucose

0

-

3.5.5.1

4,5-dimethoxybenzonitrile + 2 H2O = 4,5-dimethoxybenzoic acid + NH3

0

-

Inhibitor in Enzyme-catalyzed Reactions (3 results)

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Show Inhibitors (3 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.67

-

485518

-

2.4.1.65

-

660797

-

4.2.1.1

-

714459

-

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

2.4.1.136

0.72

-

-

488579

K_i Value (4 results)

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Show KI Value (4 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

4.2.1.1

0.00618

-

isozyme hCAII, pH 7.5, 22°C

714459

4.2.1.1

0.0067

-

isozyme hCAXII, pH 7.5, 22°C

714459

4.2.1.1

0.00683

-

isozyme hCAI, pH 7.5, 22°C

714459

4.2.1.1

0.00825

-

isozyme hCAIX, pH 7.5, 22°C

714459

4.2.1.1

4 entries

References & Links

Literature References (14)

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Show Reference (14 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

288400

10742235

Novel scheme for biosynthesis of aryl metabolites from L-phenylalanine in the fungus Bjerkandera adusta

2000

Lapadatescu, C.; Ginies, C.; Le Quere, J.L.; Bonarme, P.

Appl. Environ. Microbiol.

66

1517-1522

438344

3226294

4-Methoxybenzoate monooxygenase from Pseudomonas putida: isolation, biochemical properties, substrate specificity, and reaction mechanisms of the enzyme components

1988

Bernhardt, F.H.; Bill, E.; Trautwein, A.X.; Twilfer, H.

Methods Enzymol.

161

281-294

438352

4351526

Interactions of substrates with a purified 4-methoxybenzoate monooxygenase system (O-demethylating) from Pseudomonas putida

1973

Bernhardt, F.H.; Erdin, N.; Staudinger, H.; Ullrich, V.

Eur. J. Biochem.

35

126-134

485518

3950915

Thiopurine methyltransferase: structure-activity relationships for benzoic acid inhibitors and thiophenol substrates

1986

Ames, M.M.; Selassie, C.D.; Woodson, L.C.; Van Loon, J.A.; Hansch, C.; Weinshilboum, R.M.

J. Med. Chem.

29

354-358

488579

-

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

1983

Gross, G.

Phytochemistry

22

2179-2182

639289

10671462

Substrate range and genetic analysis of Acinetobacter vanillate demethylase

2000

Morawski, B.; Segura, A.; Ornston, L.N.

J. Bacteriol.

182

1383-1389

660797

15081893

Inhibition of fucosyltransferase VII by gallic acid and its derivatives

2004

Niu, X.; Fan, X.; Sun, J.; Ting, P.; Narula, S.; Lundell, D.

Arch. Biochem. Biophys.

425

51-57

674280

16707678

Metabolism of isovanillate, vanillate, and veratrate by Comamonas testosteroni strain BR6020

2006

Providenti, M.A.; OBrien, J.M.; Ruff, J.; Cook, A.M.; Lambert, I.B.

J. Bacteriol.

188

3862-3869

675042

-

Production and characterization of laccase and manganese peroxidase from the ligninolytic fungus Fomes sclerodermeus

2006

Papinutti, L.; Martinez, M.J.

J. Chem. Technol. Biotechnol.

81

1064-1070

714459

21282059

Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site

2011

Durdagi, S.; Sentuerk, M.; Ekinci, D.; Balaydin, H.T.; Goeksu, S.; Kuefrevioglu, Ö.I.; Innocenti, A.; Scozzafava, A.; Supuran, C.T.

Bioorg. Med. Chem.

19

1381-1389

727349

22695988

The crystal structures of 4-methoxybenzoate bound CYP199A2 and CYP199A4: Structural changes on substrate binding and the identification of an anion binding site

2012

Bell, S.; Yang, W.; Tan, A.; Zhou, R.; Johnson, E.; Zhang, A.; Zhou, W.; Rao, Z.; Wong, L.

Dalton Trans.

41

8703-8714

744457

25008238

Expression and substrate range of Streptomyces vanillate demethylase

2014

Nishimura, M.; Nishimura, Y.; Abe, C.; Kohhata, M.

Biol. Pharm. Bull.

37

1564-1568

764041

11409548

Isolation and characterization of a veratrol corrinoid protein methyl transferase from Acetobacterium dehalogenans

2001

Engelmann, T.; Kaufmann, F.; Diekert, G.

Arch. Microbiol.

175

376-383

765837

-

Microbial manganese peroxidase a ligninolytic enzyme and its ample opportunities in research

2019

Chowdhary, P.; Shukla, G.; Raj, G.; Ferreira, L.; Bharagava, R.

SN Appl. Sci.

1

45

Links to other databases for 3,4-dimethoxybenzoic acid

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Show Links (1 entry)

ChEBI

PubChem