print visible entries

print all entries

Ligand 1,4-dihydroxy-2-naphthoic acid

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

vitamin K metabolism

KEGG

Biosynthesis of cofactors, Biosynthesis of secondary metabolites, Ubiquinone and other terpenoid-quinone biosynthesis

MetaCyc

2-carboxy-1,4-naphthoquinol biosynthesis, alizarin biosynthesis, demethylmenaquinol-4 biosynthesis, demethylmenaquinol-6 biosynthesis I, demethylmenaquinol-8 biosynthesis I, demethylmenaquinol-9 biosynthesis, juglone biosynthesis, lawsone biosynthesis, menaquinol-10 biosynthesis, menaquinol-11 biosynthesis, menaquinol-12 biosynthesis, menaquinol-13 biosynthesis, menaquinol-7 biosynthesis, phylloquinol biosynthesis, superpathway of phylloquinol biosynthesis more

Show all BRENDA pathways known for 1,4-dihydroxy-2-naphthoic acid

close all tables

open all tables

Roles as Enzyme Ligand

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

top print hide

Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.5.1.74

octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate = a demethylmenaquinol + diphosphate + CO2

737563

-

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

top print hide

Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.2.28

1,4-dihydroxy-2-naphthoyl-CoA + H2O = CoA + 1,4-dihydroxy-2-naphthoate

0

-

Substrate in Enzyme-catalyzed Reactions (7 results)

top print hide

Show Substrate (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.13.11.4

1,4-dihydroxy-2-naphthoate + O2 = ?

389985, 672692

-

2.1.1.303

S-adenosyl-L-methionine + 1,4-dihydroxy-2-naphthoic acid = S-adenosyl-L-homocysteine + 1-hydroxy-4-methoxy-2-naphthoate

725380

-

2.5.1.74

all-trans-nonaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H+ = demethylmenaquinol-9 + diphosphate + CO2

696178

-

2.5.1.74

farnesyl diphosphate + 1,4-dihydroxy-2-naphthoate = ? + phosphate + CO2

698552

-

2.5.1.74

farnesyl diphosphate + 1,4-dihydroxy-2-naphthoate = demethylmenaquinone-3 + phosphate + CO2

698675

-

2.5.1.74

octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate = a demethylmenaquinol + diphosphate + CO2

737563

-

2.5.1.74

solanesyl diphosphate + 1,4-dihydroxy-2-naphthoate = demethylmenaquinone + phosphate + CO2

696178

-

2.5.1.74

5 entries

Product in Enzyme-catalyzed Reactions (1 result)

top print hide

Show Product (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.2.28

1,4-dihydroxy-2-naphthoyl-CoA + H2O = CoA + 1,4-dihydroxy-2-naphthoate

0

-

Inhibitor in Enzyme-catalyzed Reactions (5 results)

top print hide

Show Inhibitors (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.2.1.9

the potent inhibitor binds to domain II of the enzyme and inhibits its activity

757239

6o04, 3D-view

2.2.1.9

the potent inhibitor binds to domain II of the enzyme and inhibits its activity

757239

6o0g, 3D-view

2.2.1.9

the potent inhibitor binds to domain II of the enzyme and inhibits its activity

757239

6o0j, 3D-view

2.2.1.9

the potent inhibitor binds to domain II of the enzyme and inhibits its activity

757239

6o0n, 3D-view

2.2.1.9

4 entries

3.4.22.56

-

696717

-

3D Structure of Enzyme-Ligand-Complex (PDB) (12 results)

top print hide

Show 3D Structure of Enzyme-Ligand-Complex (PDB) (12 entries)

EC NUMBER

ENZYME 3D STRUCTURE

2.2.1.9

6o04, 3D-view

2.2.1.9

6o0g, 3D-view

2.2.1.9

6o0j, 3D-view

2.2.1.9

6o0n, 3D-view

2.2.1.9

6o04, 3D-view

2.2.1.9

6o0g, 3D-view

2.2.1.9

6o0j, 3D-view

2.2.1.9

6o0n, 3D-view

2.2.1.9

6o04, 3D-view

2.2.1.9

6o0g, 3D-view

2.2.1.9

6o0j, 3D-view

2.2.1.9

6o0n, 3D-view

2.2.1.9

12 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (1 result)

top print hide

Show Turnover Number (1 entry)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

2.1.1.303

0.000133

-

pH 6.0, 25°C

725380

K_M Value (3 results)

top print hide

Show KM Value (3 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.13.11.4

0.045

-

-

389985

1.13.11.4

0.29

-

-

389985

1.13.11.4

2 entries

2.1.1.303

0.024

-

pH 6.0, 25°C

725380

IC₅₀ Value (3 results)

top print hide

Show IC50 Value (3 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

2.2.1.9

0.000053

-

wild type enzyme, at pH 8.0 and 25°C

757239

2.2.1.9

0.00032

-

mutant enzyme R303A, at pH 8.0 and 25°C

757239

2.2.1.9

0.00103

-

mutant enzyme R97A, at pH 8.0 and 25°C

757239

2.2.1.9

3 entries

References & Links

Literature References (9)

top print hide

Show Reference (9 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

389985

2156846

Gentisate 1,2-dioxygenase from pseudomonas. Purification, characterization, and comparison of the enzymes from Pseudomonas testosteroni and Pseudomonas acidovorans

1990

Harpel, M.R.; Lipscomb, J.D.

J. Biol. Chem.

265

6301-6311

672692

17213679

Gentisate 1,2-dioxygenase from Xanthobacter polyaromaticivorans 127W

2007

Hirano, S.; Morikawa, M.; Takano, K.; Imanaka, T.; Kanaya, S.

Biosci. Biotechnol. Biochem.

71

192-199

696178

949474

Biosynthesis of bacterial menaquinones: the membrane-associated 1,4-dihydroxy-2-naphthoate octaprenyltransferase of Escherichia coli

1976

Shineberg, B.; Young, I.G.

Biochemistry

15

2754-2758

696717

18387304

Structure-based discovery of a novel non-peptidic small molecular inhibitor of caspase-3

2008

Sakai, J.; Yoshimori, A.; Nose, Y.; Mizoroki, A.; Okita, N.; Takasawa, R.; Tanuma, S.

Bioorg. Med. Chem.

16

4854-4859

698552

9573170

Menaquinone (vitamin K2) biosynthesis: localization and characterization of the menA gene from Escherichia coli

1998

Suvarna, K.; Stevenson, D.; Meganathan, R.; Hudspeth, M.E.S.

J. Bacteriol.

180

2782-2787

698675

7275947

Biosynthesis of menaquinones. Enzymic prenylation of 1,4-dihydroxy-2-naphthoate by Micrococcus luteus membrane fractions

1981

Saito, Y.; Ogura, K.

J. Biochem.

89

1445-1452

725380

18387946

Regiospecific O-methylation of naphthoic acids catalyzed by NcsB1, an O-methyltransferase involved in the biosynthesis of the enediyne antitumor antibiotic neocarzinostatin

2008

Luo, Y.; Lin, S.; Zhang, J.; Cooke, H.A.; Bruner. S.D.; Shen, B.

J. Biol. Chem.

283

14694-14702

737563

25772016

Isolation and functional analysis of McMenA, a gene encoding a 1,4-dihydroxy-2-naphthoate octaprenyltransferase in Mylabris cichorii

2015

Liao, Y.F.; Wang, Y.; Huang, Y.; Zha, S.F.; Liu, J.J.; Wang, Z.K.; Yin, Y.P.; Liao, Y.F.; Wang, Y.

Arch. Insect Biochem. Physiol.

89

127-137

757239

32029475

Allosteric regulation of menaquinone (vitamin K2) biosynthesis in the human pathogen Mycobacterium tuberculosis

2020

Bashiri, G.; Nigon, L.V.; Jirgis, E.N.M.; Ho, N.A.T.; Stanborough, T.; Dawes, S.S.; Baker, E.N.; Bulloch, E.M.M.; Johnston, J.M.

J. Biol. Chem.

295

3759-3770

Links to other databases for 1,4-dihydroxy-2-naphthoic acid

top print hide

Show Links (1 entry)

ChEBI

PubChem