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Ligand 3-amino-4-hydroxybenzoic acid

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for 3-amino-4-hydroxybenzoic acid

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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

1.10.3.15

3-amino-4-hydroxybenzoate + N-acetyl-L-cysteine + O2 = grixazone B + H2O + CO2

674768, 722650

-

1.14.13.249

3-amino-4-hydroxybenzoate + NADPH + H+ + O2 = 3-amino-2,4-dihydroxybenzoate + NADP+ + H2O

743674, 762905, 763490

-

2.3.1.5

acetyl-CoA + 3-amino-4-hydroxybenzoic acid = CoA + 3-acetylamino-4-hydroxybenzoic acid

674321

-

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.1.99.20

2-amino-4,5-dihydroxy-6-oxo-7-(phosphonooxy)heptanoate = 3-amino-4-hydroxybenzoate + phosphate + 2 H2O

0

-

4.1.99.20

2-amino-4,5-dihydroxy-6-oxo-7-(phosphooxy)heptanoate = 3-amino-4-hydroxybenzoate + phosphate + 2 H2O

0

-

4.1.99.20

2 entries

Substrate in Enzyme-catalyzed Reactions (8 results)

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Show Substrate (8 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.10.3.15

3-amino-4-hydroxybenzoate + N-acetyl-L-cysteine + O2 = grixazone B + H2O + CO2

674768, 722650

-

1.10.3.2

3-amino-4-hydroxybenzoic acid + O2 = ?

724662

-

1.14.13.249

3-amino-4-hydroxybenzoate + NADPH + H+ + O2 = 3-amino-2,4-dihydroxybenzoate + NADP+ + H2O

743674, 762905, 763490

-

1.14.13.64

3-Amino-4-hydroxybenzoate + NADH + O2 = ?

7428

-

1.14.13.64

3-Amino-4-hydroxybenzoate + NADPH + O2 = ?

7428

-

2.3.1.5

acetyl-CoA + 3-amino-4-hydroxybenzoic acid = CoA + 3-(acetylamino)-4-hydroxybenzoic acid

685192

-

2.3.1.5

acetyl-CoA + 3-amino-4-hydroxybenzoic acid = CoA + 3-acetylamino-4-hydroxybenzoic acid

674321

-

2.3.1.5

acetyl-CoA + 3-amino-4-hydroxybenzoic acid = CoA + N-acetyl-3-amino-4-hydroxybenzoic acid

685192

-

1.14.13.64

2 entries

2.3.1.5

3 entries

Product in Enzyme-catalyzed Reactions (2 results)

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Show Product (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.1.99.20

2-amino-4,5-dihydroxy-6-oxo-7-(phosphonooxy)heptanoate = 3-amino-4-hydroxybenzoate + phosphate + 2 H2O

0

-

4.1.99.20

2-amino-4,5-dihydroxy-6-oxo-7-(phosphooxy)heptanoate = 3-amino-4-hydroxybenzoate + phosphate + 2 H2O

0

-

4.1.99.20

2 entries

Inhibitor in Enzyme-catalyzed Reactions (3 results)

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Show Inhibitors (3 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.11.1.21

50 mM, 30% residual activity

743032

-

1.13.11.74

20% inhibition at 0.05 mM

722493

-

1.13.11.8

-

439360

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (3 results)

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Show Turnover Number (3 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.13.64

8.3

-

-

7428

2.3.1.5

1.3

-

pH 7.0, 30°C, recombinant enzyme

674321

2.3.1.5

94

-

-

685192

2.3.1.5

2 entries

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

1.14.13.64

0.013

-

4-hydroxy-3-nitrobenzoate

7428

2.3.1.5

0.32

-

-

685192

2.3.1.5

2

-

pH 7.0, 30°C, recombinant enzyme

674321

2.3.1.5

2 entries

References & Links

Literature References (12)

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Show Reference (12 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

7428

9352916

Purification and properties of 4-hydroxybenzoate 1-hydroxylase (decarboxylating), a novel flavin adenine dinucleotide-dependent monooxygenase from Candida parapsilosis CBS604

1997

Eppink, M.H.M.; Boeren, S.A.; Vervoort, J.; van Berkel, W.J.H.

J. Bacteriol.

179

6680-6687

439360

2997190

Water and nitric oxide binding by protocatechuate 4,5-dioxygenase and catechol 2,3-dioxygenase. Evidence for binding of exogenous ligands to the active site Fe2+ of extradiol dioxygenases

1985

Arciero, D.M.; Orville, A.M.; Lipscomb, J.D.

J. Biol. Chem.

260

14035-14044

674321

17158669

Arylamine N-acetyltransferase responsible for acetylation of 2-aminophenols in Streptomyces griseus

2007

Suzuki, H.; Ohnishi, Y.; Horinouchi, S.

J. Bacteriol.

189

2155-2159

674768

16282322

A novel o-aminophenol oxidase responsible for formation of the phenoxazinone chromophore of grixazone

2006

Suzuki, H.; Furusho, Y.; Higashi, T.; Ohnishi, Y.; Horinouchi, S.

J. Biol. Chem.

281

824-833

685192

18795795

Kinetic and chemical mechanism of arylamine N-acetyltransferase from Mycobacterium tuberculosis

2008

Sikora, A.L.; Frankel, B.A.; Blanchard, J.S.

Biochemistry

47

10781-10789

722493

8892823

2-Aminophenol 1,6-dioxygenase: a novel aromatic ring cleavage enzyme purified from Pseudomonas pseudoalcaligenes JS45

1996

Lendenmann, U.; Spain, J.C.

J. Bacteriol.

178

6227-6232

722650

17003031

Novel benzene ring biosynthesis from C3 and C4 primary metabolites by two enzymes

2006

Suzuki, H.; Ohnishi, Y.; Furusho, Y.; Sakuda, S.; Horinouchi, S.

J. Biol. Chem.

281

36944-36951

724662

21266052

Bacillus pumilus laccase: a heat stable enzyme with a wide substrate spectrum

2011

Reiss, R.; Ihssen, J.; Thoeny-Meyer, L.

BMC Biotechnol.

11

9-9

743032

27016935

Heterologous expression and characterization of a new heme-catalase in Bacillus subtilis 168

2016

Philibert, T.; Rao, Z.; Yang, T.; Zhou, J.; Huang, G.; Irene, K.; Samuel, N.

J. Ind. Microbiol. Biotechnol.

43

729-740

743674

21825154

Dedicated ent-kaurene and ent-atiserene synthases for platensimycin and platencin biosynthesis

2011

Smanski, M.; Yu, Z.; Casper, J.; Lin, S.; Peterson, R.; Chen, Y.; Wendt-Pienkowski, E.; Rajski, S.; Shen, B.

Proc. Natl. Acad. Sci. USA

108

13498-13503

762905

26278892

The cremeomycin biosynthetic gene cluster encodes a pathway for diazo formation

2015

Waldman, A.; Pechersky, Y.; Wang, P.; Wang, J.; Balskus, E.

ChemBioChem

16

2172-2175

763490

26689788

A nitrous acid biosynthetic pathway for diazo group formation in bacteria

2016

Sugai, Y.; Katsuyama, Y.; Ohnishi, Y.

Nat. Chem. Biol.

12

73-75

Links to other databases for 3-amino-4-hydroxybenzoic acid

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Show Links (1 entry)

ChEBI

PubChem