Ligand 4-hydroxybenzoic acid

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Basic Ligand Information

Molecular Structure

C₇H₆O₃

4-hydroxybenzoic acid

FJKROLUGYXJWQN-UHFFFAOYSA-N

Synonyms:

4-carboxyphenol, 4-hydroxybenzoate, 4-hydroxy benzoic acid, oxybenzoate, p-hydroxybenzoate, p-hydroxybenzoic acid, p-hydroxy benzoic acid

BRENDA

4-hydroxymandelate degradation, aerobic toluene degradation, phenol degradation, ubiquinone biosynthesis

KEGG

Aminobenzoate degradation, Benzoate degradation, Benzoic acid family, Biosynthesis of cofactors, Biosynthesis of phenylpropanoids

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MetaCyc

4-chlorobenzoate degradation, 4-coumarate degradation (aerobic), 4-coumarate degradation (anaerobic), 4-hydroxybenzoate biosynthesis I (eukaryotes), 4-hydroxybenzoate biosynthesis II (bacteria)

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Show all BRENDA pathways known for 4-hydroxybenzoic acid

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (103 results)

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1.1.1.24

p-hydroxybenzoate + O2 = protocatechuic acid + H2O

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

S-adenosyl-L-methionine + 4-hydroxybenzoate = S-adenosyl-L-homocysteine + methyl 4-hydroxybenzoate

725781

2.4.1.177

UDP-glucose + 4-hydroxybenzoate = UDP + 4-hydroxybenzoyl beta-D-glucoside

759563

2.4.2.54

5-phospho-alpha-D-ribose 1-diphosphate + 4-hydroxybenzoate = 4-(beta-D-ribofuranosyl)phenol 5'-phosphate + CO2 + diphosphate

geranyl diphosphate + 4-hydroxybenzoate = 3-geranyl-4-hydroxybenzoate + diphosphate

704405, 737898, 738205, 721942, 759206, 702133, 706366

6.2.1.27

ATP + 4-hydroxybenzoate + CoA = AMP + diphosphate + 4-hydroxybenzoyl-CoA

712275, 648907, 648909, 288500, 712273, 16327

6.2.1.50

2 entries

In Vivo Product in Enzyme-catalyzed Reactions (21 results)

4-hydroxybenzaldehyde + NADP+ + H2O = 4-hydroxybenzoate + NADPH + H+

4-Hydroxybenzoyl-CoA + H2O = 4-Hydroxybenzoate + CoA

3.1.2.23

3 entries

3.8.1.6

4-chlorobenzoate + H2O = 4-hydroxybenzoate + Cl-

289297, 289296

4.1.1.123

phenyl phosphate + CO2 + H2O = 4-hydroxybenzoate + phosphate

4.1.3.40

chorismate = 4-hydroxybenzoate + pyruvate

Substrate in Enzyme-catalyzed Reactions (225 results)

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1.1.1.24

p-hydroxybenzoate + O2 = protocatechuic acid + H2O

4-hydroxybenzoic acid + H2O2 + H+ = ?

4-hydroxybenzoic acid + O2 = ?

4-hydroxybenzoate + O2 = ?

671549

1.14.13.114

4-hydroxybenzoate + NADH + H+ + O2 = hydroquinone + NAD+ + H2O + CO2

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

684919

1.14.13.27

4-hydroxybenzoate + NAD(P)H + O2 = quinol + NAD(P)+ + H2O2 + CO2

4-hydroxybenzoate + ? = 3,4-dihydroxybenzoate + ?

4-hydroxybenzoate + NADH + O2 = 3,4-dihydroxybenzoate + NAD+ + H2O

438344, 438345, 438346, 438349, 438351, 438348

1.2.1.30

p-hydroxybenzoic acid + NADPH + ATP = p-hydroxybenzaldehyde + NADP+ + AMP + H2O

288180, 288182

1.2.3.9

p-hydroxybenzoic acid + ? = p-hydroxybenzaldehyde + ?

288400

1.2.99.6

4-Hydroxybenzoate + reduced carbamoyl methyl viologen = 4-Hydroxybenzaldehyde + carbamoyl methyl viologen

11943

2.1.1.274

S-adenosyl-L-methionine + 4-hydroxybenzoate = S-adenosyl-L-homocysteine + methyl 4-hydroxybenzoate

725781

2.4.1.120

UDP-alpha-D-glucose + 4-hydroxybenzoic acid = UDP + 1-O-(4-hydroxybenzoyl)-beta-D-glucose

488516

2.4.1.136

UDP-alpha-D-glucose + 4-hydroxybenzoate = UDP + 1-O-(4-hydroxybenzoyl)-beta-D-glucopyranose

UDPglucose + 4-hydroxybenzoate = UDP + 4-(beta-D-glucosyloxy)benzoate

636882, 636883

2.4.1.35

UDP-glucose + 4-hydroxybenzoic acid = UDP + 4-hydroxybenzoyl 3-O-beta-D-glucoside

757325

2.4.1.85

UDPglucose + 4-hydroxybenzoic acid = UDP + glucosyl-4-hydroxybenzoate

geranyl diphosphate + 4-hydroxybenzoate = 4-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]benzoic acid

geranyl diphosphate + 4-hydroxybenzoate = 3-geranyl-4-hydroxybenzoate + diphosphate

704405, 737898, 738205, 721942, 759206, 702133, 706366

2.8.2.22

2 entries

4.1.1.61

4-Hydroxybenzoate = Phenol + CO2

677849, 4728, 4742, 4744, 4743, 4741, 4740, 650756, 679381, 691579

6.2.1.25

ATP + 4-hydroxybenzoate + CoA = AMP + diphosphate + 4-hydroxybenzoyl-CoA

651721, 744341, 649526, 662016, 675454

ATP + 4-hydroxybenzoic acid + holo-[aryl-carrier protein] = AMP + diphosphate + 4-hydroxybenzoyl-[aryl-carrier protein]

752747

Product in Enzyme-catalyzed Reactions (104 results)

4-hydroxybenzaldehyde + NADPH + H+ + O2 = 4-hydroxybenzoate + NADP+ + H2O

0, 649387

1.14.14.1

benzoic acid + [reduced NADPH-hemoprotein reductase] + O2 = 4-hydroxybenzoic acid + [oxidized NADPH-hemoprotein reductase] + H2O

4-hydroxybenzaldehyde + NAD+ + H2O = 4-hydroxybenzoate + NADH + H+

1.17.3.2

4-hydroxybenzaldehyde + H2O + O2 = 4-hydroxybenzoate + H2O2

1.2.1.28

2 entries

1.2.1.29

4-hydroxybenzaldehyde + NAD+ + H2O = 4-hydroxybenzoic acid + NADH + H+

1.2.1.3

2 entries

1.2.1.4

4-hydroxybenzaldehyde + NADP+ + H2O = 4-hydroxybenzoate + NADPH + H+

1.2.1.5

p-hydroxybenzaldehyde + NADP+ + H2O = p-hydroxybenzoic acid + NADPH + H+

1.2.1.64

5 entries

1.2.1.65

4-hydroxybenzaldehyde + NAD+ + H2O = 4-hydroxybenzoate + NADH + 2 H+

4-hydroxybenzaldehyde + H2O + O2 = 4-hydroxybenzoate + ?

1.2.3.9

p-hydroxybenzaldehyde + O2 + H2O = p-hydroxybenzoic acid + H2O2

1.2.7.5

4-hydroxybenzaldehyde + H2O + 2 oxidized benzyl viologen = 4-hydroxybenzoate + 2 H+ + 2 reduced benzyl viologen

1.2.99.6

4-Hydroxybenzaldehyde + carbamoyl methyl viologen = 4-Hydroxybenzoate + reduced carbamoyl methyl viologen

11939

2.4.1.299

1-O-4-hydroxybenzoyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside = 4-hydroxybenzoate + cyanidin 3,5-di-O-beta-D-glucoside

4-carboxyphenyl acetate + H2O = 4-carboxyphenol + acetate

4-acetoxybenzoate + H2O = 4-hydroxybenzoate + acetate

3.1.1.6

4-acetoxybenzoic acid + H2O = 4-hydroxybenzoate + acetate

p-hydroxybenzoyl-Ala + H2O = p-hydroxybenzoate + Ala

N-4-hydroxybenzoylglycine + H2O = 4-hydroxybenzoate + glycine

4-hydroxybenzonitrile + H2O = 4-hydroxybenzoic acid + NH3

3.8.1.6

3 entries

3.8.1.7

4-chlorobenzoate + H2O = 4-hydroxybenzoate + chloride

4.1.1.103

Phenol + CO2 = 4-Hydroxybenzoate

4.1.1.123

phenyl phosphate + CO2 + H2O = 4-hydroxybenzoate + phosphate

Activator in Enzyme-catalyzed Reactions (2 results)

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2.8.2.1

activation of P-PST and M-PST

645686

3.2.1.21

109.7% activity at 2.5 mM with cellobioside as substrate

749779

Inhibitor in Enzyme-catalyzed Reactions (127 results)

47.0% inhibition at 0.015 mM, active site binding structure

product inhibition

38% inhibition at 4.5 mM

0.1 mM, 79% inhibition

695533

1.4.99.6

21.4% residual activity at 0.1 mM

5 mM, 88% loss of activity

718828

2.7.4.2

2.5 mM, 28% inhibition

competitive

isolated from seeds of Syagrus romanzoffiana

682301

3.2.1.21

97.5% residual activity at 2.5 mM with 4-nitrophenyl beta-D-glucopyranoside as substrate

3D Structure of Enzyme-Ligand-Complex (PDB) (235 results)

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (49 results)

311.7

native enzyme, at 30Â°C

696482

1.14.13.114

0.074

pH 7.5, 25Â°C, recombinant wild-type enzyme

0.002

in 100 mM Na-TAPS (pH 8.5), at 30Â°C

0.93

pH 8.0, 31Â°C, recombinant wild-type enzyme

744341

6.2.1.27

2 entries

K_M Value (87 results)

18.76

native enzyme, at 30Â°C

6.33

0.029

3.45

5.6

in 100 mM Na-TAPS (pH 8.5), at 30Â°C

0.158

pH 8.0, 31Â°C, recombinant wild-type enzyme

744341

6.2.1.27

3 entries

K_i Value (17 results)

1.1

mutant enzyme V1M, at pH 6.0 and 20Â°C

764028

1.13.11.66

0.014

pH 7.0, 25Â°C

3.2

2.3

0.07

pH 4.8, 50Â°C, Ki(slope)

0.00932

at pH 7.5 and 20Â°C

696622

IC₅₀ Value (7 results)

1.3

0.062

0.0564

pH 6.5, 37Â°C

682301

3.4.15.1

2 entries

References & Links

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Show Reference (246 entries)

Ligand 4-hydroxybenzoic acid

Basic Ligand Information

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (103 results)

In Vivo Product in Enzyme-catalyzed Reactions (21 results)

Substrate in Enzyme-catalyzed Reactions (225 results)

Product in Enzyme-catalyzed Reactions (104 results)

Activator in Enzyme-catalyzed Reactions (2 results)

Inhibitor in Enzyme-catalyzed Reactions (127 results)

3D Structure of Enzyme-Ligand-Complex (PDB) (235 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (49 results)

KM Value (87 results)

Ki Value (17 results)

IC50 Value (7 results)

References & Links

Literature References (246)

k_cat Value (Turnover Number) (49 results)

K_M Value (87 results)

K_i Value (17 results)

IC₅₀ Value (7 results)