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Ligand 4-hydroxybenzaldehyde

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

4-hydroxymandelate degradation, aerobic toluene degradation

KEGG

Aminobenzoate degradation, Biosynthesis of phenylpropanoids, Bisphenol degradation, Microbial metabolism in diverse environments, Toluene degradation

MetaCyc

4-coumarate degradation (aerobic), 4-coumarate degradation (anaerobic), 4-hydroxybenzoate biosynthesis I (eukaryotes), 4-hydroxybenzoate biosynthesis IV (plants), 4-hydroxymandelate degradation, 4-methylphenol degradation to protocatechuate, Amaryllidacea alkaloids biosynthesis, dhurrin degradation, resveratrol degradation, taxiphyllin bioactivation, vanillin biosynthesis I more

Show all BRENDA pathways known for 4-hydroxybenzaldehyde

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (9 results)

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Show Natural Substrate (9 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.2.1.64

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

743556

-

1.2.1.64

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

288313, 288311

-

1.2.1.64

2 entries

1.2.1.7

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

288334, 288333

-

1.2.1.96

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

733948

-

1.2.1.96

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

288312, 288314

-

1.2.1.96

4-hydroxybenzaldehyde + NADP+ + H2O = 4-hydroxybenzoic acid + NADPH + H+

726788

-

4.1.2.11

cyanide + 4-hydroxybenzaldehyde = (S)-4-hydroxymandelonitrile

651012

-

4.1.2.11

cyanide + 4-hydroxybenzaldehyde = (S)-p-hydroxymandelonitrile

653018

-

4.1.2.11

HCN + 4-hydroxybenzaldehyde = (S)-p-hydroxymandelonitrile

650926

-

1.2.1.96

3 entries

4.1.2.11

3 entries

In Vivo Product in Enzyme-catalyzed Reactions (12 results)

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Show Natural Product (12 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.90

4-hydroxybenzyl alcohol + NAD+ = 4-hydroxybenzaldehyde + NADH

0

-

1.1.3.19

(S)-2-hydroxy-2-(4-hydroxyphenyl)acetate + O2 = 4-hydroxybenzaldehyde + CO2 + H2O2

0

-

1.1.3.7

4-hydroxybenzyl alcohol + O2 = 4-hydroxybenzaldehyde + H2O2

0

-

1.17.9.1

4-cresol + 2 acceptor + H2O = 4-hydroxybenzaldehyde + 2 reduced acceptor

0

-

1.17.9.1

4-cresol + acceptor + H2O = 4-hydroxybenzaldehyde + reduced acceptor

0

-

1.17.9.1

4-cresol + azurin + H2O = 4-hydroxybenzaldehyde + reduced azurin

0

-

1.17.9.1

4-cresol + nitrate + H2O = 4-hydroxybenzaldehyde + ?

0

-

1.17.9.1

4-hydroxybenzyl alcohol + acceptor = 4-hydroxybenzaldehyde + reduced acceptor

0

-

1.17.9.1

4-methylphenol + acceptor + H2O = 4-hydroxybenzaldehyde + reduced acceptor

0

-

1.17.9.1

4-methylphenol + acceptor + H2O = 4-hydroxybenzaldehyde + reduced acceptor + H+

0

-

1.17.9.1

7 entries

4.1.2.11

(S)-4-Hydroxymandelonitrile = Cyanide + 4-hydroxybenzaldehyde

0, 650107

-

4.1.2.61

4-coumaroyl-CoA = 4-hydroxybenzaldehyde + acetyl-CoA

653573

-

Substrate in Enzyme-catalyzed Reactions (70 results)

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Show Substrate (70 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.184

4-hydroxybenzaldehyde + NADPH + H+ = 4-hydroxybenzyl alcohol + NADP+

761884

-

1.1.1.2

4-hydroxybenzaldehyde + NADPH + H+ = 4-hydroxybenzyl alcohol + NADP+

657019

-

1.1.1.91

4-hydroxybenzaldehyde + NADPH + H+ = 4-hydroxybenzyl alcohol + NADP+

389606

-

1.1.1.91

4-hydroxybenzaldehyde + NADPH = 4-hydroxybenzyl alcohol + NADP+

724669

-

1.1.1.91

p-hydroxybenzaldehyde + NADPH + H+ = p-hydroxybenzyl alcohol + NADP+

389598

-

1.1.1.91

3 entries

1.11.1.7

4-hydroxybenzaldehyde + H2O2 = ?

688465

-

1.14.13.7

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

764589

-

1.14.13.84

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

644553, 649387

-

1.14.13.84

4-hydroxybenzaldehyde + NADPH + H+ + O2 = ?

644553

-

1.14.18.1

4-hydroxybenzaldehyde + 1/2 O2 = 3,4-dihydroxybenzaldehyde + H2O

636450

-

1.14.18.1

4-hydroxybenzaldehyde + O2 = ?

726870

-

1.14.13.84

2 entries

1.14.18.1

2 entries

1.17.1.4

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

644562

-

1.17.3.2

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

654034

-

1.2.1.28

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

757496

-

1.2.1.28

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

390228, 389587, 390243

-

1.2.1.28

2 entries

1.2.1.29

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

711095

-

1.2.1.3

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

711095

-

1.2.1.3

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

671512

-

1.2.1.3

2 entries

1.2.1.4

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

712174

-

1.2.1.5

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

685040

-

1.2.1.64

4-hydroxybenzaldehyde + FAD + H2O = 4-hydroxybenzoate + FADH2 + ?

723889

-

1.2.1.64

4-hydroxybenzaldehyde + FMN + H2O = 4-hydroxybenzoate + FMNH2 + ?

723889

-

1.2.1.64

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

743556, 723889

-

1.2.1.64

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

688643, 688652, 288313, 288311

-

1.2.1.64

4-hydroxybenzaldehyde + NADP+ + H2O = 4-hydroxybenzoate + NADPH + 2 H+

723889

-

1.2.1.64

5 entries

1.2.1.65

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

741638

-

1.2.1.67

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

741714, 743835, 743803, 743782, 762865

-

1.2.1.67

4-hydroxybenzaldehyde + NADP+ + H2O = 4-hydroxybenzoate + NADPH + 2 H+

725035

-

1.2.1.67

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

691363

-

1.2.1.7

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

697657

-

1.2.1.7

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

288334, 288333

-

1.2.1.96

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

733948

-

1.2.1.96

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

726788

-

1.2.1.96

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

288312, 288314

-

1.2.1.96

4-hydroxybenzaldehyde + NADP+ + H2O = 4-hydroxybenzoic acid + NADPH + H+

726788

-

1.2.3.1

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

654034, 763618

-

1.2.3.1

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

699045, 656311, 700829

-

1.2.1.67

3 entries

1.2.1.7

2 entries

1.2.1.96

4 entries

1.2.3.1

2 entries

1.2.3.8

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

390446

-

1.2.3.9

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

288398

-

1.2.7.5

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

763075

-

1.2.99.6

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

11939

-

1.2.99.7

4-hydroxybenzaldehyde + H2O + phenyazine methosulfate = 4-hydroxybenzylic acid + reduced phenyazine methosulfate

762827

-

1.6.99.1

NADPH + H+ + 4-hydroxybenzaldehyde = NADP+ + ?

725313

1k03, 3D-view

1.6.99.1

NADPH + H+ + 4-hydroxybenzaldehyde = NADP+ + ?

725313

1oyb, 3D-view

1.6.99.1

NADPH + H+ + 4-hydroxybenzaldehyde = NADP+ + ?

725313

3hgj, 3D-view

1.6.99.1

NADPH + H+ + 4-hydroxybenzaldehyde = NADP+ + ?

725313

4rnv, 3D-view

1.6.99.1

NADPH + H+ + 4-hydroxybenzaldehyde = NADP+ + ?

725313

5k1k, 3D-view

1.6.99.1

NADPH + H+ + 4-hydroxybenzaldehyde = NADP+ + ?

725313

5v4p, 3D-view

2.1.2.1

D-alanine + 4-hydroxybenzaldehyde + H2O = (2S,3S)-2-amino-3-hydroxy-3-(4-hydroxyphenyl)-2-methylpropanoic acid + (2S,3R)-2-amino-3-hydroxy-3-(4-hydroxyphenyl)-2-methylpropanoic acid

755784

-

2.1.2.1

D-serine + 4-hydroxybenzaldehyde + H2O = (2S,3S)-2-amino-3-hydroxy-2-(hydroxymethyl)-3-(4-hydroxyphenyl)propanoic acid + (2S,3R)-2-amino-3-hydroxy-2-(hydroxymethyl)-3-(4-hydroxyphenyl)propanoic acid

755784

-

2.1.2.1

glycine + 4-hydroxybenzaldehyde + H2O = (2S,3S)-2-amino-3-hydroxy-3-(4-hydroxyphenyl)propanoic acid + (2S,3R)-2-amino-3-hydroxy-3-(4-hydroxyphenyl)propanoic acid

755784

-

1.6.99.1

6 entries

2.1.2.1

3 entries

2.2.1.6

4-hydroxybenzaldehyde + pyruvate = ? + CO2

733088

-

2.2.1.9

4-hydroxybenzaldehyde + 2-oxoglutarate = (5R)-5-hydroxy-5-(4-hydroxyphenyl)-4-oxopentanoic acid + CO2

705201

-

2.4.1.218

UDP-glucose + 4-hydroxybenzaldehyde = UDP + 4-beta-D-glucopyranosyloxy-benzaldehyde

658631

-

2.4.1.218

UDP-glucose + 4-hydroxybenzaldehyde = UDP + 4-formylphenyl beta-D-glucopyranoside

393094

-

2.4.1.218

2 entries

2.4.1.85

UDP-glucose + 4-hydroxybenzaldehyde = UDP + 4-formylphenyl beta-D-glucopyranoside

489458

-

2.6.1.119

(S)-1-phenylethylamine + 4-hydroxybenzaldehyde = ?

756287

-

4.1.1.7

4-Hydroxy-benzaldehyde + acetaldehyde = 2-Hydroxy-1-(4-hydroxy-phenyl)-propan-1-one

655499

-

4.1.1.7

4-hydroxybenzaldehyde + acetaldehyde = (S)-2-Hydroxy-1-(4-hydroxy-phenyl)-propan-1-one

655230

-

4.1.2.10

cyanide + 4-hydroxybenzaldehyde = (2R)-(4-hydroxyphenyl)(hydroxy)ethanenitrile

701695

-

4.1.2.10

cyanide + 4-hydroxybenzaldehyde = (R)-4-hydroxymandelonitrile

704762, 746785

-

4.1.2.11

cyanide + 4-hydroxybenzaldehyde = (S)-4-hydroxymandelonitrile

651012, 704762

-

4.1.2.11

cyanide + 4-hydroxybenzaldehyde = (S)-p-hydroxymandelonitrile

653018

-

4.1.2.11

HCN + 4-hydroxybenzaldehyde = (S)-4-hydroxymandelonitrile

651012, 650926, 650107, 653018

-

4.1.2.11

HCN + 4-hydroxybenzaldehyde = (S)-p-hydroxymandelonitrile

650926

-

4.1.1.7

2 entries

4.1.2.10

2 entries

4.1.2.11

4 entries

4.1.2.38

2 4-hydroxybenzaldehyde = (2R)-2-hydroxy-1,2-bis(4-hydroxyphenyl)ethan-1-one

762916

-

4.1.2.42

4-hydroxybenzaldehyde + glycine = D-4-hydroxyphenylserine

682892

-

4.1.2.45

4-hydroxybenzaldehyde + pyruvate = (3E)-4-(4-hydroxyphenyl)-2-oxobut-3-enoate + H2O

695728

-

4.1.2.47

cyanide + 4-hydroxybenzaldehyde = (2S)-(4-hydroxyphenyl)(hydroxy)ethanenitrile

650854

-

4.2.1.84

4-hydroxybenzaldehyde + HCN + H2O = ? + H2O

654314

-

Product in Enzyme-catalyzed Reactions (34 results)

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Show Product (34 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.90

4-hydroxybenzyl alcohol + NAD+ = 4-hydroxybenzaldehyde + NADH

0

-

1.1.1.91

salicyl alcohol + NADP+ = p-hydroxybenzaldehyde + NADPH

0

-

1.1.1.97

4-hydroxybenzyl alcohol + NADP+ = 4-hydroxybenzaldehyde + NADPH

287558, 287557

-

1.1.3.19

(S)-2-hydroxy-2-(4-hydroxyphenyl)acetate + O2 = 4-hydroxybenzaldehyde + CO2 + H2O2

0

-

1.1.3.38

4-(methoxymethyl)phenol + O2 + H2O = 4-hydroxybenzaldehyde + methanol + H2O2

0, 10669

-

1.1.3.38

4-hydroxybenzyl alcohol + O2 = 4-hydroxybenzaldehyde + H2O2

10666

-

1.1.3.7

4-hydroxybenzyl alcohol + O2 = 4-hydroxybenzaldehyde + H2O2

0

-

1.1.3.7

4-hydroxybenzyl alcohol + O2 = 4-hydroxybenzyl aldehyde + H2O2

0

-

1.1.3.38

2 entries

1.1.3.7

2 entries

1.14.17.1

1-(4-hydroxybenzyl)imidazole + ascorbate + O2 = 4-hydroxybenzaldehyde + dehydroascorbate + H2O + ?

438616

-

1.14.99.15

4-methoxybenzaldehyde + AH2 + O2 = 4-hydroxybenzaldehyde + formaldehyde + A + H2O

0

-

1.17.9.1

4-cresol + 2 acceptor + H2O = 4-hydroxybenzaldehyde + 2 reduced acceptor

0

-

1.17.9.1

4-cresol + acceptor + H2O = 4-hydroxybenzaldehyde + reduced acceptor

437867, 437868, 437870, 437872, 437873, 437875, 437876, 437877, 437878, 437879, 437880, 437883, 437884, 437886, 0, 437864, 437874, 437865, 437869, 437871, 288313, 437866, 437882, 437885

-

1.17.9.1

4-cresol + azurin + H2O = 4-hydroxybenzaldehyde + reduced azurin

0

-

1.17.9.1

4-cresol + Fe3+ + H2O = 4-hydroxybenzaldehyde + Fe2+

0

-

1.17.9.1

4-cresol + nitrate + H2O = 4-hydroxybenzaldehyde + ?

0

-

1.17.9.1

4-hydroxybenzyl alcohol + acceptor = 4-hydroxybenzaldehyde + reduced acceptor

0

-

1.17.9.1

4-hydroxybenzyl alcohol + Fe3+ + H2O = 4-hydroxybenzaldehyde + Fe2+

0

-

1.17.9.1

4-methylphenol + acceptor + H2O = 4-hydroxybenzaldehyde + reduced acceptor

0

-

1.17.9.1

4-methylphenol + acceptor + H2O = 4-hydroxybenzaldehyde + reduced acceptor + H+

0

-

1.17.9.1

4-methylphenol + phenazine methosulfate + H2O = 4-hydroxybenzaldehyde + reduced phenazine methosulfate + H+

0

-

1.17.9.1

10 entries

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 + ?

0

-

1.2.99.6

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

0

-

3.1.1.2

4-acetoxybenzaldehyde + H2O = 4-hydroxybenzaldehyde + acetate

0

-

3.1.8.1

diethyl 4-formylphenyl phosphate + H2O = diethyl phosphate + 4-formylphenol

0

-

3.1.8.1

4-diethyl phosphate benzaldehyde + H2O = 4-hydroxybenzaldehyde + diethyl phosphate

0

-

3.2.1.21

dhurrin + H2O = 4-hydroxybenzaldehyde + hydrogen cyanide + D-glucose

0

-

3.2.1.21

dhurrin + H2O = HCN + beta-D-glucose + 4-hydroxybenzaldehyde

326271

-

3.2.1.21

taxiphyllin + H2O = 4-hydroxybenzaldehyde + hydrogen cyanide + D-glucose

0

-

3.1.8.1

2 entries

3.2.1.21

3 entries

4.1.2.10

(R)-4-hydroxymandelonitrile = cyanide + 4-hydroxybenzaldehyde

0

-

4.1.2.11

(S)-4-Hydroxymandelonitrile = Cyanide + 4-hydroxybenzaldehyde

0, 4892, 4895, 650107, 4889

-

4.1.2.61

4-coumaroyl-CoA + H2O = 4-hydroxybenzaldehyde + acetyl-CoA

0

-

4.1.2.61

4-coumaroyl-CoA = 4-hydroxybenzaldehyde + acetyl-CoA

653573

-

4.1.2.61

4-hydroxycinnamoyl-CoA + H2O = 4-hydroxybenzaldehyde + acetyl-CoA

210668

-

4.1.2.61

3 entries

Inhibitor in Enzyme-catalyzed Reactions (24 results)

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Show Inhibitors (24 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.10.3.15

-

674768, 713565

-

1.10.3.4

-

713565

-

1.10.3.4

-

674768

-

1.10.3.4

2 entries

1.13.11.27

50% inhibition above 10 mM, noncompetitive

395375

-

1.14.13.2

2 mM, 27% inhibition

390040

-

1.14.13.2

slight

390019

-

1.14.13.2

2 entries

1.14.17.1

-

438616

-

1.14.18.1

-

696650, 697303, 699195

-

1.14.18.1

16.4% inhibition at 0.2 mM

697744

-

1.14.18.1

2 entries

1.2.1.16

-

288048

-

1.2.1.24

-

288150, 288158, 288163, 288165, 288166, 288170

-

1.2.1.24

10 mM, 82% inhibition

288173

-

1.2.1.24

linear dead-end inhibition, competitive versus succinate semialdehyde, uncompetitive versus NAD+

742640

-

1.2.1.24

more than 95% inhibition at 0.05 mM

700082

-

1.2.1.24

4 entries

1.2.1.60

-

288300

-

1.3.1.20

-

349254

-

1.3.1.42

-

699588

-

2.4.1.219

strong inhibition at 5 mM

488935

-

2.4.1.85

potent inhibitor, 1 mg/ml bovine serum albumin protects

489461

-

2.6.1.19

competitive inhibitor of GABA transaminase

702606

-

2.6.1.19

IC50: 0.0165 mM, competitive inhibition

672609

-

2.6.1.19

potent inhibitor

672598

-

2.6.1.19

3 entries

2.7.4.2

2.5 mM, 11% inhibition

645179

-

4.1.3.40

-

650373

-

3D Structure of Enzyme-Ligand-Complex (PDB) (42 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (42 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.11.1.5

4jqn, 3D-view

1.3.1.92

5dy3, 3D-view

1.5.1.30

5k1k, 3D-view

1.6.99.1

1k03, 3D-view

1.6.99.1

1oyb, 3D-view

1.6.99.1

3hgj, 3D-view

1.6.99.1

4rnv, 3D-view

1.6.99.1

5k1k, 3D-view

1.6.99.1

5v4p, 3D-view

1.6.99.1

1k03, 3D-view

1.6.99.1

1oyb, 3D-view

1.6.99.1

3hgj, 3D-view

1.6.99.1

4rnv, 3D-view

1.6.99.1

5k1k, 3D-view

1.6.99.1

5v4p, 3D-view

1.6.99.1

1k03, 3D-view

1.6.99.1

1oyb, 3D-view

1.6.99.1

3hgj, 3D-view

1.6.99.1

4rnv, 3D-view

1.6.99.1

5k1k, 3D-view

1.6.99.1

5v4p, 3D-view

1.6.99.1

1k03, 3D-view

1.6.99.1

1oyb, 3D-view

1.6.99.1

3hgj, 3D-view

1.6.99.1

4rnv, 3D-view

1.6.99.1

5k1k, 3D-view

1.6.99.1

5v4p, 3D-view

1.6.99.1

1k03, 3D-view

1.6.99.1

1oyb, 3D-view

1.6.99.1

3hgj, 3D-view

1.6.99.1

4rnv, 3D-view

1.6.99.1

5k1k, 3D-view

1.6.99.1

5v4p, 3D-view

1.6.99.1

1k03, 3D-view

1.6.99.1

1oyb, 3D-view

1.6.99.1

3hgj, 3D-view

1.6.99.1

4rnv, 3D-view

1.6.99.1

5k1k, 3D-view

1.6.99.1

5v4p, 3D-view

1.6.99.1

36 entries

3.4.19.12

7oft, 3D-view

4.2.1.37

1eb9, 3D-view

4.2.1.78

2vq5, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (10 results)

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Show Turnover Number (10 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.13.84

7.6

-

pH 8, 30°C

649387, 644553

1.14.18.1

0.19

-

pH and temperature not specified in the publication

726870

1.2.1.28

20

-

-

389587

1.2.1.7

4

-

apparent Kcat

697657

1.2.1.96

0.0017

-

with NAD+ as cosubstrate, at pH 8.0 and 30°C

726788

1.2.1.96

0.26

-

with NADP+ as cosubstrate, at pH 8.0 and 30°C

726788

1.2.3.1

0.53

-

wild-type, pH 8.0, 37°C

763618

1.2.3.1

0.91

-

pH 8, 37°C

763618

1.2.3.1

1.94

-

pH 8, 37°C

763618

1.2.3.1

4.31

-

pH 8, 37°C

763618

1.2.1.96

2 entries

1.2.3.1

4 entries

K_M Value (22 results)

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Show KM Value (22 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.2

21.8

-

pH 6.5, 30°C

657019

1.1.1.91

0.09

-

-

389598

1.14.13.84

0.1

-

pH 8, 30°C

649387

1.14.13.84

0.101

-

pH 8, 30°C

644553

1.14.18.1

1.14

-

pH and temperature not specified in the publication

726870

1.14.18.1

6.37

-

-

636450

1.14.13.84

2 entries

1.14.18.1

2 entries

1.17.3.2

0.17

-

-

654034

1.2.1.28

0.018

-

-

389587

1.2.1.64

0.0548

-

apparent Km-value, pH 7.5 and 35°C

723889

1.2.1.7

0.006

-

apparent KM

697657

1.2.1.96

0.00357

-

with NADP+ as cosubstrate, at pH 8.0 and 30°C

726788

1.2.1.96

0.01311

-

with NAD+ as cosubstrate, at pH 8.0 and 30°C

726788

1.2.3.1

0.0019

-

wild-type, pH 8.0, 37°C

763618

1.2.3.1

0.0026

-

30°C, pH 7.0

699045

1.2.3.1

0.0027

-

pH 8, 37°C

763618

1.2.3.1

0.0028

-

pH 8, 37°C

763618

1.2.3.1

0.008

-

37°C, pH 7.0

654034

1.2.3.1

0.0346

-

pH 8, 37°C

763618

1.2.1.96

2 entries

1.2.3.1

6 entries

1.2.99.6

12

-

with carbamoyl methyl viologen as cosubstrate

11939

1.2.99.7

0.75

-

pH 6, 30°C

762827

4.1.2.10

6

-

pH 5.0, 25°C

704762

4.1.2.11

5.9

-

pH 5.0, 25°C

704762

K_i Value (6 results)

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Show KI Value (6 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.10.3.15

1.9

-

at pH 7.0 and 55°C

674768

1.10.3.4

1.9

-

-

674768

1.14.17.1

2.3

-

-

438616

1.2.1.24

3.37

-

pH 9.0, 37°C, versus succinate semmialdehyde

742640

1.2.1.24

3.9

-

pH 9.0, 37°C, versus NAD+

742640

1.2.1.24

2 entries

4.1.3.40

0.33

-

pH 7.5, wild-type enzyme

650373

IC₅₀ Value (6 results)

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Show IC50 Value (6 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.14.18.1

1.12

-

-

696650

1.14.18.1

1.15

-

-

699195

1.14.18.1

1.22

-

in 50 mM Na2HPO4-NaH2PO4 buffer (pH 6.8), at 25°C

697744

1.14.18.1

1.22

-

in 50 mM phosphate buffer (pH 6.8), at 25°C

697303

2.6.1.19

0.0165

-

-

702606

2.6.1.19

0.0165

-

IC50: 0.0165 mM, competitive inhibition

672609

1.14.18.1

4 entries

2.6.1.19

2 entries

References & Links

Literature References (137)

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Show Reference (137 entries)

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PUBMED ID

TITLE

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AUTHORS

JOURNAL

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Potato tuber succinate semialdehyde dehydrogenase: purification and characterization

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Purification and properties of two succinate semialdehyde dehydrogenases from human brain

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Biochim. Biophys. Acta

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288166

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Purification and properties of rat brain succinic semialdehyde dehydrogenase

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288173

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Formation and reduction of intermediate acyladenylate by aryl-aldehyde. NADP oxidoreductase from Neurospora crassa

1972

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Reduction of aromatic acids to aldehydes and alcohols in the cell-free system. 1. Purification and properties of aryl-aldehyde: NADP-oxidoreductase from Neurospora crassa

1969

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Eur. J. Biochem.

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288300

6756482

Carboxymethylhydroxymuconic semialdehyde dehydrogenase in the 4-hydroxyphenylacetate catabolic pathway of Escherichia coli

1982

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Biochim. Biophys. Acta

719

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288311

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Formation of p-hydroxybenzoic acid from p-coumaric acid by cell free extract of Lithospermum erythrorhizon cell cultures

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Phytochemistry

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288312

10565539

Organization and sequences of p-hydroxybenzaldehyde dehydrogenase and other plasmid-encoded genes for early enzymes of the p-cresol degradative pathway in Pseudomonas putida NCIMB 9866 and 9869

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DNA Seq.

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288313

2722739

Anaerobic oxidation of p-cresol mediated by a partially purified methylhydroxylase from a denitrifying bacterium

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4383635

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5294-5300

288398

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Production of an aromatic aldehyde oxidase by Streptomyces viridosporus

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349254

7852295

Purification and characterization of dimeric dihydrodiol dehydrogenase from dog liver

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389587

3060114

Benzyl alcohol dehydrogenase and benzaldehyde dehydrogenase II from Acinetobacter calcoaceticus. Substrate specificities and inhibition studies

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653-661

389598

-

Aromatic alcohol dehydrogenase from potato tubers

1973

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Phytochemistry

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531-536

389606

1997322

Purification and properties of an aryl-alcohol dehydrogenase from the white-rot fungus Phanerochaete chrysosporium

1991

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4402938

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1972

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390040

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Properties of NADH/NADPH-dependent p-hydroxybenzoate hydroxylase from Moraxella sp

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17

77-90

390228

2597133

Purification and characterization of benzaldehyde dehydrogenase I from Acinetobacter calcoaceticus [published erratum appears in Biochem J 1990 Feb 1;265(6):931]

1989

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Biochem. J.

263

913-919

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11882941

Benzoic acid biosynthesis in cell cultures of Hypericum androsaemum

2002

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Planta

214

727-733

390446

6808989

Tissue-specific and substrate-specific detection of aldehyde and pyridoxal oxidase in larval and imaginal tissues of Drosophila melanogaster

1982

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393094

11937332

Arbutin synthase, a novel member of the NRD1beta glycosyltransferase family, is a unique multifunctional enzyme converting various natural products and xenobiotics

2002

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10

1731-1741

395375

7118918

Blue color, metal content, and substrate binding in 4-hydroxyphenylpyruvate dioxygenase from Pseudomonas sp. strain P. J. 874

1982

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257

11922-11931

437864

588247

The purification and properties of p-cresol-(acceptor) oxidoreductase (hydroxylating), a flavocytochrome from Pseudomonas putida

1977

Hopper, D.J.; Taylor, D.G.

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167

155-162

437865

736904

Incorporation of [18O]water in the formation of p-hydroxybenzyl alcohol by the p-cresol methylhydroxylase from Pseudomonas putida

1978

Hopper, D.J.

Biochem. J.

175

345-347

437866

7391034

8 alpha-O-Tyrosyl-FAD: a new form of covalently bound flavin from p-cresol methylhydroxylase

1980

McIntire, W.; Edmondson, D.E.; Singer, T.P.; Hopper, D.J.

J. Biol. Chem.

255

6553-6555

437867

7248267

8 alpha-(O-Tyrosyl)flavin adenine dinucleotide, the prosthetic group of bacterial p-cresol methylhydroxylase

1981

McIntire, W.; Edmondson, D.E.; Hopper, D.J.; Singer, T.P.

Biochemistry

20

3068-3075

437868

6309572

Redox potential of the cytochrome c in the flavocytochrome p-cresol methylhydroxylase

1983

Hopper, D.J.

FEBS Lett.

161

100-102

437869

-

Azurin from Pseudomonas putida: an electron acceptor for p-cresol methylhydroxylase

1984

Causer, M.J.; Hopper, D.J.; McIntire, W.S.; Singer, T.P.

Biochem. Soc. Trans.

12

1131-1132

437870

6083780

Stereochemistry of 1-(4-hydroxyphenyl)ethanol produced by hydroxylation of 4-ethylphenol by p-cresol methylhydroxylase

1984

McIntire, W.; Hopper, D.J.; Craig, J.C.; Everhart, E.T.; Webster, R.V.; Causer, M.J.; Singer, T.P.

Biochem. J.

224

617-621

437871

3920077

Periplasmic location of p-cresol methylhydroxylase in Pseudomonas putida

1985

Hopper, D.J.; Jones, M.R.; Causer, M.J.

FEBS Lett.

182

485-488

437872

2990445

Laser-flash-photolysis studies of p-cresol methylhydroxylase. Electron-transfer properties of the flavin and haem components

1985

Bhattacharyya, A.; Tollin, G.; McIntire, W.; Singer, T.P.

Biochem. J.

228

337-345

437873

4020868

Preliminary X-ray study of p-cresol methylhydroxylase (flavocytochrome c) from Pseudomonas putida N.C.I.B. 9869

1985

Shamala, N.; Lim, L.W.; Mathews, F.S.

J. Mol. Biol.

183

517-518

437874

2990444

p-Cresol methylhydroxylase. assay and general properties

1985

McIntire, W.; Hopper, D.J.; Singer, T.P.

Biochem. J.

228

325-335

437875

4074695

Resolution of the flavocytochrome p-cresol methylhydroxylase into subunits and reconstitution of the enzyme

1985

Koerber, S.C.; McIntire, W.; Bohmont, C.; Singer, T.P.

Biochemistry

24

5276-5280

437876

7929007

Cloning, sequencing, and expression of the structural genes for the cytochrome and flavoprotein subunits of p-cresol methylhydroxylase from two strains of Pseudomonas putida

1994

Kim, J.; Fuller, J.H.; Cecchini, G.; McIntire, W.S.

J. Bacteriol.

176

6349-6361

437877

3460061

Structure of an intermolecular electron-transfer complex: p-cresol methylhydroxylase at 6.0-A resolution

1986

Shamala, N.; Lim, L.W.; Mathews, F.S.; McIntire, W.; Singer, T.P.; Hopper, D.J.

Proc. Natl. Acad. Sci. USA

83

4626-4630

437878

3790500

Amino acid and sequence analysis of the cytochrome and flavoprotein subunits of p-cresol methylhydroxylase

1986

McIntire, W.; Singer, T.P.; Smith, A.J.; Mathews, F.S.

Biochemistry

25

5975-5981

437879

3651440

Steady-state and stopped-flow kinetic measurements of the primary deuterium isotope effect in the reaction catalyzed by p-cresol methylhydroxylase

1987

McIntire, W.S.; Hopper, D.J.; Singer, T.P.

Biochemistry

26

4107-4117

437880

743215

p-Cresol and 3,5-xylenol methylhydroxylases in Pseudomonas putida N.C.I.B. 9896

1978

Keat, M.J.; Hopper, D.J.

Biochem. J.

175

649-658

437882

10623531

Structures of the flavocytochrome p-cresol methylhydroxylase and its enzyme-substrate complex: Gated substrate entry and proton relays support the proposed catalytic mechanism

2000

Cunane, L.M.; Chen, Z.W.; Shamala, N.; Mathews, F.S.; Cronin, C.N.; McIntire, W.S.

J. Mol. Biol.

295

357-374

437883

10600124

Properties of p-cresol methylhydroxylase flavoprotein overproduced by Escherichia coli

1999

Engst, S.; Kuusk, V.; Efimov, I.; Cronin, C.N.; McIntire, W.S.

Biochemistry

38

16620-16628

437884

8537385

The cytochrome subunit is necessary for covalent FAD attachment to the flavoprotein subunit of p-cresol methylhydroxylase

1995

Kim, J.; Fuller, J.H.; Kuusk, V.; Cunane, L.; Chen, Z.; Mathews, F.S.; McIntire, W.S.

J. Biol. Chem.

270

31202-31209

437885

11329284

Effects of noncovalent and covalent FAD binding on the redox and catalytic properties of p-cresol methylhydroxylase

2001

Efimov, I.; Cronin, C.N.; McIntire, W.S.

Biochemistry

40

2155-2166

437886

10833393

Heterologous expression in Pseudomonas aeruginosa and purification of the 9.2-kDa c-type cytochrome subunit of p-cresol methylhydroxylase

2000

Cronin, C.N.; McIntire, W.S.

Protein Expr. Purif.

19

74-83

438616

3593236

Interaction of dopamine beta-mono-oxygenase with substituted imidazoles and pyrazoles. Catalysis and inhibition

1987

Sirimanne, S.R.; Herman, H.H.; May, S.W.

Biochem. J.

242

227-233

488935

-

Enzymatic formation of Raucaffricine, the major indole alkaloid of Rauwolfia serpentina cell-suspension cultures

1991

Ruyter, C.M.; Stoeckigt, J.H.H.

Helv. Chim. Acta

74

1707-1712

489458

4416442

The purification and properties of a uridine diphosphate glucose: aldehyde cyanohydrin beta-glucosyltransferase from sorghum seedlings

1974

Reay, P.F.; Conn, E.E.

J. Biol. Chem.

249

5826-5830

489461

10585420

The UDP-glucose:p-hydroxymandelonitrile-O-glucosyltransferase that catalyzes the last step in synthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor. Isolation, cloning, heterologous expression, and substrate specificity

1999

Jones, P.R.; Moller, B.L.; Hoj, P.B.

J. Biol. Chem.

274

35483-35491

636450

11453787

Properties of diphenolase from Vanilla planifolia (Andr.) shoot primordia cultured in vitro

2001

Debowska, R.; Podstolski, A.

J. Agric. Food Chem.

49

3432-3437

644553

11322873

4- Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB: a novel flavoprotein catalyzing Baeyer-Villiger oxidation of aromatic compounds

2001

Kamerbeek, N.M.; Moonen, M.J.; van der Ven, J.G.; van Berkel, W.J.H.; Fraaije, M.W.; Janssen, D.B.

Eur. J. Biochem.

268

2547-2557

644562

11341925

Xanthine dehydrogenase from Pseudomonas putida 86: Specificity, oxidation-reduction potentials of its redox-active centers, and first EPR characterization

2001

Parschat, K.; Canne, C.; Huttermann, J.; Kappl, R.; Fetzner, S.

Biochim. Biophys. Acta

1544

151-165

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

649387

12514023

Substrate specificity and enantioselectivity of 4-hydroxyacetophenone monooxygenase

2003

Kamerbeek, N.M.; Olsthoorn, A.J.J.; Fraaije, M.W.; Janssen, D.B.

Appl. Environ. Microbiol.

69

419-426

650107

12356304

Crystal structure of hydroxynitrile lyase from Sorghum bicolor in complex with the inhibitor benzoic acid: a novel cyanogenic enzyme

2002

Lauble, H.; Miehlich, B.; Foerster, S.; Wajant, H.; Effenberger, F.

Biochemistry

41

12043-12050

650373

11825618

Chorismate lyase: kinetics and engineering for stability

2002

Holden, M.J.; Mayhew, M.P.; Gallagher, D.T.; Vilker, V.L.

Biochim. Biophys. Acta

1594

160-167

650854

12616635

Substrate specificity of mutants of the hydroxynitrile lyase from Manihot esculenta

2003

Bühler, H.; Effenberger, F.; Förster, S.; Roos, J.; Wajant, H.

ChemBioChem

4

211-216

650926

11102786

Hydroxynitrile lyases in stereoselective catalysis

2000

Effenberger, F.; Foerster, S.; Wajant, H.

Curr. Opin. Biotechnol.

11

532-539

651012

-

Hydroxynitrile lyase-catalyzed synthesis of cyanohydrins in organic solvents. Parameters influencing activity and enantiospecificity

1999

Costes, D.; Wehtje, E.; Adlercreutz, P.

Enzyme Microb. Technol.

25

384-391

653018

-

Biopolymers for biocatalysis: Structure and catalytic mechanism of hydroxynitrile lyases

2004

Gruber, K.; Kratky, C.

J. Polym. Sci. A

42

479-486

653573

12012244

4-Hydroxycinnamoyl-CoA hydratase/lyase, an enzyme of phenylpropanoid cleavage from Pseudomonas, causes formation of C(6)-C(1) acid and alcohol glucose conjugates when expressed in hairy roots of Datura stramonium L.

2002

Mitra, A.; Mayer, M.J.; Mellon, F.A.; Michael, A.J.; Narbad, A.; Parr, A.J.; Waldron, K.W.; Walton, N.J.

Planta

215

79-89

654034

15448727

Kinetics and specificity of guinea pig liver aldehyde oxidase and bovine milk xanthine oxidase towards substituted benzaldehydes

2004

Panoutsopoulos, G.I.; Beedham, C.

Acta Biochim. Pol.

51

649-663

654314

14666389

Characterisation of nitrilase and nitrile hydratase biocatalytic systems

2004

Brady, D.; Beeton, A.; Zeevaart, J.; Kgaje, C.; van Rantwijk, F.; Sheldon, R.A.

Appl. Microbiol. Biotechnol.

64

76-85

655230

10840971

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