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Ligand phenylhydrazine

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

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

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Show Natural Substrate (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.2.B3

(S)-ureidoglycolate + phenylhydrazine = ureidoglycoylphenylhydrazide

715761

-

2.3.2.B3

phenylhydrazine + (S)-ureidoglycolate = 1-[(1S)-hydroxy-2-oxo-2-(2-phenylhydrazinyl)ethyl]urea + H2O

715761

-

2.3.2.B3

2 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

2.3.2.2

5-D/L-glutamyl-phenylhydrazine + acceptor = phenylhydrazine + 5-L-glutamyl-acceptor

487966

-

Substrate in Enzyme-catalyzed Reactions (13 results)

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Show Substrate (13 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.3.15

glycolate + phenylhydrazine = glyoxylate + phenylhydrazone

763602

-

1.1.3.15

L-lactate + phenylhydrazine = pyruvate + phenylhydrazone

763602

-

1.14.13.8

phenylhydrazine + NADPH + H+ + O2 = phenylhydrazine N-oxide + NADP+ + H2O

348490

-

1.14.13.8

phenylhydrazine + NADPH + O2 = ?

348490

-

1.1.3.15

2 entries

1.14.13.8

2 entries

2.3.1.5

acetyl-CoA + phenylhydrazine = CoA + N-acetyl-phenylhydrazine

685029

-

2.3.2.9

gamma-benzyl-L-glutamate + phenylhydrazine = benzoic acid + gamma-L-glutamylphenylhydrazine

488026

-

2.3.2.9

gamma-L-glutamyl-p-hydroxyaniline + phenylhydrazine = p-hydroxyaniline + gamma-L-glutamylphenylhydrazine

488026

-

2.3.2.9

glutamine + phenylhydrazine = beta-N-(gamma-L-glutamyl)phenylhydrazine

488026

-

2.3.2.9

N-gamma-L-glutamylcyclohexylamine + phenylhydrazine = cyclohexylamine + gamma-L-glutamylphenylhydrazine

488026

-

2.3.2.B3

(S)-ureidoglycolate + phenylhydrazine = ureidoglycoylphenylhydrazide

715761

-

2.3.2.B3

phenylhydrazine + (S)-ureidoglycolate = 1-[(1S)-hydroxy-2-oxo-2-(2-phenylhydrazinyl)ethyl]urea + H2O

715761

-

2.3.2.B3

ureidoglycolate + phenylhydrazine = ureidoglycolyl phenylhydrazide + H2O

715761

-

2.3.2.9

4 entries

2.3.2.B3

3 entries

4.1.3.1

isocitrate + phenylhydrazine = ? + glyoxylate phenylhydrazone

653163

-

Product in Enzyme-catalyzed Reactions (2 results)

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Show Product (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.2.2

5-D/L-glutamyl-phenylhydrazine + acceptor = phenylhydrazine + 5-L-glutamyl-acceptor

487966

-

2.3.2.9

beta-N-(gamma-L-glutamyl)phenylhydrazine + H2O = L-glutamate + phenylhydrazine

488026

-

Activator in Enzyme-catalyzed Reactions (3 results)

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Show Activating Compound (3 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.2.3.4

0.1 mM concentration 280% activation

288392

-

3.5.3.9

completely dependent on phenylhydrazine, which acts as an activator at low concentrations and decreases the affinity of the enzyme for the substrate at higher concentrations, the activation is reduced by pyridoxamine-5'-phosphate and pyridoxal-5'-phosphate

689677

-

4.6.1.2

acivation

34843

-

Inhibitor in Enzyme-catalyzed Reactions (148 results)

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Show Inhibitors (148 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.169

carbonyl reagent

286103

-

1.1.1.26

-

286411

-

1.1.1.28

up to 45% inhibition

656314

-

1.1.1.29

-

286506

-

1.1.3.13

-

724083

-

1.1.3.13

1 mM, complete inhibition

484907, 688123

-

1.1.3.13

1% residual activity at 1 mM

740872

-

1.1.3.13

3 entries

1.1.3.39

92.5% inhibition at 2 mM

287628

-

1.1.3.4

-

696865

-

1.1.3.4

30% inhibition at 1 mM

389814

-

1.1.3.4

partial

389806

-

1.1.3.4

3 entries

1.1.3.50

1 mM, 11% inhibition

765689

-

1.1.3.9

1 mM, 91% inhibition

687852

-

1.11.1.11

a suicide substrate

765196

-

1.11.1.13

rapid inactivation, concentration-dependent, no heme adducts detectable, inactivation is slightly stimulated by Co2+

439824

-

1.11.1.19

AnaPX is highly sensitive to the suicide substrate phenylhydrazine (complete inhibition at 1 mM)

695785

-

1.11.1.7

competitive

673966

-

1.11.1.7

100% inhibition at 1 mM

439741

-

1.11.1.7

complete inhibition at 1 mM

695785

-

1.11.1.7

3 entries

1.13.11.88

1 mM, 95% loss of activity

749754

-

1.14.12.17

-

658747

-

1.14.13.105

1 mM, 10% inhibition

684953

-

1.14.18.1

1 mM, 86% inhibition, noncompetitive inhibition

636338

-

1.17.1.5

1 mM, 10 min at 35°C, 15% loss of activity

644529

-

1.17.3.2

-

644645

-

1.2.2.B1

-

288469

-

1.2.3.1

1 mM, 12% residual activity

699045

-

1.2.3.1

1 mM, 6% residual activity

740776

-

1.2.3.1

2 entries

1.21.4.1

-

484927, 484928

-

1.4.3.13

-

391739, 742424

-

1.4.3.19

-

725913

-

1.4.3.2

complete inhibition at 1 mM (pH 5.5)

725575

-

1.4.3.21

-

391914, 391916, 725314

-

1.4.3.21

complete inhibition at 1 mM

742933

-

1.4.3.21

irreversible inactivation most likely due to hydrazone formation

391915

-

1.4.3.22

-

391909, 391925, 391935, 391940, 391941, 391954

-

1.4.3.22

1 mM, complete inhibition; 1 mM, complete inhibition

391953

-

1.4.3.22

10 mM, complete inhibition

656323

-

1.4.3.22

69% inhibition at 0.01 mM

720756

-

1.4.3.4

-

394573

-

1.4.3.4

weak binding; weak binding

702238

-

1.4.9.1

-

396585

-

1.4.9.1

O6 of cysteine tryptophylquinone is the site of inhibitory attack by phenylhydrazine

654076

-

1.4.9.2

-

396589, 396591, 396592

-

1.4.9.2

0.02 mM

685206

-

1.4.3.21

3 entries

1.4.3.22

4 entries

1.4.3.4

2 entries

1.4.9.1

2 entries

1.4.9.2

2 entries

1.5.3.1

slight

392384

-

1.5.3.15

0.1 mM, 95% inhibition

694075

-

1.5.8.2

irreversible inactivation of both wild-type and mutant C30A, 10 times more potent than N-cyclopropyl-alpha-methylbenzylamine

393897

-

1.5.8.2

lowers the requirement of reducing equivalents from three to 0.9

393900

-

1.5.8.2

potent inhibition at very low concentration

393923

-

1.5.8.2

progressive loss of activity by reaction with FMN, trimethylamine or tetramethylammonium chloride protect against inactivation

393913

-

1.5.8.2

4 entries

1.5.99.12

-

288533

-

1.5.99.6

-

392547

-

1.7.2.1

irreversible

665461

-

1.7.2.6

N2H3 protects

394341

-

1.7.2.6

an HAO enzyme specific inhibitor

741829

-

1.7.2.6

an HAO enzyme specific inhibitor, inhibits about 60% of enzyme NeHAO activity at 0.01 mM

741829

-

1.7.2.6

an HAO enzyme specific inhibitor, slight inhibition of enzyme NoHAO activity at 0.01 mM

741829

-

1.7.2.6

4 entries

2.1.1.3

0.01 M

485244

-

2.1.2.1

partially reversible by pyridoxal 5'-phosphate

441410

-

2.3.1.29

-

486740

-

2.3.1.47

-

487052

-

2.3.2.9

strong inhibition

736651

-

2.5.1.47

73% inhibition by 1 mM, 97.4% inhibition by 10 mM

637383

-

2.5.1.48

-

637439

-

2.5.1.49

-

637830, 637834, 637837, 637838, 637839

-

2.5.1.49

95% inhibition at 10 mM, 12% at 1 mM

661358

-

2.5.1.49

2 entries

2.6.1.113

-

739832

-

2.6.1.13

fully reversed by addition of pyridoxal phosphate

637121

-

2.6.1.19

-

637056, 637059

-

2.6.1.2

-

636715

-

2.6.1.21

1 mM; 30% inhibition

636738

-

2.6.1.21

2 mM, 85% inhibition

636742

-

2.6.1.21

2 entries

2.6.1.23

84% inhibition at 1 mM

639934

-

2.6.1.37

1 mM, 20% inhibition

636706

-

2.6.1.4

pyridoxal phosphate restores activity

639987

-

2.6.1.42

-

639995, 640003, 640020, 640032

-

2.6.1.42

1 mM, 0% residual activity

661957

-

2.6.1.42

2 entries

2.6.1.45

weak inhibition

636693

-

2.6.1.5

1 mM, complete inhibition

657704

-

2.6.1.55

0.5 mM, 17% inhibition

636678, 636679

-

2.6.1.57

-

636653

-

2.6.1.57

0.15 mM, 78% inhibition of aromatic aminotransferase from strain CB 60, 56% inhibition of enzyme from strain CB 6

636655

-

2.6.1.57

2 entries

2.6.1.6

-

640167

-

2.6.1.62

-

1335

-

2.6.1.62

100% inhibition at 1 mM

637090

-

2.6.1.62

2 entries

2.6.1.7

0.1 mM, 81% inhibition, reversible by pyridoxal phosphate

636613

-

2.6.1.70

irreversible inhibitor; retains 56% activity at 0.01 mM, retains 18% activity at 0.1 mM

640191

-

2.7.3.1

inhibits phosphorylation of ADP

642366

-

3.1.1.83

1 mM, 17% inhibition

684542

-

3.5.1.101

1 mM, complete inhibition

692156

-

3.5.1.4

complete inhibition at 1 mM

733127

-

3.5.1.6

49% inhibition

172065

-

3.5.1.76

-

31889

-

3.5.1.87

5 mM, 48% inhibition

288945

-

3.5.1.91

23% inhibition at 1 mM

733172

-

3.5.1.91

25% inhibition

660362

-

3.5.1.91

2 entries

3.5.2.14

1 mM

246616

-

3.5.4.4

competitive inhibition

688040

-

3.5.5.1

43% residual activity at 1 mM

684594

-

3.5.5.1

slight inhibition at 1 mM

209746

-

3.5.5.1

2 entries

3.5.5.5

-

32503

-

3.5.5.7

53% residual activity at 5 mM; 5 mM, 47% inhibition

670792

-

3.5.99.11

10 mM, 80% inhibition

172186

-

3.5.99.5

10 mM, 20% inhibition

172186

-

4.1.1.11

-

3947, 3948

-

4.1.1.19

-

4083

-

4.1.1.36

-

4408, 4411, 4415

-

4.1.1.50

-

4672, 4680, 4691

-

4.1.1.50

strong

4668

-

4.1.1.57

-

4721

-

4.1.1.57

1 mM, 29% activity

651387

-

4.1.1.50

2 entries

4.1.1.57

2 entries

4.1.1.64

-

4757

-

4.1.1.92

1 mM, 87% inhibition

711507

-

4.1.1.93

1 mM, 84% inhibition

711887

-

4.1.2.26

1 mM, 52% inhibition

663708

-

4.1.2.49

1 mM, 91% inhibition

715045

-

4.2.1.28

-

5627

-

4.2.1.49

-

5744, 5747, 5754, 5757, 5758

-

4.2.1.84

68% inhibition at 1 mM

703995

-

4.2.1.84

1 mM

648437, 648439, 648440

-

4.2.1.84

1 mM, 20 min at 15ºC, irreversible

648438

-

4.2.1.84

100% inhibition

648450

-

4.2.1.84

4 entries

4.3.1.15

-

6046

-

4.3.1.18

5 mM, DsdSC activity with pyridoxal 5'-phosphate 97.1%, without 4.2%

678079

-

4.3.1.19

-

210839

-

4.3.1.19

reversed by pyridoxal 5'-phosphate

210792, 210846

-

4.3.1.2

-

6059

-

4.3.1.2

20 mM, complete inhibition after 20 min

650542

-

4.3.1.19

2 entries

4.3.1.2

2 entries

4.3.1.3

-

34278

-

4.4.1.1

-

34484

-

4.4.1.1

2.8% residual activity at 5 mM

652626

-

4.4.1.1

alpha,beta-elimination L-homoserine as substrate

586904

-

4.4.1.13

-

34689, 34691

-

4.4.1.13

complete inhibition at 1 mM

34685

-

4.4.1.1

3 entries

4.4.1.13

2 entries

4.4.1.15

-

648731

-

4.5.1.2

-

34751, 34753

-

4.8.1.2

-

677719, 763288

-

4.8.1.2

1 mM, 71.1% inhibition

648793

-

4.8.1.2

inhibits dehydration of (Z)-3-phenylpropionaldoxime, but not of (E/Z)-n-valeraldoxime

650189

-

5.1.1.1

-

673766, 676382

-

5.1.1.1

1 mM, 72% inhibition

650876

-

4.8.1.2

3 entries

5.1.1.1

2 entries

5.1.1.13

-

650892

-

5.1.1.15

-

2088

-

5.4.3.3

-

3397

-

5.4.3.6

-

3405

-

6.1.1.16

-

190

-

6.1.1.16

weak

58

-

6.1.1.16

2 entries

3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (2 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.4.99.4

2agl, 3D-view

1.7.3.4

4n4m, 3D-view

Enzyme Kinetic Parameters

K_M Value (5 results)

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Show KM Value (5 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.13.8

3

-

-

348490

2.3.2.B3

4

-

at pH 7.8 and 22°C

715761

2.3.2.B3

4

-

pH 7.8, 30°C

715761

2.3.2.B3

8.5

-

at pH 7.8 and 22°C

715761

2.3.2.B3

8.5

-

pH 7.8, 30°C

715761

2.3.2.B3

4 entries

K_i Value (8 results)

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Show KI Value (8 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.4.3.22

0.0000015

-

-

391925

1.4.3.22

0.00004

-

-

391940

1.4.3.22

0.00006

-

-

391940

1.4.3.22

0.00025

-

-

391935

1.4.3.4

0.205

-

pH 7.5, MAO-A, determined from competitive inhibition data of substrate oxidation at 25°C

702238

1.4.3.4

0.523

-

pH 7.5, MAO-A, determined from Kitz-Wilson plots of the hydrazine concentration dependence on rates in enzyme inhibition at 15°C

702238

1.4.3.4

0.791

-

pH 7.5, MAO-B, determined from Kitz-Wilson plots of the hydrazine concentration dependence on rates in enzyme inhibition at 15°C

702238

1.4.3.22

4 entries

1.4.3.4

3 entries

3.5.4.4

0.25

-

pH 7.5, 25°C

688040

IC₅₀ Value (4 results)

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Show IC50 Value (4 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.7.2.6

0.00092

-

pH 7.0, 25°C

741829

1.7.2.6

0.00101

-

pH 7.0, 25°C

741829

1.7.2.6

0.00123

-

pH 7.0, 25°C

741829

1.7.2.6

0.00289

-

pH 7.0, 25°C

741829

1.7.2.6

4 entries

References & Links

Literature References (191)

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Show Reference (191 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

58

14693

Sulphur metabolism in Paracoccus denitrificans. Purification, properties and regulation of cysteinyl- and methionyl-tRNA synthetase

1977

Burnell, J.N.; Whatley, F.R.

Biochim. Biophys. Acta

481

266-278

190

16660161

Cysteinyl-tRNA synthetase from Phaseolus aureus. Purification and properties

1977

Burnell, J.N.; Shrift, A.

Plant Physiol.

60

670-674

1335

108512

Microbiological biosynthesis of biotin

1979

Izumi, Y.; Tani, Y.; Ogata, K.

Methods Enzymol.

62

326-338

2088

-

Properties of alpha-amino-epsilon-caprolactam racemase from Achromobacter obae

1983

Ahmed, S.A.; Esaki, N.; Tanaka, H.; Soda, K.

Agric. Biol. Chem.

47

1887-1893

3397

4540127

Purification and properties of beta-lysine mutase, a pyridoxal phosphate and B12 coenzyme dependent enzyme

1973

Baker, J.J.; van der Drift, C.; Stadtman, T.C.

Biochemistry

12

1054-1063

3405

5021987

Biosynthesis of beta-tyrosine

1972

Kurylo-Borowska, Z.; Abramsky, T.

Biochim. Biophys. Acta

264

1-10

3947

3003510

L-Aspartate alpha-decarboxylase

1985

Williamson, J.M.

Methods Enzymol.

113

589-595

3948

381298

Purification and properties of L-aspartate-alpha-decarboxylase, an enzyme that catalyzes the formation of beta-alanine in Escherichia coli

1979

Williamson, J.M.; Brown, G.M.

J. Biol. Chem.

254

8074-8082

4083

1252

Arginine decarboxylase from Lathyrus sativus seedlings. Purification and properties

1975

Ramakrishna, S.; Adiga, P.R.

Eur. J. Biochem.

59

377-386

4408

4459135

Pantothenoylcysteine-4'-phosphate decarboxylase from horse liver

1974

Scandurra, R.; Barboni, E.; Granata, F.; Pensa, B.; Costa, M.

Eur. J. Biochem.

49

1-9

4411

440105

Phosphopantothenoylcysteine decarboxylase from horse liver [4'-phospho-N-(D-pantothenoyl)-L-cysteine carboxy-lyase, EC 4.1.1.36]

1979

Scandurra, R.; Moriggi, M.; Consalvi, V.; Politi, L.

Methods Enzymol.

62

245-248

4415

3307915

Purification and properties of Escherichia coli 4'-phosphopantothenoylcysteine decarboxylase: presence of covalently bound pyruvate

1987

Yang, H.; Abeles, R.H.

Biochemistry

26

4076-4081

4668

6364703

Methionine adenosyltransferase (S-adenosylmethionine synthetase) and S-adenosylmethionine decarboxylase

1984

White Tabor, C.; Tabor, H.

Adv. Enzymol. Relat. Areas Mol. Biol.

56

251-282

4672

6353153

S-Adenosylmethionine decarboxylase (Escherichia coli)

1983

Markham, G.D.; Tabor, C.W.; Tabor, H.

Methods Enzymol.

94

228-230

4680

-

Adenosylmethionine decarboxylase (Escherichia coli W)

1971

Wickner, R.B.; Tabor, C.W.; Tabor, H.

Methods Enzymol.

17B

647-651

4691

1764068

Purification of S-adenosylmethionine decarboxylase from soybean

1991

Yang, Y.G.; Cho, Y.D.

Biochem. Biophys. Res. Commun.

181

1181-1186

4721

-

Purification and properties of L-methionine decarboxylase of Streptomyces sp.

1980

Misono, H.; Kawabata, Y.; Toyosato, M.; Yamamoto, T.; Soda, K.

Bull. Inst. Chem. Res. Kyoto Univ.

58

323-333

4757

-

Fungal thermostable alpha-dialkylamino acid aminotransferase: occurence, purification and characterization

1994

Esaki, N.; Watanabe, M.; Kurihara, T.; Soda, K.

Arch. Microbiol.

161

110-115

5627

-

Purification and properties of propanediol dehydratase from Propionibacterium freudenreichii

1985

Ichikawa, Y.; Horike, Y.; Mori, N.; Hosoi, N.; Kitamoto, Y.

J. Ferment. Technol.

63

135-141

5744

5412708

Identification of alpha-ketobutyrate as the prosthetic group of urocanase from Pseudomonas putida

1970

George, D.J.; Phillips, A.T.

J. Biol. Chem.

245

528-537

5747

-

Urocanase (Pseudomonas putida)

1971

Phillips, A.T.; George, D.J.

Methods Enzymol.

17B

73-79

5754

18470

Presence of tightly bound NAD+ in urocanase of Pseudomonas putida

1977

Egan, R.M.; Phillips, A.T.

J. Biol. Chem.

252

5701-5707

5757

27186

Thioglycolate, competitive inhibitor of urocanase

1978

Hug, D.H.; O'Donnell, P.S.; Hunter, J.K.

Biochem. Biophys. Res. Commun.

81

1435-1442

5758

25660

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Aldoxime dehydratase co-existing with nitrile hydratase and amidase in the iron-type nitrile hydratas(E)-producer Rhodococcus sp. N-771

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FAD-dependent C-glycoside-metabolizing enzymes in microorganisms Screening, characterization, and crystal structure analysis

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