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Roles as Enzyme Ligand
Enzyme Kinetic Parameters
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Ligand 4-nitrophenyl beta-D-glucuronide

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Basic Ligand Information

Molecular Structure

Picture of 4-nitrophenyl beta-D-glucuronide (click for magnification)

Molecular Formula

BRENDA Name

InChIKey

C₁₂H₁₃NO₉

4-nitrophenyl beta-D-glucuronide

QSUILVWOWLUOEU-GOVZDWNOSA-N

Synonyms:

(4-nitrophenyl beta-D-glucopyranoside)uronate, 4-nitrophenol beta-D-glucuronide, 4-nitrophenyl-beta-D-glucuronide, 4-nitrophenyl-beta-glucuronide, 4-nitrophenyl beta-D-glucopyranosiduronic acid, 4-nitrophenyl beta-D-glucuronic acid, 4-nitrophenyl beta-D-glucuronopyranoside, 4-nitrophenyl beta-D-glucuronoside, 4-nitrophenyl beta-O-D-glucuronoside, 4-nitrophenyl O-beta-D-glucuronoside, beta-D-glucuronosyl-(4-nitrophenol), p-nitrophenyl-beta-D-glucuronide, p-nitrophenyl beta-D-glucuronic acid, p-nitrophenyl beta-D-glucuronide

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Roles as Enzyme Ligand

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

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EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.17

UDP-D-glucuronate + 4-nitrophenol = UDP + 4-nitrophenyl O-beta-D-glucuronoside

Substrate in Enzyme-catalyzed Reactions (19 results)

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EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.2.1.139

p-nitrophenyl-beta-D-glucuronide + H2O = p-nitrophenol + D-glucuronate

26102

3.2.1.167

4-nitrophenyl beta-D-glucuronide + H2O = 4-nitrophenol + beta-D-glucuronic acid

666782, 709499

3.2.1.167

4-nitrophenyl beta-D-glucuronide + H2O = 4-nitrophenol + D-glucuronate

731207

3.2.1.23

4-nitrophenyl beta-D-glucuronide + H2O = 4-nitrophenol + beta-D-glucuronate

713883

3.2.1.23

4-nitrophenyl beta-D-glucuronide + H2O = 4-nitrophenol + beta-D-glucuronic acid

704135

3.2.1.23

p-nitrophenyl beta-D-glucuronide + H2O = p-nitrophenol + ?

656940

3.2.1.23

p-nitrophenyl-beta-D-glucuronide + H2O = p-nitrophenol + beta-D-glucose

665014

3.2.1.31

4-nitrophenol beta-D-glucuronide + H2O = 4-nitrophenol + beta-D-glucuronate

751117

3.2.1.31

4-nitrophenyl beta-D-glucopyranosiduronic acid + 4-nitrophenyl beta-D-glucopyranosiduronic acid = 4-nitrophenol + 4-nitrophenyl 3-O-beta-D-glucopyranuronosyl-beta-D-glucopyranosiduronic acid + 4-nitrophenyl 2-O-beta-D-glucopyranuronosyl-beta-D-glucopyranosiduronic acid

26869, 657383

3.2.1.31

4-nitrophenyl beta-D-glucuronic acid + H2O = 4-nitrophenol + D-glucuronic acid

697118

3.2.1.31

4-nitrophenyl beta-D-glucuronide + H2O = 4-nitrophenol + beta-D-glucuronate

731480, 752284, 709499, 752283

3.2.1.31

4-nitrophenyl beta-D-glucuronide + H2O = 4-nitrophenol + beta-D-glucuronic acid

26865, 665527, 666274, 664529

3.2.1.31

4-nitrophenyl beta-D-glucuronide + H2O = 4-nitrophenol + D-glucuronic acid

26854, 682636, 26849, 26859, 697926, 26868, 26869, 680040, 26871, 681051, 700710, 26857, 26847, 679993, 677746, 747459

3.2.1.31

p-nitrophenyl-beta-D-glucuronide + H2O = D-glucuronate + ?

655962

3.2.1.31

p-nitrophenyl-beta-D-glucuronide + H2O = p-nitrophenol + beta-D-glucuronic acid

655172, 654250

3.2.1.31

p-nitrophenyl-beta-D-glucuronide + H2O = p-nitrophenol + D-glucuronate

654922

3.2.1.31

p-nitrophenyl-beta-D-glucuronide + H2O = p-nitrophenol + D-glucuronic acid

4-nitrophenyl beta-D-glucuronide + H2O = 4-nitrophenol + D-glucose

724764

3.2.1.B44

4-nitrophenyl beta-D-glucuronopyranoside + H2O = 4-nitrophenol + D-glucuronate

749672

Product in Enzyme-catalyzed Reactions (11 results)

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EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.17

UDP-glucuronate + 4-nitrophenol = UDP + 4-nitrophenol beta-D-glucuronide

2.4.1.17

4-nitrophenol + UDP-glucuronate = 4-nitrophenyl beta-D-glucuronide + UDP

488729, 488747, 488748, 488750, 488722, 488751, 488696, 488761, 488786, 0, 488695, 488697, 488698, 488704, 488706, 488712, 488715, 488718, 488719, 488730, 488734, 488735, 488737, 488738, 488739, 488740, 488745, 488756, 488760, 488771, 488705, 488708, 488714, 488726, 488728, 488731, 488765, 488775, 488782, 488759, 488702, 488725

2.4.1.17

4-nitrophenol + UDP-glucuronate = UDP + 4-nitrophenyl beta-D-glucuronide

2.4.1.17

UDP-glucuronate + 4-nitrophenol = UDP + 4-nitrophenyl beta-D-glucuronide

2.4.1.17

UDP-D-glucuronate + 4-nitrophenol = UDP + 4-nitrophenyl beta-D-glucuronoside

2.4.1.17

UDP-D-glucuronate + 4-nitrophenol = UDP + 4-nitrophenyl beta-O-D-glucuronoside

2.4.1.17

UDP-D-glucuronate + 4-nitrophenol = UDP + 4-nitrophenyl O-beta-D-glucuronoside

2.4.1.17

UDP-glucuronate + 4-nitrophenol = UDP + beta-D-glucuronosyl-(4-nitrophenol)

2.4.1.17

8 entries

2.4.1.35

UDPglucuronic acid + p-nitrophenol = dTDP + p-nitrophenyl beta-D-glucuronic acid

3.1.1.117

methyl (4-nitrophenyl beta-D-glucopyranoside)uronate + H2O = methanol + (4-nitrophenyl beta-D-glucopyranoside)uronate

3.1.1.117

methyl (4-nitrophenyl beta-D-glucopyranosid)uronate + H2O = 4-nitrophenyl beta-D-glucopyranosiduronic acid + methanol

3.1.1.117

2 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (14 results)

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EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

3.2.1.167

31.8

recombinant His-tagged enzyme, pH 5.0, 37Â°C

731207

3.2.1.167

53.7

native enzyme, pH 5.0, 37Â°C

731207

3.2.1.31

0.001

wild-type enzyme

665527

3.2.1.31

0.33

65Â°C, pH 6.5, mutant enzyme E383A

747459

3.2.1.31

0.67

pH 7.2, 37Â°C

697926

3.2.1.31

0.98

65Â°C, pH 6.5, mutant enzyme E383Q

747459

3.2.1.31

65Â°C, pH 6.5, wild-type enzyme

747459

3.2.1.31

pH 6.5, 65Â°C, recombinant His6-tagged enzyme

664529

3.2.1.31

75Â°C, pH 6.5, wild-type enzyme

747459

3.2.1.31

pH 6.5, 75Â°C, recombinant His6-tagged enzyme

200

1100

mutant enzyme Q493R/T509A/M532T/N550S/G559S/N566S

682636

3.2.1.31

1500

wild type enzyme

0.26

pH 4.5, 45Â°C

749672

K_M Value (15 results)

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EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.2.1.167

0.154

native enzyme, pH 5.0, 37Â°C

731207

3.2.1.167

0.156

recombinant His-tagged enzyme, pH 5.0, 37Â°C

731207

3.2.1.31

0.0046

65Â°C, pH 6.5, mutant enzyme E383Q

747459

3.2.1.31

0.0065

65Â°C, pH 6.5, mutant enzyme E383A

747459

3.2.1.31

0.083

65Â°C, pH 6.5, wild-type enzyme

747459

3.2.1.31

0.13

2.9

26854, 26849, 26859, 26868, 26869, 26857, 26847

3.2.1.31

0.15

75Â°C, pH 6.5, wild-type enzyme

747459

3.2.1.31

0.152

pH 6.5, 75Â°C, recombinant His6-tagged enzyme

664529

3.2.1.31

0.208

wild type enzyme

682636

3.2.1.31

0.22

pH 7.0, 37Â°C

654922

3.2.1.31

0.23

pH 4.6, 37Â°C

655172

3.2.1.31

0.36

wild-type enzyme

665527

3.2.1.31

0.414

mutant enzyme Q493R/T509A/M532T/N550S/G559S/N566S

682636

3.2.1.31

1.4

pH 7.2, 37Â°C

25.56

pH 4.5, 45Â°C

749672

References & Links

Literature References (82)

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BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

26102

9300126

Bacteroides J-37, a human intestinal bacterium, produces alpha-glucuronidase

1997

Kim, D.H.; Jang, H.S.; Lee, S.W.

Biol. Pharm. Bull.

834-837

26847

6530397

exo-beta-D-Glucuronidase from the fungus Kobayasia nipponica

1984

Tsuchihashi, H.; Yadome, T.; Miyazaki, T.

J. Biochem.

1789-1797

26849

6416296

Isolation and characterization of the major form of beta-glucuronidase from human seminal plasma

1983

Gupta, G.S.; Singh, G.P.

Biochim. Biophys. Acta

748

398-404

26854

Characterization of immobilized beta-glucuronidase in aqueous and mixed solvent systems

1981

Bowers, L.D.; Johnson, P.R.

Biochim. Biophys. Acta

661

100-105

26857

428383

Properties of two molecular forms of beta-glucuronidase from the mollusc Littorina littorea L

1979

Diez, T.; Cabezas, J.A.

Eur. J. Biochem.

301-311

26859

413568

Purification and properties of beta-glucuronidase from human placenta

1978

Brot, F.E.; Bell, C.E.; Sly, W.S.

Biochemistry

385-391

26865

1194264

Purification and chemical properities of mouse liver lysosomal (L form) beta-glucuronidase

1975

Tomino, S.; Paigen, K.

J. Biol. Chem.

250

8503-8509

26868

236293

beta-Glucuronidase of rat preputial gland. Crystallization, properties, carbohydrate composition, and subunits

1975

Himeno, M.; Ohhara, H.; Arakawa, Y.; Kato, K.

J. Biochem.

427-438

26869

4457546

beta-Glucuronidase of bovine liver. Purification, properties, carbohydrate composition

1974

Himeno, M.; Hashiguchi, Y.; Kato, K.

J. Biochem.

766

1243-1252

26871

4215418

Rabbit beta-glucuronidase. Purification and properties, and the existence of multiple forms

1974

Dean, R.T.

Biochem. J.

138

395-405

488695

6404284

UDP-glucuronosyltransferase activities. Guidelines for consistent interim terminology and assay conditions

1983

Bock, K.W.; Burchell, B.; Dutton, G.J.; HÃ¤nninen, O.; Mulder, G.J.; Owens, I.S.; Siest, G.; Tephly, T.R.

Biochem. Pharmacol.

953-955

488696

Identification and purification of multiple forms of UDP-glucuronosyltransferase

1981

Burchell, B.

Rev. Biochem. Toxicol.

1-32

488697

3931633

Strain differences in purified rat hepatic 3alpha-hydroxysteroid UDP-glucuronosyltransferase

1985

Green, M.D.; Falany, C.N.; Kirkpatrick, R.B.; Tephly, T.R.

Biochem. J.

230

403-409

488698

111930

Purification of rat-liver microsomal UDP-glucuronyltransferase. Separation of two enzyme forms inducible by 3-methylcholanthrene or phenobarbital

1979

Bock, K.W.; Josting, D.; Lilienblum, W.; Pfeil, H.

Eur. J. Biochem.

19-26

488702

1599427

Multiplicity of UDP-glucuronosyltransferases in fish. Purification and characterization of a phenol UDP-glucuronosyltransferase from the liver of a marine teleost, Pleuronectes platessa

1992

Clarke, D.J.; George, S.G.; Burchell, B.

Biochem. J.

284

417-423

488704

1939026

Differential effects of phospholipids on two similar forms of UDP-glucuronyltransferase purified from rat liver and kidney microsomes

1991

Yokota, H.; Fukuda, T.; Yuasa, A.

J. Biochem.

110

50-53

488705

1900286

Effects of cholesterol on the function and thermotropic properties of pure UDP-glucuronosyltransferase

1991

Rotenberg, M.; Zakim, D.

J. Biol. Chem.

266

4159-4161

488706

2108023

Inhibition of UDP-glucuronosyltransferase activity by possible transition-state analogues in rat-liver microsomes

1990

Noort, D.; Coughtrie, M.W.H.; Burchell, B.; van der Marel, G.A.; van Boom, J.H.; van der Gen, A.; Mulder, G.J.

Eur. J. Biochem.

188

309-312

488708

2106830

Effect of brief treatment at alkaline pH on the properties of UDP-glucuronosyltransferase

1990

Dannenberg, A.; Wong, T.; Zakim, D.

Arch. Biochem. Biophys.

277

312-317

488712

2509439

Purification and properties of UDP-glucuronyltransferase from kidney microsomes of beta-naphthoflavone-treated rat

1989

Yokota, H.; Ohgiya, N.; Ishihara, G.; Ohta, K.; Yuasa, A.

J. Biochem.

106

248-252

488714

2491848

Regulation of UDP-glucuronosyltransferase by lipid-protein interactions. Comparison of the thermotropic properties of pure reconstituted enzyme with microsomal enzyme

1989

Dannenberg, A.; Rotenberg, M.; Zakim, D.

J. Biol. Chem.

264

238-242

488715

3149280

Purification and properties of a form of UDP-glucuronyltransferase from liver microsomes of 3-methylcholanthrene-treated rats

1988

Yokota, H.; Yuasa, A.; Sato, R.

J. Biochem.

104

531-536

488718

3099767

Substrate specificity and characterization of rat liver p-nitrophenol, 3alpha-hydroxysteroid and 17beta-hydroxysteroid UDP-glucuronosyltransferases

1986

Falany, C.N.; Green, M.D.; Swain, E.; Tephly, T.R.

Biochem. J.

238

65-73

488719

3085655

Isolation and characterization of multiple forms of rat liver UDP-glucuronate glucuronosyltransferase

1986

Roy Chowdhury, J.; Roy Chowdhury, N.; Falany, C.N.; Tephly, T.R.; Arias, I.M.

Biochem. J.

233

827-837

488722

6428319

Purification and immunochemical characterization of a low-pI form of UDP glucuronosyltransferase from mouse liver

1984

Mackenzie, P.I.; Hjelmeland, L.M.; Owens, I.S.

Arch. Biochem. Biophys.

231

487-497

488725

6416180

Separation, purification and characterization of three isoenzymes of UDP-glucuronyltransferase from rat liver microsomes

1983

Falany, C.N.; Tephly, T.R.

Arch. Biochem. Biophys.

227

248-258

488726

6403523

A comparison of the kinetic properties of two different forms of microsomal UDPglucuronyltransferase

1983

Hochman, Y.; Zakim, D.

J. Biol. Chem.

258

4143-4146

488728

6794456

Purification of properties of rabbit liver estrone and p-nitrophenol UDP-glucuronyltransferases

1981

Tukey, R.H.; Tephly, T.R.

Arch. Biochem. Biophys.

209

565-578

488729

6788550

The phospholipid-dependence of UDP glucuronosyltransferase. Purification, delipidation and reconstitution of microsomal enzyme from guinea-pig liver

1981

Singh, O.M.; Graham, A.B.; Wood, G.C.

Eur. J. Biochem.

116

311-316

488730

6799732

4-Nitrophenol UDPglucuronyltransferase (rat liver)

1981

Burchell, B.; Weatherill, P.

Methods Enzymol.

169-177

488731

6799733

Estrone and 4-nitrophenol UDPglucuronyltransferases (rabbit liver)

1981

Tukey, R.H.; Tephly, T.R.

Methods Enzymol.

177-188

488734

6779813

The separation and purification of rat liver UDP-glucuronyltransferase activities towards testosterone and oestrone

1980

Weatherill, P.J.; Burchell, B.

Biochem. J.

189

377-380

488735

6766875

Isolation and purification of bilirubin UDP-glucuronyl-transferase from rat liver

1980

Burchell, B.

FEBS Lett.

111

131-135

488737

101208

Substrate specificity and properties of uridine diphosphate glucuronyltransferase purified to apparent homogeneity from phenobarbital-treated rat liver

1978

Burchell, B.

Biochem. J.

173

749-757

488738

402364

Purification and properties of microsomal UDP-glucuronosyltransferase from rat liver

1977

Gorski, J.P.; Kasper, C.B.

J. Biol. Chem.

252

1336-1343

488739

406146

Purification of UDP-glucuronyltransferase from untreated rat liver

1977

Burchell, B.

FEBS Lett.

101-104

488740

403910

Studies on the purification of rat liver uridine diphosphate glucuronyltransferase

1977

Burchell, B.

Biochem. J.

161

543-549

488745

Heterogeneity of hepatic microsomal uridine diphosphate glucuronosyltransferase: a critical evaluation

1974

Mulder, G.J.

Biochem. Soc. Trans.

1172-1176

488747

4196676

Kinetic properties of microsomal UDP-glucuronyltransferase. Evidence for cooperative kinetics and activation by UDP-N-acetylglucosamine

1973

Vessey, D.A.; Goldenberg, J.; Zakim, D.

Biochim. Biophys. Acta

309

58-66

488748

4200892

Effects of metals on the properties of hepatic microsomal uridine diphosphate glucuronyltransferase

1973

Zakim, D.; Goldenberg, J.; Vessey, D.A.

Biochemistry

4068-4074

488750

4635820

Kinetic properties of different forms of hepatic UDPglucuronyltransferase

1972

Winsnes, A.

Biochim. Biophys. Acta

284

394-405

488751

5086951

Inhibition of hepatic UDPglucuronyltransferase by nucleotides

1972

Winsnes, A.

Biochim. Biophys. Acta

289

88-96

488756

1906977

Purification and properties of a rat liver phenobarbital-inducible 4-hydroxybiphenyl UDP-glucuronosyltransferase

1991

Styczynski, P.; Green, M.; Puig, J.; Coffman, B.; Tephly, T.

Mol. Pharmacol.

80-84

488759

3105537

Subcellular localization and properties of cytochrome P-450 and UDP glucuronosyltransferase in the rainbow trout kidney

1987

Pesonen, M.; Andersson, T.

Biochem. Pharmacol.

823-829

488760

3101703

Purification and properties of rat kidney UDP-glucuronosyltransferase

1987

Coughtrie, M.W.H.; Burchell, B.; Bend, J.R.

Biochem. Pharmacol.

245-251

488761

3100939

Isolation and purification of two human liver UDP-glucuronosyltransferases

1987

Irshaid, Y.M.; Tephly, T.R.

Mol. Pharmacol.

27-34

488765

6783797

Phospholipid dependency of purified estrone and p-nitrophenol UDP-glucuronyltransferases

1980

Tukey, R.; Tephly, T.

Life Sci.

2471-2476

488771

1717446

Molecular basis for the lack of bilirubin-specific and 3-methylcholanthrene-inducible UDP-glucuronosyltransferase activities in Gunn rats. The two isoforms are encoded by distinct mRNA species that share an identical single base deletion

1991

Roy-Chowhury, J.; Huang, T.; Kesari, K.; Lederstein, M.; Arias, I.M.; Roy-Chowhury, N.

J. Biol. Chem.

266

18294-18298

488775

96815

Separation of oestrone UDP-glucuronyltransferase and p-nitrophenol UDP-glucuronyltransferase activities

1978

Tukey, R.H.; Billings, R.E.; Tephly, T.R.

Biochem. J.

171

659-663

488782

9264550

Characterization of rabbit UDP-glucuronosyltransferase UGT1A7: tertiary amine glucuronidation is catalyzed by UGT1A7 and UGT1A4

1997

Bruck, M.; Li, Q.; Lamb, J.G.; Tukey, R.H.

Arch. Biochem. Biophys.

344

357-364

488786

9895303

Cloning and characterization of a simian UDP-glucuronosyltransferase enzyme UGT2B20, a novel C19 steroid-conjugating protein

1999

Barbier, O.; Belanger, A.; Hum, D.W.

Biochem. J.

337

567-574

654250

11229918

Identification and cloning of gusA, encoding a new beta-glucuronidase from Lactobacillus gasseri ADH

2001

Russell, W.M.; Klaenhammer, T.E.

Appl. Environ. Microbiol.

1253-1261

654922

8845801

Purification and characterization of beta-glucuronidase from Escherichia coli HGU-3, a human intestinal bacterium

1995

Kim, D.H.; Jin, Y.H.; Jung, E.A.; Han, M.J.; Kobashi, K.

Biol. Pharm. Bull.

1184-1188

655172

11423108

Purification and characterization of a beta-glucuronidase from Aspergillus niger

2001

Kuroyama, H.; Tsutsui, N.; Hashimoto, Y.; Tsumuraya, Y.

Carbohydr. Res.

333

27-39

655962

2108135

A new type of exo-beta-glucuronidase acting only on non-sulfated glycosaminoglycans

1990

Nakamura, T.; Takagaki, K.; Majima, M.; Kimura, S.; Kubo, K.; Endo, M.

J. Biol. Chem.

265

5390-5397

656940

11393513

Purification and characterization of isoforms of beta-galactosidases in mung bean seedlings

2001

Li, S.C.; Han, J.W.; Chen, K.C.; Chen, C.S.

Phytochemistry

349-359

657383

Transfer activity of bovine liver beta-glucuronidase: synthesis of disaccharides containing a beta-D-glucopyranuronate unit

2002

Langlois, V.; Parisot, J.; Bonnet, V.; Rabiller, C.

Tetrahedron

2369-2373

664529

16303119

Cloning and characterization of Thermotoga maritima beta-glucuronidase

2005

Salleh, H.M.; Muellegger, J.; Reid, S.P.; Chan, W.Y.; Hwang, J.; Warren, R.A.; Withers, S.G.

Carbohydr. Res.

341

49-59

665014

Purification and properties of b-galactosidase from Tilapia intestine: Digestive enzyme of Tilapia-X

2004

Taniguchi, A.Y.; Takano, K.

Fish. Sci.

688-694

665527

15069062

Rapid evolution of beta-glucuronidase specificity by saturation mutagenesis of an active site loop

2004

Geddie, M.L.; Matsumura, I.

J. Biol. Chem.

279

26462-26468

666274

16000722

Genetic characterization of the beta-glucuronidase enzyme from a human intestinal bacterium, Ruminococcus gnavus

2005

Beaud, D.; Tailliez, P.; Anba-Mondoloni, J.

Microbiology

151

2323-2330

666782

Purification and characterization of baicalin-b-D-glucuronidase hydrolyzing baicalin to baicalein from fresh roots of Scutellaria viscidula Bge

2005

Zhang, C.; Zhang, Y.; Chen, J.; Liang, X.

Process Biochem.

1911-1915

677746

17221200

Characterization of the new beta-glucuronidase from Streptococcus equi subsp. zooepidemicus

2007

Krahulec, J.; Krahulcova, J.

Appl. Microbiol. Biotechnol.

1016-1022

679993

17174482

Modification of Lactobacillus beta-glucuronidase activity by random mutagenesis

2007

Callanan, M.J.; Russell, W.M.; Klaenhammer, T.R.

Gene

389

122-127

680040

16774908

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