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Ligand taurocholate

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for taurocholate

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Natural Substrate (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.8.2.14

3'-phosphoadenylyl sulfate + taurocholic acid = adenosine 3',5'-bisphosphate + taurocholate 3-sulfate

761661, 761662, 760733

-

3.5.1.24

taurocholate + H2O = taurine + cholate

668059

-

3.5.1.24

taurocholic acid + H2O = 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanate + taurine

720148, 712204, 720209

-

3.5.1.24

taurocholic acid + H2O = cholate + taurine

754684, 755337, 755518, 733164, 752522, 753680, 753623, 753622, 753621, 753684, 755276, 755516

-

3.5.1.24

3 entries

7.6.2.2

ATP + H2O + taurocholate/in = ADP + phosphate + taurocholate/out

701356

-

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

2.3.1.65

choloyl-CoA + taurine = CoA + taurocholate

-

-

7.6.2.2

ATP + H2O + taurocholate/in = ADP + phosphate + taurocholate/out

-

-

Substrate in Enzyme-catalyzed Reactions (19 results)

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Show Substrate (19 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.159

taurocholic acid + NAD+ = 2[[3alpha,12alpha-dihydroxy-7,24-dioxo-5beta-cholan-24-yl]amino]ethane sulfonic acid + NADH

286085, 286073, 286077, 286080, 286079, 286075

-

1.1.1.176

taurocholic acid + NAD(P)+ = 3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanoyl taurine + NAD(P)H

347741, 347744, 286075, 347740

-

1.1.1.176

taurocholic acid + NAD+ = ? + NADH + H+

761221

-

1.1.1.176

taurocholic acid + NADP+ = ?

760397

-

1.1.1.176

3 entries

1.1.1.270

taurocholic acid + NADP+ = ?

760397

-

1.1.1.395

taurocholic acid + NAD+ = 3-oxotaurocholic acid + NADH + H+

739615

-

1.1.1.50

taurocholic acid + NAD(P)+ = 2[[7alpha,12alpha-dihydroxy-3,24-dioxo-5beta-cholan-24-yl]amino]ethane sulfonic acid + NADPH

389548, 389522

-

1.1.1.50

taurocholic acid + NAD+ = 7alpha,12alpha-dihydroxy-5beta-cholan-3-one-24-oyl-taurine + NADH

656300

-

1.1.1.50

2 entries

1.1.3.6

taurocholate + O2 = ? + H2O2

742195

-

1.3.1.20

taurocholic acid + NADP+ = ?

349256

-

2.8.2.14

3'-phosphoadenylyl-sulfate + taurocholate = adenosine 3',5'-bisphosphate + taurocholate monosulfate + taurocholate disulfate + taurocholate trisulfate

645714, 645709

-

2.8.2.14

3'-phosphoadenylyl sulfate + taurocholic acid = adenosine 3',5'-bisphosphate + taurocholate 3-sulfate

761661, 761662, 760733

-

3.5.1.24

cholyltaurine + H2O = cholic acid + taurine

209039

-

3.5.1.24

taurocholate + H2O = taurine + cholate

670898, 669644, 669499, 668059, 710870

-

3.5.1.24

taurocholic acid + H2O = 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanate + taurine

720148, 209038, 209043, 712204, 209037, 209039, 209046, 695682, 697838, 695744, 681363, 720209

-

3.5.1.24

taurocholic acid + H2O = cholate + taurine

754684, 755337, 734499, 755518, 735128, 733164, 752522, 753680, 753623, 753622, 753621, 753684, 755276, 755516

-

2.8.2.14

2 entries

3.5.1.24

4 entries

3.5.1.74

taurocholic acid + H2O = taurine + cholic acid

209234

-

7.6.2.2

ATP + H2O + taurocholate/in = ADP + phosphate + taurocholate/out

701356

-

7.6.2.2

ATP + H2O + taurocholic acid[side 1] = ADP + phosphate + taurocholic acid[side 2]

748825

-

7.6.2.2

2 entries

Product in Enzyme-catalyzed Reactions (3 results)

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Show Product (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.65

choloyl-CoA + taurine = CoA + taurocholate

, 487364, 487365, 487368, 487367, 487372

-

7.6.2.2

ATP + H2O + taurocholate/in = ADP + phosphate + taurocholate/out

-

-

7.6.2.2

ATP + H2O + taurocholic acid[side 1] = ADP + phosphate + taurocholic acid[side 2]

-

-

7.6.2.2

2 entries

Activator in Enzyme-catalyzed Reactions (32 results)

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Show Activating Compound (32 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.344

about 36% as effective as G-3634-A

489346

-

2.4.1.78

stimulates solubilized activity

489379

-

2.7.8.1

-

644354

-

2.7.8.2

stimulates

644343

-

3.1.1.1

activates

170990

2dr0, 3D-view

3.1.1.1

non-essential activator

170990

2dr0, 3D-view

3.1.1.13

activates CRL3, not CRL1

650378

1aql, 3D-view

3.1.1.13

increasing the bile salt concentration (0-50 mM taurocholate) in assay mixture using desalted extracts gives a correlated increase in the hydrolase activity up to 20 mM and remains more or less constant at a higher concentration of bile

690604

1aql, 3D-view

3.1.1.13

up to 100 mM, enhancement of the activity, bile salt is absolutely required for activity

650638

1aql, 3D-view

3.1.1.3

absolutely necessary both for lipase stability in the gel and for optimum activity, 10 mM improves the lipase activity approximately 130fold

715063

-

3.1.1.3

activates carboxyl esterase activity

649985

-

3.1.1.3

activates 50% at 0.1 mM

666216

-

3.1.1.3

strong activation, 2.7fold at 10 mM

653693

-

3.1.1.1

2 entries

3.1.1.13

3 entries

3.1.1.3

4 entries

3.1.1.4

bile salt regulation of lipid metabolism via both activation and inhibition of PLA2, interaction and binding structure analysis, overview

681436

2azz, 3D-view

3.1.1.50

20 mM

690604

-

3.1.1.50

activity is dependent on the presence of primary bile salts such as cholate, taurocholate and taurochenodeoxycholate

94406

-

3.1.3.2

114% activity at 1% (w/v)

677425

-

3.1.3.2

136.3% activity at 1% (w/v)

677425

-

3.1.3.2

168.3% activity at 1% (w/v)

677425

-

3.1.1.50

2 entries

3.1.3.2

3 entries

3.1.3.4

stimulates

134862

-

3.1.4.12

-

135179, 663974, 135172

-

3.1.4.12

required for enzyme activity, and probably to prevent enzyme dissociation from the membranes

678434

-

3.1.4.12

stimulates hydrolysis of sphingomyelin and platelet-activating factor

663974

-

3.1.4.12

strong activation, maximal activation at approx. 10 mM

652706

-

3.1.4.12

the enzyme activity is specifically stimulated by 6 mM taurocholate

692009

-

3.1.4.12

5 entries

3.2.1.23

required for hydrolysis of lipid substrates

171319

-

3.2.1.46

-

171507, 171514, 171506

-

3.2.1.46

in combination with oleic acid

171517

-

3.2.1.46

2 entries

3.2.1.52

concentrations of 0.05 M and 0.1 M cause 140% and 160% of activity

393700

-

3.5.1.23

-

667153

-

7.6.2.1

increases the efflux of phospholipids and cholesterol from cells, the taurocholate monomer plays an important role in ABCB4-mediated lipid secretion

687006

-

7.6.2.3

103% activity at 0.1 mM

746704

-

Inhibitor in Enzyme-catalyzed Reactions (24 results)

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Show Inhibitors (24 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.14.19.77

-

438312

-

2.3.1.22

-

486603

-

2.3.1.22

2%

486598

-

2.3.1.22

2 entries

2.3.1.5

-

487116

-

2.3.1.65

-

487365, 487367

-

2.4.1.131

-

638568

-

2.7.1.227

0.1% w/v, 70% loss of activity

752588

-

3.1.1.13

-

650378

1aql, 3D-view

3.1.1.13

inhibits CRL1, not CRL3

650378

1aql, 3D-view

3.1.1.4

bile salt regulation of lipid metabolism via both activation and inhibition of PLA2, interaction and binding structure analysis, overview

681436

2azz, 3D-view

3.1.1.4

plasmalogen-specific PLA2

133875

2azz, 3D-view

3.1.1.13

2 entries

3.1.1.4

2 entries

3.1.1.60

-

170988

-

3.1.3.2

-

134750

-

3.1.3.76

IC50 is above 0.1 mM

661168

-

3.1.4.12

in presence of Triton X-100

135172

-

3.2.1.21

74% inhibition at 1%, w/v

326366

-

3.2.1.21

90% inhibition at 18 mM

326349

-

3.2.1.21

2 entries

3.2.1.46

high concentrations, above 0.3% w/v

171514

-

3.3.2.10

IC50 is 0.09 mM

661168

-

3.4.22.56

at low concentrations of 0.00001-0.1 mM it increases caspase-3 activity, but at larger doses of 0.5-10 mM it reverses stimulation to inhibition. It inhibits the caspase-3 pathway and prevents ethanol-induced caspase-3 activation leading to inhibition of apoptosis, overview

697570

-

3.5.1.23

20 mM, 50% inhibition

685419

-

3.5.1.23

inhibits in vitro neutral ceramidase activity

719197

-

3.5.1.23

2 entries

3.5.1.24

competitive inhibition of glycocholic acid hydrolysis

670898

-

6.2.1.7

-

838

-

Metals and Ions (1 result)

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Show Metals Ions (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.3

1.6fold stimulation at 200 mM

650654

-

3D Structure of Enzyme-Ligand-Complex (PDB) (4 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (4 entries)

EC NUMBER

ENZYME 3D STRUCTURE

2.3.1.28

6pxa, 3D-view

3.1.1.1

2dr0, 3D-view

3.1.1.13

1aql, 3D-view

3.1.1.4

2azz, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (11 results)

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Show Turnover Number (11 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.1.1.159

3.13

-

-

286085

1.1.1.395

0.15

-

wild type enzyme isoform BaiA2, at pH 8.7 and 37°C

739615

1.1.1.395

0.4

-

wild type enzyme isoform BaiA1, at pH 8.7 and 37°C

739615

1.1.1.395

2 entries

1.1.1.50

74

-

pH 8.5, 37°C, with cofactor NAD+

656300

1.3.1.20

0.07

-

DD1

349256

3.5.1.24

9.75

-

pH 5.4, 37°C, recombinant enzyme

733164

3.5.1.24

40

-

pH 6.5, 40°C, recombinant mutant T2A

669499

3.5.1.24

70.03

-

pH 6.5, 37°C, recombinant isozyme BSH1

734499

3.5.1.24

76

-

pH 6.5, 40°C, recombinant wild-type enzyme

669499

3.5.1.24

93.14

-

pH 6.5, 37°C, recombinant isozyme BSH2

734499

3.5.1.24

2500

-

about, pH 5.0, 50°C, recombinant enzyme

755276

3.5.1.24

6 entries

K_M Value (18 results)

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Show KM Value (18 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.159

1

-

-

286080

1.1.1.159

2

-

-

286085

1.1.1.159

2 entries

1.1.1.176

4

-

-

347741

1.1.1.395

0.201

-

wild type enzyme isoform BaiA2, at pH 8.7 and 37°C

739615

1.1.1.395

0.329

-

wild type enzyme isoform BaiA1, at pH 8.7 and 37°C

739615

1.1.1.395

2 entries

1.1.1.50

0.043

-

pH 8.5, 37°C, with cofactor NAD+

656300

1.1.3.6

0.5

-

pH 6.75, 35°C

742195

1.3.1.20

0.21

-

DD1

349256

3.5.1.24

0.03

-

pH 6.5, 40°C, recombinant mutant T2A

669499

3.5.1.24

0.032

-

pH 6.5, 40°C, recombinant wild-type enzyme

669499

3.5.1.24

0.45

-

-

209038

3.5.1.24

0.76

-

hydrolase A

209043

3.5.1.24

0.95

-

hydrolase B

209043

3.5.1.24

3.21

-

pH 5.4, 37°C, recombinant enzyme

733164

3.5.1.24

13.16

-

about, pH 5.0, 50°C, recombinant enzyme

755276

3.5.1.24

13.57

-

pH 6.5, 37°C, recombinant isozyme BSH1

734499

3.5.1.24

15.92

-

pH 6.5, 37°C, recombinant isozyme BSH2

734499

3.5.1.24

37

-

-

209037

3.5.1.24

10 entries

K_i Value (1 result)

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Show KI Value (1 entry)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.5.1.24

2.5

-

pH 8.0, 50°C

670898

IC₅₀ Value (2 results)

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Show IC50 Value (2 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

3.1.3.76

0.1

-

IC50 is above 0.1 mM

661168

3.3.2.10

0.09

-

IC50 is 0.09 mM

661168

References & Links

Literature References (109)

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Show Reference (109 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

838

6639941

Subcellular distribution of cholic acid:Coenzyme A ligase and deoxycholic acid:coenzyme A ligase activities in rat liver

1983

Simion, F.A.; Fleischer, B.; Fleischer, S.

Biochemistry

22

5029-5034

94406

-

Studies on triacylglycerol, wax ester and sterol ester hydrolases in intestinal caeca of rainbow trout (Salmo gairdneri) fed diets rich in triacylglycerols and wax esters

1984

Tocher, D.R.; Sargent, J.R.

Comp. Biochem. Physiol. B

77

561-571

133875

9131165

Characterization of plasmalogen-selective phospholipase A2 from bovine brain

1996

Yang, H.C.; Farooqui, A.A.; Horrocks, L.A.

Adv. Exp. Med. Biol.

416

309-313

134750

-

Acid phosphatases

1971

Hollander, V.P.

The Enzymes, 3rd Ed. (Boyer, P. D. , ed. )

4

449-498

134862

3002481

Phosphatidate phosphatase activity in isolated rod outer segment from bovine retina

1986

Pasquare de Garcia, S.J.; Giusto, N.M.

Biochim. Biophys. Acta

875

195-202

135172

5916388

Enzymatic hydrolysis of sphingolipids. II. Hydrolysis of sphingomyelin by an enzyme from rat brain

1966

Barnholz, Y.; Roitman, A.; Gatt, S.

J. Biol. Chem.

241

3731-3737

135179

9328299

Purification of a newly identified alkaline sphingomyelinase in human bile and effects of bile salts and phosphatidylcholine on enzyme activity

1997

Duan, R.D.; Nilsson, A.

Hepatology

26

823-830

170988

6468391

Plant biochemistry of xenobiotics. Purification and properties of a wheat esterase hydrolyzing the plasticizer chemical, bis(2-ethylhexyl)phthalate

1984

Krell, H.W.; Sandermann, H.

Eur. J. Biochem.

143

57-62

170990

6689130

Kinetic properties of human pancreatic carboxylesterase

1983

Wang, C.S.; Kloer, H.U.

Biochim. Biophys. Acta

754

142-149

171319

-

beta-Galactosidase from rat brain

1969

Gatt, S.

Methods Enzymol.

14

156-161

171506

3111543

Hydrolysis of galactosylsphingosine and lactosylsphingosine by beta-galactosidases in human brain and cultured fibroblasts

1987

Goda, S.; Kobayashi, T.; Goto, I.

Biochim. Biophys. Acta

920

259-265

171507

3094585

Metabolism of galactosylceramide in the twitcher mouse, an animal model of human globoid cell leukodystrophy

1986

Kobayashi, T.; Shinnoh, N.; Kuroiwa, Y.

Biochim. Biophys. Acta

879

215-220

171514

236034

Glycosphinoglipid beta-galactosidases of cultured mammalian cells. Characterization of the enzymes from mouse cell line lmtk and human Lesch-Nyhan fibroblasts

1975

Rushton, A.R.; Dawson, G.

Biochim. Biophys. Acta

388

92-105

171517

1521344

Characterization of 6-hexadecanoylamino-4-methylumbelliferyl-beta-D-galactopyranoside as fluorogenic substrate of galactocerebrosidase for the diagnosis of Krabbe disease

1992

Wiederschain, G.; Raghavan, S.; Kolodny, E.

Clin. Chim. Acta

205

87-96

209037

6016335

The enzymatic cleavage of the carbon-nitrogen bond in 3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oylglycine

1967

Nair, P.P.; Gordon, M.; Reback, J.

J. Biol. Chem.

242

7-11

209038

10993

Purification and characterization of bile salt hydrolase from Bacteroides fragilis subsp. fragilis

1976

Stellwag, E.J.; Hylemon, P.B.

Biochim. Biophys. Acta

452

165-176

209039

6096355

Substrate specificity of cholylglycine hydrolase for the hydrolysis of bile acid conjugates

1984

Batta, A.K.; Salen, G.; Shefer, S.

J. Biol. Chem.

259

15035-15039

209043

2376558

Characterization and purification of bile salt hydrolase from Lactobacillus sp. strain 100-100

1990

Lundeen, S.G.; Savage, D.S.

J. Bacteriol.

172

4171-4177

209046

10194664

Bile salt hydrolase activity of three strains of Lactobacillus acidophilus

1999

Corzo, G.; Gilliland, S.E.

J. Dairy Sci.

82

472-480

209234

2628421

Purification and characterization of a new hydrolase for conjugated bile acids, chenodeoxycholyltaurine hydrolase, from Bacteroides vulgatus

1989

Kawamoto, K.; Horibe, I.; Uchida, K.

J. Biochem.

106

1049-1053

286073

2698265

Kinetic properties of 7alpha-hydroxysteroid dehydrogenase from Escherichia coli 080

1989

Prabha, V.; Gupta, M.; Gupta, K.G.

Can. J. Microbiol.

35

1076-1080

286075

-

Purification and properties of three kinds of alpha-hydroxysteroid dehydrogenase from Brevibacterium fuscum DC33

1988

Kinoshita, S.; Kadota, K.; Inoue, T.; Sawada, H.; Taguchi, H.

J. Ferment. Technol.

66

145-152

286077

786279

The specificity of a 7alpha-hydroxy steroid dehydrogenase from Escherichia coli

1976

Haslewood, E.S.; Haslewood, G.A.D.

Biochem. J.

157

207-210

286079

236764

NAD- and NADP-dependent 7alpha-hydroxysteroid dehydrogenases from bacteroides fragilis

1975

MacDonald, I.A.; Williams, C.N.; Mahony, D.E.; Christie, W.M.

Biochim. Biophys. Acta

384

12-24

286080

4581498

7alpha-hydroxysteroid dehydrogenase from Escherichia coli B: preliminary studies

1973

MacDonald, I.A.; Williams, C.N.; Mahony, D.E.

Biochim. Biophys. Acta

309

243-253

286085

2007545

Cloning and sequencing of the 7alpha-hydroxysteroid dehydrogenase gene from Escherichia coli HB101 and characterization of the expressed enzyme

1991

Yoshimoto, T.; Higashi, H.; Kanatani, A.; Lin, X.S.; Nagai, H.; Oyama, H.; Kurazono, K.; Tsuru, D.

J. Bacteriol.

173

2173-2179

326349

6406230

Substrate specificity of the human splenic non-specific soluble beta-glucosidase

1983

Maret, A.; Salvayre, R.; Negre, A.; Douste-Blazy, L.

Eur. J. Biochem.

133

283-287

326366

2304

Isolation and characterization of beta-glucosidase from the cytosol of rat kidney cortex

1976

Glew, R.H.; Peters, S.P.; Christopher, A.R.

Biochim. Biophys. Acta

422

179-199

347740

39496

Bile salt 3alpha- and 12alpha-hydroxysteroid dehydrogenases from Eubacterium lentum and related organisms

1979

MacDonald, I.A.; Jellett, J.F.; Mahony, D.E.; Holdeman, L.V.

Appl. Environ. Microbiol.

37

992-1000

347741

23170

Partial purification and characterization of NADP-dependent 12alpha-hydroxysteroid dehydrogenase from Clostridium leptum

1978

Harris, J.N.; Hylemon, P.B.

Biochim. Biophys. Acta

528

148-157

347744

10985

3alpha-, 7alpha- and 12alpha-hydroxysteroid dehydrogenase activities from Clostridium perfringens

1976

MacDonald, I.A.; Meier, E.C.; Mahony, D.E.; Costain, G.A.

Biochim. Biophys. Acta

450

142-153

349256

7766669

Enzymic characterization of a novel bovine liver dihydrodiol dehydrogenase - reaction mechanism and bile acid dehydrogenase activity

1995

Nanjo, H.; Adachi, H.; Morihana, S.; Mizoguchi, T.; Nishihara, T.; Terada, T.

Biochim. Biophys. Acta

1244

53-61

389522

-

Properties of crystalline 3alpha-hydroxysteroid dehydrogenase from Pseudomonas putida

1979

Uwajima, T.; Terada, O.

Agric. Biol. Chem.

43

1521-1528

389548

-

Purification and properties of 3alpha-hydroxysteroid dehydrogenase from Pseudomonas putida

1997

Adachi, O.; Toyama, H.; Matsushita, K.

Biosci. Biotechnol. Biochem.

61

131-137

393700

1837501

Characteristics of hexosaminidase A in homogenates of white blood cells using methylumbelliferyl-N-acetyl-beta-D-glucosaminide-6-sulphate as substrate

1991

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Links to other databases for taurocholate

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PubChem

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