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Ligand 12-ketochenodeoxycholic acid

Basic Ligand Information

Molecular Structure

Related pathways

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Roles as Enzyme Ligand

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

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Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.176

12-ketochenodeoxycholic acid + NADH = cholic acid + NAD+

347748

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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

1.1.1.176

cholate + NAD+ = 3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanate + NADH + H+

-

-

1.1.1.176

cholate + NADP+ = 3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanate + NADPH + H+

-

-

1.1.1.176

2 entries

Substrate in Enzyme-catalyzed Reactions (6 results)

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Show Substrate (6 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.159

12-ketochenodeoxycholic acid + NAD+ = 7,12-diketochenodeoxycholic acid + NADH

286075, 286077

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1.1.1.176

12-ketochenodeoxycholic acid + NADH = cholic acid + NAD+

347748

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1.1.1.176

12-oxo-cholic acid + NAD(P)H + H+ = cholic acid + NAD(P)+

760397

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1.1.1.176

12-oxochenodeoxycholic acid + NADP+ = (3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxycholan-24-oic acid + NADPH + H+

347737

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1.1.1.176

12-oxochenodeoxycholic acid + NADPH + H+ = 7-oxodeoxycholic acid + NADP+

760391

-

1.1.1.176

4 entries

1.1.1.238

3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanoate + NADPH = 3alpha,7alpha,12beta-trihydroxy-5beta-cholanoate + NADP+

286353

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Product in Enzyme-catalyzed Reactions (7 results)

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Show Product (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.159

(3alpha,5beta)-3-hydroxy-7,12-dioxocholan-24-oic acid + NADH = (3alpha,5beta,7alpha)-3,7-dihydroxy-12-oxocholan-24-oic acid + NAD+

-

-

1.1.1.159

7,12-diketolithocholic acid + NADH = 12-ketochenodeoxycholic acid + NAD+

286075

-

1.1.1.176

cholic acid + NADP+ = 12-ketochenodeoxycholic acid + NADPH + H+

-

-

1.1.1.176

cholic acid + NAD(P)+ = 12-oxocholic acid + NAD(P)H + H+

-

-

1.1.1.176

cholic acid + NAD(P)+ = 3alpha,7alpha-dihydroxy-12-oxo-5beta-cholan-24-oic acid + NAD(P)H

286075, -

-

1.1.1.176

cholate + NAD+ = 3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanate + NADH + H+

-

-

1.1.1.176

cholate + NADP+ = 3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanate + NADPH + H+

-

-

1.1.1.159

2 entries

1.1.1.176

5 entries

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.2

inhibition of the ADH from Lactobacillus brevis by bile acids, acetone prevents partially

668040

-

Enzyme Kinetic Parameters

K_M Value (2 results)

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Show KM Value (2 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.176

0.0012

-

-

347737

1.1.1.238

0.274

-

-

286353

References & Links

Literature References (9)

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Show Reference (9 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

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

286353

3167086

Characterization of NADP-dependent 12beta-hydroxysteroid dehydrogenase from Clostridium paraputrificum

1988

Edenharder, R.; Pfutzner, A.

Biochim. Biophys. Acta

962

362-370

347737

2007406

12 alpha-hydroxysteroid dehydrogenase from Clostridium group P, strain C 48-50. Production, purification and characterization

1991

Braun, M.; Lunsdorf, H.; Buckmann, A.F.

Eur. J. Biochem.

196

439-450

347748

-

Bile acids induction of 12 alpha-hydroxysteroid dehydrogenase in Brevibacterium fuscum

1993

Panichajakul, S.; Tawat, K.; Yoshida, T.; Taguchi, H.

Microb. Util. Renewable Resour.

8

112-118

668040

16245351

Exploitation of the alcohol dehydrogenase-acetone NADP-regeneration system for the enzymatic preparative-scale production of 12-ketochenodeoxycholic acid

2006

Fossati, E.; Polentini, F.; Carrea, G.; Riva, S.

Biotechnol. Bioeng.

93

1216-1220

760391

29549099

Metabolism of oxo-bile acids and characterization of recombinant 12alpha-hydroxysteroid dehydrogenases from bile acid 7alpha-dehydroxylating human gut bacteria

2018

Doden, H.; Sallam, L.A.; Devendran, S.; Ly, L.; Doden, G.; Daniel, S.L.; Alves, J.M.P.; Ridlon, J.M.

Appl. Environ. Microbiol.

84

e00235-18

760397

29330189

Targeted synthesis and characterization of a gene cluster encoding NAD(P)H-dependent 3alpha-, 3beta-, and 12alpha-hydroxysteroid dehydrogenases from Eggerthella CAG 298, a gut metagenomic sequence

2018

Mythen, S.; Devendran, S.; Méndez-García, C.; Cann, I.; Ridlon, J.

Appl. Environ. Microbiol.

84

e02475-17

760397

29330189

Targeted synthesis and characterization of a gene cluster encoding NAD(P)H-dependent 3alpha-, 3beta-, and 12alpha-hydroxysteroid dehydrogenases from Eggerthella CAG 298, a gut metagenomic sequence

2018

Mythen, S.; Devendran, S.; Méndez-García, C.; Cann, I.; Ridlon, J.

Appl. Environ. Microbiol.

84

e02475-17

760397

2 entries

Links to other databases for 12-ketochenodeoxycholic acid

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Show Links (1 entry)