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Ligand hyodeoxycholic acid

Basic Ligand Information

Molecular Structure

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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

2.4.1.17

UDP-D-glucuronate + hyodeoxycholic acid = UDP + hyodeoxycholic acid 6-O-glucuronoside

694264

-

Substrate in Enzyme-catalyzed Reactions (11 results)

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Show Substrate (11 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.213

hyodeoxycholic acid + NADH = ?

684676

-

1.1.1.50

hyodeoxycholic acid + NADH = ?

684676

-

2.4.1.17

hyodeoxycholic acid + UDP-glucuronate = ?

673582, 671661

-

2.4.1.17

hyodeoxycholic acid + UDPglucuronate = UDP + hyodeoxycholic acid O-glucuronide

488783

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2.4.1.17

UDP-D-glucuronate + hyodeoxycholic acid = UDP + hyodeoxycholic acid 24-carboxy-glucuronoside

694264

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2.4.1.17

UDP-D-glucuronate + hyodeoxycholic acid = UDP + hyodeoxycholic acid 3-O-glucuronoside

694264

-

2.4.1.17

UDP-D-glucuronate + hyodeoxycholic acid = UDP + hyodeoxycholic acid 6-O-glucuronoside

694264

-

2.4.1.17

UDP-glucuronate + hyodeoxycholic acid = UDP + beta-D-glucuronosyl-hyodeoxycholic acid

657879

-

2.4.1.17

UDP-glucuronate + hyodeoxycholic acid = UDP + hyodeoxycholic acid 24G-beta-D-glucuronoside

736006

-

2.4.1.17

UDP-glucuronate + hyodeoxycholic acid = UDP + hyodeoxycholoyl beta-D-glucuronoside

735649

-

2.4.1.17

8 entries

2.8.2.14

3'-phosphoadenylyl-sulfate + hyodeoxycholate = adenosine 3',5'-bisphosphate + ?

725821

-

Product in Enzyme-catalyzed Reactions (5 results)

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Show Product (5 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.57

chenodeoxycholate + [reduced NADPH-hemoprotein reductase] + O2 = hyocholate + [oxidized NADPH-hemoprotein reductase] + H2O

0

-

1.14.14.57

lithocholate + [reduced NADPH-hemoprotein reductase] + O2 = hyocholate + [oxidized NADPH-hemoprotein reductase] + H2O

0

-

1.14.14.57

lithocholate + [reduced NADPH-hemoprotein reductase] + O2 = hyodeoxycholate + [oxidized NADPH-hemoprotein reductase] + H2O

0

-

1.14.14.57

3 entries

3.5.1.24

glycohyodeoxycholate + H2O = glycine + hyodeoxycholate

0

-

3.5.1.74

taurohyodeoxycholic acid + H2O = taurine + hyodeoxycholic acid

0

-

Inhibitor in Enzyme-catalyzed Reactions (3 results)

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Show Inhibitors (3 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.21

i.e. hyodeoxycholic acid

695881

-

2.4.1.17

-

706097

-

2.8.2.34

-

659656

-

Enzyme Kinetic Parameters

K_M Value (9 results)

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Show KM Value (9 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.4.1.17

0.011

-

apparent Km for UGT2B7(H)

488790

2.4.1.17

0.021

-

native UGT2B4

673582

2.4.1.17

0.025

-

native UGT2B4

673582

2.4.1.17

0.029

-

mutant UGT2B4(Y33L)

673582

2.4.1.17

0.039

-

mutant UGT2B4(Y33F)

673582

2.4.1.17

0.044

-

recombinant genetic variant UGT2A3.2

694264

2.4.1.17

0.069

-

recombinant genetic variant UGT2A3.1

694264

2.4.1.17

0.091

-

mutant UGT2B4(F33Y)

673582

2.4.1.17

0.27

-

apparent Km for UGT2B4

488790

2.4.1.17

9 entries

IC₅₀ Value (3 results)

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Show IC50 Value (3 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.1.1.21

0.00026

-

in 0.1 M potassium phosphate, pH 7.4, at 25°C

695881

2.4.1.17

0.0614

-

isoform UGT2B4, substrate (S)-propanolol, pH 7.4, 37°C

706097

2.4.1.17

0.102

-

isoform UGT2B4, substrate (R)-propanolol, pH 7.4, 37°C

706097

2.4.1.17

2 entries

References & Links

Literature References (13)

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Show Reference (13 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

488783

9394029

Glucuronidation of opioids, carboxylic acid-containing drugs, and hydroxylated xenobiotics catalyzed by expressed monkey UDP-glucuronosyltransferase 2B9 protein

1997

Green, M.D.; Belanger, G.; Hum, D.W.; Belanger, A.; Tephly, T.R.

Drug Metab. Dispos.

25

1389-1394

488790

10575553

Structural and functional studies of UDP-Glucuronosyltransferases

1999

Radominska-Pandya, A.; Czernik, P.J.; Little, J.M.; Battaglia, E.; Mackenzie, P.I.

Drug Metab. Rev.

31

817-899

657879

12694866

Cloning and characterisation of the first drug-metabolising canine UDP-glucuronosyltransferase of the 2B subfamily

2003

Soars, M.G.; Fettes, M.; O'Sullivan, A.C.; Riley, R.J.; Ethell, B.T.; Burchell, B.

Biochem. Pharmacol.

65

1251-1259

659656

2754334

Bile acid sulfotransferase I from rat liver sulfates bile acids and 3-hydroxy steroids: purification, N-terminal amino acid sequence, and kinetic properties

1989

Barnes, S.; Buchina, E.S.; King, R.J.; McBurnett, T.; Taylor, K.B.

J. Lipid Res.

30

529-540

671661

16897040

Identification of the human liver UDP-glucuronosyltransferase involved in the metabolism of p-ethoxyphenylurea (dulcin)

2007

Uesawa, Y.; Staines, A.G.; Lockley, D.; Mohri, K.; Burchell, B.

Arch. Toxicol.

81

163-168

673582

17263731

Substrate specificity of the human UDP-glucuronosyltransferase UGT2B4 and UGT2B7. Identification of a critical aromatic amino acid residue at position 33

2007

Barre, L.; Fournel-Gigleux, S.; Finel, M.; Netter, P.; Magdalou, J.; Ouzzine, M.

FEBS J.

274

1256-1264

684676

17475203

Rat NAD+-dependent 3alpha-hydroxysteroid dehydrogenase (AKR1C17): a member of the aldo-keto reductase family highly expressed in kidney cytosol

2007

Sanai, M.; Endo, S.; Matsunaga, T.; Ishikura, S.; Tajima, K.; El-Kabbani, O.; Hara, A.

Arch. Biochem. Biophys.

464

122-129

694264

18523138

Novel polymorphic human UDP-glucuronosyltransferase 2A3: cloning, functional characterization of enzyme variants, comparative tissue expression, and gene induction

2008

Court, M.H.; Hazarika, S.; Krishnaswamy, S.; Finel, M.; Williams, J.A.

Mol. Pharmacol.

74

744-754

695881

19464995

Kinetic studies of AKR1B10, human aldose reductase-like protein: endogenous substrates and inhibition by steroids

2009

Endo, S.; Matsunaga, T.; Mamiya, H.; Ohta, C.; Soda, M.; Kitade, Y.; Tajima, K.; Zhao, H.T.; El-Kabbani, O.; Hara, A.

Arch. Biochem. Biophys.

487

1-9

706097

18936551

Stereoselective glucuronidation of propranolol in human and cynomolgus monkey liver microsomes: role of human hepatic UDP-glucuronosyltransferase isoforms, UGT1A9, UGT2B4 and UGT2B7

2008

Hanioka, N.; Hayashi, K.; Shimizudani, T.; Nagaoka, K.; Koeda, A.; Naito, S.; Narimatsu, S.

Pharmacology

82

293-303

725821

21839837

A comparative study of the sulfation of bile acids and a bile alcohol by the Zebra danio (Danio rerio) and human cytosolic sulfotransferases (SULTs)

2011

Kurogi, K.; Krasowski, M.D.; Injeti, E.; Liu, M.Y.; Williams, F.E.; Sakakibara, Y.; Suiko, M.; Liu, M.C.

J. Steroid Biochem. Mol. Biol.

127

307-314

735649

25937523

Roles of human UDP-glucuronosyltransferases in clearance and homeostasis of endogenous substrates, and functional implications

2015

Bock, K.W.

Biochem. Pharmacol.

96

77-82

736006

23756265

The human UDP-glucuronosyltransferase UGT2A1 and UGT2A2 enzymes are highly active in bile acid glucuronidation

2013

Perreault, M.; Gauthier-Landry, L.; Trottier, J.; Verreault, M.; Caron, P.; Finel, M.; Barbier, O.

Drug Metab. Dispos.

41

1616-1620

Links to other databases for hyodeoxycholic acid

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Show Links (1 entry)

ChEBI

PubChem