print visible entries

print all entries

Ligand glycolithocholic acid

Basic Ligand Information

Molecular Structure

close all tables

open all tables

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (4 results)

top print hide

Show Natural Substrate (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.8.2.14

3'-phosphoadenylyl sulfate + glycolithocholate = adenosine 3',5'-bisphosphate + glycolithocholate 3-sulfate

676007

-

2.8.2.14

3'-phosphoadenylyl sulfate + glycolithocholic acid = adenosine 3',5'-bisphosphate + glycolithocholate 3-sulfate

761727

-

2.8.2.14

2 entries

2.8.2.2

3'-phosphoadenylyl sulfate + glycolithocholic acid = adenosine 3',5'-bisphosphate + glycolithocholate 3-sulfate

761727

-

3.5.1.24

glycolithocholic acid + H2O = lithocholate + glycine

753412

-

Substrate in Enzyme-catalyzed Reactions (17 results)

top print hide

Show Substrate (17 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.112

glycolithocholic acid + NAD(P)+ = N[3-oxo-5beta-cholan-24-oyl]glycine + NAD(P)H

285759

-

1.1.1.209

glycolithocholic acid + NADP+ = N-[(5beta)-3,24-dioxocholan-24-yl]glycine + NADPH

286234

-

1.1.1.213

glycolithocholic acid + NADH = ?

684676

-

1.1.1.213

glycolithocholic acid + NADP+ = 3-oxo-5beta-cholanoyl glycine + NADPH

286354

-

1.1.1.213

2 entries

1.1.1.239

glycolithocholic acid + NAD+ = 3-oxo-5beta-cholanoyl glycine + NADH

286354

-

1.1.1.50

glycolithocholic acid + NADH = ?

684676

-

1.1.1.50

glycolithocholic acid + NADP+ = 3-oxo-glycocholanoic acid + NADPH

389527, 389526

-

1.1.1.50

2 entries

1.3.1.20

glycolithocholic acid + NAD(P)+ = 3-oxo-glycocholanoic acid + NAD(P)H

349239

-

2.4.1.17

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

488763

-

2.8.2.14

3'-phosphoadenylyl-sulfate + glycine conjugated lithocholate = adenosine 3',5'-bisphosphate + ?

726539

-

2.8.2.14

3'-phosphoadenylyl sulfate + glycolithocholate = adenosine 3',5'-bisphosphate + glycolithocholate 3-sulfate

676007

-

2.8.2.14

3'-phosphoadenylyl-sulfate + glycolithocholate = adenosine 3',5'-bisphosphate + glycolithocholate 3-sulfate

645712, 645714, 645710, 645711, 645715, 645721, 645709, 645713, 645717, 645719, 645716

-

2.8.2.14

3'-phosphoadenylyl sulfate + glycolithocholic acid = adenosine 3',5'-bisphosphate + glycolithocholate 3-sulfate

761727

-

2.8.2.14

4 entries

2.8.2.15

3'-phosphoadenylylsulfate + glycolithocholate = adenosine 3',5'-bisphosphate + ?

645726

-

2.8.2.2

3'-phosphoadenylyl sulfate + glycolithocholic acid = adenosine 3',5'-bisphosphate + glycolithocholate 3-sulfate

761727

-

2.8.2.34

3'-phosphoadenylyl 5'-phosphosulfate + glycolithocholate = adenosine 3',5'-bisphosphate + glycolithocholate 3-sulfate

645728, 659656

-

3.5.1.24

glycolithocholic acid + H2O = lithocholate + glycine

753412

-

Product in Enzyme-catalyzed Reactions (1 result)

top print hide

Show Product (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.65

lithocholoyl-CoA + glycine = CoA + glycolithocholate

0

-

Inhibitor in Enzyme-catalyzed Reactions (5 results)

top print hide

Show Inhibitors (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.21

competitive inhibition with respect to geraniol

695881

-

2.8.2.14

-

645715

-

2.8.2.14

substrate inhibition

761727

-

2.8.2.14

2 entries

2.8.2.2

substrate inhibition

761727

-

2.8.2.34

competitive, 50% inhibition at 0.04 mM

659655

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (2 results)

top print hide

Show Turnover Number (2 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.1.1.213

0.233

-

-

286354

1.1.1.239

0.25

-

-

286354

K_M Value (14 results)

top print hide

Show KM Value (14 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.209

0.0004

-

cofactor NADP+

286234

1.1.1.239

0.003

-

-

286354

1.1.1.50

0.0052

0.0059

-

389527

1.1.1.50

0.0052

0.0059

also in this range: 3alpha-hydroxy-5alpha-pregnan-20-one

389530

2.8.2.14

0.00048

-

recombinant SULT2A1, pH 7.4, 37°C

761727

2.8.2.14

0.00099

-

liver cytosol, pH 7.4, 37°C

761727

2.8.2.14

0.0018

-

pH 7.5, 37°C

645711

2.8.2.14

0.00192

-

apparent value, in 50 mM NaH2PO4 buffer (pH 5.5), 2 mM MgCl2, at 37°C

726539

2.8.2.14

0.002

-

pH 6.5, 37°C

645715

2.8.2.14

0.0028

-

pH 7.5, 37°C

645721

2.8.2.14

0.0033

-

pH 6.8, 37°C

645710

2.8.2.14

0.02

-

pH 6.5, 37°C

645709

2.8.2.2

0.00048

-

recombinant SULT2A1, pH 7.4, 37°C

761727

2.8.2.2

0.00099

-

liver cytosol, pH 7.4, 37°C

761727

1.1.1.50

2 entries

2.8.2.14

8 entries

2.8.2.2

2 entries

K_i Value (6 results)

top print hide

Show KI Value (6 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.8.2.14

0.0022

-

pH 6.5, 37°C

645715

2.8.2.14

0.0096

-

recombinant SULT2A1, pH 7.4, 37°C

761727

2.8.2.14

0.0123

-

liver cytosol, pH 7.4, 37°C

761727

2.8.2.2

0.0096

-

recombinant SULT2A1, pH 7.4, 37°C

761727

2.8.2.2

0.0123

-

liver cytosol, pH 7.4, 37°C

761727

2.8.2.14

3 entries

2.8.2.2

2 entries

2.8.2.34

0.018

-

pH 7.0, 37°C

659655

IC₅₀ Value (1 result)

top print hide

Show IC50 Value (1 entry)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.1.1.21

0.00071

-

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

695881

References & Links

Literature References (29)

top print hide

Show Reference (29 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

285759

2559080

3(20)alpha-hydroxysteroi dehydrogenase activity of monkey liver indanol dehydrogenase

1989

Hara, A.; Nakagawa, M.; Taniguchi, H.; Saweda, H.

J. Biochem.

106

900-903

286234

2691507

Identification of two dihydrodiol dehydrogenases associated with 3(17)alpha-hydoxysteroid dehydrogenase activity in mouse kidney

1989

Nakagawa, M.; Tsukuda, F.; Nakayama, T.; Matsuura, K.; Hara, A.; Sawada, H.

J. Biochem.

106

633-638

286354

2317205

Demonstration of 3alpha(17beta)-hydroxysteroid dehydrogenase distinct from 3alpha-hydroxysteroid dehydrogenase in hamster liver

1990

Ohmura, M.; Hara, A.; Nakagawa, M.; Sawada, H.

Biochem. J.

266

583-589

349239

2691507

Identification of two dihydrodiol dehydrogenases associated with 3(17)alpha-hydroxysteroid dehydrogenase activity in mouse kidney

1989

Nakagawa, M.; Tsukada, F.; Nakayama, T.; Matsuura, K.; Hara, A.; Sawada, H.

Biochem. J.

106(4)

633-638

389526

6586631

Purification and characterization of the multiple forms of 3alpha-hydroxysteroid dehydrogenase in rat liver cytosol

1984

Ikeda, M.; Hattori, H.; Ikeda, N.; Hayakawa, S.; Ohmori, S.

Hoppe-Seyler's Z. Physiol. Chem.

365

377-391

389527

3170514

Purification and characterization of NADP+-dependent 3alpha-hydroxysteroid dehydrogenase from mouse liver cytosol

1988

Hara, A.; Inoue, Y.; Nakagawa, M.; Naganeo, F.; Sawada, H.

J. Biochem.

103

1027-1034

389530

240965

Separation and characterization of two 3-hydroxysteroid oxidoreductases from the soluble fraction of rat ovarian cells

1975

Nimrod, A.; Lamprecht, S.A.; Lindner, H.R.

J. Steroid Biochem.

6

1205-1209

488763

6430960

Hepatic and extrahepatic glucuronidation of bile acids in man. Characterization of bile acid uridine 5-diphosphate-glucuronosyltransferase in hepatic, renal, and intestinal microsomes

1984

Matern, S.; Matern, H.; Farthmann, E.H.; Gerok, W.

J. Clin. Invest.

74

402-410

645709

23845

Enzymatic sulfation of bile salts. II. Studies on bile salt sulfotranferase from rat kidney

1978

Chen, L.J.; Imperato, T.J.; Bolt, R.J.

Biochim. Biophys. Acta

522

443-451

645710

698243

Enzymatic sulphation of bile salts in human liver

1978

Loeoef, L.; Wengle, B.

Biochim. Biophys. Acta

530

451-460

645711

6928376

Partial purification of a human liver sulphotransferase active towards bile salts

1980

Loeoef, L.; Hjerten, S.

Biochim. Biophys. Acta

617

192-204

645712

6948990

Bile salt sulfotransferase

1981

Chen, L.J.

Methods Enzymol.

77

213-218

645713

6954993

Evidence for heterogeneity of hepatic bile salt sulfotransferases in female hamsters and rats

1982

Barnes, S.; Spenney, J.G.

Biochim. Biophys. Acta

704

353-360

645714

6956371

Bile salt sulfotransferase in guinea pig liver

1982

Chen, L.J.

Biochim. Biophys. Acta

717

316-321

645715

3862362

Purification and characterization of bile salt sulfotransferase from human liver

1985

Chen, L.J.; Segel, I.H.

Arch. Biochem. Biophys.

241

371-379

645716

3470420

Evidence for an ordered reaction mechanism for bile salt:3phosphoadenosine-5-phosphosulfate:sulfotransferase from rhesus monkey liver that catalyzes the sulfation of the hepatotoxin glycolithocholate

1986

Barnes, S.; Waldrop, R.; Crenshaw, J.; King, R.J.; Taylor, K.B.

J. Lipid Res.

27

1111-1123

645717

2051277

Hepatic bile salt sulfotransferases in the rat: sulfation of 3beta-hydroxy-5-cholenoate during development

1991

Kane, R.E.; Chen, L.J.

J. Ped. Gastroent. Nutri.

12

260-268

645719

1417875

Fatty acid binding protein inhibits glycolithocholate sulfation

1992

Singer, S.S.; Dravis, D.; Henkels, K.; Trulzsch, D.V.

Biochem. Int.

27

373-383

645721

7939371

Bile salt sulphotransferase activity in the liver of cholestatic infants

1994

Obinata, K.; Nemeth, A.; Ellin, A.; Strandvik, B.

Scand. J. Clin. Lab. Invest.

54

285-290

645726

6948578

Enzymatic sulfation of steroids. XV. Studies differentiating between rat liver androgen, estrogen, bile acid, glucocorticoid and phenol sulfotransferases

1982

Singer, S.S.; Federspiel, M.J.; Green, J.; Lewis, W.G.; Martin, V.; Witt, K.R.; Tappel, J.

Biochim. Biophys. Acta

700

110-117

645728

3464463

Purification of a 32.5 kDa monomeric sulfotransferase from rat liver with activity for bile acids and phenolic steroids

1986

Takikawa, H.; Stolz, A.; Kaplowitz, N.

FEBS Lett.

207

193-197

659655

533830

Enzymic sulfation of glycochenodeoxycholic acid by tissue fractions from adult hamsters

1979

Barnes, S.; Burhol, P.G.; Zander, R.; Haggstrom, G.; Settine, R.L.; Hirschowitz, B.I.

J. Lipid Res.

20

952-959

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

676007

17595319

The xenobiotic-sensing nuclear receptors pregnane X receptor, constitutive androstane receptor, and orphan nuclear receptor hepatocyte nuclear factor 4alpha in the regulation of human steroid-/bile acid-sulfotransferase

2007

Echchgadda, I.; Song, C.S.; Oh, T.; Ahmed, M.; De La Cruz, I.J.; Chatterjee, B.

Mol. Endocrinol.

21

2099-2111

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

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

726539

20102295

Kinetic analysis of bile acid sulfation by stably expressed human sulfotransferase 2A1 (SULT2A1)

2010

Huang, J.; Bathena, S.P.; Tong, J.; Roth, M.; Hagenbuch, B.; Alnouti, Y.

Xenobiotica

40

184-194

753412

30014852

A selective gut bacterial bile salt hydrolase alters host metabolism

2018

Yao, L.; Seaton, S.C.; Ndousse-Fetter, S.; Adhikari, A.A.; DiBenedetto, N.; Mina, A.I.; Banks, A.S.; Bry, L.; Devlin, A.S.

eLife

7

e37182

761727

30918069

Inhibition of human sulfotransferase 2A1-catalyzed sulfonation of lithocholic acid, glycolithocholic acid, and taurolithocholic acid by selective estrogen receptor modulators and various analogs and metabolites

2019

Bansal, S.; Lau, A.J.

J. Pharmacol. Exp. Ther.

369

389-405

Links to other databases for glycolithocholic acid

top print hide

Show Links (1 entry)

ChEBI

PubChem