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Ligand 11alpha-hydroxyprogesterone

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

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Show Natural Substrate (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.146

11alpha-hydroxy-pregn-4-ene-3,20-dione + ? = pregn-4-ene-3,11,20-trione + ?

285966

-

2.4.1.17

11alpha-hydroxyprogesterone + UDP-glucuronate = UDP + 11alpha-hydroxyprogesterone-11-O-D-glucuronate

673304

-

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

1.14.99.14

progesterone + AH2 + O2 = 11alpha-hydroxyprogesterone + A + H2O

-

-

1.14.99.14

progesterone + NADPH + O2 = 11alpha-hydroxyprogesterone + NADP+ + H2O

438354, 288562, 438356, 438362, 438355, 438358, 438359, 438361, 438363, 438360

-

1.14.99.14

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

1.1.1.146

11alpha-hydroxy-pregn-4-ene-3,20-dione + ? = pregn-4-ene-3,11,20-trione + ?

285966

-

1.14.99.14

11alpha-hydroxyprogesterone + NADPH + O2 = 6beta,11alpha-dihydroxyprogesterone

438354

-

1.3.1.22

11alpha-hydroxyprogesterone + NADPH + H+ = 11alpha-hydroxydihydroprogesterone + NADP+

763398

-

1.3.99.4

11alpha-hydroxyprogesterone + acceptor = 11alpha-hydroxy-1,4-pregnene-3,20-dione + reduced acceptor

391375

-

2.4.1.17

11alpha-hydroxyprogesterone + UDP-glucuronate = UDP + 11alpha-hydroxyprogesterone-11-O-D-glucuronate

673304

-

2.4.1.17

UDP-D-glucuronate + 11alpha-hydroxyprogesterone = UDP + 11alpha-hydroxyprogesterone 11-O-beta-D-glucuronoside

690847

-

2.4.1.17

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

1.14.15.8

progesterone + reduced adrenodoxin + O2 = 15beta-hydroxy-progesterone + 11alpha-hydroxy-progesterone + oxidized adrenodoxin + H2O

-

-

1.14.99.14

progesterone + AH2 + O2 = 11alpha-hydroxyprogesterone + A + H2O

-

-

1.14.99.14

progesterone + NADPH + O2 = 11alpha-hydroxyprogesterone + NADP+ + H2O

438354, 288562, 438356, 438362, 438355, 438358, 438359, 438360, 438361, 438363

-

1.14.99.14

2 entries

Activator in Enzyme-catalyzed Reactions (1 result)

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Show Activating Compound (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.14.99.14

induced by

438354

-

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.146

-

761757

-

Enzyme Kinetic Parameters

K_M Value (3 results)

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Show KM Value (3 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.3.99.4

0.0196

-

i.e. 4-pregnene-11alpha-ol-3,20-dione, 11beta-hydroxy-4-androstene-3,17-dione, 4-estren-3,17-dione

391375

2.4.1.17

0.0069

-

37°C, pH 7.4

673304

2.4.1.17

0.093

-

37°C, pH 7.4

673304

2.4.1.17

2 entries

References & Links

Literature References (16)

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Show Reference (16 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

285966

6946265

Specificity of human 11beta-hydroxysteroid dehydrogenase

1981

Pearson Murphy, B.E.

J. Steroid Biochem.

14

807-809

288562

6810893

Microsomal 11alpha-hydroxylation of progesterone in Aspergillus ochraceus: Part I: Characterization of the hydroxylase system

1982

Jayanthi, C.R.; Madyastha, P.; Madyastha, K.M.

Biochem. Biophys. Res. Commun.

106

1262-1268

391375

2317517

Purification and characterization of 3-ketosteroid-delta 1-dehydrogenase from Nocardia corallina

1990

Itagaki, E.; Wakabayashi, T.; Hatta, T.

Biochim. Biophys. Acta

1038

60-67

438354

5417182

Microbial hydroxylations. V. 11alpha-hydroxylation of progesterone by cell-free preparations of Aspergillus ochraceus

1979

Shibahara, M.; Moody, J.A.; Smith, L.L.

Biochim. Biophys. Acta

202

172-179

438355

-

Regeneration of the progesterone 11alpha-hydroxylase of Rhizopus nigricans by the use of periodate

1980

Hanisch, W.H.; Dunnill, P.

Biotechnol. Lett.

2

123-126

438356

7300325

11alpha-Hydroxylation of progesterone by cell free preparation of Aspergillus ochraceus TS

1981

Ghosh, D.; Samanta, T.B.

J. Steroid Biochem.

14

1063-1067

438358

3936501

Resolution and reconstitution of the NADPH-cytochrome c (P-450) reductase induced by progesterone in Rhizopus nigricans

1985

Cresnar, B.; Breskvar, K.; Hudnik-Plevnik, T.

Biochem. Biophys. Res. Commun.

133

1057-1063

438359

6810893

Studies for the large scale isolation of membrane-associated progesterone 11alpha-hydroxylase:enzyme stability in Rhizopus nigricans ATCC 6277b cells

1986

Broad, D.F.; Pontin, S.; Dunnill, P.

Enzyme Microb. Technol.

9

546-548

438360

3936501

Poly(ethylene glycol) precipitation and two aquaeous-phase separation of progesterone 11-alpha hydroxylase from Rhizopus nigricans

1988

Bonnerjea, J.; Pontin, S.; Hoare, M.; Dunnill, P.

Appl. Microbiol. Biotechnol.

27

362-365

438361

8651707

Identification and partial characterization of cytosolic progesterone-binding sites in the filamentous fungus Rhizopus nigricans

1996

Lenasi, H.; Hudnik-Plevnik, T.

Arch. Biochem. Biophys.

330

80-86

438362

10525834

Bioconversion of progesterone by the activated immobilized conidia of Aspergillus ochraceus TS

1999

Dutta, T.K.; Samanta, T.B.

Curr. Microbiol.

39

309-312

438363

10653158

Comparison of two monooxygenase systems with cytochrome P450 in filamentous fungus Rhizopus nigricans

2000

Kunic, B.; Makovec, T.; Breskvar, K.

Pflugers Arch.

439

R107-108

673304

17151189

The glucuronidation of DELTA4-3-keto C19- and C21-hydroxysteroids by human liver microsomal and recombinant UDP-glucuronosyltransferases (UGTs): 6alpha- and 21-hydroxyprogesterone are selective substrates for UGT2B7

2007

Bowalgaha, K.; Elliot, D.J.; Mackenzie, P.I.; Knights, K.M.; Miners, J.O.

Drug Metab. Dispos.

35

363-370

690847

17223084

Amino terminal domains of human UDP-glucuronosyltransferases (UGT) 2B7 and 2B15 associated with substrate selectivity and autoactivation

2007

Lewis, B.C.; Mackenzie, P.I.; Elliot, D.J.; Burchell, B.; Bhasker, C.R.; Miners, J.O.

Biochem. Pharmacol.

73

1463-1473

761757

30825506

The 11beta-hydroxysteroid dehydrogenase isoforms pivotal catalytic activities yield potent C11-oxy C19 steroids with 11betaHSD2 favouring 11-ketotestosterone, 11-ketoandrostenedione and 11-ketoprogesterone biosynthesis

2019

Gent, R.; du Toit, T.; Bloem, L.M.; Swart, A.C.

J. Steroid Biochem. Mol. Biol.

189

116-126

763398

31039398

11alpha-Hydroxyprogesterone, a potent 11alpha-hydroxysteroid dehydrogenase inhibitor, is metabolised by steroid-5alpha-reductase and cytochrome P450 17alpha-hydroxylase/17,20-lyase to produce C11alpha-derivatives of 21-deoxycortisol and 11-hydroxyandrostenedione in vitro

2019

Gent, R.; du Toit, T.; Swart, A.C.

J. Steroid Biochem. Mol. Biol.

191

105369

Links to other databases for 11alpha-hydroxyprogesterone

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