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Ligand 11-deoxycorticosterone

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for 11-deoxycorticosterone

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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

1.14.15.4

11-deoxycorticosterone + reduced adrenal ferredoxin + O2 = corticosterone + oxidized adrenal ferredoxin + H2O

285401

4dvq, 3D-view

1.14.15.4

11-deoxycorticosterone + reduced adrenodoxin + O2 = corticosterone + oxidized adrenodoxin + H2O

725981, 725828

4dvq, 3D-view

1.14.15.4

2 entries

1.14.99.14

11-deoxycorticosterone + AH2 + O2 = ? + A + H2O

715693

-

1.3.99.5

deoxycorticosterone + reduced acceptor = 21-hydroxy-5alpha-pregnan-3,20-dione + acceptor

655526

-

2.4.1.17

21-hydroxyprogesterone + UDP-glucuronate = UDP + 21-hydroxyprogesterone-21-O-D-glucuronate

673304

-

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

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Show Natural Product (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.16

progesterone + NADPH + H+ + O2 = 11-deoxycorticosterone + NADP+ + H2O

0

-

1.14.14.16

progesterone + [reduced NADPH-hemoprotein reductase] + O2 = 11-deoxycorticosterone + [oxidized NADPH-hemoprotein reductase] + H2O

0

-

1.14.14.16

progesterone + [reduced NADPH-P450 reductase] + O2 = 11-deoxycorticosterone + [oxidized NADPH-P450 reductase] + H2O

0

-

1.14.14.16

3 entries

1.14.15.4

corticosterone + reduced adrenal ferredoxin + O2 = 11-deoxycorticosterone + adrenal ferredoxin + ?

0

4dvq, 3D-view

Substrate in Enzyme-catalyzed Reactions (35 results)

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Show Substrate (35 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.149

11-deoxycorticosterone + NAD(P)H = 4-pregnen-20alpha,21-diol-3-one + NAD(P)+

668428

-

1.1.1.53

deoxycorticosterone + NADPH = 20,21-dihydroxypregn-4-ene-3-one + NADP+

287092, 287084

-

1.14.13.54

deoxycorticosterone + NADPH + O2 = ?

7390

-

1.14.15.4

11-deoxycorticosterone + adrenal ferredoxin + H2O = corticosterone + reduced adrenal ferredoxin + O2

686714

4dvq, 3D-view

1.14.15.4

11-deoxycorticosterone + NADPH + O2 = 18-hydroxycorticosterone + NADP+ + H2O

655347

4dvq, 3D-view

1.14.15.4

11-deoxycorticosterone + reduced adrenal ferredoxin + 2 H+ + 2 O2 = aldosterone + oxidized adrenal ferredoxin + 2 H2O

285395, 285396, 285392, 285397, 285399, 285400, 285403

4dvq, 3D-view

1.14.15.4

11-deoxycorticosterone + reduced adrenal ferredoxin + O2 = ?

695555

4dvq, 3D-view

1.14.15.4

11-deoxycorticosterone + reduced adrenal ferredoxin + O2 = corticosterone + oxidized adrenal ferredoxin + H2O

285392, 285410, 285391, 285407, 285393, 285394, 285402, 285404, 285401, 285406, 285389, 285390

4dvq, 3D-view

1.14.15.4

11-deoxycorticosterone + reduced adrenodoxin + O2 = corticosterone + oxidized adrenodoxin + H2O

725981, 725828

4dvq, 3D-view

1.14.15.4

deoxycorticosterone + oxidized adrenodoxin + H2O = corticosterone + reduced adrenodoxin + O2

761755

4dvq, 3D-view

1.14.15.8

11-deoxycorticosterone + reduced adrenodoxin + O2 = 15beta-hydroxy-11-deoxycorticosterone + 7beta,15beta-dihydroxy-11-deoxycorticosterone + oxidized adrenodoxin + H2O

744148

-

1.14.15.8

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

725584, 697323, 695980

-

1.14.15.8

11-deoxycorticosterone + reduced ferredoxin + O2 = 15beta-hydroxy-11-deoxycorticosterone + oxidized ferredoxin + H2O

696462

-

1.14.15.8

11-deoxycorticosterone + reduced flavodoxin + O2 = 15beta-hydroxy-11-deoxycorticosterone + oxidized flavodoxin + H2O

696462

-

1.14.15.8

11-deoxycorticosterone + reduced megaredoxin + O2 = 15beta-hydroxy-11-deoxycorticosterone + oxidized megaredoxin + H2O

698682

-

1.14.15.8

deoxycorticosterone + reduced ferredoxin + O2 = 15beta-hydroxy-11-deoxycorticosterone + oxidized ferredoxin + H2O

696462

-

1.14.15.8

deoxycorticosterone + reduced flavodoxin + O2 = 15beta-hydroxy-11-deoxycorticosterone + oxidized flavodoxin + H2O

696462

-

1.14.15.4

7 entries

1.14.15.8

7 entries

1.14.99.14

11-deoxycorticosterone + AH2 + O2 = ? + A + H2O

715693

-

1.14.99.4

deoxycorticosterone + NADPH + O2 = testosterone + NADP+ + ?

438216

-

1.3.1.22

21-hydroxypregn-4-ene-3,20-dione + NADPH = 21-hydroxy-5alpha-pregnan-3,20-dione + NADP+

390765

-

1.3.1.22

deoxycorticosterone + NADPH = 21-hydroxy-5alpha-pregnan-3,20-dione

396218, 396219, 396193

-

1.3.1.3

cortexone + NADPH = 21-trihydroxy-5beta-pregnane-3,20-dione + NADP+

676735, 676376

-

1.3.1.3

deoxycorticosterone + NADPH = pregnan-21-ol-3,20-dione + NADP+

390646

-

1.3.99.4

11-deoxycorticosterone + acceptor = 21-hydroxypregna-1,4-diene-3,20-dione + reduced acceptor

763735

-

1.3.99.4

deoxycorticosterone + 2,6-dichlorophenol-indophenol = 1,4-pregnadiene-21-ol-3,20-dione + reduced 2,6-dichlorophenol-indophenol

743236

-

1.3.99.4

deoxycorticosterone + 2,6-dichlorophenol-indophenol = 1,4-pregnene-21-ol-3,20-dione + reduced 2,6-dichlorophenol-indophenol

743236

-

1.3.99.4

deoxycorticosterone + acceptor = 1,4-pregnene-21-ol-3,20-dione + reduced acceptor

391383

-

1.3.1.22

2 entries

1.3.1.3

2 entries

1.3.99.4

4 entries

1.3.99.5

deoxycorticosterone + reduced acceptor = 21-hydroxy-5alpha-pregnan-3,20-dione + acceptor

655526

-

2.4.1.17

21-hydroxyprogesterone + UDP-glucuronate = UDP + 21-hydroxyprogesterone-21-O-D-glucuronate

673304

-

2.4.1.385

UDP-alpha-D-glucose + 21-hydroxyprogesterone = UDP + 3,20-dioxopregn-4-en-21-yl beta-D-glucopyranoside

691052

-

2.8.2.15

3'-phosphoadenylylsulfate + 11-deoxycorticosterone = adenosine 3',5'-bisphosphate + 11-deoxycorticosterone sulfate

645724

-

2.8.2.18

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

645768, 645769

-

2.8.2.2

3'-phosphoadenylylsulfate + 11-deoxycorticosterone = adenosine 3',5'-bisphosphate + 11-deoxycorticosterone sulfate

645773, 645774, 645776

-

5.3.1.21

11-Deoxycorticosterone = 20-Hydroxy-3-oxopregn-4-en-21-al

2654, 2652, 2655, 2656, 2657, 2651, 2653

-

7.6.2.2

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

733268

-

Product in Enzyme-catalyzed Reactions (14 results)

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Show Product (14 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.150

pregn-4-ene-3,20,21-trione + NADH = 21-hydroxy-pregn-4-ene-3,20-dione + NAD+

286004

-

1.1.1.151

pregn-4-ene-3,20,21-trione + NADPH = 21-hydroxy-pregn-4-ene-3,20-dione + NADP+

286004

-

1.14.14.16

progesterone + NADH + O2 = 11-deoxycorticosterone + NAD+ + H2O

0

-

1.14.14.16

progesterone + NADPH + H+ + O2 = 11-deoxycorticosterone + NADP+ + H2O

0

-

1.14.14.16

progesterone + [reduced NADPH-hemoprotein reductase] + O2 = 11-deoxycorticosterone + [oxidized NADPH-hemoprotein reductase] + H2O

0

-

1.14.14.16

progesterone + [reduced NADPH-P450 reductase] + O2 = 11-deoxycorticosterone + [oxidized NADPH-P450 reductase] + H2O

0

-

1.14.14.16

DELTA5-pregnen-3beta-ol-20-one + NADH + O2 = deoxycorticosterone + NAD+ + H2O

285439, 0

-

1.14.14.16

progesterone + AH2 + O2 = deoxycorticosterone + A + H2O

0

-

1.14.14.16

progesterone + NADH + O2 = deoxycorticosterone + NAD+ + H2O

0, 285446, 285439, 285440

-

1.14.14.16

progesterone + NADPH + H+ + O2 = deoxycorticosterone + NADP+ + H2O

0

-

1.14.14.16

progesterone + NADPH + O2 = deoxycorticosterone + NADP+ + H2O

285447, 285448, 0

-

1.14.14.16

9 entries

1.14.15.4

corticosterone + reduced adrenal ferredoxin + O2 = 11-deoxycorticosterone + adrenal ferredoxin + ?

0

4dvq, 3D-view

1.3.99.6

21-hydroxy-5beta-pregnan-3,20-dione + acceptor = 21-hydroxy-pregn-4-en-3,20-dione + reduced acceptor

0

-

7.6.2.2

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

0

-

Activator in Enzyme-catalyzed Reactions (1 result)

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Show Activating Compound (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.2.1.3

activates

348717

-

Inhibitor in Enzyme-catalyzed Reactions (18 results)

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Show Inhibitors (18 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.145

-

389394

-

1.1.1.146

-

285949

-

1.1.1.146

IC50: 0.031 mM

285948

-

1.1.1.146

2 entries

1.1.1.21

i.e. 11-deoxycorticosterone

695881

-

1.1.1.213

-

286354

-

1.1.1.239

0.010 mM, 73% inhibition

286354

-

1.1.1.50

-

389527

-

1.1.1.B40

-

285949

-

1.1.1.B40

IC50: 0.001 mM

285948

-

1.1.1.B40

2 entries

1.10.3.3

-

439889

-

1.14.15.4

competitive substrate inhibition

285390

4dvq, 3D-view

1.14.15.8

-

698682

-

1.2.1.3

this inhibition may play a role in cataract formation in patients maintained on systemic corticosteroids and in tablet-dependent diabetics

348709

-

2.3.1.26

-

486676, 486679

-

2.3.1.26

inhibits esterification of endogenous cholesterol

486676

-

2.3.1.26

2 entries

2.8.2.15

competitive inhibitor, inhibits cortisol sulfotransferase activity

645722

-

2.8.2.18

cortisol as substrate, strong

645768, 645769

-

3.4.15.1

-

81234

-

3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (2 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.14.15.4

4dvq, 3D-view

1.14.15.5

4dvq, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (7 results)

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Show Turnover Number (7 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.15.4

0.133

-

dipalmitoyl phosphatidylcholine vesicles + diphosphatidyl glycerol

285398

1.14.15.4

0.3

-

18-hydroxylation

285391

1.14.15.4

0.583

-

dipalmitoyl phosphatidylcholine vesicles

285398

1.14.15.4

0.66

-

+/-2.112, calculatetd from Kcat/Km

285402

1.14.15.4

0.85

-

pH 7.4, recombinant enzyme

686714

1.14.15.4

1.83

-

11beta-hydroxylation

285391

1.14.15.4

6 entries

2.8.2.2

0.183

-

pH 7.5, 37°C

645774

K_M Value (33 results)

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Show KM Value (33 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.149

0.0033

-

pH 7.4, 37°C

668428

1.1.1.53

0.0086

-

-

287084

1.1.1.53

0.0251

-

-

287092

1.14.15.4

0.0008

-

presence of methyltrienolone

285405

1.14.15.4

0.00087

-

without phospholipids

285402

1.14.15.4

0.0011

-

with phospholipids

285402

1.14.15.4

0.0015

-

+/-0.00008

285402

1.14.15.4

0.00197

-

+/-0.00026

285404

1.14.15.4

0.002

-

absence of methyltrienolone

285405

1.14.15.4

0.005

-

dipalmitoyl-phosphatidylcholine vesicles

285398

1.14.15.4

0.006

-

identical for both enzyme activities

285391

1.14.15.4

0.0073

-

37°C

655347

1.14.15.4

0.01

-

dipalmitoyl/diphytanoyl-phosphatidylcholine vesicles

285398

1.14.15.4

0.02

-

identical for both enzymes activities

285389

1.14.15.4

0.033

-

dipalmitoyl phosphatidylcholine/diphosphatidyl glycerol vesicles

285398

1.14.15.4

0.18

-

pH 7.4, recombinant enzyme

686714

1.14.15.8

0.0012

-

pH 7.4, 30°C, mutant I86T

697323

1.14.15.8

0.0015

-

pH 7.4, 30°C, wild-type enzyme

697323

1.14.15.8

0.0019

-

pH 7.4, 30°C, mutant E90V/D185G

697323

1.14.15.8

0.0024

-

pH 7.4, 30°C, mutant K27R/I71T/I215T

697323

1.14.15.8

0.0042

-

pH 7.4, 30°C, mutant A395L

697323

1.14.15.8

0.0046

-

pH 7.4, 30°C, mutant G397P

697323

1.14.15.8

0.0047

-

pH 7.4, 30°C, mutant S394I

697323

1.14.15.8

0.0056

-

pH 7.4, 30°C, mutant Q398S

697323

1.14.15.8

0.06

-

22°C

698682

1.3.1.3

1.597

-

-

676376

1.3.1.3

2.373

-

-

676735

1.3.99.4

0.0216

-

pH 7.0, 30°C

743236

1.3.99.4

0.0425

-

pH 7.0, 30°C

743236

1.3.99.4

0.1113

-

pH 7.0, 30°C

743236

1.1.1.53

2 entries

1.14.15.4

13 entries

1.14.15.8

9 entries

1.3.1.3

2 entries

1.3.99.4

3 entries

2.4.1.385

0.07

-

pH 8.0, 30°C

691052

2.8.2.2

0.52

-

pH 7.5, 37°C

645774

5.3.1.21

0.0038

-

-

2651

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

1.14.15.8

0.11

-

22°C

698682

IC₅₀ Value (3 results)

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Show IC50 Value (3 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.1.1.146

0.031

-

IC50: 0.031 mM

285948

1.1.1.21

0.0025

-

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

695881

1.1.1.B40

0.001

-

IC50: 0.001 mM

285948

References & Links

Literature References (84)

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Show Reference (84 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

2651

901753

Studies on 21-3H-labeled corticosteroids: evidence for isomerization of the ketol side chain of 11-deoxycorticosterone by a hamster liver

1977

Martin, K.O.; Oh, S.W.; Lee, H.J.; Monder, C.

Biochemistry

16

3803-3809

2652

6712249

Stimulation of mouse liver corticosteroid side chain isomerase by cobaltous and nickelous ions: evidence for an endogenous inhibitor of isomerase activity

1984

Iohan, F.; Monder, C.

Arch. Biochem. Biophys.

230

440-445

2653

7391077

Presence of epimerase activity in hamster liver corticosteroid side chain isomerase

1980

Monder, C.; Martin, K.O.; Bogumil, J.

J. Biol. Chem.

255

7192-7198

2654

2028477

Corticosteroid side-chain isomerase in the circulatory system

1991

Monder, C.M; Marandici, A.

Steroids

56

12-16

2655

2075619

Corticosteroid side-chain isomerase in mouse organs: kinetic and immunologic studies

1990

Marandici, A.; Monder, C.

Steroids

55

516-521

2656

2322553

Purification and characterization of corticosteroid side chain isomerase

1990

Marandici, A.; Monder, C.

Biochemistry

29

1147-1154

2657

8461263

Corticosteroid side chain oxidations - 3. Evidence for isomerization and direct oxidation reactions in the formation of steroid 21-oic acids by rabbit liver cytosol

1993

Senciall, I.R.; Rahal, S.

J. Steroid Biochem. Mol. Biol.

44

305-313

7390

3486863

Studies on steroid monooxygenase from Cylindrocarpon radicicola ATCC 11011. Purification and characterization

1986

Itagaki, E.

J. Biochem.

99

815-824

81234

2823638

Isolation of human liver angiotensin-converting enzyme by chromatofocusing

1987

Sakharov, I.Y.; Danilov, S.M.; Sukhova, N.V.

Anal. Biochem.

166

14-17

285389

889836

Purification and properties of cytochrome p-450 (11beta- and 18-hydroxylase) from bovine adrenocortical mitochondria

1977

Watanuki, M.; Tilley, B.E.; Hall, P.F.

Biochim. Biophys. Acta

483

236-247

285390

412519

Cytochrome P-450 for 11beta- and 18-hydroxylase activities of bovine adrenocortical mitochondria: one enzyme or two?

1978

Watanuki, M.; Tilley, B.E.; Hall, P.F.

Biochemistry

17

127-130

285391

708075

Properties of an adrenal cytochrome P-450 (P-45011beta) for the hydroxylations of corticosteroids

1978

Sato, H.; Ashida, N.; Suhara, K.; Itagaki, E.; Takemori, S.; Katagiri, M.

Arch. Biochem. Biophys.

190

307-314

285392

2738055

Isolation of aldosterone synthase cytochrome P-450 from zona glomerulosa mitochondria of rat adrenal cortex

1989

Ogishima, T.; Mitani, F.; Ishimura, Y.

J. Biol. Chem.

264

10935-10938

285393

4155923

Studies on the partially purified heme protein P-450 from the adrenal cortex

1973

Cooper, D.Y.; Schleyer, H.; Levin, S.S.; Rosenthal, O.

Ann. N. Y. Acad. Sci.

212

227-242

285394

6978716

Integration of purified adrenocortical cytochrome P-45011beta into phospholipid vesicles

1982

Lombardo, A.; Defaye, G.; Guidicelli, C.; Monnier, N.; Chambaz, E.M.

Biochem. Biophys. Res. Commun.

104

1638-1645

285395

3485096

The synthesis of aldosterone by the adrenal cortex. Two zones (fasciculata and glomerulosa) possess one enzyme for 11beta-, 18-hydroxylation, and aldehyde synthesis

1986

Yanigabashi, K.; Haniu, M.; Shively, J.E.; Shen, W.H.; Hall, P.

J. Biol. Chem.

261

3556-3562

285396

2788159

Isolation of two distinct cytochromes P-45011beta with aldosterone synthase activity from bovine adrenocortical mitochondria

1989

Ogishima, T.; Mitani, F.; Ishimura, Y

J. Biochem.

105

497-499

285397

2789017

Purification and characterization of two distinct forms of rat adrenal cytochrome P450(11) beta: functional and structural aspects

1989

Lauber, M.; Muller, J.

Arch. Biochem. Biophys.

274

109-119

285398

2337351

Lipid regulation of bovine cytochrome P45011beta activity

1990

Seybert, D.

Arch. Biochem. Biophys.

279

188-194

285399

2176837

Active site of bovine adrenocortical cytochrome P-45011beta studied by resonance Raman and electron paramagnetic resonance spectroscopies: distinction from cytochrome P-450scc

1990

Tsubaki, M.; Ichikawa, Y.; Fujimoto, Y.; Yu, N.T.; Hori, H.

Biochemistry

29

8805-8812

285400

2390091

Ascorbate as a source of reducing equivalents for the synthesis of aldosterone

1990

Yanigabashi, K.; Kobayashi, Y.; Hall, P.F.

Biochem. Biophys. Res. Commun.

170

1256-1262

285401

9430822

Functional and expression analysis of ovine steroid 11beta-hydroxylase (cytochrome P 45011beta)

1997

Boon, W.C.; Roche, P.J.; Butkus, A.; McDougall, J.G.; Jeyaseelan, K.; Coghlan, J.P.

Endocr. Res.

23

325-347

285402

7556158

Inhibition of bovine cytochrome P-45011beta by 18-unsaturated progesterone derivatives

1995

Delorme, C.; Piffeteau, A.; Viger, A.; Marquet, A.

Eur. J. Biochem.

232

247-256

285403

9310386

Mechanism-based inactivation of bovine cytochrome P-45011beta by 18-unsaturated progesterone derivatives

1997

Delorme, C.; Piffeteau, A.; Sobrio, F.; Marquet, A.

Eur. J. Biochem.

248

252-260

285404

9839008

18-Vinyldeoxycorticosterone: a potent inhibitor of the bovine cytochrome P-45011beta

1998

Davioud, E.; Piffeteau, A.; Delorme, C.; Coustal, S.; Marquet, A.

Bioorg. Med. Chem.

6

1781-1788

285405

8431474

Photoaffinity labeling of cytochrome P-45011beta with methyltrienolone as a probe for the substrate binding region

1993

Ohnishi, T.; Miura, S.; Ichikawa, Y.

Biochim. Biophys. Acta

1161

257-264

285406

9057984

Stereoselective reductive metabolism of metyrapone and inhibitory activity of metyrapone metabolites, metyrapol enantiomers, on steroid 11beta-hydroxylase in the rat

1997

Nagamine, S.; Horisaka, E.; Fukuyama, Y.; Maetani, K.; Matsuzawa, R.; Iwakawa, S.; Asada, S.

Biol. Pharm. Bull.

20

188-192

285407

7663533

Cloning and stable expression of the human mitochondrial cytochrome P45011B1 cDNA in V79 Chinese hamster cells and their application for testing of potential inhibitors

1995

Denner, K.; Vogel, R.; Schmalix, W.; Doehmer, J.; Bernhardt, R.

Pharmacogenetics

5

89-96

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