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Ligand pregnenolone

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

androgen and estrogen metabolism

KEGG

Aldosterone synthesis and secretion, Cortisol synthesis and secretion, Cushing syndrome, Ovarian steroidogenesis, Steroid hormone biosynthesis

MetaCyc

11-oxyandrogens biosynthesis, androgen biosynthesis, backdoor pathway of androgen biosynthesis, pregnenolone biosynthesis, progesterone biosynthesis, superpathway of steroid hormone biosynthesis more

Show all BRENDA pathways known for pregnenolone

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (16 results)

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Show Natural Substrate (16 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.145

pregnenolone + NAD(P)+ = pregn-5-en-3,20-dione + NAD(P)H + H+

389373, 389383, 389384, 389399, 389371, 389372, 389385, 389386, 389387, 389388, 389389, 389395, 389401, 389377, 389378, 389379, 389380, 389396, 389392, 389393, 389369, 389374, 389376, 389390, 389391, 2884, 389370, 2898, 389397, 389381, 389382, 389400, 389402

-

1.1.1.145

pregnenolone + NAD+ = pregn-5-en-3,20-dione + NADH + H+

656091, 740914, 740998, 741261, 656586, 656652, 741250

-

1.1.1.145

pregnenolone + NAD+ = progesterone + NADH + H+

656652, 656091

-

1.1.1.51

pregnenolone + NAD+ = progesterone + NADH + H+

677079

-

1.1.1.51

pregnenolone + NADPH + H+ = isoprogesterone + NADP+

713329

-

1.1.3.6

pregnenolone + O2 = 5-pregnen-3,20-dione + H2O2

710959

-

1.1.3.6

pregnenolone + O2 = ? + H2O2

725869

-

1.14.14.19

pregnenolone + AH2 + O2 = 17alpha-hydroxypregnenolone + A + H2O

686364, 390119, 390123, 390131, 390137, 390145, 680978, 685308, 686511, 688979, 691232, 704824, 716053, 390122, 390138, 390144, 675512, 390121, 390132, 390133, 390136, 5129, 390126, 390140, 390127, 390120, 691670, 692540

-

1.14.14.19

pregnenolone + ferrocytochrome b5 + O2 = ?

703551

-

1.14.14.19

pregnenolone + [reduced NADPH-hemoprotein reductase] + O2 = 17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O

735281, 732996, 726886, 726923, 726997, 727947, 728213, 734260, 734283, 734289, 735204, 727701

-

1.14.14.32

pregnenolone + reduced acceptor + O2 = 17alpha-hydroxypregnenolone + oxidized acceptor + H2O

714275

-

1.14.14.32

pregnenolone + [reduced NADPH-hemoprotein reductase] + O2 = 17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O

735283, 734569

-

2.8.2.15

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

738099

-

2.8.2.15

3'-phosphoadenylylsulfate + pregnenolone = adenosine 3',5'-bisphosphate + pregnenolone 3-sulfate

724959

-

2.8.2.2

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

661823, 761704

-

2.8.2.2

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

738296

-

1.1.1.145

3 entries

1.1.1.51

2 entries

1.1.3.6

2 entries

1.14.14.19

3 entries

1.14.14.32

2 entries

2.8.2.15

2 entries

2.8.2.2

2 entries

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

1.14.15.6

(20R,22R)-20,22-dihydroxy-cholesterol + 2 reduced adrenodoxin + O2 = pregnenolone + 4-methylpentanal + 2 oxidized adrenodoxin + 2 H2O

-

-

1.14.15.6

cholesterol + 6 reduced adrenodoxin + 3 O2 = pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O

285425, 285429, 285430, 285432, 285433, 285431, 285412, 285415, 285417, 285418, 285420, 285421, 285422, 285423, 285428, 285426,

-

1.14.15.6

cholesterol + reduced adrenal ferredoxin + O2 = pregnenolone + 4-methylpentanal + oxidized adrenal ferredoxin

-

-

1.14.15.6

cholesterol + reduced ferredoxin + O2 = pregnenolone + 4-methylpentanal + oxidized ferredoxin

-

-

1.14.15.6

4 entries

Substrate in Enzyme-catalyzed Reactions (49 results)

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Show Substrate (49 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.145

pregnenolone + NAD(P)+ = pregn-5-en-3,20-dione + NAD(P)H

389373, 389383, 389384, 389399, 389371, 389372, 389385, 389386, 389387, 389388, 389389, 389395, 389401, 389377, 389378, 389379, 389380, 389396, 389392, 389393, 389369, 389374, 389376, 389390, 389391, 2884, 389370, 2898, 389397, 389381, 389382, 389400, 389402

-

1.1.1.145

pregnenolone + NAD+ = isoprogesterone + NADH + H+

713329

-

1.1.1.145

pregnenolone + NAD+ = isoprogesterone + progesterone + NADH

689697

-

1.1.1.145

pregnenolone + NAD+ = pregn-5-en-3,20-dione + NADH

656091, 656586, 656652

-

1.1.1.145

pregnenolone + NAD+ = pregn-5-en-3,20-dione + NADH + H+

740914, 740998, 741261, 741250, 740503

-

1.1.1.145

pregnenolone + NAD+ = progesterone + NADH

724302, 725511

-

1.1.1.145

pregnenolone + NAD+ = progesterone + NADH + H+

670037, 699845, 656652, 685186, 700557, 699111, 656091

-

1.1.1.145

7 entries

1.1.1.270

pregnenolone + NADH + H+ = progesterone + NAD+

725813

-

1.1.1.278

pregnenolone + NADP+ = ?

691108

-

1.1.1.51

5-pregnen-3beta-ol-20-one + NAD(P)+ = 5-pregnene-3,20-dione + NAD(P)H + H+

689697

-

1.1.1.51

pregnenolone + NAD(P)+ = progesterone + NAD(P)H + H+

699146, 691108, 700177

-

1.1.1.51

pregnenolone + NAD+ = progesterone + NADH + H+

677079, 712092

-

1.1.1.51

pregnenolone + NADP+ = progesterone + NADPH + H+

712881

-

1.1.1.51

pregnenolone + NADPH + H+ = isoprogesterone + NADP+

713329

-

1.1.1.51

pregnenolone + NADPH = progesterone + NADP+

670037

-

1.1.1.51

6 entries

1.1.1.53

pregnenolone + NADPH = 3beta,20beta-Dihydroxypregn-5-ene + NADP+

287084

-

1.1.3.6

3beta-hydroxypregn-5-en-20-one + O2 = pregn-5-en-3,20-dione + H2O2

723968

-

1.1.3.6

pregnenolone + O2 = 5-pregnen-3,20-dione + H2O2

657224, 2892, 287653, 287657, 287648, 287646, 710959

-

1.1.3.6

pregnenolone + O2 = ?

697915, 287670, 287674, 697914, 655611, 684653

-

1.1.3.6

pregnenolone + O2 = ? + H2O2

725869

-

1.1.3.6

4 entries

1.14.13.54

Pregnenolone + NADPH + O2 = ?

7389

-

1.14.14.16

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

285439, 285440

-

1.14.14.19

pregnenolone + AH2 + O2 = 17alpha-hydroxypregnenolone + A + H2O

686364, 390119, 390123, 390131, 390137, 390145, 657657, 680978, 685308, 686511, 688979, 691232, 704824, 716053, 390122, 390138, 390144, 675512, 658149, 746506, 390121, 390132, 390133, 390136, 5129, 390126, 390140, 390127, 390120, 691670, 692540

-

1.14.14.19

pregnenolone + ferrocytochrome b5 + O2 = ?

703551

-

1.14.14.19

pregnenolone + [reduced NADPH-hemoprotein reductase] + O2 = 17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O

735281, 732996, 726886, 726923, 726997, 727947, 728213, 734260, 734283, 734289, 735204, 745365, 727701, 734316

-

1.14.14.32

pregnenolone + AH2 + O2 = 17alpha-hydroxypregnenolone + A + H2O

714352

-

1.14.14.32

pregnenolone + reduced acceptor + O2 = 17alpha-hydroxypregnenolone + oxidized acceptor + H2O

714275

-

1.14.14.32

pregnenolone + [reduced NADPH-hemoprotein reductase] + O2 = 17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O

735283, 734569, 745365

-

1.14.14.32

pregnenolone + [reduced NADPH-hemoprotein reductase] + O2 = 3beta-hydroxyandrost-5-en-17-one + acetate + [oxidized NADPH-hemoprotein reductase] + H2o

745365

-

1.14.14.19

3 entries

1.14.14.32

4 entries

1.14.15.30

pregnenolone + 2 reduced ferredoxin [iron-sulfur] cluster + H+ + O2 = ?

745648

-

1.14.15.8

pregnenolone + reduced adrenodoxin + O2 = 7beta-hydroxy-pregnenolone + oxidized adrenodoxin + H2O

745699

-

2.3.1.26

acyl-CoA + pregnenolone = CoA + pregnenolyl 3-O-acyl ester

736702

-

2.3.1.26

pregnenolone + oleoyl-CoA = 20-oxopregn-5-en-3beta-yl (9Z)-octadec-9-enoate + CoA

720018

-

2.4.1.173

pregn-5-en-3beta-ol-20-one + UDP-glucose = ?

690224

-

2.4.1.173

pregnenolone + UDP-glucose = UDP + pregnenolone 3-beta-D-glucoside

672427

-

2.4.1.173

UDP-glucose + pregnenolone = UDP + pregnenolone 3-beta-D-glucoside

671624

-

2.4.1.173

UDP-glucose + pregnenolone = UDP + pregnenolone 3-beta-glucoside

637770

-

2.3.1.26

2 entries

2.4.1.173

4 entries

2.4.1.192

pregn-5-en-3beta-ol-20-one + UDP-glucose = UDP + pregn-5-en-3beta-ol-20-one 3-O-beta-D-glucoside

488871

-

2.8.2.1

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

762517

-

2.8.2.15

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

738102, 738099

-

2.8.2.15

3'-phosphoadenylylsulfate + pregnenolone = adenosine 3',5'-bisphosphate + pregn-5-en-20-one 3-sulfate

663165

-

2.8.2.15

3'-phosphoadenylylsulfate + pregnenolone = adenosine 3',5'-bisphosphate + pregnenolone 3-sulfate

724959

-

2.8.2.15

3'-phosphoadenylylsulfate + pregnenolone = adenosine 3',5'-bisphosphate + pregnenolone sulfate

645733, 645730, 645723, 645729, 645725, 645739, 645736, 645724

-

2.8.2.2

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

675604, 675680, 661823, 761704

-

2.8.2.2

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

738296

-

2.8.2.2

3'-phosphoadenylylsulfate + pregnenolone = adenosine 3',5'-bisphosphate + 5-pregnen-20-one 3-sulfate

645792, 645781, 645773

-

2.8.2.2

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

661823

-

2.8.2.15

4 entries

2.8.2.2

4 entries

2.8.2.4

3'-phosphoadenylylsulfate + pregnenolone = adenosine 3',5'-bisphosphate + pregnenolone 3-sulfate

645881, 645883, 645900

-

5.3.3.1

pregnenolone = progesterone

725807

-

Product in Enzyme-catalyzed Reactions (17 results)

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Show Product (17 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.53

3beta,20alpha-dihydroxypregn-5-ene + NADP+ = 3beta-hydroxypregn-5-en-20-one + NADPH

-

-

1.1.3.6

5-pregnen-3,20-dione + O2 = pregnenolone + H2O2

-

-

1.14.15.6

(20R,22R)-20,22-dihydroxy-cholesterol + 2 reduced adrenodoxin + O2 = pregnenolone + 4-methylpentanal + 2 oxidized adrenodoxin + 2 H2O

-

-

1.14.15.6

20alpha-hydroxycholesterol + reduced adrenodoxin + O2 = pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O

-

-

1.14.15.6

20alpha-hydroxycholesterol + reduced adrenodoxin + O2 = pregnenolone + oxidized adrenodoxin + H2O

285418

-

1.14.15.6

22(R)-hydroxycholesterol + reduced adrenodoxin + O2 = pregnenolone + oxidized adrenodoxin + H2O

-

-

1.14.15.6

25-hydroxycholesterol + O2 + reduced ferredoxin = pregnenolone + H2O + ferredoxin + 4-hydroxy-4-methylpentanal

-

-

1.14.15.6

25-hydroxycholesterol + reduced adrenodoxin + O2 = pregnenolone + oxidized adrenodoxin + H2O

-

-

1.14.15.6

cholesterol + 6 reduced adrenodoxin + 3 O2 = pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O

285425, 285429, 285430, 285432, 285433, 285431, 285412, 285415, 285417, 285418, 285420, 285421, 285422, 285423, 285428, 285426,

-

1.14.15.6

cholesterol + 6 reduced adrenodoxin mutant S112W + 3 O2 = pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin mutant S112W + 4 H2O

-

-

1.14.15.6

cholesterol + reduced adrenal ferredoxin + O2 = pregnenolone + 4-methylpentanal + oxidized adrenal ferredoxin

-

-

1.14.15.6

cholesterol + reduced adrenal ferredoxin + O2 = pregnenolone + adrenal ferredoxin + H2O

-

-

1.14.15.6

cholesterol + reduced adrenodoxin + O2 + H+ = pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O

-

-

1.14.15.6

cholesterol + reduced adrenodoxin + O2 = pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O

, 285412, 285413, 285414, 285415, 285419, 285420, 285423, 285424, 285426, 285427, 285428, 285429, 285430, 285431, 285432, 285433, 285422, 285421, 285425, 285416, 285418, 285417

-

1.14.15.6

cholesterol + reduced ferredoxin + O2 = pregnenolone + 4-methylpentanal + oxidized ferredoxin

-

-

3.1.6.2

pregnenolone 3-sulfate + H2O = pregnenolone + sulfate

-

-

3.1.6.2

pregnenolone sulfate + H2O = pregnenolone + sulfate

-

-

1.14.15.6

13 entries

3.1.6.2

2 entries

Inhibitor in Enzyme-catalyzed Reactions (10 results)

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Show Inhibitors (10 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.145

competitive inhibition

389369

-

1.14.13.54

and other C21-20-ketosteroids which are the substrates for oxygenative esterification of the enzyme, strongly inhibit lactonization of androstenedione

7389

-

1.14.14.19

-

390145

-

1.14.99.12

-

7389

-

1.4.1.3

-

743356

-

2.3.1.26

-

486679

-

2.3.1.26

inhibits esterification of endogenous cholesterol

486676

-

2.3.1.26

2 entries

2.3.1.5

-

685029

-

2.8.2.15

substrate inhibition

645729

-

3.1.6.2

1 mM, 10% inhibition

656643

-

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

1.14.99.9

4nkw, 3D-view

4.1.2.30

4nkw, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (31 results)

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Show Turnover Number (31 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.1.1.145

0.04

-

-

389390

1.1.1.145

1.48

-

pH 8.5, 37°C

685186

1.1.3.6

9

-

pH 7.0, 37°C, mutant enzyme P357N

657224

1.1.3.6

9

-

pH 7.0, 37°C, mutant enzyme V145D

657224

1.1.3.6

11

-

pH 7.0, 37°C, mutant enzyme V145E

657224

1.1.3.6

12

-

pH 7.0, 37°C, mutant enzyme V145Q

657224

1.1.3.6

13

-

pH 7.0, 37°C, mutant enzyme L119A

657224

1.1.3.6

19

-

pH 7.0, 37°C, mutant enzyme Q286R

657224

1.1.3.6

21

-

assay relies on spectroscopic detection of 4-cholesten-3-one formation

287670

1.1.3.6

21

-

pH 7.0, 37°C, mutant enzyme L119F

657224

1.1.3.6

21

-

product formation followed at 240 nm in the presence of 0.02 ml H2O2, substrate dissolved in Triton X-100, 100 mM phosphate buffer

287674

1.1.3.6

21

-

substrate pregnenolone, detection of product formation at 240 nm. 0.1 M potassium phosphate, 1% Triton X-100, 1.25% propan-2-ol, 25°C and pH 7.5

697914

1.1.3.6

21

-

substrate pregnenolone, rate of H2O2 formation detected with o-dianisidine and horseradish peroxidase. 0.1 M potassium phosphate, 1% Triton X-100, 1.25% propan-2-ol, 25°C and pH 7.5

697914

1.1.3.6

24

-

assay relies on spectroscopic detection of 4-cholesten-3-one formation

287670

1.1.3.6

24

-

product formation followed at 240 nm in the presence of 0.02 ml H2O2, substrate dissolved in Triton X-100, 100 mM phosphate buffer

287674

1.1.3.6

24

-

substrate pregnenolone, detection of product formation at 240 nm. 0.1 M potassium phosphate, 1% Triton X-100, 1.25% propan-2-ol, 25°C and pH 7.5

697914

1.1.3.6

30

-

pH 7.0, 37°C, wild-type enzyme

657224

1.1.3.6

35

-

pH 7.0, 37°C, mutant enzyme S379A

657224

1.1.3.6

35

-

substrate pregnenolone, rate of H2O2 formation detected with o-dianisidine and horseradish peroxidase. 0.1 M potassium phosphate, 1% Triton X-100, 1.25% propan-2-ol, 25°C and pH 7.5

697914

1.1.3.6

39

-

pH 7.0, 37°C, mutant enzyme S379V

657224

1.1.3.6

45

-

pH 7.0, 37°C, mutant enzyme S379T

657224

1.14.14.19

0.0037

-

pH 7.4, 37°C

745365

1.14.14.19

0.0065

-

mutant enzyme A105L, at pH 7.4 and 37°C

734283

1.14.14.19

0.0065

-

wild type enzyme, at pH 7.4 and 37°C

734283

1.14.14.19

0.03

-

isoform P450 17A1, at pH 7.4 and 37°C

734316

1.14.14.19

0.11

-

pH 7.4, 37°C, presence of cytochrome b5

745365

1.14.14.19

0.85

-

isoform P450 17A2, at pH 7.4 and 37°C

734316

1.14.14.32

0.0037

-

17alpha-hydroxylation, pH 7.4, 37°C

745365

1.14.14.32

0.045

-

lyase reaction, pH 7.4, 37°C, presence of cytochrome b5

745365

1.14.14.32

0.11

-

17alpha-hydroxylation, pH 7.4, 37°C, presence of cytochrome b5

745365

1.1.1.145

2 entries

1.1.3.6

19 entries

1.14.14.19

6 entries

1.14.14.32

3 entries

2.4.1.173

0.0047

-

for the cytosolic enzyme

672427

K_M Value (83 results)

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Show KM Value (83 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.145

0.00004

-

3betaHSD VI

389384

1.1.1.145

0.00007

-

-

389372

1.1.1.145

0.00008

-

3betaHSD I

389383

1.1.1.145

0.00013

-

-

389396

1.1.1.145

0.00047

-

37°C, pH 7.25

657352

1.1.1.145

0.001

-

37°C

656586, 656652

1.1.1.145

0.00102

-

-

389382

1.1.1.145

0.00103

-

3betaHSD III

389383

1.1.1.145

0.0011

-

37°C

656652

1.1.1.145

0.002

-

-

389369, 389390

1.1.1.145

0.002

-

mitochondria

389391

1.1.1.145

0.0028

-

27°C, pH 7.4

656091

1.1.1.145

0.0032

-

microsomes

389391

1.1.1.145

0.0055

-

type I

389400

1.1.1.145

0.0088

-

type II

389400

1.1.1.145

0.02

-

NAD+ as cofactor

389402

1.1.1.145

0.023

-

pH 8.5, 37°C

685186

1.1.1.145

0.04534

-

pH 7.2, 30°C

763569

1.1.1.145

0.05

-

27°C, pH 7.4

656091

1.1.1.145

0.09

-

pH 7.8, 30°C

689697

1.1.1.145

0.2313

-

pH 7.8, 30°C

763139

1.1.1.51

0.00067

-

pH and temperature not specified in the publication

712881

1.1.1.51

0.09

-

50°C, pH 7.8

689697

1.1.1.145

21 entries

1.1.1.51

2 entries

1.1.1.53

0.004

-

-

287084

1.1.3.6

0.0000058

-

pH 7.0, 37°C, mutant enzyme S379T

657224

1.1.3.6

0.000023

-

pH 7.0, 37°C, mutant enzyme S379A

657224

1.1.3.6

0.000023

-

pH 7.0, 37°C, wild-type enzyme

657224

1.1.3.6

0.00004

-

pH 7.0, 37°C, mutant enzyme L119A

657224

1.1.3.6

0.00004

-

pH 7.0, 37°C, mutant enzyme S379V

657224

1.1.3.6

0.000056

-

pH 7.0, 37°C, mutant enzyme Q286R

657224

1.1.3.6

0.000058

-

pH 7.0, 37°C, mutant enzyme V145Q

657224

1.1.3.6

0.000077

-

pH 7.0, 37°C, mutant enzyme L119F

657224

1.1.3.6

0.000083

-

pH 7.0, 37°C, mutant enzyme V145E

657224

1.1.3.6

0.000098

-

pH 7.0, 37°C, mutant enzyme P357N

657224

1.1.3.6

0.0001

-

pH 7.0, 37°C, mutant enzyme V145D

657224

1.1.3.6

0.0017

-

-

2892

1.1.3.6

0.19061

-

pH 7.5, temperature not specified in the publication, mutant enzyme F70V

763712

1.1.3.6

0.2

-

-

287674

1.1.3.6

0.2

-

assay relies on spectroscopic detection of 4-cholesten-3-one formation

287670

1.1.3.6

0.2

-

substrate pregnenolone, detection of product formation at 240 nm. 0.1 M potassium phosphate, 1% Triton X-100, 1.25% propan-2-ol, 25°C and pH 7.5

697914

1.1.3.6

0.2

-

substrate pregnenolone, rate of H2O2 formation detected with o-dianisidine and horseradish peroxidase. 0.1 M potassium phosphate, 1% Triton X-100, 1.25% propan-2-ol, 25°C and pH 7.5

697914

1.1.3.6

0.22842

-

pH 7.5, temperature not specified in the publication, mutant enzyme V64C

763712

1.1.3.6

0.29455

-

pH 7.5, temperature not specified in the publication, wild-type enzyme

763712

1.1.3.6

0.33

-

pH 7.5, 37°C, full-length isozyme ChoM2

725869

1.1.3.6

0.35

-

pH 7.5, 37°C, truncated isozyme ChoM2

725869

1.1.3.6

0.38

-

pH 7.5, 37°C

725869

1.1.3.6

0.4

-

-

287674

1.1.3.6

0.4

-

assay relies on spectroscopic detection of 4-cholesten-3-one formation

287670

1.1.3.6

0.4

-

substrate pregnenolone, detection of product formation at 240 nm. 0.1 M potassium phosphate, 1% Triton X-100, 1.25% propan-2-ol, 25°C and pH 7.5

697914

1.1.3.6

0.5

-

-

287653

1.1.3.6

4

-

in the presence of undecanol

287653

1.14.14.19

0.00008

-

wild type enzyme

390124

1.14.14.19

0.00022

-

R200N mutant

390124

1.14.14.19

0.00025

-

-

390124

1.14.14.19

0.00038

-

mutant enzyme A105L, at pH 7.4 and 37°C

734283

1.14.14.19

0.0005

-

pH 7.4, 37°C

745365

1.14.14.19

0.00055

-

-

704824

1.14.14.19

0.0008

-

adrenal gland

390140

1.14.14.19

0.00093

-

wild type enzyme, at pH 7.4 and 37°C

734283

1.14.14.19

0.0011

-

pH 7.4, 37°C, presence of cytochrome b5

745365

1.14.14.19

0.0017

-

isozyme 1, pH 7.4, temperature not specified in the publication

727701

1.14.14.19

0.0019

-

isozyme 2, pH 7.4, temperature not specified in the publication

727701

1.14.14.19

0.002

-

isoform P450 17A1, at pH 7.4 and 37°C

734316

1.14.14.19

0.0025

-

-

390145

1.14.14.19

0.0077

-

-

390132

1.14.14.19

0.0093

-

isoform P450 17A2, at pH 7.4 and 37°C

734316

1.14.14.32

0.00049

-

lyase reaction, pH 7.4, 37°C, presence of cytochrome b5

745365

1.14.14.32

0.0005

-

17alpha-hydroxylation, pH 7.4, 37°C

745365

1.14.14.32

0.0011

-

17alpha-hydroxylation, pH 7.4, 37°C, presence of cytochrome b5

745365

1.1.3.6

27 entries

1.14.14.19

15 entries

1.14.14.32

3 entries

2.3.1.26

0.0012

-

pH 7.4, 37°C, with cholesterol (0.32 mM). Without cholesterol, the Km for pregnenolone is too high to be measurable

720018

2.4.1.173

0.005

-

for the cytosolic enzyme

672427

2.4.1.173

0.006

-

activity is assayed radiometrically using UDP-[U-14C] glucose, at pH 8.0 and 37°C

671624

2.4.1.173

0.008

-

-

671624

2.8.2.15

0.00025

-

pH 7.7, 37°C, 3-betaHST isoform

645736

2.8.2.15

0.0018

-

pH 7.4, 37°C, isoenzyme His-SULT2B1b

645739

2.8.2.15

0.0027

-

pH 7.4, 37°C, isoenzyme SULT2B1b

645739

2.8.2.15

0.003

-

pH 7.4, 37°C, isoenzyme His-SULT2B1a

645739

2.8.2.15

0.0049

-

pH 7.4, 37°C, isoenzyme DHEA-ST

645739

2.8.2.15

0.0072

-

pH 7.4, 37°C, isoenzyme SULT2B1a

645739

2.8.2.15

0.014

-

pH 7.5, 25°C, BNST4

663165

2.8.2.2

0.000257

-

pH 7.7, 37°C

645781

2.8.2.2

0.0016

-

pH 7.5, 37°C

645792

2.8.2.2

0.0089

-

pH 7.5, 37°C, recombinant isozyme SULT2B1a

661823

2.4.1.173

3 entries

2.8.2.15

7 entries

2.8.2.2

3 entries

K_i Value (1 result)

top print hide

Show KI Value (1 entry)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.14.19

0.0008

-

competitive substrate with progesterone

390145

IC₅₀ Value (5 results)

top print hide

Show IC50 Value (5 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.4.1.3

0.0117

-

pH 8.0, temperature not specified in the publication

743356

1.4.1.3

0.0541

-

presence of 0.1 M ADP, pH 8.0, temperature not specified in the publication

743356

1.4.1.3

0.104

-

pH 8.0, temperature not specified in the publication

743356

1.4.1.3

0.287

-

presence of 0.1 M ADP, pH 8.0, temperature not specified in the publication

743356

1.4.1.3

4 entries

2.3.1.5

0.1

-

value above 0.1 mM

685029

References & Links

Literature References (192)

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Show Reference (192 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

2884

4274151

Purification and properties of the DELTA5-3-beta-hydroxysteroid dehydrogenase-isomerase system of sheep adrenal cortical microsomes

1974

Ford, H.C.; Engel, L.L.

J. Biol. Chem.

249

1363-1368

2892

588244

The substrate specificity and stereochemistry, reversibility and inhibition of the 3-oxo steroid DELTA 4-DELTA 5-isomerase component of cholesterol oxidase

1977

Smith, A.G.; Brooks, C.J.W.

Biochem. J.

167

121-129

2898

2050270

Characterization of macaque 3beta-hydroxy-5-ene steroid dehydrogenase/DELTA5-DELTA4-isomerase: structure and expression in steroidogenic and peripheral tissues in primate

1991

Simard, J.; Melner, M.H.; Breton, N.; Low, K.G.; Zhao, H.F.; Periman, L.M.; Labrie, F.

Mol. Cell. Endocrinol.

75

101-110

5129

8918985

Kinetic analysis of duodenal and testicular cytochrome P450c17 in the rat

1996

Dalla Valle, L.; Ramina, A.; Vianello, S.; Belvedere, P.; Colombo, L.

J. Steroid Biochem. Mol. Biol.

58

577-584

7389

3486864

Studies on steroid monooxygenase from Cylindrocarpon radicicola ATCC 11011. Oxygenative lactonization of androstenedione to testololactone

1986

Itagaki, E.

J. Biochem.

99

825-832

285412

6766943

Mitochondrial cytochrome P-450sec. Mechanism of electron transport by adrenodoxin

1980

Hanukoglu, I.; Jefcoate, C.R.

J. Biol. Chem.

255

3057-3061

285413

7217084

Adrenal mitochondrial cytochrome P-450scc. Cholesterol and adrenodoxin interactions at equilibrium and during turnover

1981

Hanukoglu, I.; Spitsberg, V.; Bumpus, J.A.; Dus, K.M.; Jefcoate, C.R.

J. Biol. Chem.

256

4321-4328

285414

6783659

Mechanisms of ionic activation of adrenal mitochondrial cytochromes P-450scc and P-45011beta

1981

Hanukoglu, I.; Privalle, C.T.; Jefcoate, C.R.

J. Biol. Chem.

256

4329-4335

285415

184090

Purification and characterization of adrenal cortex mitochondrial cytochrome P-450 specific for cholesterol side chain cleavage activity

1976

Wang, H.P.; Kimura, T.

J. Biol. Chem.

251

6068-6074

285416

444237

Binding of Triton X-100 to purified cytochrome P-450scc and enhancement of the cholesterol side chain cleavage activity

1979

Nakajin, S.; Ishii, Y.; Shinoda, M.

Biochem. Biophys. Res. Commun.

87

524-531

285417

6723652

The catalytic cycle of cytochrome P-450scc and intermediates in the conversion of cholesterol to pregnenolone

1984

Hume, R.; Kelly, R.W.; Taylor, P.L.; Boyd, G.S.

Eur. J. Biochem.

140

583-591

285418

4723901

Cytochrome P-450 from bovine adrenocortical mitochondria: an enzyme for the side chain cleavage of cholesterol. I. Purification and properties

1973

Shikita, M.; Hall, P.F.

J. Biol. Chem.

248

5598-5604

285419

1131251

Purification of cytochrome P-450 from bovine adrenocortical mitochondria by an aniline-Sepharose and the properties

1975

Takemori, S.; Sukara, K.; Hashimoto, K.; Hashimoto, M.; Sato, H.; Gomi, T.; Katagiri, M.

Biochem. Biophys. Res. Commun.

63

588-593

285420

2605191

Cholesterol metabolism by purified cytochrome P-450scc is highly stimulated by octyl glucoside and stearic acid exclusively in large unilamellar phospholipid vesicles

1989

Dhariwal, M.S.; Jefcoate, C.R.

Biochemistry

28

8397-8402

285421

4019455

Cytochrome P-450scc-adrenodoxin interactions. Ionic effects on binding, and regulation of cytochrome reduction by bound steroid substrates

1985

Lambeth, J.D.; Kriengsiri, S.

J. Biol. Chem.

260

8810-8816

285422

3968069

Competitive inhibition of cytochrome P-450scc by (22R)- and (22S)-22-aminocholesterol. Side-chain stereochemical requirements for C-22 amine coordination to the active-site heme

1985

Nagahisa, A.; Foo, T.; Gut, M.; Orme-Johnson, W.H.

J. Biol. Chem.

260

846-851

285423

6244284

Purification and characterization of mitochondrial cytochrome P-450 associated with cholesterol side chain cleavage from bovine corpus luteum

1980

Kashiwagi, K.; Dafeldecker, W.P.; Salhanick, H.A.

J. Biol. Chem.

255

2606-2611

285424

6688621

Active site-directed inhibitors of cytochrome P-450scc. Structural and mechanistic implications of a side chain-substituted series of amino-steroids

1983

Sheets, J.J.; Vickery, L.E.

J. Biol. Chem.

258

11446-11452

285425

6822531

C-22-Substituted steroid derivatives as substrate analogues and inhibitors of cytochrome P-450scc

1983

Sheets, J.J.; Vickery, L.E.

J. Biol. Chem.

258

1720-1725

285426

6572949

Modulation of the kinetics of cholesterol side-chain cleavage by an activator and by an inhibitor isolated from the cytosol of the cortex of bovine adrenals

1983

Warne, P.A.; Greenfield, N.J.; Lieberman, S.

Proc. Natl. Acad. Sci. USA

80

1877-1881

285427

4723902

Cytochrome P-450 from bovine adrenocortical mitochondria: an enzyme for the side chain cleavage of cholesterol. II. Subunit structure

1973

Shikita, M.; Hall, P.F.

J. Biol. Chem.

248

5605-5609

285428

7599132

Cytochrome P-450scc-mediated oxidation of (20S)-22-thiacholesterol: Characterization of mechanism-based inhibition

1995

Miao, E.; Joardar, S.; Zuo, C.; Cloutier, N.J.; Nagahisa, A.; Byon, C.; Wilson, S.R.; Orme-Johnson, W.H.

Biochemistry

34

8415-8421

285429

8662703

alpha-Branched 1,2-diacyl phosphatidylcholines as effectors of activity of cytochrome P450SCC (CYP11A1). Modeling the structure of the fatty acyl chain region of cardiolipin

1996

Schwarz, D.; Kisselev, P.; Wessel, R.; Jueptner, O.; Schmid, R.D.

J. Biol. Chem.

271

12840-12846

285430

11173513

Site-directed mutagenesis of cytochrome P450scc (CYP11A1). Effect of lysine residue substitution on its structural and functional properties

2000

Lepesheva, G.I.; Azeva, T.N.; Strushkevich, N.V.; Gilep, A.A.; Usanov, S.A.

Biochemistry (Moscow)

65

1409-1418

285431

10924360

The use of the novel substrate-heme complex approach in the derivation of a representation of the active site of the enzyme cholesterol side chain cleavage

2000

Ahmed, S.

Biochem. Biophys. Res. Commun.

274

821-824

285432

8431464

Substrate-binding region of cytochrome P-450scc (P-450 XIA1). Identification and primary structure of the cholesterol binding region in cytochrome P-450scc

1993

Tsujita, M.; Ichikawa, Y.

Biochim. Biophys. Acta

1161

124-130

285433

12081479

Probing the interaction of bovine cytochrome P450scc (CYP11A1) with adrenodoxin: evaluating site-directed mutations by molecular modeling

2002

Usanov, S.A.; Graham, S.E.; Lepesheva, G.I.; Azeva, T.N.; Strushkevich, N.V.; Gilep, A.A.; Estabrook, R.W.; Peterson, J.

Biochemistry

41

8310-8320

285439

13416221

Hydroxylation of steroids at carbon 21

1957

Ryan, K.J.; Engel, L.L.

J. Biol. Chem.

225

103-114

285440

6972231

Purification and reconstitution of the steroid 21-hydroxylase system (cytochrome P-450-linked mixed function oxidase system) of bovine adrenocortical microsomes

1981

Hiwatashi, A.; Ichikawa, Y.

Biochim. Biophys. Acta

664

33-48

287084

3240999

20beta-Hydroxysteroid dehydrogenase of neonatal pig testis: purification and some properties

1988

Nakajin, S.; Ohno, S.; Shinoda, M.

J. Biochem.

104

565-569

287646

-

Properties of crystalline 3beta-hydroxysteroid oxidase of Brevibacterium sterolicum

1974

Uwajima, T.; Yagi, H.; Terado, O.

Agric. Biol. Chem.

38

1149-1156

287648

956143

Some enzymatic properties of 3beta-hydroxysteroid oxidase produced by Streptomyces violascens

1976

Tomioka, H.; Kagawa, M.; Nakamura, S.

J. Biochem.

79

903-915

287653

-

Influence of long-chain primary alcohols on cholesterol oxidase from Schizophyllum commune

1983

Abe, T.; Nihira, T.; Tanaka, A.; Fukui, S.

Biochim. Biophys. Acta

749

69-76

287657

36375

Purification and some properties of cholesterol oxidase from Schizophyllum commune with covalently bound flavin

1979

Fukuyama, M.; Miyake, Y.

J. Biochem.

85

1183-1193

287670

9428686

Characterization of cholesterol oxidase from Streptomyces hygroscopicus and Brevibacterium sterolicum

1997

Gadda, G.; Wels, G.; Pollegioni, L.; Zucchelli, S.; Amrosius, D.; Pilone, M.S.; Ghisla, S.

Eur. J. Biochem.

250

369-376

287674

10447682

Kinetic mechanisms of cholesterol oxidase from Streptomyces hygroscopicus and Brevibacterium sterolicum

1999

Pollegioni, L.; Wels, G.; Pilone, M.S.; Ghisla, S.

Eur. J. Biochem.

264

140-151

389369

3867664

Purification and kinetic properties of 3beta-hydroxysteroid dehydrogenase from bovine adrenocortical microsomes

1985

Hiwatashi, A.; Hamamoto, I.; Ichikawa, Y.

J. Biochem.

98

1519-1526

389370

495965

Preparation of highly purified 3alpha- and 3beta-hydroxysteroid dehydrogenases from Pseudomonas sp

1979

Shikita, M.; Talalay, P.

Anal. Biochem.

95

286-292

389371

1610797

Affinity labeling of human placental 3beta-hydroxy-DELTA5-steroid dehydrogenase and steroid delta-isomerase: evidence for bifunctional catalysis by a different conformation of the same protein for each enzyme activity

1992

Thomas, J.L.; Strickler, R.C.; Myers, R.P.; Covey, D.F

Biochemistry

31

5522-5527

389372

6957697

Partial characterization of placental 3beta-hydroxysteroid dehydrogenase (EC 1.1.1.145), delta 4-5isomerase (EC 5.3.3.1) in human term placental mitochondria

1982

Rabe, T.; Brandstetter, K.; Kellermann, J.; Runnebaum, B.

J. Steroid Biochem.

17

427-433

389373

6955572

Properties of 5-ene-3beta-hydroxysteroid dehydrogenase in granulosa tissue from the domestic fowl (Gallus domesticus)

1982

Armstrong, D.G.

J. Steroid Biochem.

17

225-230

389374

28762

Role of thiol group(s) in the enzymatic activity of the membrane-bound delta5-3beta-hydroxysteroid dehydrogenase from bovine adrenal cortex microsomes

1978

Vincent, M.; Gallay, J.; de Paillerets, C.; Alfsen, A.; Biellmann, J.F.

Biochim. Biophys. Acta

525

1-8

389376

4226148

Purification and properties of 3-beta-hydroxysteroid dehydrogenase and delta-5-3-ketosteroid isomerase from bovine corpora lutea

1966

Cheatum, S.G.; Warren, J.C.

Biochim. Biophys. Acta

122

1-13

389377

14220672

The conversion of pregnenolone to progesterone by small particles from rat adrenal

1964

Koritz, S.B.

Biochemistry

3

1098-1102

389378

2961942

Testicular and adrenal 3beta-hydroxy-5-ene-steroid dehydrogenase and 5-ene-4-ene isomerase

1987

Ishii-Ohba, H.; Inano, H.; Bunichi, T.

J. Steroid Biochem.

27

775-779

389379

2945972

Purification and properties of testicular 3beta-hydroxy-5-ene-steroid dehydrogenase and 5-ene-4-ene isomerase

1986

Ishii-Ohba, H.; Inano, H.; Tamaoki, B.

J. Steroid Biochem.

25

555-560

389380

6603965

Differences in inhibition by various steroids of rat testis and Pseudomonas testosteroni DELTA5-3beta-hydroxysteroid dehydrogenase

1983

Spona, J.

Endocrinol. Exp.

17

107-118

389381

5856

Properties of delta5-3beta-hydroxysteroid oxidoreductase isolated from Streptomyces griseocarneus

1975

Kerenyi, G.; Szentirmai, A.; Natonek, M.

Acta Microbiol. Acad. Sci. Hung.

22

487-496

389382

11070354

Kinetic properties of microsomal 3beta hydroxysteroid dehydrogenase-isomerase from the testis of Bufo arenarum H

2000

Pozzi, A.G.; Canosa, L.F.; Calvo, J.C.; Ceballos, N.R.

J. Steroid Biochem. Mol. Biol.

73

257-264

389383

8477648

Enzyme characteristics of two distinct forms of mouse 3beta-hydroxysteroid dehydrogenase/DELTA5-DELTA4-isomerase complementary deoxyribonucleic acids expressed in COS-1 cells

1993

Clarke, T.R.; Bain, P.A.; Sha, L.; Payne, A.H.

Endocrinology

132

1971-1976

389384

9075693

Isolation of a new mouse 3beta-hydroxysteroid dehydrogenase isoform, 3beta-HSD VI, expressed during early pregnancy

1997

Abbaszade, I.G.; Arensburg, J.; Park, C.H.; Kasa-Vubu, J.Z.; Orly, J.; Payne, A.H.

Endocrinology

138

1392-1399

389385

10686147

Membrane-bound human 3beta-hydroxysteroid dehydrogenase: overexpression with his-tag using a baculvirus system and single-step purification

2000

Huang, Y.W.; Lu, M.L.; Qi, H.; Lin, S.X.

Protein Expr. Purif.

18

169-174

389386

11463578

The engineered, cytosolic form of human type I 3beta-hydroxysteroid dehydrogenase/isomerase: purification, characterization and crystallization

2001

Thomas, J.L.; Mason, J.I.; Blanco, G.; Veisaga, M.L.

J. Mol. Endocrinol.

27

77-83

389387

10514560

Creation of a fully active, cytosolic form of human type I 3beta-hydroxysteroid dehydrogenase/isomerase by the deletion of a membrane-spanning domain

1999

Thomas, J.L.; Evans, B.W.; Blanco, G.; Mason, J.I.; Strickler, R.C.

J. Mol. Endocrinol.

23

231-239

389388

1381375

Immunohistochemical localization of 3beta-hydroxy-5-ene-steroid dehydrogenase/DELTA5-DELTA4 isomerase in human placenta and fetal membranes throughout gestation

1992

Riley, S.C.; Dupont, E.; Walton, J.C.; Luu-The, V.; Labrie, F.; Pelletier, G.; Challis, J.R.

J. Clin. Endocrinol.

75

956-961

389389

11061520

3beta-Hydroxysteroid dehydrogenase/DELTA5---4-isomerase activity associated with the human 17beta-hydroxysteroid dehydrogenase type 2 isoform

2000

Suzuki, T.; Sasana, H.; Andersson, S.; Mason, J.I.

J. Clin. Endocrinol.

85

3669-3672

389390

10704908

Bovine adrenal 3beta-hydroxysteroid dehydrogenase (E.C. 1.1.1.145)/5-ene-4-ene isomerase (E.C. 5.3.3.1): characterization and its inhibition by isoflavones

1999

Wong, C.K.; Keung, W.M.

J. Steroid Biochem. Mol. Biol.

71

191-202

389391

8119176

Characterization of the 3beta-hydroxysteroid dehydrogenase activity associated with bovine adrenocortical mitochondria

1994

Cherradi, N.; Defaye, G.; Chambaz, E.M.

Endocrinology

134

1358-1364

389392

8702847

Purification of a 3beta-hydroxy-D5-C27-steroid dehydrogenase from pig liver microsomes active in major and alternative pathways of bile acid biosynthesis

1996

Furster, C.; Zhang, J.; Toll, A.

J. Biol. Chem.

271

20903-20907

389393

1388046

Kinetic evidence for separate 3beta-hydroxysteroid dehydrogenase-isomerases in androgen and 16-androstene biosynthetic pathways in the pig testis

1992

Hebert, P.; Cooke, G.M.

J. Steroid Biochem. Mol. Biol.

42

901-910

389395

1562516

Structure and tissue-specific expression of 3beta-hydroxysteroid dehydrogenase/5-ene-4-ene isomerase genes in human and rat classical and peripheral steroidogenic tissues

1992

Labrie, F.; Simard, J.; Luu-The, V.; Pelletier, G.; Belanger, A.; Lachance, Y.; Zhao, H.F.; Labrie, C.; Breton, N.; de Launoit, Y.; et al.

J. Steroid Biochem. Mol. Biol.

41

421-435

389396

1955079

3beta-Hydroxysteroid dehydrogenase/DELTA 5-4-isomerase expression in rat and characterization of the testis isoform

1991

Lorence, M.C.; Naville, D.; Graham-Lorence, S.E.; Mack, S.O.; Murry, B.A.; Trant, J.M.; Mason, J.I.

Mol. Cell. Endocrinol.

80

21-31

389397

8070583

Ovarian 3beta-hydroxysteroid dehydrogenase/DELTA5-4-isomerase of rainbow trout: its cDNA cloning and properties of the enzyme expressed in a mammalian cell

1994

Sakai, N.; Tanaka, M.; Takahashi, M.; Fukada, S.; Mason, J.I.; Nagahama, Y.

FEBS Lett.

350

309-313

389399

1926230

Subcellular distribution of 3beta-hydroxysteroid dehydrogenase-isomerase in bovine and murine adrenocortical tissue: species differences in the localization of activity and immunoreactivity

1991

Perry, J.E.; Ishii-Ohba, H.; Stalvey, J.R.

Steroids

56

329-336

389400

8547173

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