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Ligand 17beta-hydroxy-5alpha-androstan-3-one

Basic Ligand Information

Molecular Structure

Show all pathways known for 17beta-hydroxy-5alpha-androstan-3-one

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (27 results)

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Show Natural Substrate (27 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.210

17beta-hydroxy-5alpha-androstan-3-one + NADPH = 5alpha-androstan-3beta,17beta-diol + NADP+

286265, 286266

-

1.1.1.213

17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+ = 3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+

347988, 347990, 347981, 347982, 347989

-

1.1.1.213

5alpha-dihydrotestosterone + NAD(P)H = 5alpha-androstane-3alpha,17beta-diol + NAD(P)+

674674

-

1.1.1.213

5alpha-dihydrotestosterone + NADPH + H+ = 3alpha-androstanediol + NADP+

654726

-

1.1.1.213

5alpha-dihydrotestosterone + NADPH = 3alpha-androstanediol + NADP+

672088, 676812

-

1.1.1.213

5alpha-dihydrotestosterone + NADPH = 5alpha-androstane-3alpha,17beta-diol + NADP+

673349, 676002, 668392, 677001

-

1.1.1.213

5 entries

1.1.1.239

5alpha-dihydrotestosterone + NAD+ = androstandione + NADH

287209

-

1.1.1.270

2 17beta-hydroxy-5alpha-androstan-3-one + 2 NADPH + 2 H+ = 5alpha-androstane-3beta,17beta-diol + 5alpha-androstane-3alpha,17beta-diol + 2 NADP+

656200

-

1.1.1.270

5alpha-dihydrotestosterone + NADPH = 3alpha-androstanediol + NADP+

655348

-

1.1.1.357

5alpha-dihydrotestosterone + NADPH + H+ = 3alpha-androstanediol + NADP+

740017

-

1.1.1.357

5alpha-dihydrotestosterone + NAD(P)H + H+ = 3alpha-androstanediol + NAD(P)+

724711, 724208

-

1.1.1.357

5alpha-dihydrotestosterone + NADPH + H+ = 5alpha-androstane-3alpha,17beta-diol + NADP+

743179

-

1.1.1.50

5alpha-dihydrotestosterone + NAD(P)H = 5alpha-androstane-3alpha,17beta-diol + NAD(P)+

389551, 389525, 674674, 389557, 389540, 389528

-

1.1.1.50

5alpha-dihydrotestosterone + NADH = 3alpha-androstanediol + NAD+

655348

-

1.1.1.50

5alpha-dihydrotestosterone + NADPH = 3alpha-androstanediol + NADP+

672088, 676812

-

1.1.1.50

5alpha-dihydrotestosterone + NADPH = 5alpha-androstane-3alpha,17beta-diol + NADP+

673349

-

1.1.1.50

5alpha-dihydrotestosterone + NADPH + H+ = 5alpha-androstane-3alpha,17beta-diol + NADP+

740017, 738928

-

1.1.1.270

2 entries

1.1.1.357

3 entries

1.1.1.50

5 entries

1.1.1.51

dihydrotestosterone + NADPH + H+ = 5alpha-androstane-3beta,17beta-diol + NADP+

670033

-

1.1.1.62

5alpha-dihydrotestosterone + NADP+ = 5alpha-androstan-3,17-dione + NADPH

670033

1dht, 3D-view

1.1.1.62

5alpha-dihydrotestosterone + NADP+ = 5alpha-androstan-3,17-dione + NADPH

670033

3dey, 3D-view

1.1.1.62

5alpha-dihydrotestosterone + NADP+ = 5alpha-androstan-3,17-dione + NADPH

670033

3klm, 3D-view

1.1.1.62

3 entries

1.3.1.20

5alpha-dihydrotestosterone + NADPH = 5alpha-androstan-3alpha,17beta-diol + NADP+

349263

-

1.3.99.5

5alpha-dihydrotestosterone + NADP+ = testosterone + NADPH + H+

712093, 713520, 713519, 713595

-

1.3.99.5

dihydrotestosterone + NADP+ = testosterone + NADPH + H+

713080, 711736, 712094

-

1.3.99.5

2 entries

1.6.2.2

5alpha-dihydrotestosterone + acceptor = ?

394211

-

2.4.1.17

UDP-D-glucuronate + dihydrotestosterone = UDP + dihydrotestosterone 17-O-beta-D-glucuronoside

693011

-

4.1.1.17

5alpha-dihydrotestosterone = ?

697772

-

In Vivo Product in Enzyme-catalyzed Reactions (10 results)

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Show Natural Product (10 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.213

3alpha-androstanediol + NAD+ = 5alpha-dihydrotestosterone + NADH + H+

-

-

1.1.1.35

5alpha-androstane-3,17-diol + NAD+ = 5alpha-dihydrotestosterone + NADH

-

-

1.1.1.357

3alpha-androstanediol + NAD(P)+ = 5alpha-dihydrotestosterone + NAD(P)H + H+

-

-

1.1.1.357

5alpha-androstane-3alpha,17beta-diol + NADP+ = (5alpha)-androstan-17-beta-ol-3-one + NADPH + H+

-

-

1.1.1.51

5-androstenedione + NADPH = 5alpha-dihydrotestosterone + NADP+

-

-

1.1.1.51

androstane-3,17-dione + NADPH = dihydrotestosterone + NADP+

-

-

1.3.1.22

testosterone + NADPH = 5alpha-dihydrotestosterone + NADP+

-

-

1.3.1.22

testosterone + NADPH = 17beta-hydroxy-5alpha-androstan-3-one + NADP+

-

-

1.3.1.22

testosterone + NADPH + H+ = 5alpha-dihydrotestosterone + NADP+

-

-

1.1.1.357

2 entries

1.1.1.51

2 entries

1.3.1.22

3 entries

1.3.99.5

testosterone + reduced acceptor = 5alpha-dihydrotestosterone + acceptor

-

-

Substrate in Enzyme-catalyzed Reactions (108 results)

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Show Substrate (108 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

17beta-hydroxyetiocholan-3-one + NAD+ = ethiocholan-3,17-dione + NADH

285571

-

1.1.1.1

5alpha-androstan-17beta-ol-3-one + NADH + H+ = 3beta,17beta-dihydroxy-5alpha-androstan + NAD+

655206, 285606

-

1.1.1.112

5alpha-dihydrotestosterone + NAD(P)+ = 5alpha-dihydro-17-oxo-testosterone + NADH

285760

-

1.1.1.112

5alpha-dihydrotestosterone + NAD+ = 5alpha-17-oxo-dihydrotestosterone + NADH + H+

285760

-

1.1.1.145

5alpha-dihydrotestosterone + NADPH = ? + NADP+

684725

-

1.1.1.145

5alpha-dihydrotestosterone + NADPH = 5alpha-androstane-3beta,17beta-diol + NADP+

389394

-

1.1.1.145

17beta-hydroxy-5alpha-androstane-3-one + NADPH = 3beta,17beta-dihydroxy-5alpha-androstane + NADP+

389394

-

1.1.1.1

2 entries

1.1.1.112

2 entries

1.1.1.145

3 entries

1.1.1.148

5alpha-dihydrotestosterone + NADPH = 5alpha-androstane-3alpha,17alpha-diol + NADP+

668078

-

1.1.1.149

dihydrotestosterone + NADPH = ? + NADP+

656526

-

1.1.1.149

5alpha-dihydrotestosterone + NADP+ = ?

740126

-

1.1.1.149

5alpha-dihydrotestosterone + NADPH + H+ = ?

740126

-

1.1.1.149

5alpha-dihydrotestosterone + NADPH + H+ = ? + NADP+

740522

-

1.1.1.149

4 entries

1.1.1.150

dihydrotestosterone + NADH = androstanediol + NAD+

688677

-

1.1.1.184

5alpha-androstan-17beta-ol-3-one + NADPH = ?

347770, 347755, 655213

-

1.1.1.184

5alpha-dihydrotestosterone + NADPH = ?

347762

-

1.1.1.184

5alpha-androstane-17beta-ol-3-one + NADPH = ? + NADP+

697269

-

1.1.1.184

3 entries

1.1.1.189

5alpha-dihydrotestosterone + NADPH = ?

347776

-

1.1.1.2

5alpha-dihydrotestosterone + NADPH = ? + NADP+

286184

-

1.1.1.209

5alpha-dihydrotestosterone + NAD(P)H = androstanedione + NAD(P)+

389547

-

1.1.1.209

5alpha-androstan-17beta-ol-3-one + NADP+ = 5alpha-androstan-3,17-dione + NADPH + H+

710716, 695325

-

1.1.1.210

17beta-hydoxy-5alpha-androstan-3-one + NADPH = 5alpha-androstan-3beta,17beta-diol + NADP+

286265, 286266, 286267

-

1.1.1.210

17beta-hydroxy-5alpha-androstan-3-one + NADPH = 5alpha-androstan-3beta,17beta-diol + NADP+

286265, 286266

-

1.1.1.213

17beta-hydroxy-5alpha-androstan-3-one + NADPH = 3alpha,17beta-dihydroxy-5alpha-androstan + NADP+

347979

-

1.1.1.213

5alpha-androstan-17beta-ol-3-one + NADPH + H+ = 5alpha-androstan-3alpha,17beta-diol + NADP+

286354

-

1.1.1.213

androstan-17beta-ol-3-one + NADH = androstan-3alpha,17beta-diol + NAD+

347984

-

1.1.1.213

17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H = 5alpha-androstane-3alpha,17beta-diol + NAD(P)+

347987

-

1.1.1.213

17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+ = 3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+

347988, 347990, 347981, 347982, 347989

-

1.1.1.213

5alpha-dihydrotestosterone + NAD(P)H = 5alpha-androstane-3alpha,17beta-diol + NAD(P)+

674674

-

1.1.1.213

5alpha-dihydrotestosterone + NADPH + H+ = 3alpha-androstanediol + NADP+

654726

-

1.1.1.213

5alpha-dihydrotestosterone + NADPH = 3alpha-androstanediol + NADP+

672088, 676812

-

1.1.1.213

5alpha-dihydrotestosterone + NADPH = 5alpha-androstane-3alpha,17beta-diol + NADP+

673349, 676002, 668392, 677001, 675687

-

1.1.1.213

5alpha-dihydrotestosterone + NADH = ?

684676

-

1.1.1.239

5alpha-dihydrotestosterone + NAD+ = androstanedione + NADH

287209, 287216

-

1.1.1.239

5alpha-dihydrotestosterone + NAD+ = 5alpha-androstane-3,17-dione + NADH

287214

-

1.1.1.239

5alpha-dihydrotestosterone + NAD+ = androstandione + NADH

287209

-

1.1.1.239

5alpha-androstan-17beta-ol-3-one + NAD+ = 5alpha-androstan-3,17-dione + NADH + H+

739953

-

1.1.1.239

5alpha-androstane-17beta-ol-3-one + NAD+ = 5alpha-androstan-3,17-dione + NADH + H+

739953

-

1.1.1.239

5alpha-dihydrotestosterone + NADH + H+ = testosterone + NADH + H+

740637

-

1.1.1.270

17beta-hydroxy-5alpha-androstan-3-one + NADPH = 5alpha-androstane-3beta,17beta-diol + NADP+

286475, 286478

-

1.1.1.270

5alpha-dihydrotestosterone + NADPH = 5alpha-androstan-3alpha,17beta-diol + NADP+

677144

-

1.1.1.270

2 17beta-hydroxy-5alpha-androstan-3-one + 2 NADPH + 2 H+ = 5alpha-androstane-3beta,17beta-diol + 5alpha-androstane-3alpha,17beta-diol + 2 NADP+

656200

-

1.1.1.270

5alpha-dihydrotestosterone + NADPH = 3alpha-androstanediol + NADP+

655348

-

1.1.1.270

5alpha-dihydrotestosterone + NADPH = 5alpha-androstan-3beta,17beta-diol + NADP+

677144

-

1.1.1.270

5alpha-dihydrotestosterone + NADPH + H+ = 3beta,17beta-dihydroxy-5alpha-androstane + NADP+

724124

-

1.1.1.209

2 entries

1.1.1.210

2 entries

1.1.1.213

10 entries

1.1.1.239

6 entries

1.1.1.270

6 entries

1.1.1.35

5alpha-dihydrotestosterone + NADH = (3beta,5alpha,17beta)-androstane-3,17-diol + NAD+

286589

-

1.1.1.357

5alpha-dihydrotestosterone + NADPH + H+ = 3alpha-androstanediol + NADP+

724711, 740017

-

1.1.1.357

5alpha-dihydrotestosterone + NAD(P)H + H+ = (5alpha,17beta)-androstane-3,17-diol + NAD(P)+

722166

-

1.1.1.357

5alpha-dihydrotestosterone + NAD(P)H + H+ = 3alpha-androstanediol + NAD(P)+

724711, 724208

-

1.1.1.357

5alpha-dihydrotestosterone + NADPH + H+ = 5alpha-androstane-3alpha,17beta-diol + NADP+

743179, 725333

-

1.1.1.357

dihydrotestosterone + NAD(P)H + H+ = 5alpha-androstane-3alpha,17beta-diol + NAD(P)+

725345

-

1.1.1.357

5alpha-androstan-17-beta-ol-3-one + NADH + H+ = 5alpha-androstane-3alpha,17beta-diol + NAD+

739957

-

1.1.1.357

5alpha-androstan-17-beta-ol-3-one + NADPH + H+ = 5alpha-androstane-3alpha,17beta-diol + NADP+

739957

-

1.1.1.50

5alpha-dihydrotestosterone + NAD(P)H = 5alpha-androstan-3alpha,17beta-diol + NAD(P)+

389545, 389540, 389541, 389547, 389551, 389546, 389525, 389528, 389531, 389532, 389522, 389529

-

1.1.1.50

5alpha-dihydrotestosterone + NAD(P)H = 3beta-adiol + NAD(P)+

389545, 389540, 389541, 389547, 389546, 389525, 389528, 389531, 389532, 389522, 389529

-

1.1.1.50

17beta-hydroxy-dihydrotestosterone + NAD+ = 5alpha-androstan-3,17-dione + NADH

389541

-

1.1.1.50

5alpha-dihydrotestosterone + NAD(P)H = 5alpha-androstane-3alpha,17beta-diol + NAD(P)+

389551, 389525, 674674, 389557, 389540, 389528

-

1.1.1.50

5alpha-dihydrotestosterone + NADH = 3alpha-androstanediol + NAD+

655348

-

1.1.1.50

5alpha-dihydrotestosterone + NADPH = 3alpha-androstanediol + NADP+

672088, 676812

-

1.1.1.50

5alpha-dihydrotestosterone + NADPH = 5alpha-androstane-3alpha,17beta-diol + NADP+

673349

-

1.1.1.50

5alpha-dihydrotestosterone + NADH = ?

684676

-

1.1.1.50

5alpha-dihydrotestosterone + NADPH + H+ = 5alpha-androstane-3alpha,17beta-diol + NADP+

740017, 738928

-

1.1.1.51

5alpha-dihydrotestosterone + NADP+ = 5alpha-androstane-3,17-dione + NADPH

287073

-

1.1.1.51

5alpha-dihydrotestosterone + NAD(P)H = 5alpha-androstane-3beta,17beta-diol + NADP+

287073

-

1.1.1.51

dihydrotestosterone + NAD+ = 5alpha-androstan-3,17-dione + NADH

659176

-

1.1.1.51

dihydrotestosterone + NADP+ = 5alpha-androstan-3,17-dione + NADPH

659176

-

1.1.1.51

dihydrotestosterone + NADPH + H+ = 5alpha-androstane-3beta,17beta-diol + NADP+

670033

-

1.1.1.51

5alpha-dihydrotestosterone + NADH + H+ = ? + NAD+

740637

-

1.1.1.53

5alpha-androstan-17beta-ol-3-one + NAD(P)H + H+ = 5alpha-androstan-3alpha,17beta-diol + NAD(P)+

287103, 287106, 287097

-

1.1.1.53

5alpha-dihydrotestosterone + NADPH = 5alpha-androstan-3alpha,17beta-diol + NADP+

654932

-

1.1.1.53

5alpha-dihydrotestosterone + NADP+ = 5alpha-androstan-3alpha,17beta-diol + NADPH + H+

738928

-

1.1.1.62

5alpha-dihydrotestosterone + NADP+ = 5alpha-androstan-3,17-dione + NADPH

287176, 670033

1dht, 3D-view

1.1.1.62

5alpha-dihydrotestosterone + NADP+ = 5alpha-androstan-3,17-dione + NADPH

287176, 670033

3dey, 3D-view

1.1.1.62

5alpha-dihydrotestosterone + NADP+ = 5alpha-androstan-3,17-dione + NADPH

287176, 670033

3klm, 3D-view

1.1.1.62

5alpha-dihydrotestosterone + NADH = 5alpha-androstanedione + NAD+

287206

1dht, 3D-view

1.1.1.62

5alpha-dihydrotestosterone + NADH = 5alpha-androstanedione + NAD+

287206

3dey, 3D-view

1.1.1.62

5alpha-dihydrotestosterone + NADH = 5alpha-androstanedione + NAD+

287206

3klm, 3D-view

1.1.1.62

5alpha-dihydrotestosterone + NADPH = 5alpha-androstane-3,17-dione + NADP+

287208

1dht, 3D-view

1.1.1.62

5alpha-dihydrotestosterone + NADPH = 5alpha-androstane-3,17-dione + NADP+

287208

3dey, 3D-view

1.1.1.62

5alpha-dihydrotestosterone + NADPH = 5alpha-androstane-3,17-dione + NADP+

287208

3klm, 3D-view

1.1.1.62

dihydrotestosterone + NAD(P)H + H+ = androstane-3beta,17beta-diol + NAD(P)+

670265

1dht, 3D-view

1.1.1.62

dihydrotestosterone + NAD(P)H + H+ = androstane-3beta,17beta-diol + NAD(P)+

670265

3dey, 3D-view

1.1.1.62

dihydrotestosterone + NAD(P)H + H+ = androstane-3beta,17beta-diol + NAD(P)+

670265

3klm, 3D-view

1.1.1.62

dihydrotestosterone + NADPH + H+ = 5alpha-androstane-3beta,17beta-diol + NADP+

686263

1dht, 3D-view

1.1.1.62

dihydrotestosterone + NADPH + H+ = 5alpha-androstane-3beta,17beta-diol + NADP+

686263

3dey, 3D-view

1.1.1.62

dihydrotestosterone + NADPH + H+ = 5alpha-androstane-3beta,17beta-diol + NADP+

686263

3klm, 3D-view

1.1.1.62

5alpha-dihydrotestosterone + NAD+ = 5alpha-androstan-3,17-dione + NADH

688956

1dht, 3D-view

1.1.1.62

5alpha-dihydrotestosterone + NAD+ = 5alpha-androstan-3,17-dione + NADH

688956

3dey, 3D-view

1.1.1.62

5alpha-dihydrotestosterone + NAD+ = 5alpha-androstan-3,17-dione + NADH

688956

3klm, 3D-view

1.1.1.62

5alpha-dihydrotestosterone + NADPH + H+ = 5alpha-androstane-3beta,17beta-diol + 5alpha-androstane-3,17-dione + NADP+

726374

1dht, 3D-view

1.1.1.62

5alpha-dihydrotestosterone + NADPH + H+ = 5alpha-androstane-3beta,17beta-diol + 5alpha-androstane-3,17-dione + NADP+

726374

3dey, 3D-view

1.1.1.62

5alpha-dihydrotestosterone + NADPH + H+ = 5alpha-androstane-3beta,17beta-diol + 5alpha-androstane-3,17-dione + NADP+

726374

3klm, 3D-view

1.1.1.64

5alpha-dihydrotestosterone + NADP+ = 5alpha-17-oxo-dihydrotestosterone + NADPH

287226

-

1.1.1.64

5alpha-androstane-17beta-ol-3-one + NADP+ = 5alpha-androstane-3,17-dione + NADPH

287228

-

1.1.1.357

7 entries

1.1.1.50

9 entries

1.1.1.51

6 entries

1.1.1.53

3 entries

1.1.1.62

21 entries

1.1.1.64

2 entries

1.14.15.30

5alpha-androstane-17beta-ol-3-one + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = 9alpha,17beta-dihydroxy-5alpha-androstane-3-one + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O

717737, 717735

-

1.14.99.4

5alpha-dihydrotestosterone + NADPH + O2 = ?

438221

-

1.3.1.20

5alpha-dihydrotestosterone + NADPH = 5alpha-androstan-3alpha,17beta-diol + NADP+

349255, 349263

-

1.3.99.4

5alpha-androstan-3-one-17beta-ol + 2,6-dichlorophenol-indophenol = (5alpha,17beta)-17-hydroxyandrost-1-en-3-one + reduced 2,6-dichlorophenol-indophenol

684994

-

1.3.99.4

(5alpha,17beta)-17-hydroxyandrostan-3-one + 2,6-dichlorophenol-indophenol = ? + reduced 2,6-dichlorophenol-indophenol

743236

-

1.3.99.4

5alpha-androstane-17beta-ol-3-one + 2,6-dichlorophenol-indophenol = 5alpha-androst-1-ene-17beta-ol-3-one + reduced 2,6-dichlorophenol-indophenol

743221

-

1.3.99.5

5alpha-dihydrotestosterone + NADP+ = testosterone + NADPH + H+

713520, 713519, 713595, 712093

-

1.3.99.5

dihydrotestosterone + NADP+ = testosterone + NADPH + H+

713080, 711736, 712094

-

1.3.99.4

3 entries

1.3.99.5

2 entries

1.6.2.2

5alpha-dihydrotestosterone + acceptor = ?

394211

-

2.4.1.17

17beta-hydroxy-5alpha-androstan-3-one + UDPglucuronate = UDP + 17beta-hydroxy-5alpha-androstan-3-one 17O-glucuronide

488718

-

2.4.1.17

dihydrotestosterone + UDPglucuronate = UDP + dihydrotestosterone O-glucuronide

488783

-

2.4.1.17

UDP-D-glucuronate + dihydrotestosterone = UDP + dihydrotestosterone 17-O-beta-D-glucuronoside

693011

-

2.4.1.17

dihydrotestosterone + UDP-alpha-D-glucuronate = dihydrotestosterone D-glucuronate + UDP

719346

-

2.4.1.17

UDP-glucuronate + dihydrotestosterone = UDP + dihydrotestosterone beta-D-glucuronoside

735649

-

2.4.1.17

5 entries

4.1.1.17

5alpha-dihydrotestosterone = ?

697772

-

Product in Enzyme-catalyzed Reactions (35 results)

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Show Product (35 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.145

5alpha-androstanediol + NAD+ = 5alpha-dihydrotestosterone + NADH

-

-

1.1.1.145

5alpha-androstane-3beta,17beta-diol + NADP+ = 5alpha-androstane-17beta-ol-3-one + NADPH

-

-

1.1.1.209

5alpha-androstan-3alpha,17beta-diol + NAD(P)+ = 17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H

286233

-

1.1.1.209

5alpha-androstane-3alpha,17beta-diol + NADP+ = 5alpha-androstane-17beta-ol-3-one + NADPH

286234

-

1.1.1.213

5alpha-androstane-3alpha,17beta-diol + NADP+ = 5alpha-androstane-17beta-ol-3-one + NADPH

286354

-

1.1.1.213

3alpha-androstanediol + NAD+ = 5alpha-dihydrotestosterone + NADH + H+

-

-

1.1.1.145

2 entries

1.1.1.209

2 entries

1.1.1.213

2 entries

1.1.1.270

3alpha-androstanediol + NAD+ = 5alpha-dihydrotestosterone + NADH

-

-

1.1.1.35

5alpha-androstane-3,17-diol + NAD+ = 5alpha-dihydrotestosterone + NADH

-

-

1.1.1.357

3alpha-androstanediol + NAD+ = 5alpha-dihydrotestosterone + NADH + H+

-

-

1.1.1.357

androstandiol + NAD(P)+ = (5alpha,17beta)-17-hydroxyandrostan-3-one + NAD(P)H + H+

-

-

1.1.1.357

3alpha-androstanediol + NAD(P)+ = 5alpha-dihydrotestosterone + NAD(P)H + H+

-

-

1.1.1.357

5alpha-androstane-3alpha,17beta-diol + NADP+ = (5alpha)-androstan-17-beta-ol-3-one + NADPH + H+

-

-

1.1.1.357

5alpha-androstane-3alpha,17beta-diol + NAD+ = 5alpha-androstan-17-beta-ol-3-one + NADH + H+

-

-

1.1.1.357

5alpha-androstane-3alpha,17beta-diol + NADP+ = 5alpha-androstan-17-beta-ol-3-one + NADPH + H+

-

-

1.1.1.50

3alpha-adiol + NAD(P)+ = dihydrotestosterone + NAD(P)H

389540

-

1.1.1.50

5alpha-androstan-3alpha,17beta-diol + NAD(P)H = 5alpha-dihydrotestosterone + NAD(P)+

389541

-

1.1.1.50

5alpha-androstan-3alpha,17beta-diol + NAD(P)+ = 17beta-hydroxy-5alpha-androstan-3-one + NADPH

389527, 389541

-

1.1.1.50

3alpha-androstanediol + NAD+ = 5alpha-dihydrotestosterone + NADH

-

-

1.1.1.50

3alpha,17beta-androstene-3,17-diol + NAD(P)+ = dihydrotestosterone + NAD(P)H + H+

-

-

1.1.1.51

androstanedione + NADPH = dihydrotestosterone + NADP+

-

-

1.1.1.51

5-androstenedione + NADPH = 5alpha-dihydrotestosterone + NADP+

-

-

1.1.1.51

androstane-3,17-dione + NADPH = dihydrotestosterone + NADP+

-

-

1.1.1.51

dihydroepiandrostendione + NADPH = dihydrotestosterone + NADP+

-

-

1.1.1.62

5alpha-androstane-3,17-dione + NADH + H+ = 5alpha-androstane-17beta-ol-3-one + NAD+

-

1dht, 3D-view

1.1.1.62

5alpha-androstane-3,17-dione + NADH + H+ = 5alpha-androstane-17beta-ol-3-one + NAD+

-

3dey, 3D-view

1.1.1.62

5alpha-androstane-3,17-dione + NADH + H+ = 5alpha-androstane-17beta-ol-3-one + NAD+

-

3klm, 3D-view

1.1.1.357

6 entries

1.1.1.50

5 entries

1.1.1.51

4 entries

1.1.1.62

3 entries

1.1.1.64

androstanedione + NADPH = dihydrotestosterone + NADP+

-

-

1.3.1.22

testosterone + NADPH = 5alpha-dihydrotestosterone + NADP+

390657

-

1.3.1.22

testosterone + NADPH = androstan-3alpha,17beta-diol + androstan-3beta,17beta-diol + 5alpha-dihydrotestosterone

390765, 390766

-

1.3.1.22

testosterone + NADPH = 17beta-hydroxy-5alpha-androstan-3-one + NADP+

396202, 396216, 396193

-

1.3.1.22

testosterone + NADPH + H+ = 5alpha-dihydrotestosterone + NADP+

-

-

1.3.1.22

testosterone + NADPH = 5alpha-dihydrotestosterone + NADP+ + H+

-

-

1.3.99.5

testosterone + reduced acceptor = 5alpha-dihydrotestosterone + acceptor

-

-

1.3.99.5

testosterone + NADPH + H+ = 5alpha-dihydrotestosterone + NADP+

-

-

1.3.99.5

testosterone + NADPH + H+ = dihydrotestosterone + NADP+

-

-

1.3.1.22

5 entries

1.3.99.5

3 entries

Activator in Enzyme-catalyzed Reactions (9 results)

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Show Activating Compound (9 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.141

-

285939

-

1.15.1.1

-

715089

-

1.3.1.22

significantly increases 5alpha-R1 mRNA and 5alpha-R2 mRNA expression in male rats

676162

-

3.3.1.1

stimulating and stabilizing, promotes formation of ternary complexes, restores specific activity after hypophysectomy

137149

-

3.4.21.77

hormonal treatment of BT-474 cells with dihydrotestosterone (an androgen) for 48 h triggers an increase of prostate-specific antigen concentration in the supernatant of these cells

708155

-

3.4.24.11

induces a time-dependent increase in neprilysin expression. Dihydrotestosterone also significantly decreases levels of amyloid beta in androgen receptor-expressing cells transfected with amyloid precursor protein, but does not affect levels of either full-length or non-amyloidogenic, soluble amyloid precursor protein. The dihydrotestosterone-induced decrease of amyloid beta is blocked by pharmacological inhibition of neprilysin. The dihydrotestosterone-mediated increase in neprilysin expression and decrease in amyloid beta levels are not observed in rat pheochromocytoma cell 12 lacking androgen receptor and blocked in androgen receptor-expressing cells by the antagonists, cyproterone acetate and flutamide

699666

-

3.4.24.81

10 nM, in the presence of 10 or 50 ng/ml insulin-like growth factor, 1.8fold upregulation of the 100-kDa proform and 3 to 4 fold stimulation of the active 60-kDa form

668275

-

3.4.24.B10

regulation in a bell-shaped, dose-dependent manner, maximal, 5fold increase in activity at 0.000001 mM

653225

-

3.4.24.B9

upregulation, 1.5fold increase in activity at 0.000001 mM, 1.7fold at 0.00001 mM

653225

-

Inhibitor in Enzyme-catalyzed Reactions (14 results)

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Show Inhibitors (14 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

i.e. 5alpha-dihydrotestosterone, allosteric, competitive against substrate cyclohexanone, noncompetitive against NAD+ nd ethanol

655206

-

1.1.1.146

-

740915

-

1.1.1.149

-

285981

-

1.1.1.21

i.e. 5alpha-dehydrotestosterone

695881

-

1.1.1.210

inhibition of 20alpha-reductase activity

286265, 286266

-

1.1.1.218

-

286287

-

1.1.1.218

0.1 mM, complete inhibition

667890

-

1.1.1.218

2 entries

1.1.1.51

inhibits oxidation of testosterone

658489

-

1.3.1.22

significantly decreases 5alpha-R1 mRNA and 5alpha-R2 mRNA expression in female rats

676162

-

1.3.1.3

0.01 mM, 57% inhibition

390649

-

2.3.1.26

inhibits esterification of endogenous cholesterol

486676

-

2.8.2.34

inhibits the hepatic enzyme in sham-operated and castrated male rats, prevents activation by 6-methylene-4-pregnene-3,20-dione

657876

-

2.8.2.4

-

645872

-

5.3.3.1

-

2882

-

3D Structure of Enzyme-Ligand-Complex (PDB) (5 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (5 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.1.1.62

1dht, 3D-view

1.1.1.62

3dey, 3D-view

1.1.1.62

3klm, 3D-view

2.3.1.48

3l3x, 3D-view

2.3.1.48

3l3z, 3D-view

1.1.1.62

3 entries

2.3.1.48

2 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (43 results)

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Show Turnover Number (43 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.1.1.145

0.095

-

pH 7.4, 25°C

684725

1.1.1.149

0.025

-

at pH 7.4 and 37°C

740126

1.1.1.149

0.047

-

at pH 7.4 and 37°C

740126

1.1.1.209

0.0025

-

mutant Y224D, pH 7.0, 25°C

710716

1.1.1.209

0.0027

-

mutant Y224F, pH 7.0, 25°C

710716

1.1.1.209

0.003

-

-

389547

1.1.1.209

0.0367

-

mutant Q222N, pH 7.0, 25°C

710716

1.1.1.209

0.167

-

wild-type, pH 7.0, 25°C

710716

1.1.1.209

0.383

-

mutant G225P/G226P

695325

1.1.1.213

0.033

-

pH 7.0, 25°C, recombinant enzyme

672088

1.1.1.213

0.35

-

-

286354

1.1.1.213

5.9

-

pH 7.5, recombinant mutant R304L

677001

1.1.1.213

22.1

-

pH 7.5, recombinant mutant R301L

677001

1.1.1.213

1339

-

pH 7.5, recombinant wild-type enzyme

677001

1.1.1.239

0.0052

-

pH 7.4, 25°C

739953

1.1.1.239

0.0103

-

pH 7.4, 25°C

739953

1.1.1.239

0.065

-

pH 7.4, 25°C

739953

1.1.1.270

0.003

-

pH 7.0, 37°C, radiometric analysis, formation of 3beta-androstanediol

656200

1.1.1.270

0.0493

-

pH 7.0, 37°C, radiometric analysis, formation of 3alpha-androstanediol

656200

1.1.1.270

0.052

-

pH 7.0, 37°C, spectrophotometric analysis, formation of 3beta-androstanediol or 3alpha-androstanediol

656200

1.1.1.357

0.004

-

mutant F217S, pH 7.4, 25°C

739957

1.1.1.357

0.025

-

pH 7.5, 37°C

725345

1.1.1.357

0.033

-

isoform AKR1C4, at pH 7.4 and 25°C

724208

1.1.1.357

0.0612

-

pH 7.4, 37°C, recombinant wild-type enzyme

743179

1.1.1.357

0.1153

-

pH 7.4, 37°C, recombinant mutant V54L

743179

1.1.1.357

0.367

-

wild-type, pH 7.4, 25°C

739957

1.1.1.50

0.0038

-

pH 7.0, 37°C, with NAD(P)H

655348

1.1.1.50

0.0167

-

-

389540

1.1.1.50

0.02

-

isozyme AKR1C2

655214

1.1.1.50

0.033

-

pH 7.0, 25°C, recombinant enzyme

672088

1.1.1.50

0.0398

-

detection fluorometrically

389547

1.1.1.50

0.0612

-

pH 7.4, 37°C, recombinant wild-type enzyme

738928

1.1.1.50

0.0965

-

detection spectrophotometrically

389547

1.1.1.50

0.114

-

detection radiometrically

389547

1.1.1.50

0.1153

-

pH 7.4, 37°C, recombinant mutant V54L

738928

1.1.1.50

1

-

isozyme AKR1C9

655214

1.1.1.51

0.057

-

pH 7.4, 25°C, recombinant enzyme

740637

1.1.1.51

2.4

-

pH 7.4, with NAD+ as cofactor

659176

1.1.1.53

0.061

-

wild type enzyme, at pH 7.4 and 37°C

738928

1.1.1.53

0.115

-

mutant enzyme, at pH 7.4 and 37°C

738928

1.1.1.62

0.33

-

wild-type enzyme

670265

1.1.1.62

0.34

-

mutant enzyme L149V

670265

1.1.1.62

1.13

-

recombinant enzyme

287208

1.1.1.149

2 entries

1.1.1.209

6 entries

1.1.1.213

5 entries

1.1.1.239

3 entries

1.1.1.270

3 entries

1.1.1.357

6 entries

1.1.1.50

10 entries

1.1.1.51

2 entries

1.1.1.53

2 entries

1.1.1.62

3 entries

K_M Value (88 results)

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Show KM Value (88 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.1

0.0036

-

pH 7.3, 37°C, ADH1C*2 (gamma2gamma2)

655206

1.1.1.1

0.021

-

isoenzyme 2

285606

1.1.1.1

0.025

-

isoenzyme 2

285606

1.1.1.1

0.027

-

isoenzyme 4

285606

1.1.1.1

0.04

-

isoenzyme 1

285606

1.1.1.145

0.0055

-

3betaHSD I

389383

1.1.1.145

0.0068

-

3betaHSD III

389383

1.1.1.145

0.016

-

pH 7.4, 25°C

684725

1.1.1.145

0.684

-

-

389394

1.1.1.149

0.0034

-

at pH 7.4 and 37°C

740126

1.1.1.149

0.018

-

at pH 7.4 and 37°C

740126

1.1.1.149

0.069

-

wild type, pH 7.5, 37°C

656526

1.1.1.149

0.151

-

mutant R304L, pH 7.5, 37°C

656526

1.1.1.184

0.05

-

form CR2

347770

1.1.1.184

0.1

-

-

347770

1.1.1.2

0.11

-

AR2

286184

1.1.1.2

4

-

AR3

286184

1.1.1.209

0.0047

-

mutant Y224F, pH 7.0, 25°C

710716

1.1.1.209

0.026

-

-

389547

1.1.1.209

0.027

-

mutant G225P/G226P

695325

1.1.1.209

0.08

-

mutant Q222N, pH 7.0, 25°C

710716

1.1.1.209

0.096

-

mutant Y224D, pH 7.0, 25°C

710716

1.1.1.1

5 entries

1.1.1.145

4 entries

1.1.1.149

4 entries

1.1.1.184

2 entries

1.1.1.2

2 entries

1.1.1.209

5 entries

1.1.1.210

0.074

-

-

286266

1.1.1.213

0.0012

-

cloned human liver enzyme type I

347989

1.1.1.213

0.0013

-

recombinant enzyme in intact COS-1 cells

676812

1.1.1.213

0.0029

-

pH 7.0, 25°C, recombinant enzyme

672088

1.1.1.213

0.0057

-

pH 7.5, recombinant wild-type enzyme

677001

1.1.1.213

0.0059

-

pH 7.5, recombinant mutant R301L

677001

1.1.1.213

0.012

-

pH 7.5, recombinant mutant R304L

677001

1.1.1.213

0.0192

-

cloned human liver enzyme type II

347989

1.1.1.213

0.505

-

NAD(H), prostate

347987

1.1.1.213

0.614

-

NADP(H), prostate

347987

1.1.1.213

0.645

-

NADP(H), epididymis

347987

1.1.1.213

0.726

-

NAD(H), epididymis

347987

1.1.1.213

11 entries

1.1.1.218

0.002

-

similar values of other 17beta-hydroxysteroids

286288

1.1.1.239

0.00067

-

pH 7.4, 25°C

739953

1.1.1.239

0.0078

-

pH 7.4, 25°C

739953

1.1.1.239

0.13

-

pH 7.4, 25°C

739953

1.1.1.239

3 entries

1.1.1.270

0.0043

-

pH 7.0, 37°C, spectrophotometric analysis, formation of 3beta-androstanediol or 3alpha-androstanediol

656200

1.1.1.357

0.0001

-

mutant F217S, pH 7.4, 25°C

739957

1.1.1.357

0.0011

-

pH 7.5, 37°C

725345

1.1.1.357

0.0012

-

apparent Km-value, pH 7.4, 37°C

725333

1.1.1.357

0.00218

-

pH 7.4, 37°C, recombinant wild-type enzyme

743179

1.1.1.357

0.003

-

wild-type, pH 7.4, 25°C

739957

1.1.1.357

0.0034

-

isoform AKR1C4, at pH 7.4 and 25°C

724208

1.1.1.357

0.0161

-

pH 7.0, temperature not specified in the publication, NAD(P)H

722166

1.1.1.357

0.019

-

pH 7.0, temperature not specified in the publication, NAD(P)H

722166

1.1.1.357

0.0192

-

apparent Km-value, pH 7.4, 37°C

725333

1.1.1.357

0.07103

-

pH 7.4, 37°C, recombinant mutant V54L

743179

1.1.1.50

0.0001

-

-

389540

1.1.1.50

0.00062

0.00065

-

389529

1.1.1.50

0.0013

-

recombinant enzyme in intact COS-1 cells

676812

1.1.1.50

0.002

0.0024

also in this range: 3alpha,7alpha-dihydroxy-5beta-cholanoyl glycine

347743

1.1.1.50

0.002

0.0024

-

389527

1.1.1.50

0.00218

-

pH 7.4, 37°C, recombinant wild-type enzyme

738928

1.1.1.50

0.0029

-

pH 7.0, 25°C, recombinant enzyme

672088

1.1.1.50

0.006

-

NADP+, detection radiometrically

389547

1.1.1.50

0.007

0.0083

also in this range: 3alpha,12alpha-dihydroxy-5beta-cholanoyl glycine

347743

1.1.1.50

0.007

0.0083

-

389525

1.1.1.50

0.007

0.0083

also in this range: 3alpha-hydroxy-5beta-pregnan-17-one

389527

1.1.1.50

0.007

0.0083

also in this range: 3alpha-hydroxy-5alpha-androstan-17-one

389530

1.1.1.50

0.007

0.0083

also in this range: androstanedione

389533

1.1.1.50

0.012

-

-

389541

1.1.1.50

0.018

-

NADPH, detection radiometrically

389547

1.1.1.50

0.019

-

NADPH, detection spectrophotometrically

389547

1.1.1.50

0.0223

-

-

389546

1.1.1.50

0.026

-

pH 7.0, 37°C, with NAD(P)H

655348

1.1.1.50

0.07103

-

pH 7.4, 37°C, recombinant mutant V54L

738928

1.1.1.51

0.00025

-

pH 7.4, with NAD+ as cofactor

659176

1.1.1.51

0.0076

-

pH 7.4, 25°C, recombinant enzyme

740637

1.1.1.51

0.14

-

-

287073

1.1.1.51

0.2

-

cofactor NAD+ or NADP+

287076

1.1.1.53

0.00018

-

reduction

287097

1.1.1.53

0.00218

-

wild type enzyme, at pH 7.4 and 37°C

738928

1.1.1.53

0.07103

-

mutant enzyme, at pH 7.4 and 37°C

738928

1.1.1.62

0.0043

-

mutant enzyme L149V

670265

1.1.1.62

0.0067

-

recombinant enzyme

287208

1.1.1.62

0.033

-

wild-type enzyme

670265

1.1.1.62

0.118

-

-

287176

1.1.1.357

10 entries

1.1.1.50

19 entries

1.1.1.51

4 entries

1.1.1.53

3 entries

1.1.1.62

4 entries

1.1.1.64

0.077

-

-

287228

1.3.99.4

0.006

-

apparent value, in 50 mM Tris (pH 7.4), at 30°C

684994

1.3.99.4

0.0246

-

pH 7.0, 30°C

743236

1.3.99.4

0.035

-

pH 7.0, 30°C

743221

1.3.99.4

0.036

-

apparent value, in 50 mM Tris (pH 7.4), at 30°C

684994

1.3.99.4

0.0379

-

pH 7.0, 30°C

743221

1.3.99.4

0.07

-

apparent value, in 50 mM Tris (pH 7.4), at 30°C

684994

1.3.99.4

0.166

-

apparent value, in 50 mM Tris (pH 7.4), at 30°C

684994

1.3.99.4

7 entries

2.4.1.17

0.0196

-

isoform UGT1A4, pH 7.4, 37°C

719346

K_i Value (4 results)

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Show KI Value (4 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.1

0.0047

-

pH 7.3, 37°C, versus cyclohexanone

655206

1.1.1.1

0.014

-

pH 7.3, 37°C, versus ethanol

655206

1.1.1.1

0.028

-

pH 7.3, 37°C, versus NAD+

655206

1.1.1.1

3 entries

2.8.2.4

0.038

-

pH 8.1, 37°C

645872

IC₅₀ Value (1 result)

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Show IC50 Value (1 entry)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.1.1.21

0.00051

-

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

695881

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Literature References (149)

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Show Reference (149 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

2882

5017704

Inhibition of the 3-ketosteroid DELTA5->DELTA4 isomerase of Pseudomonas testosteroni by some bromo-3-ketosteroid derivatives

1972

Jones, J.B.; Ship, S.

Biochim. Biophys. Acta

258

800-809

137149

7259183

S-Adenosylhomocysteine hydrolases as the primary target enzymes in androgen regulation of methylation complexes

1981

Liau, M.C.; Chang, C.F.; Saunders, G.F.; Tsai, Y.H.

Arch. Biochem. Biophys.

208

261-272

285571

6375718

Physical and enzymatic properties of a class III isozyme of human liver alcohol dehydrogenase: chi-ADH

1984

Wagner, F.W.; Pares, X.; Holmquist, B.; Vallee, B.L.

Biochemistry

23

2193-2199

285606

6354095

Separation and partial characterization of multiple forms of rat liver alcohol dehydrogenase

1983

Mezey, E.; Potter, J.J.

Arch. Biochem. Biophys.

225

787-794

285760

3527067

Isolation of multiple forms of indanol dehydrogenase associated with 17-beta-hydroxysteroid dehydrogenase activity from male rabbit

1986

Hara, A.; Kariya, K.; Nakamura, M.; Nakayama, T.; Saweda, H.

Arch. Biochem. Biophys.

249

225-236

285939

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Induction of NAD+-linked 15-hydroxyprostaglandin dehydrogenase expression by androgens in human prostate cancer cells

2000

Tong, M.; Tai, H.H.

Biochem. Biophys. Res. Commun.

276

77-81

285981

3859247

17beta-Hydroxysteroid and 20alpha-hydroxysteroid dehydrogenase activities of human placental microsomes: kinetic evidence for two enzymes differing in substrate specificity

1985

Blomquist, C.H.; Lindemann, N.J.; Hakanson, E.Y.

Arch. Biochem. Biophys.

239

206-215

286184

6343086

Isolation and characterization of multiforms of aldehyde reductase in chicken kidney

1983

Hara, A.; Deyashiki, Y.; Nakayama, T.; Sawada, H.

Eur. J. Biochem.

133

207-214

286233

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Comparison of the multiple forms of the soluble 3(17)alpha-hydroxysteroid dehydrogenases of female rabbit kidney and liver

1982

Lau, P.C.K.; Layne, D.S.; Williamson, D.G.

J. Biol. Chem.

257

9450-9456

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

286265

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Dual activity at an enzyme active site: 3beta,20alpha-hydroxysteroid oxidoreductase from fetal blood

1982

Sharaf, M.A.; Sweet, F.

Biochemistry

21

4615-4620

286266

3483295

Isolation of 3beta,20alpha-hydroxysteroid oxidoreductase from sheep fetal blood

1987

Chen, Q.; Nancarrow, C.D.; Sweet, F.

Steroids

49

477-496

286267

2605227

Fetal lamb 3beta,20alpha-hydroxysteroid oxidoreductase: dual activity at the same active site examined by affinity labeling with 16alpha-(bromo[2-14C]acetoxy)progesterone

1989

Chen, Q.; Rosik, L.O.; Nancarrow, C.D.; Sweet, F.

Biochemistry

28

8856-8863

286287

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In vivo and in vitro formation of morphinone from morphine in rat

1997

Yamano, S.; Takahashi, A.; Todaka, T.; Toki, S.

Xenobiotica

27

645-656

286288

10666297

Purification and characterization of NAD-dependent morphine 6-dehydrogenase from hamster liver cytosol, a new member of the aldo-keto reductase superfamily

2000

Todaka, T.; Yamano, S.; Toki, S.

Arch. Biochem. Biophys.

374

189-197

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

286475

6942531

A DNA-binding of mouse kidney 3-ketosteroid reductase: comparison with androgen receptors

1981

Wieland, S.J.; Fox, T.O.

Steroids

37

527-538

286478

1537836

Expression of liver-specific member of the 3beta-hydroxysteroid dehydrogenase family, an isoform possessing an almost exclusive 3-ketosteroid reductase activity

1992

De Launoit, Y.; Zhao, H.F.; Belanger, A.; Labrie, F.; Simard, J.

J. Biol. Chem.

267

4513-4517

286589

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Human brain short chain L-3-hydroxyacyl Coenzyme A dehydrogenase is a singl-domain multifunctional enzyme

1999

He, X.Y.; Merz, G.; Mehta, P.; Schulz, H.; Yang, S.Y.

J. Biol. Chem.

274

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287073

4152755

A 3(17)beta-hydroxysteroid dehydrogenase in rat erythrocytes. Conversion of 5alpha-dihydrotestosterone into 5alpha-androstane-3beta,17beta-diol and purification of the enzyme by affinity chromatography

1974

Heyns, W.; de Moor, P.

Biochim. Biophys. Acta

358

1-13

287076

513731

The induction, purification and characterization of 17beta-hydroxy-C19-steroid dehydrogenase of the female guinea pig kidney

1979

Shen, C.C.; Kochakian, C.D.

J. Steroid Biochem.

10

187-193

287097

2064995

20beta-Hydroxysteroid dehydrogenase of neonatal pig testis: 3alpha/beta-hydroxysteroid dehydrogenase activities catalyzed by highly purified enzyme

1991

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

J. Steroid Biochem. Mol. Biol.

38

787-794

287103

1558817

Ontogeny of testicular steroid dehydrogenase enzymes in pig (3alpha/beta-, 20alpha- and 20beta-): evidence for two forms of 3alpha/beta-hydroxysteroid dehydrogenase

1992

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

J. Steroid Biochem. Mol. Biol.

42

17-21

287106

1377683

Pig testicular 20beta-hydroxysteroid dehydrogenase exhibits carbonyl reductase-like structure and activity

1992

Tanaka, M.; Ohno, S.; Adachi, S.; Nakajin, S.; Shinoda, M.; Nagahama, Y.

J. Biol. Chem.

267

13451-13455

287176

6231029

Dehydroepiandrosterone is a substrate for estradiol 17beta-dehydrogenase from human placenta

1984

Mendoza-Hernandez, G.; Calcagno, M.; Sanchez-Nuncio, H.R.; Diaz-Zagoya, J.C.

Biochem. Biophys. Res. Commun.

119

83-87

287206

1463443

Purification and properties of oestradiol 17beta-dehydrogenase extracted from cytoplasmic vesicles of porcine endometrial cells

1992

Adamski, J.; Husen, B.; Marks, F.; Jungblut, P.W.

Biochem. J.

288

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287208

7737980

Molecular cloning and characterization of mouse estradiol 17beta-dehydrogenase (A-specific), a member of the aldoketoreductase family

1995

Deyashiki, Y.; Ohshima, K.; Nakanishi, M.; Sato, K.; Matsuura, K.; Hara, A.

J. Biol. Chem.

270

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287209

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Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5

2001

Krazeisen, A.; Breitling, R.; Möller, G.; Adamski, J.

Mol. Cell. Endocrinol.

171

151-162

287214

2997177

Isolation of novel microbiol 3alpha-, 3beta, and 17beta-hydroxysteroid dehydrogenases

1985

Payne, D.W.; Talalay, P.

J. Biol. Chem.

260

13648-13655

287216

-

Enzyminduktion bei Streptomyces hydrogenans, V. Charakterisierung der Testosteron-17beta-Dehydrogenase und ihre Induktion durch Steroide

1975

Markert, C.; Träger, L.

Hoppe-Seyler's Z. Physiol. Chem.

356

1843-1852

287226

2983661

Guinea-pig liver testosterone 17beta-dehydrogenase (NADP+) and aldehyde reductase exhibit benzene dihydrodiol dehydrogenase activity

1985

Hara, A.; Hayashibara, M.; Nakayama, T.; Hasabe, K.; Usui, s.; Sawada, H.

Biochem. J.

225

177-181

287228

18133

Purification and properties of a new testosterone 17beta-dehydrogenase (NADP+) from guinea-pig liver

1977

Kageura, E.; Toki, S.

Biochem. J.

163

401-407

347743

201289

NAD-dependent 3alpha- and 12alpha-hydroxysteroid dehydrogenase activities from Eubacterium lentum ATCC no. 25559

1977

MacDonald, I.A.; Mahony, D.E.; Jellet, J.F.; Meier, C.E.

Biochim. Biophys. Acta

489

466-476

347755

1731616

Purification and characterization of pig lung carbonyl reductase

1992

Oritani, H.; Deyashiki, Y.; Nakayama, T.; Hara, A.; Sawada, H.; Matsuura, K.; Bunai, Y.; Ohya, I.

Arch. Biochem. Biophys.

292

539-547

347762

1338044

Characterization of multiple forms of carbonyl reductase from chicken liver

1993

Nishinaka, T.; Kinoshita, Y.; Terada, N.; Terada, T.; Mizoguchi, T.; Nishihara, T.

Enzyme

46

221-228

347770

7990149

Expression, crystallization and preliminary crystallographic analysis of human carbonyl reductase

1994

Bohren, K.M.; Wermuth, B.; Harrison, D.; Ringe, D.; Petsko, G.A.; Gabbay, K.H.

J. Mol. Biol.

244

659-664

347776

1597188

Purification and properties of prostaglandin 9-ketoreductase from pig and human kidney. Identity with human carbonyl reductase

1992

Schieber, A.; Frank, R.W.; Ghisla, S.

Eur. J. Biochem.

206

491-502

347979

1898369

The kinetic mechanism catalysed by homogeneous rat liver 3alpha-hydroxysteroid dehydrogenase. Evidence for binary and ternary dead-end complexes containing non-steroidal anti-inflammatory drugs

1991

Askonas, L.J.; Ricigliano, J.W.; Penning, T.M.

Biochem. J.

278

835-841

347981

1840601

Cloning and sequencing of the cDNA for rat liver 3alpha-hydroxysteroid/dihydrodiol dehydrogenase

1991

Pawlowski, J.E.; Huizinga, M.; Penning, T.M.

J. Biol. Chem.

266

8820-8825

347982

6435601

Purification and properties of a 3alpha-hydroxysteroid dehydrogenase of rat liver cytosol and its inhibition by anti-inflammatory drugs

1984

Penning, T.M.; Mukharji, I.; Barrows, S.; Talalay, P.

Biochem. J.

222

601-611

347984

13278351

A mammalian 3alpha-hydroxysteroid dehydrogenase

1956

Tomkins, G.M.

J. Biol. Chem.

218

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347987

8836171

3alpha-Hydroxysteroid oxidoreductase activities in dihydrotestosterone degradation and back-formation in rat prostate and epididymis

1996

Span, P.N.; Sweep, C.G.J.; Benraad, T.J.; Smals, A.G.H.

J. Steroid Biochem. Mol. Biol.

58

319-324

347988

8939970

Characterization of the substrate binding site in rat liver 3alpha-hydroxysteroid/dihydrodiol dehydrogenase. The roles of tryptophans in ligand binding and protein fluorescence

1996

Jez, J.M.; Schlegel, B.P.; Penning, T.M.

J. Biol. Chem.

271

30190-30198

347989

9029723

Structure and function of 3alpha-hydroxysteroid dehydrogenase

1997

Penning, T.M.; Bennett, M.J.; Smith-Hoog, S.; Schlegel, B.P.; Jez, J.M.; Lewis, M.

Steroids

62

101-111

347990

10625484

Mutation of nicotinamide pocket residues in rat liver 3alpha-hydroxysteroid dehydrogenase reveals different modes of cofactor binding

2000

Ma, H.; Ratnam, K.; Penning, T.M.

Biochemistry

39

102-109

349255

8543560

Expression and kinetic properties of a recombinant 3alpha-hydroxysteroid/dihydrodiol dehydrogenase isoenzyme of human liver

1995

Deyashiki, Y.; Tamada, Y.; Miyabe, Y.; Nakanishi, M.; Matsuura, K.; Hara, A.

J. Biochem.

118

285-290

349263

9261071

Steroid recognition and regulation of hormone action: crystal structure of testosterone and NADP+ bound to 3alpha-hydroxysteroid/dihydrodiol dehydrogenase

1997

Bennett, M.J.; Albert, R.H.; Jez, J.M.; Ma, H.; Penning, T.M.; Lewis, M.

Structure

5

799-812

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

389394

7841933

Purification and characterization of 5alpha-dihydrotestosterone 3beta-hydroxysteroid dehydrogenase from mature pig testicular cytosol

1994

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

Biol. Pharm. Bull.

17

1155-1160

389522

-

Properties of crystalline 3alpha-hydroxysteroid dehydrogenase from Pseudomonas putida

1979

Uwajima, T.; Terada, O.

Agric. Biol. Chem.

43

1521-1528

389525

2933398

Purification and properties of 3alpha-hydroxysteroid dehydrogenase from rat brain cytosol. Inhibition by nonsteroidal anti-inflammatory drugs and progestins

1985

Penning, T.M.; Sharp, R.B.; Krieger, N.R.

J. Biol. Chem.

260

15266-15272

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

389528

6946263

Kinetic properties of the soluble 3alpha-hydroxysteroid dehydrogenase from rat testis and epididymis

1981

Hastings, C.; Hansson, V.

J. Steroid Biochem.

14

705-711

389529

592799

Characterization of the 3alpha-hydroxysteroid dehydrogenase of dog prostate

1977

Jacobi, G.H.; Moore, R.J.; Wilson, J.D.

J. Steroid Biochem.

8

719-723

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

389531

16168

Prostate 3alpha-hydroxysteroid dehydrogenase: its partial purification and properties

1977

Inano, H.; Hayashi, S.; Tamaoki, B.

J. Steroid Biochem.

8

41-46

389532

2535

Solubilization and purification of a 3alpha-hydroxysteroid dehydrogenase in rat liver microsomes

1976

Golf, S.W.; Graef, V.; Nowotny, E.

Hoppe-Seyler's Z. Physiol. Chem.

357

35-40

389533

234846

3alpha-Hydroxysteroid dehydrogenase from Pseudomonas testosteroni: kinetic properties with NAD and its thionicotinamide analogue

1975

Skalhegg, B.A.

Eur. J. Biochem.

50

603-609

389540

9188497

Expression cloning and characterization of oxidative 17beta- and 3alpha-hydroxysteroid dehydrogenase from rat and human prostate

1997

Biswas, M.G.; Russel, D.W.

J. Biol. Chem.

272

15959-15966

389541

11294878

Characterization of a novel type of human microsomal 3alpha-hydroxysteroid dehydrogenase

2001

Chetyrkin, S.V.; Belyaeva, O.V.; Gough, W.H.; Kedishvili, N.Y.

J. Biol. Chem.

276

22278-22286

389545

1390284

Purification and properties of human hepatic 3alpha-hydroxysteroid dehydrogenase

1992

Iyer, R.B.; Binstock, J.M.; Schwartz, I.S.; Gordon, G.G.; Weinstein, B.I.; Southern, A.L.

J. Steroid Biochem. Mol. Biol.

43

343-349

389546

10833462

Functional expression, purification, and characterization of 3alpha-hydroxysteroid dehydrogenase/Carbonyl reductase from Comamonas testosteroni

2000

Maser, E.; Mobus, E.; Xiong, G.

Biochem. Biophys. Res. Commun.

272

622-628

389547

9415401

Expression and characterization of recombinant type 2: 3alpha-hydroxysteroid dehydrogenase (HSD) from human prostate: demonstration of bifunctional 3alpha/17beta-HSD activity and cellular distribution

1997

Lin, H.K.; Jez, J.M.; Schlegel, B.P.; Peehl, D.M.; Pachter, J.A.; Penning, T.M.

Mol. Endocrinol.

11

1971-1984

389551

11264591

Crystallization and preliminary X-ray crystallographic analysis of the human type 3 3alpha-hydroxysteroid dehydrogenase at 1.8 A resolution

2001

Zhu, D.W.; Cantin, L.; Nahoum, V.; Rehse, P.; Luu-The, V.; Labrie, F.; Breton, R.; Lin S.X.

Acta Crystallogr. Sect. D

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589-591

389557

9219922

Regional distribution of cytosolic and particulate 5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductases in female rat brain

1997

Li, X.; Bertics, P.J.; Karavolas, H.J.

J. Steroid Biochem. Mol. Biol.

60

311-318

390649

4152608

Transformation of testosterone into 17beta-hydroxy-5beta-androstan-3-one by Rana esculenta skeletal muscle

1974

Ozon, R.; Fouchet, C.; Perin, F.

Biochim. Biophys. Acta

348

425-437

390657

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Potent inhibition of human steroid 5alpha-reductase (EC 1.3.1.30) by 3-androstene-3-carboxylic acids

1989

Metcalf, B.W.; Holt, D.A.; Levy, M.A.; Erb, J.M.; Heaslip, J.I.; Brandt, M.; Oh, H.J.

Bioorg. Chem.

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390765

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Some characteristics of the microsomal steroid reductase (5alpha) of rat liver

1960

McGuire, J.S.; Hollis, V.W.; Tomkins, G.M.

J. Biol. Chem.

235

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390766

4156680

Studies on the mechanism of the DELTA-4-3-oxosteroid-5alpha-reduction in rat liver microsomes

1974

Golf, S.W.; Graef, V.; Staudinger, H.

Hoppe-Seyler's Z. Physiol. Chem.

355

1499-1507

394211

4041239

Properties and biochemical characterization of NADH 5alpha-reductase from rat liver microsomes

1985

Golf, S.W.; Graf, V.; Rempeters, G.; Mersdorf, S.

Biol. Chem. Hoppe-Seyler

366

647-653

396193

234171

Reduced nicotinamide adenine dinucleotide phosphate delta4-3-ketosteroid 5alpha-oxidoreductase (rat ventral prostate)

1975

Moore, R.J.; Wilson, J.D.

Methods Enzymol.

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396202

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Interferences of zearalenone, zearalanol or estradiol-17beta with the steroid-metabolizing enzymes of the human prostate gland

1980

Thouvenot, D.; Morfin, R.F.

J. Steroid Biochem.

13

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396216

8110760

Natural mutagenesis study of the human steroid 5alpha-reductase 2 isozyme

1994

Wigley, W.C.; Prihoda, J.S.; Mowszowicz, I.; Mendonca, B.B.; New, M.I.; Wilson, J.D.; Russel, D.W.

Biochemistry

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438221

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cDNA cloning, heterologous expression, and characterization of mouse CYP2G1, an olfactory-specific steroid hydroxylase

1997

Hua, Z.; Zhang, Q.; Su, T.; Lipinskas, T.W.; Ding, X.

Arch. Biochem. Biophys.

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486676

3897773

Cholesterol acyltransferase

1985

Billheimer, J.T.

Methods Enzymol.

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488718

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Substrate specificity and characterization of rat liver p-nitrophenol, 3alpha-hydroxysteroid and 17beta-hydroxysteroid UDP-glucuronosyltransferases

1986

Falany, C.N.; Green, M.D.; Swain, E.; Tephly, T.R.

Biochem. J.

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488783

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

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

Drug Metab. Dispos.

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903358

Studies on bovine adrenal estrogen sulfotransferase. Inhibition and possible involvement of adenine-estrogen stacking

1977

Rozhin, J.; Huo, A.; Zemlicka, J.; Brooks, S.C.

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252

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The expression of the ADAMs proteases in prostate cancer cell lines and their regulation by dihydrotestosterone

2000

McCulloch, D.R.; Harvey, M.; Herington, A.C.

Mol. Cell. Endocrinol.

167

11-21

654726

15379543

Dissection of the physiological interconversion of 5alpha-DHT and 3alpha-diol by rat 3alpha-HSD via transient kinetics shows that the chemical step is rate-determining: effect of mutating cofactor and substrate-binding pocket residues on catalysis

2004

Heredia, V.V.; Penning, T.M.

Biochemistry

43

12028-12037

654932

12297521

Ovarian carbonyl reductase-like 20beta-hydroxysteroid dehydrogenase shows distinct surge in messenger RNA expression during natural and gonadotropin-induced meiotic maturation in Nile tilapia

2002

Senthilkumaran, B.; Sudhakumari, C.C.; Chang, X.T.; Kobayashi, T.; Oba, Y.; Guan, G.; Yoshiura, Y.; Yoshikuni, M.; Nagahama, Y.

Biol. Reprod.

67

1080-1086

655206

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Specificity of human alcohol dehydrogenase 1C*2 (gamma2gamma2) for steroids and simulation of the uncompetitive inhibition of ethanol metabolism

2003

Plapp, B.V.; Berst, K.B.

Chem. Biol. Interact.

143-144

183-193

655213

12604224

Further characterization of chinese hamster carbonyl reductases (CHCRs)

2003

Terada, T.; Sugihara, Y.; Nakamura, K.; Mizobuchi, H.; Maeda, M.

Chem. Biol. Interact.

143-144

373-381

655214

12604225

Examination of the differences in structure-function of human and rat 3alpha-hydroxysteroid dehydrogenase

2003

Jin, Y.; Cooper, W.C.; Penning, T.M.

Chem. Biol. Interact.

143-144

383-392

655348

12810547

Human type 3 3alpha-hydroxysteroid dehydrogenase (aldo-keto reductase 1C2) and androgen metabolism in prostate cells

2003

Rizner, T.L.; Lin, H.K.; Peehl, D.M.; Steckelbroeck, S.; Bauman, D.R.; Penning, T.M.

Endocrinology

144

2922-2932

656200

14672942

Human cytosolic 3alpha-hydroxysteroid dehydrogenases of the aldo-keto reductase superfamily display significant 3beta-hydroxysteroid dehydrogenase activity: implications for steroid hormone metabolism and action

2004

Steckelbroeck, S.; Jin, Y.; Gopishetty, S.; Oyesanmi, B.; Penning, T.M.

J. Biol. Chem.

279

10784-10795

656526

12899831

Human 20alpha-hydroxysteroid dehydrogenase: crystallographic and site-directed mutagenesis studies lead to the identification of an alternative binding site for C21-steroids

2003

Couture, J.F.; Legrand, P.; Cantin, L.; Luu-The, V.; Labrie, F.; Breton, R.

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Effect of 6-methylene-4-pregnene-3,20-dione treatment on hepatic bile acid sulfotransferase activity in male rats

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McKinney, S.C.; Collins, R.H.; Killenberg, P.G.; Lack, L.

Biochem. Pharmacol.

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658489

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Inhibitors of 17beta-hydroxysteroid dehydrogenases

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Poirier, D.

Curr. Med. Chem.

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Purification, reconstitution, and steady-state kinetics of the trans-membrane 17beta-hydroxysteroid dehydrogenase 2

2002

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

J. Biol. Chem.

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22123-22130

667890

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Bioactivation of morphine in human liver: isolation and identification of morphinone, a toxic metabolite

2005

Todaka, T.; Ishida, T.; Kita, H.; Narimatsu, S.; Yamano, S.

Biol. Pharm. Bull.

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1275-1280

668078

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Characterization of 17alpha-hydroxysteroid dehydrogenase activity (17alpha-HSD) and its involvement in the biosynthesis of epitestosterone

2005

Bellemare, V.; Faucher, F.; Breton, R.; Luu-The, V.

BMC Biochem.

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12

668275

14734484

Expression of the disintegrin metalloprotease, ADAM-10, in prostate cancer and its regulation by dihydrotestosterone, insulin-like growth factor I, and epidermal growth factor in the prostate cancer cell model LNCaP

2004

McCulloch, D.R.; Akl, P.; Samaratunga, H.; Herington, A.C.; Odorico, D.M.

Clin. Cancer Res.

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Multiplicity of mammalian reductases for xenobiotic carbonyl compounds

2006

Matsunaga, T.; Shintani, S.; Hara, A.

Drug Metab. Pharmacokinet.

21

1-18

670033

15862963

Cloning and characterization of human form 2 type 7 17beta-hydroxysteroid dehydrogenase, a primarily 3beta-keto reductase and estrogen activating and androgen inactivating enzyme

2005

Liu, H.; Robert, A.; Luu-The, V.

J. Steroid Biochem. Mol. Biol.

94

173-179

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Structural basis of the multispecificity demonstrated by 17beta-hydroxysteroid dehydrogenase types 1 and 5

2006

Lin, S.X.; Shi, R.; Qiu, W.; Azzi, A.; Zhu, D.W.; Dabbagh, H.A.; Zhou, M.

Mol. Cell. Endocrinol.

248

38-46

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Multiple steps determine the overall rate of the reduction of 5alpha-dihydrotestosterone catalyzed by human type 3 3alpha-hydroxysteroid dehydrogenase: implications for the elimination of androgens

2006

Jin, Y.; Penning, T.M.

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