Ligand view of 5alpha-androstane-3,17-dione (1859 - RAJWOBJTTGJROA-WZNAKSSCSA-N)

C₁₉H₂₈O₂

5alpha-androstane-3,17-dione

RAJWOBJTTGJROA-WZNAKSSCSA-N

KEGG

Microbial metabolism in diverse environments, Steroid degradation, Steroid hormone biosynthesis

MetaCyc

testosterone and androsterone degradation to androstendione (aerobic)

1.1.1.357

5alpha-androstane-3,17-dione + NAD(P)H + H+ = androsterone + NAD(P)+

724208

4xo6, 3D-view

1.1.1.145

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

-

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

-

1qyw, 3D-view

1.14.14.32

17alpha-hydroxy-5alpha-dihydroprogesterone + [reduced NADPH-hemoprotein reductase] + O2 = 5alpha-androstanedione + acetate + [oxidized NADPH-hemoprotein reductase] + H2O

-

1.1.1.112

5alpha-androstane-3,17-dione + NAD(P)H = 5alpha-androstane-3alpha-ol-17-one + NAD(P)+

-

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

739953

-

1.1.1.252

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

-

5alpha-androstane-3,17-dione + NAD(P)H + H+ = androsterone + NAD(P)+

5alpha-androstane-3,17-dione + NADPH = ?

287097

-

1.1.1.62

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

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

349251

4xo6, 3D-view

1.3.99.4

5alpha-androstane-3,17-dione + 2,6-dichlorophenol-indophenol = 5beta-androst-1-en-3,17-dione + reduced 2,6-dichlorophenol-indophenol

684994

-

1.3.99.5

5alpha-androstane-3,17-dione + N,N,N',N'-tetramethyl-1,4-phenylendiamine = androst-4-ene-3,17-dione + reduced N,N,N',N'-tetramethyl-1,4-phenylendiamine

-

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

287228

-

1.1.3.6

5alpha-androstan-3-ol-17-one + O2 = 5alpha-androstan-3,17-dione + H2O2

-

1.14.14.32

17alpha-hydroxy-5alpha-dihydroprogesterone + [reduced NADPH-hemoprotein reductase] + O2 = 5alpha-androstanedione + acetate + [oxidized NADPH-hemoprotein reductase] + H2O

-

1.3.1.22

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

-

1.1.1.21

competitive inhibition with respect to geraniol

-

-

-

DD3

30% inhibition

-

-

0.097

-

pH 7.4, 25Â°C

0.03

-

isoform AKR1C4, at pH 7.4 and 25Â°C

724208

1.1.1.50

0.42

-

pH 7.0, 25, reduction reaction

687635

1.14.15.30

0.8

-

isoform KshA5, at pH 7.0 and 22Â°C

0.15

-

form CR2

0.00144

-

isoform AKR1C4, at pH 7.4 and 25Â°C

0.0061

-

isoform KshA5, at pH 7.0 and 22Â°C

745308

1.3.1.20

0.0031

-

DD1

0.0161

-

reaction with N,N,Nâ,Nâ-tetramethyl-1,4-phenylenediamine

391399

1.3.1.20

0.011

-

DD3

349251

1.1.1.21

0.00039

-

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

695881

285759

2559080

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

1989

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

J. Biochem.

106

900-903

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

286233

6955303

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

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

286355

1917902

Kinetic and stereochemical characterization of hamster liver 3alpha-hydroxysteroid dehydrogenase and 3alpha(17beta)-hydroxysteroid dehydrogenase

1991

Sawada, H.; Hara, A.; Ohmura, M.; Nakayama, T.; Deyashi, Y.

J. Biochem.

109

770-775

286477

11513953

Gene structure, chromosomal localization and analysis of 3-ketosteroid reductase activity of the human 3(alpha->beta)-hydroxysteroid epimerase

2001

Huang, X.F.; Luu-The, V.

Biochim. Biophys. Acta

1520

124-130

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

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

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

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

375-381

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

10461-10467

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.; TrÃ¤ger, L.

Hoppe-Seyler's Z. Physiol. Chem.

356

1843-1852

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

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

347763

1540623

Carbonyl reductase from human testis: purification and comparison with carbonyl reductase from human brain and rat testis

1992

Inazu, N.; Ruepp, B.; Wirth, H.; Wermuth, B.

Biochim. Biophys. Acta

1116

50-56

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

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

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

349251

8493915

Unique dihydrodiol specific dehydrogenase of bovine liver: Inhibition studies and comparison with aldo/keto reductase

1993

Nanjo, H.; Nishinaka, T.; Nagai, M.; Terada, T.; Mizoguchi, T.; Nishihara, T.

Adv. Exp. Med. Biol.

328

371-377

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

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

389534

14406805

Stereospecificity of hydrogen transfer by pyridine nucleotide-linked hydroxysteroid dehydrogenase

1960

Jarabak, J.; Talalay, P.

J. Biol. Chem.

235

2147-2151

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

389549

1592159

Characterization of bovine liver cytosolic 3alpha-hydroxysteroid dehydrogenase and its aldo-keto reductase activity

1992

Nanjo, H.; Terada, T.; Umemura, T.; Nishinaka, T.; Mizoguchi, T.; Nishihara, T.

Int. J. Biochem.

24

815-820

390765

-

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

3112-3117

391399

8655514

Comamonas testosteroni 3-ketosteroid-DELTA4(5alpha)-dehydrogenase

1996

Florin, C.; Koehler, T.; Grandguillot, M.; Plesiat, P.

J. Bacteriol.

178

3322-3330

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

675687

16191478

Isolation and characterization of a cDNA encoding mouse 3alpha-hydroxysteroid dehydrogenase: an androgen-inactivating enzyme selectively expressed in female tissues

2006

Bellemare, V.; Labrie, F.; Luu-The, V.

J. Steroid Biochem. Mol. Biol.

98

18-24

684676

17475203

Rat NAD+-dependent 3alpha-hydroxysteroid dehydrogenase (AKR1C17): a member of the aldo-keto reductase family highly expressed in kidney cytosol

2007

Sanai, M.; Endo, S.; Matsunaga, T.; Ishikura, S.; Tajima, K.; El-Kabbani, O.; Hara, A.

Arch. Biochem. Biophys.

464

122-129

684725

18571493

Characterization of human DHRS4: An inducible short-chain dehydrogenase/reductase enzyme with 3beta-hydroxysteroid dehydrogenase activity

2008

Matsunaga, T.; Endo, S.; Maeda, S.; Ishikura, S.; Tajima, K.; Tanaka, N.; Nakamura, K.T.; Imamura, Y.; Hara, A.

Arch. Biochem. Biophys.

477

339-347

684994

18031290

3-Keto-5alpha-steroid DELTA(1)-dehydrogenase from Rhodococcus erythropolis SQ1 and its orthologue in Mycobacterium tuberculosis H37Rv are highly specific enzymes that function in cholesterol catabolism

2008

Knol, J.; Bodewits, K.; Hessels, G.I.; Dijkhuizen, L.; van der Geize, R.

Biochem. J.

410

339-346

687635

17848571

Elucidation of a complete kinetic mechanism for a mammalian hydroxysteroid dehydrogenase (HSD) and identification of all enzyme forms on the reaction coordinate: the example of rat liver 3alpha-HSD (AKR1C9)

2007

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

J. Biol. Chem.

282

33484-33493

687869

17196285

Rational design of novel mutants of fungal 17beta-hydroxysteroid dehydrogenase

2007

Kristan, K.; Stojan, J.; Adamski, J.; Lanisnik Rizner, T.

J. Biotechnol.

129

123-130

695881

19464995

Kinetic studies of AKR1B10, human aldose reductase-like protein: endogenous substrates and inhibition by steroids

2009

Endo, S.; Matsunaga, T.; Mamiya, H.; Ohta, C.; Soda, M.; Kitade, Y.; Tajima, K.; Zhao, H.T.; El-Kabbani, O.; Hara, A.

Arch. Biochem. Biophys.

487

1-9

696459

19520191

Role of S114 in the NADH-induced conformational change and catalysis of 3alpha-hydroxysteroid dehydrogenase/carbonyl reductase from Comamonas testosteroni

2009

Chang, Y.H.; Huang, T.J.; Chuang, L.Y.; Hwang, C.C.

Biochim. Biophys. Acta

1794

1459-1466

697269

18983987

Investigation of the role of the amino acid residue at position 230 for catalysis in monomeric carbonyl reductase 3

2009

Miura, T.; Itoh, Y.; Takada, M.; Tsutsui, H.; Yukimura, T.; Nishinaka, T.; Terada, T.

Chem. Biol. Interact.

178

211-214

697279

18973748

Two homologous fungal carbonyl reductases with different substrate specificities

2009

Kristan, K.; Brunskole, M.; Stojan, J.; Rizner, T.L.

Chem. Biol. Interact.

178

295-302

711310

19853671

Contributions of active site residues to cofactor binding and catalysis of 3alpha-hydroxysteroid dehydrogenase/carbonyl reductase

2010

Chang, Y.H.; Wang, C.Z.; Chiu, C.C.; Chuang, L.Y.; Hwang, C.C.

Biochim. Biophys. Acta

1804

235-241

716250

19906176

3-Ketosteroid 9alpha-hydroxylase is an essential factor in the pathogenesis of Mycobacterium tuberculosis

2010

Hu, Y.; Van Der Geize, R.; Besra, G.; Gurcha, S.; Liu, A.; Rohde, M.; Singh, M.; Coates, A.

Mol. Microbiol.

75

107-121

717735

21642460

Multiplicity of 3-ketosteroid-9alpha-hydroxylase enzymes in Rhodococcus rhodochrous DSM43269 for specific degradation of different classes of steroids

2011

Petrusma, M.; Hessels, G.; Dijkhuizen, L.; van der Geize, R.

J. Bacteriol.

193

3931-3940

717737

22020644

Structural features in the KshA terminal oxygenase protein that determine substrate preference of 3-ketosteroid 9alpha-hydroxylase enzymes

2012

Petrusma, M.; Dijkhuizen, L.; van Der Geize, R.

J. Bacteriol.

194

115-121

724124

22874434

Characterization of rabbit aldose reductase-like protein with 3beta-hydroxysteroid dehydrogenase activity

2012

Endo, S.; Matsunaga, T.; Kumada, S.; Fujimoto, A.; Ohno, S.; El-Kabbani, O.; Hu, D.; Toyooka, N.; Mano, J.; Tajima, K.; Hara, A.

Arch. Biochem. Biophys.

527

23-30

724208

10998348

Human 3alpha-hydroxysteroid dehydrogenase isoforms (AKR1C1-AKR1C4) of the aldo-keto reductase superfamily: Functional plasticity and tissue distribution reveals roles in the inactivation and formation of male and female sex hormones

2000

Penning, T.; Burczynski, M.; Jez, J.; Hung, C.; Lin, H.; Ma, H.; Moore, M.; Palackal, N.; Ratnam, K.

Biochem. J.

351

67-77

727480

23356661

QM/MM modelling of ketosteroid isomerase reactivity indicates that active site closure is integral to catalysis

2013

van der Kamp, M.W.; Chaudret, R.; Mulholland, A.J.

FEBS J.

280

3120-3131

739953

23228597

Characterization of rabbit morphine 6-dehydrogenase and two NAD+-dependent 3alpha(17beta)-hydroxysteroid dehydrogenases

2013

Endo, S.; Matsunaga, T.; Fujimoto, A.; Kumada, S.; Arai, Y.; Miura, Y.; Mikamo, H.; El-Kabbani, O.; Yamano, S.; Iinuma, M.; Hara, A.

Arch. Biochem. Biophys.

529

131-139

745308

25049233

Substrate specificities and conformational flexibility of 3-ketosteroid 9alpha-hydroxylases

2014

Penfield, J.S.; Worrall, L.J.; Strynadka, N.C.; Eltis, L.D.

J. Biol. Chem.

289

25523-25536

-

Ligand 5alpha-androstane-3,17-dione

Basic Ligand Information

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

In Vivo Product in Enzyme-catalyzed Reactions (12 results)

Substrate in Enzyme-catalyzed Reactions (24 results)

Product in Enzyme-catalyzed Reactions (46 results)

Inhibitor in Enzyme-catalyzed Reactions (5 results)

3D Structure of Enzyme-Ligand-Complex (PDB) (4 results)

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (8 results)

K_M Value (27 results)

K_i Value (1 result)

IC₅₀ Value (1 result)

References & Links

Literature References (50)

Links to other databases for 5alpha-androstane-3,17-dione

Ligand 5alpha-androstane-3,17-dione

Basic Ligand Information

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

In Vivo Product in Enzyme-catalyzed Reactions (12 results)

Substrate in Enzyme-catalyzed Reactions (24 results)

Product in Enzyme-catalyzed Reactions (46 results)

Inhibitor in Enzyme-catalyzed Reactions (5 results)

3D Structure of Enzyme-Ligand-Complex (PDB) (4 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (8 results)

KM Value (27 results)

Ki Value (1 result)

IC50 Value (1 result)

References & Links

Literature References (50)

Links to other databases for 5alpha-androstane-3,17-dione

k_cat Value (Turnover Number) (8 results)

K_M Value (27 results)

K_i Value (1 result)

IC₅₀ Value (1 result)