Ligand view of 5beta-androstane-3,17-dione (2468 - RAJWOBJTTGJROA-QJISAEMRSA-N)

C₁₉H₂₈O₂

5beta-androstane-3,17-dione

RAJWOBJTTGJROA-QJISAEMRSA-N

KEGG

Steroid hormone biosynthesis

1.1.1.152

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

286009

-

1.1.1.357

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

-

1.3.1.3

4-androstene-3,17-dione + NADPH = 5beta-androstan-3,17-dione + NADP+

-

1.1.1.112

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

-

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

347755, 347762, 655213

-

1.1.1.188

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

389448

-

1.1.1.209

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

-

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

739953

-

1.1.1.270

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

724124

-

1.1.1.357

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

-

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

717737, 717735

-

1.3.1.20

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

349255, 349251

-

1.3.99.4

5beta-androstan-3,17-dione + acceptor = 5beta-androst-1-en-3,17-dione + reduced acceptor

-

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

-

1.1.1.152

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

286009

-

1.1.1.209

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

-

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

-

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

287228

-

1.3.1.20

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

-

-

-

product inhibition, forward reaction

-

DD3

-

0.077

-

pH 7.4, 25Â°C

0.167

-

0.047

-

pH 7.4, 25Â°C, recombinant wild-type AKR1C17

0.0031

-

389448

1.1.1.213

0.0021

-

pH 7.4, 25Â°C, recombinant wild-type AKR1C17

684676

1.1.1.239

0.0066

-

0.0029

-

DD1

349251

1.3.1.20

0.041

-

DD3

349251

1.1.1.21

0.0021

-

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.

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285760

3527067

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

1986

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Arch. Biochem. Biophys.

249

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286009

5365796

Purification and substrate specificities of bacterial hydroxysteroid dehydrogenases

1969

Roe, C.R.; Kaplan, N.O.

Biochemistry

8

5093-5103

286234

2691507

Identification of two dihydrodiol dehydrogenases associated with 3(17)alpha-hydoxysteroid dehydrogenase activity in mouse kidney

1989

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286354

2317205

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1990

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Biochem. J.

266

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286355

1917902

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

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287214

2997177

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287228

18133

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

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Kageura, E.; Toki, S.

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347755

1731616

Purification and characterization of pig lung carbonyl reductase

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

Arch. Biochem. Biophys.

292

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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

347984

13278351

A mammalian 3alpha-hydroxysteroid dehydrogenase

1956

Tomkins, G.M.

J. Biol. Chem.

218

437-447

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

349255

8543560

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

1995

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J. Biochem.

118

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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

389448

10622721

cDNA cloning, expression and characterization of human prostaglandin F synthase

1999

Suzuki-Yamamoto, T.; Nishizawa, M.; Fukui, M.; Okuda-Ashitaka, E.; Nakajima, T.; Ito, S.; Watanabe, K.

FEBS Lett.

462

335-340

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

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

389549

1592159

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

1992

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Int. J. Biochem.

24

815-820

389552

9928117

Purification and properties of 3alpha-hydroxysteroid dehydrogenase and 3-keto-5beta-steroid-DELTA4-dehydrogenase

1998

Gao, X.; Liu, J.; Li, G.

Ann. N. Y. Acad. Sci.

864

383-392

389555

2308341

In vitro metabolism of testosterone on hepatic tissue of chicken (Gallus domesticus)

1990

Sugimoto, Y.; Ohta, Y.; Morikawa, T.; Yamashita, T.; Yoshida, M.; Tamaoki, B.

J. Steroid Biochem.

35

271-279

390590

3828348

Identification of cortisone 5beta-reductase as DELTA4-3-ketosteroid 5beta-reductase

1987

Furuebisu, M.; Deguchi, S.; Okuda, K.

Biochim. Biophys. Acta

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390646

13805063

The DELTA4-hydrogenases of guinea pig adrenal gland

1960

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235

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391381

-

Degradation of steroids by intestinal bacteria. III. 3-Oxo-5beta-steroid DELTA1-dehydrogenase and 3-oxo-5beta-steroid DELTA4-dehydrogenase

1971

Aries, V.C.; Goddard, P.; Hill, M.J.

Biochim. Biophys. Acta

248

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391402

5907467

Purification and mechanism of action of a steroid delta-4-5-beta-dehydrogenase

1966

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241

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587068

2278841

Purification and characterization of 3alpha-hydroxysteroid dehydrogenase from chicken hepatic cytosol

1990

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J. Steroid Biochem. Mol. Biol.

37

569-574

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

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

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

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

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.

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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

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

739957

25660042

Identification of a determinant for strict NADP(H)-specificity and high sensitivity to mixed-type steroid inhibitor of rabbit aldo-keto reductase 1C33 by site-directed mutagenesis

2015

Endo, S.; Matsunaga, T.; Ikari, A.; El-Kabbani, O.; Hara, A.; Kitade, Y.

Arch. Biochem. Biophys.

569

19-25

-

Ligand 5beta-androstane-3,17-dione

Basic Ligand Information

Roles as Enzyme Ligand

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

Substrate in Enzyme-catalyzed Reactions (21 results)

Product in Enzyme-catalyzed Reactions (27 results)

Inhibitor in Enzyme-catalyzed Reactions (3 results)

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (7 results)

K_M Value (16 results)

K_i Value (1 result)

IC₅₀ Value (1 result)

References & Links

Literature References (36)

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

Ligand 5beta-androstane-3,17-dione

Basic Ligand Information

Roles as Enzyme Ligand

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

Substrate in Enzyme-catalyzed Reactions (21 results)

Product in Enzyme-catalyzed Reactions (27 results)

Inhibitor in Enzyme-catalyzed Reactions (3 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (7 results)

KM Value (16 results)

Ki Value (1 result)

IC50 Value (1 result)

References & Links

Literature References (36)

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

k_cat Value (Turnover Number) (7 results)

K_M Value (16 results)

K_i Value (1 result)

IC₅₀ Value (1 result)