BRENDA - Reference to 1.1.1.213; Id = 697310

expression of recombinant wild type and mutants of AKR1C9

Rattus norvegicus

F118A

largest changes in kcat/Km

Rattus norvegicus

F129A

largest changes in kcat/Km, F129A alters the stereochemical preference from oxidizing predominantly the S,S-stereoisomer to oxidizing predominantly the R,R-stereoisomer of benzo[g]chrysene-11,12-dihydrodiol

Rattus norvegicus

L54A

mutant shows intermediate changes in kcat/Km versus wild type

Rattus norvegicus

N306A

mutant shows intermediate changes in kcat/Km versus wild type

Rattus norvegicus

T226A

smallest change in kcat/Km is observed when alanine is used to substitute hydrophilic residues

Rattus norvegicus

T24A

smallest change in kcat/Km is observed when alanine is used to substitute hydrophilic residues

Rattus norvegicus

W227A

largest changes in kcat/Km

Rattus norvegicus

Y310A

mutant shows intermediate changes in kcat/Km versus wild type

Rattus norvegicus

DMSO

33% inhibition

Rattus norvegicus

naphthalene-1,2-dione

naphthalene-1,2-dione leads to the time and concentration dependent irreversible inactivation of AKR1C9 via alkylation

Rattus norvegicus

additional information

-

(11S,12S)-11,12-dihydrobenzo[g]chrysene-11,12-diol

racemic benzo[g]chrysene-11,12-dihydrodiol derived from the fjord-region parent hydrocarbon benzo[g]chrysene is oxidized with a kcat/Km of 1520 min/mM, which is more than 100 times greater than that observed with benzo[a]pyrene-7,8-dihydrodiol

Rattus norvegicus

additional information

-

benzo[a]pyrene-7,8-dihydrodiol

kcat/Km of 39 min/mM

Rattus norvegicus

P23457

-

purification of recombinant wild type and mutants of AKR1C9

Rattus norvegicus

liver

-

Rattus norvegicus

-

1.6

-

wild type homogeneous recombinant AKR1C9, at 25°C

Rattus norvegicus

(11S,12S)-11,12-dihydrobenzo[g]chrysene-11,12-diol + NADP+

enzyme is stereoselective for benzo[g]chrysene-11S,12S-dihydrodiol

697310

Rattus norvegicus

? + NADPH + H+

-

?

benzo[c]phenanthrene-3,4-dihydrodiol + NADP+

enzyme metabolizes both stereoisomers of benzo[c]phenanthrene-3,4-dihydrodiol

697310

Rattus norvegicus

? + NADPH + H+

-

?

37

-

assay at

Rattus norvegicus

9

-

assay at

Rattus norvegicus

NADP+

-

Rattus norvegicus

expression of recombinant wild type and mutants of AKR1C9

Rattus norvegicus

NADP+

-

Rattus norvegicus

F118A

largest changes in kcat/Km

Rattus norvegicus

F129A

largest changes in kcat/Km, F129A alters the stereochemical preference from oxidizing predominantly the S,S-stereoisomer to oxidizing predominantly the R,R-stereoisomer of benzo[g]chrysene-11,12-dihydrodiol

Rattus norvegicus

L54A

mutant shows intermediate changes in kcat/Km versus wild type

Rattus norvegicus

N306A

mutant shows intermediate changes in kcat/Km versus wild type

Rattus norvegicus

T226A

smallest change in kcat/Km is observed when alanine is used to substitute hydrophilic residues

Rattus norvegicus

T24A

smallest change in kcat/Km is observed when alanine is used to substitute hydrophilic residues

Rattus norvegicus

W227A

largest changes in kcat/Km

Rattus norvegicus

Y310A

mutant shows intermediate changes in kcat/Km versus wild type

Rattus norvegicus

DMSO

33% inhibition

Rattus norvegicus

naphthalene-1,2-dione

naphthalene-1,2-dione leads to the time and concentration dependent irreversible inactivation of AKR1C9 via alkylation

Rattus norvegicus

additional information

-

(11S,12S)-11,12-dihydrobenzo[g]chrysene-11,12-diol

racemic benzo[g]chrysene-11,12-dihydrodiol derived from the fjord-region parent hydrocarbon benzo[g]chrysene is oxidized with a kcat/Km of 1520 min/mM, which is more than 100 times greater than that observed with benzo[a]pyrene-7,8-dihydrodiol

Rattus norvegicus

additional information

-

benzo[a]pyrene-7,8-dihydrodiol

kcat/Km of 39 min/mM

Rattus norvegicus

purification of recombinant wild type and mutants of AKR1C9

Rattus norvegicus

liver

-

Rattus norvegicus

-

1.6

-

wild type homogeneous recombinant AKR1C9, at 25°C

Rattus norvegicus

(11S,12S)-11,12-dihydrobenzo[g]chrysene-11,12-diol + NADP+

enzyme is stereoselective for benzo[g]chrysene-11S,12S-dihydrodiol

697310

Rattus norvegicus

? + NADPH + H+

-

?

benzo[c]phenanthrene-3,4-dihydrodiol + NADP+

enzyme metabolizes both stereoisomers of benzo[c]phenanthrene-3,4-dihydrodiol

697310

Rattus norvegicus

? + NADPH + H+

-

?

37

-

assay at

Rattus norvegicus

9

-

assay at

Rattus norvegicus

724719

Matsunaga

Pathophysiological roles of al ...

Homo sapiens

Chem. Biol. Interact.

202

234-242

2013

-

1

-

1

-

1

-

2

-

1

-

1

-

1

-

1

-

2

-

1

-

1

-

1

724915

Heinrich

Synthesis and structure-activi ...

Homo sapiens

Eur. J. Med. Chem.

62

738-744

2013

-

1

-

3

-

1

-

3

-

1

-

3

-

724916

Gazvoda

2,3-diarylpropenoic acids as s ...

Homo sapiens

Eur. J. Med. Chem.

62

89-97

2013

-

1

-

4

-

1

-

4

-

1

-

4

-

723866

Jackson

Structure of AKR1C3 with 3-phe ...

Homo sapiens

Acta Crystallogr. Sect. F

68

409-413

2012

-

1

-

1

-

1

-

1

-

1

-

1

-

724533

Chen

Crystal structures of AKR1C3 c ...

Homo sapiens

Bioorg. Med. Chem. Lett.

22

3492-3497

2012

-

1

-

2

-

1

-

1

-

1

-

1

2

-

724538

Sinreih

N-Benzoyl anthranilic acid der ...

Homo sapiens

Bioorg. Med. Chem. Lett.

22

5948-5951

2012

-

4

-

1

-

4

-

4

-

725153

Miller

Aldo-keto reductase family 1 m ...

Homo sapiens

Int. J. Clin. Exp. Pathol.

5

278-289

2012

-

1

-

2

-

8

-

1

-

8

-

725671

Brozic

Selective inhibitors of aldo-k ...

Homo sapiens

J. Med. Chem.

55

7417-7424

2012

-

1

-

2

-

1

-

1

-

2

-

2

-

1

-

2

-

1

-

725825

Byrns

Overexpression of aldo-keto re ...

Homo sapiens

J. Steroid Biochem. Mol. Biol.

130

7-15

2012

-

1

-

2

-

2

-

1

-

724517

Adeniji

Discovery of substituted 3-(ph ...

Homo sapiens

Bioorg. Med. Chem. Lett.

21

1464-1468

2011

-

3

-

1

-

1

-

3

-

3

-

1

-

725152

Zakharov

Suppressed expression of type ...

Homo sapiens

Int. J. Clin. Exp. Pathol.

3

608-617

2010

-

1

-

1

-

2

-

1

-

2

-

1

-

1

-

697265

Skarydova

AKR1C3 as a potential target f ...

Homo sapiens

Chem. Biol. Interact.

178

138-144

2009

-

1

-

15

-

2

-

1

-

1

-

7

-

1

-

7

15

-

1

-

685529

Uwai

Electronic effects of para-sub ...

Rattus norvegicus

Bioorg. Med. Chem.

16

1084-1089

2008

-

1

-

2

-

2

-

8

-

1

-

1

-

1

-

1

-

1

-

2

-

8

-

1

-

1

-

688137

Azzarello

Tissue distribution of human A ...

Homo sapiens, Rattus norvegicus

J. Histochem. Cytochem.

56

853-861

2008

-

1

-

6

-

2

-

7

-

14

-

2

1

-

1

-

6

-

2

-

14

-

2

1

-

689169

Meyer

The biological activity of 3al ...

Rattus norvegicus

Neurobiol. Dis.

30

30-41

2008

-

1

-

1

-

3

-

2

-

2

1

-

2

-

1

-

2

-

1

-

2

-

2

1

-

697310

Shultz

Fjord-region benzo[g]chrysene- ...

Rattus norvegicus

Chem. Res. Toxicol.

21

668-677

2008

-

1

-

8

-

2

-

3

-

1

-

2

1

-

2

-

1

-

1

-

1

-

1

-

8

-

2

-

2

-

1

-

2

1

-

2

-

1

-

1

-

684676

Sanai

Rat NAD+-dependent 3alpha-hydr ...

Rattus norvegicus

Arch. Biochem. Biophys.

464

122-129

2007

-

1

-

3

-

3

9

3

-

2

-

2

-

1

-

3

2

-

31

1

-

9

1

-

4

3

-

1

4

-

3

-

3

9

3

-

2

-

1

-

3

2

-

31

1

-

9

1

-

687635

Cooper

Elucidation of a complete kine ...

Rattus norvegicus

J. Biol. Chem.

282

33484-33493

2007

-

3

-

1

-

2

-

1

-

2

-

1

-

1

-

2

1

-

2

-

2

-

3

-

1

-

2

-

1

-

1

-

2

1

-

687639

McCarthy

3-ketosteroid reductase activi ...

Rattus norvegicus

J. Biol. Chem.

282

34003-34012

2007

1

-

1

-

2

-

2

-

2

-

3

-

2

-

1

-

1

2

-

2

-

2

-

3

-

687642

Chang

Mechanism of proton transfer i ...

Comamonas testosteroni

J. Biol. Chem.

282

34306-34314

2007

-

1

-

2

-

3

-

1

-

1

-

1

-

1

-

2

-

1

-

1

-

2

-

1

2

-

2

-

3

-

1

-

1

-

1

-

2

-

1

-

1

-

687870

Hoffmann

Understanding oligomerization ...

Comamonas testosteroni

J. Biotechnol.

129

131-139

2007

-

1

-

1

-

1

-

1

-

2

-

1

-

1

-

1

-

2

-

668392

Matsunaga

Multiplicity of mammalian redu ...

Homo sapiens

Drug Metab. Pharmacokinet.

21

1-18

2006

-

1

-

1

-

16

-

4

-

4

-

30

-

1

-

1

-

1

-

16

-

4

-

30

-

672088

Jin

Multiple steps determine the o ...

Homo sapiens

Biochemistry

45

13054-13063

2006

-

1

-

3

-

1

-

1

-

1

-

1

-

3

-

1

-

2

1

-

2

-

1

2

-

3

-

1

-

1

-

1

-

3

-

1

-

2

1

-

673349

Papari-Zareei

Arginine 276 controls the dire ...

Rattus norvegicus

Endocrinology

147

1591-1597

2006

-

1

-

3

-

1

-

1

-

3

-

1

-

4

1

-

2

-

1

-

1

-

3

-

1

-

1

-

4

1

-

2

-

673967

Rani

Discrete analysis of bile acid ...

Comamonas testosteroni

Indian J. Biochem. Biophys.

43

98-104

2006

-

1

-

1

-

3

-

1

-

1

-

1

-

1

-

1

-

1

-

674674

Nakamura

Apo- and holo-structures of 3a ...

Pseudomonas sp., Pseudomonas sp. B-0831

J. Biol. Chem.

281

31876-31884

2006

-

1

-

1

2

-

8

-

2

-

1

-

1

-

1

2

-

2

-

674981

Okochi

Enhanced activity of 3alpha-hy ...

Comamonas testosteroni

J. Biotechnol.

128

376-382

2006

3

1

-

1

-

1

-

1

-

1

-

1

-

1

-

2

-

3

1

-

2

-

1

-

1

-

1

-

1

-

1

-

675595

Steckelbroeck

Tibolone metabolism in human l ...

Homo sapiens

J. Pharmacol. Exp. Ther.

316

1300-1309

2006

-

3

-

2

-

1

-

2

-

3

1

-

2

-

1

-

1

-

1

-

2

-

1

-

2

3

-

2

-

1

-

3

1

-

2

-

1

-

1

-

675678

Wiebe

Dutasteride affects progestero ...

Homo sapiens

J. Steroid Biochem. Mol. Biol.

100

129-140

2006

-

1

-

2

-

1

-

1

-

1

-

675687

Bellemare

Isolation and characterization ...

Mus musculus

J. Steroid Biochem. Mol. Biol.

98

18-24

2006

-

1

-

1

-

4

-

3

-

5

-

1

-

1

-

3

-

5

-

676002

Bauman

Identification of the major ox ...

Homo sapiens

Mol. Endocrinol.

20

444-458

2006

-

1

-

1

-

2

-

3

-

3

-

3

-

2

-

1

2

-

1

-

2

-

3

-

3

-

676812

Yee

Fluorogenic metabolic probes f ...

Homo sapiens

Proc. Natl. Acad. Sci. USA

103

13304-13309

2006

-

1

-

6

2

-

2

-

1

-

1

-

4

-

1

-

5

-

1

-

5

6

-

2

-

2

-

1

-

4

-

669389

Hwang

Mechanistic roles of Ser-114, ...

Comamonas testosteroni

J. Biol. Chem.

280

3522-3528

2005

-

1

-

5

-

7

-

1

-

1

-

1

-

3

1

-

6

1

-

2

-

1

2

-

5

-

7

-

1

-

1

-

3

1

-

6

1

-

673101

Uwai

Purification and characterizat ...

Rattus norvegicus

Chirality

17

494-500

2005

-

1

-

2

-

3

-

1

-

1

-

6

1

-

1

-

1

-

1

-

1

-

2

-

1

-

1

-

6

1

-

1

-

677001

Couture

Comparison of crystal structur ...

Homo sapiens

Protein Sci.

14

1485-1497

2005

-

1

2

-

3

-

1

-

1

-

2

-

1

-

1

-

5

1

-

3

1

-

2

-

1

2

1

2

-

3

-

1

-

1

-

1

-

1

-

5

1

-

3

1

-

654726

Heredia

Dissection of the physiologica ...

Rattus norvegicus

Biochemistry

43

12028-12037

2004

-

2

-

1

-

2

-

3

-

1

-

3

-

1

-

9

1

-

5

-

5

-

2

-

1

-

2

-

1

-

3

-

1

-

9

1

-

654756

Heredia

Alanine scanning mutagenesis o ...

Rattus norvegicus

Biochemistry

43

5832-5841

2004

-

1

-

8

-

2

-

2

-

1

-

9

-

5

-

5

1

-

2

-

1

2

-

8

-

2

-

1

-

9

-

5

-

5

1

-

347990

Ma

Mutation of nicotinamide pocke ...

Rattus norvegicus

Biochemistry

39

102-109

2000

-

5

-

8

-

1

2

-

2

-

1

-

2

4

1

3

1

-

5

-

5

-

5

-

8

-

1

2

-

1

-

2

4

1

3

1

-

347989

Penning

Structure and function of 3alp ...

Rattus norvegicus

Steroids

62

101-111

1997

-

1

13

-

5

11

1

2

-

1

-

1

-

1

-

3

2

-

8

-

5

-

1

5

1

13

-

5

-

11

1

2

-

1

-

3

2

-

8

-

347987

Span

3alpha-Hydroxysteroid oxidored ...

Rattus norvegicus

J. Steroid Biochem. Mol. Biol.

58

319-324

1996

-

8

2

-

1

-

2

-

1

-

1

-

4

-

4

-

8

2

-

2

-

1

-

1

-

347988

Jez

Characterization of the substr ...

Rattus norvegicus

J. Biol. Chem.

271

30190-30198

1996

-

1

-

3

-

11

4

-

2

-

2

-

1

-

2

4

1

8

1

-

1

-

4

-

1

4

-

3

-

11

-

4

-

2

-

1

-

2

4

1

8

1

-

1

-

347986

Mallonee

Expression in Escherichia coli ...

Eubacterium sp., Eubacterium sp. VPI 12708

Curr. Microbiol.

30

259-263

1995

1

-

1

-

1

-

1

-

12

-

1

-

8

1

-

1

-

1

-

1

-

1

-

1

-

8

1

-

286355

Sawada

Kinetic and stereochemical cha ...

Mesocricetus auratus

J. Biochem.

109

770-775

1991

-

2

4

1

-

1

-

1

-

1

-

1

-

1

-

1

-

2

5

-

2

-

2

5

4

1

-

1

-

1

-

1

-

1

-

347979

Askonas

The kinetic mechanism catalyse ...

Rattus norvegicus

Biochem. J.

278

835-841

1991

-

2

4

1

-

1

-

1

-

1

-

2

-

1

-

2

1

-

2

-

2

1

4

1

-

1

-

1

-

2

-

1

-

347981

Pawlowski

Cloning and sequencing of the ...

Rattus norvegicus, Rattus norvegicus Sprangue-Dawley

J. Biol. Chem.

266

8820-8825

1991

-

1

-

1

-

2

4

-

7

-

1

-

2

-

6

1

-

1

-

1

-

1

-

2

4

-

2

-

6

1

-

286354

Ohmura

Demonstration of 3alpha(17beta ...

Mesocricetus auratus

Biochem. J.

266

583-589

1990

-

9

2

1

-

1

-

1

-

1

-

1

5

1

13

1

-

1

17

-

2

-

2

-

9

-

2

1

-

1

-

1

-

1

5

1

13

1

-

1

17

-

347985

Ricigliano

Evidence that enzyme-generated ...

Rattus norvegicus, Rattus norvegicus Sprangue-Dawley

Biochem. J.

269

749-755

1990

-

5

-

4

-

1

-

1

-

1

4

-

1

-

2

-

2

-

5

-

1

-

1

-

1

4

-

1

-

347980

Penning

Prostaglandin dehydrogenase ac ...

Rattus norvegicus

Biochem. Biophys. Res. Commun.

148

646-652

1987

-

5

1

-

1

-

1

-

1

-

1

3

-

3

1

-

1

3

-

1

-

5

3

1

-

1

-

1

-

1

3

-

3

1

-

347982

Penning

Purification and properties of ...

Rattus norvegicus, Rattus norvegicus Sprangue-Dawley

Biochem. J.

222

601-611

1984

-

25

-

1

-

2

-

5

-

1

-

1

2

1

15

1

-

5

17

-

2

-

5

-

2

25

17

-

1

-

2

-

1

-

1

2

1

15

1

-

722157

Björkhem

Stereochemistry of hydrogen tr ...

Rattus norvegicus

Eur. J. Biochem.

12

80-4

1970

-

1

-

1

-

2

-

1

-

2

-

347984

Tomkins

A mammalian 3alpha-hydroxyster ...

Rattus norvegicus

J. Biol. Chem.

218

437-447

1956

-

3

4

-

1

-

1

-

2

-

4

5

-

4

-

4

-

3

-

4

-

1

-

2

-

4

5

-

Fjord-region benzo[g]chrysene-11,12-dihydrodiol and benzo[c]phenanthrene-3,4-dihydrodiol as substrates for rat liver dihydrodiol dehydrogenase (AKR1C9): structural basis for stereochemical preference

Data extracted from this reference: