Information on EC 1.3.1.22 - 3-oxo-5alpha-steroid 4-dehydrogenase (NADP+) and Organism(s) Rattus norvegicus and UniProt Accession P24008

-

689176

-

?

testosterone + NADPH + H+

5alpha-dihydrotestosterone + NADP+

-

-

?

testosterone + NADPH + H+

dihydrotestosterone + NADP+

-

762009, 762014

-

?

17-epitestosterone + NADPH

?

-

-

?

17alpha,21-dihydroxypregn-4-ene-3,11,20-trione + NADPH

17alpha,21-dihydroxy-5alpha-pregnan-3,11,20-trione + NADP+

-

trivial name cortisone

-

ir

17alpha,21-dihydroxypregn-4-ene-3,20-dione + NADPH

17alpha,21-dihydroxy-5alpha-pregnane-3,20-dione

-

-

?

17alpha-hydroxyprogesterone + NADPH

17alpha-hydroxy-5alpha-pregnan-3,20-dione + NADP+

-

-

ir

17beta-methyl-androsta-4,9-dien-3-one + NADPH

17beta-methyl-5alpha-androst-9-en-3-one + NADP+

-

-

?

20-alpha-hydroxypregn-4-ene-3one + NADPH

20-alpha-hydroxy-5alpha-pregnan-3-one + NADP+

-

-

ir

20alpha-hydroxy-4-pregnen-3-one + NADPH

20alpha-hydroxy-5-beta-pregnan-3-one + NADP+

-

more reactive than progesterone

390660, 390662

-

?

21-hydroxypregn-4-ene-3,20-dione + NADPH

21-hydroxy-5alpha-pregnan-3,20-dione + NADP+

-

-

?

androstenediol + NADPH

5alpha-androstan-3beta,17beta-diol + NADP+

-

-

ir

androstenedione + NADPH + H+

5alpha-androstan-3,17-dione + NADP+

cholest-4-en-3-one + NADPH

5-alpha-cholestan-3-one + NADP+

cortexolone + NADPH

17alpha,21-dihydroxy-5alpha-pregnan-3,20-dione + NADP+

-

-

ir

deoxycorticosterone + NADPH

21-hydroxy-5alpha-pregnan-3,20-dione

epitestosterone + NADPH

?

-

-

ir

progesterone + NADPH + H+

5alpha-pregnan-3,20-dione + NADP+

progesterone + NADPH + H+

5alpha-pregnan-3-20-dione + NADP+

6 entries

testosterone + NADPH + H+

17beta-hydroxy-5alpha-androstan-3-one + NADP+

testosterone + NADPH + H+

5alpha-dihydrotestosterone + NADP+

4 entries

testosterone + NADPH + H+

5alpha-dihydrotestosterone + NADP+ + H+

-

685457, 688719

-

?

testosterone + NADPH + H+

androstan-3alpha,17beta-diol + androstan-3beta,17beta-diol + 5alpha-dihydrotestosterone

additional information

?

-

4 entries

testosterone + NADPH + H+

dihydrotestosterone + NADP+

-

762009, 762014

-

?

progesterone + NADPH + H+

5alpha-pregnan-3-20-dione + NADP+

testosterone + NADPH + H+

17beta-hydroxy-5alpha-androstan-3-one + NADP+

-

-

ir

testosterone + NADPH + H+

5alpha-dihydrotestosterone + NADP+

-

5alpha-dihydrotestosterone is a more potent androgen, regulatory function, overview

-

?

additional information

?

-

-

role of enzyme in initiation of spermatogenensis

654933

-

?

NADPH

coenzyme Q10

-

NADPH

additional information

8 entries

-

EDTA

-

K+

-

stimulate

Li+

-

stimulate

apigenin

-

tert-butyl-4-hydroxyanisole

a mixture of two isomers of tert-butyl-4-hydroxyanisole. Competitive inhibitor

(+)-methysticin

-

(-)-epigallocatechin-3-gallate

-

i.e. EGCG, from Thea sativa, slightly inhibits the liver microsomal enzyme

(2E,4E,6E,8E)-((2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoate

-

compound shows moderate anti-tumour activity in vivo

(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl palmitoate

-

activity of 3-O-acylated (e)-epigallocatechins increases with the increasing carbon numbers of the fatty acid moiety, reaching maximum for palmitoate

(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(1,3,5-benzotrioxepin-6-ylmethyl)tetrahydrofuran-2-ol

-

(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(1,3,5-benzotrioxepin-7-ylmethyl)tetrahydrofuran-2-ol

-

i.e. (-)-cubebin

(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(2,3-dimethoxybenzyl)tetrahydrofuran-2-ol

-

(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(3,4-dimethoxybenzyl)tetrahydrofuran-2-ol

-

i.e. (-)-3,4-dimethoxy-3,4-desmethylenedioxycubebin

(5'S)-17beta-(2-chlorophenyl-4,5-dihydrooxazol-5-yl)androst-5-en-3-one

-

(5'S)-17beta-(4-bromophenyl-4,5-dihydrooxazol-5-yl)androst-5-en-3-one

-

(5alpha,20-R)-4-Diazo-21-hydroxy-20-methylpregnan-3-one

-

RMI18,341

396204

(Z)-((2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl) hexadec-9-enoate

-

11-ketoprogesterone

-

complete inhibition

17alpha-hydroxyprogesterone

-

396210

17alpha-methyltestosterone

-

17beta-Carbamoyl-1,3,5(10)-estratriene-3-carboxylic acids

-

formation of enzyme-NADP+-inhibitor complex

390656

17beta-estradiol

17beta-hydroxyandrosta-1,4-dien-3-one

-

50% inhibition

19-norandrost-4-ene-3,17-dione

-

complete inhibition

19-nortestosterone

-

complete inhibition

20alpha-hydroxypregn-4-en-3-one

-

competitive

21,21-pentamethylene-4-aza-5alpha-pregn-1-ene-3,20-dione

-

i.e. L685,273, suppresses testicular enzyme activity during puberty by 75-86%

654933

3-Androstene-3-carboxylic acids

-

uncompetitive

396214

4-(4'-formylphenoxy)benzoic acid

-

37°C, pH 6.6, 7% inhibition at 0.01 mM, isoform I, 37°C, pH 5.5, 16% inhibition at 0.01 mM, isoform II

4-(biphenyl-4'-yloxy)phenylacetic acid

-

37°C, pH 6.6, 29% inhibition at 0.01 mM, isoform I, 37°C, pH 5.5, 50% inhibition at 0.0096 mM, isoform II

4-(biphenyl-4'-yloxy)phenylformic acid

-

37°C, pH 6.6, 21% inhibition at 0.01 mM, isoform I, 37°C, pH 5.5, 15% inhibition at 0.01 mM, isoform II

4-(N-(diphenyl)acetyl-4-piperidinyloxy)benzoic acid

-

isoform 1, pH 6.6, 37°C, 62% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 58% inhibition at 0.01 mM

4-(N-(diphenyl)carbamoyl-4-piperidinyloxy)benzoic acid

-

isoform 1, pH 6.6, 37°C, 53% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 50% inhibition at 0.01 mM

4-(N-(tert-butyloxycarbonyl)-4-piperidinyloxy)benzoic acid

-

isoform 1, pH 6.6, 37°C, 4% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 12% inhibition at 0.01 mM

4-(N-adamantanoyl-4-piperidinyloxy)benzoic acid

-

isoform 1, pH 6.6, 37°C, 18% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 21% inhibition at 0.01 mM

4-Aza-4-methyl-5alpha-pregnane-3,20-dione

4-carboxy-4'-(N,N-dicyclohexyl)-aminobiphenyl

-

pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.0014 mM, DU145 cells, 44% inhibition at 0.003 mM

4-carboxy-4'-(N,N-diisobutyl)-aminobiphenyl

-

37°C, pH 6.6, 24% inhibition at 0.001 mM, isoform I, 37°C, pH 5.5, 37% inhibition at 0.001 mM, isoform II

4-carboxy-4'-(N,N-diisopropyl)-aminobiphenyl

-

37°C, pH 6.6, 4% inhibition at 0.01 mM, isoform I, 37°C, pH 5.5, 10% inhibition at 0.01 mM, isoform II

4-carboxy-4'-(N,N-diphenyl)-aminobiphenyl

-

37°C, pH 6.6, 50% inhibition at 0.00046 mM, isoform I, 37°C, pH 5.5, 50% inhibition at 0.003 mM, isoform II

4-carboxy-4'-(N-adamantyl)-aminobiphenyl

-

37°C, pH 6.6, 50% inhibition at 0.0056 mM, isoform I, 37°C, pH 5.5, 50% inhibition at 0.01 mM, isoform II

4-Ene-3-keto-steroids

-

17beta-estradiol in high concentrations functions as an uncompetitive inhibitor

4-methyl-4-azasteroids

-

competitive

396214, 396219

-

4-methyl-azasteroid

-

396219

5alpha-androstane-3,17-dione

-

30% inhibition

5beta-cholestan-3-one

-

6alpha-methyl-11-ketoprogesterone

-

25% inhibition

6beta-methyl-11-ketoprogesterone

-

50% inhibition

acrylate episteride

-

396219

androst-1-ene-3,17dione

-

55% inhibition

androst-4-en-3,17-dione

-

androst-4-ene-3,17-dione

-

complete inhibition

androst-4-enedione

-

asclepic acid

-

50% inhibition at 0.50 mM

Biochanin A

-

Ca2+

-

1 mM: less than 20% inhibition

Cd2+

-

1 mM: less than 20% inhibition

cholest-5-en-3-one

-

cholestanone

-

Cu2+

Detergents

-

e.g.: Lubrol WX, Nonidet P-40, octyl D-glucopyranoside, L-alpha-lysophosphatidylcholine, CHAPS, concentration-dependent inhibition

dihydrotestosterone

-

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

676162

dutasteride

-

dual 5alpha-reductase inhibitor

688719

EDTA

-

slightly inhibitory

equol

-

estradiol-17beta

-

high concentration

ethinylestradiol

finasteride

flavins

-

and flavin analogs, high concentration

390652, 390653

-

genistein

-

ginsenoside Rg3

-

a unique ginsenoside in red ginseng

ginsenoside Ro

-

predominant ginsenoside in the rhizome of ginseng

kaikasaponin III

-

0.1 mM, 66.8% inhibition

725765

linoleic acid

-

50% inhibition at 0.37 mM

MK-434

-

Mn2+

-

1 mM: less than 20% inhibition

N(dicyclohexyl)acetylpiperidine-4-(2-methoxybenzylidene-4-carboxylic acid)

-

isoform 1, pH 6.6, 37°C, 55% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 43% inhibition at 0.01 mM

N,N-dicyclohexyl-4-(4'-carboxyphenoxy)benzamide

-

37°C, pH 6.6, 50% inhibition at 0.0041 mM, isoform I, 37°C, pH 5.5, 50% inhibition at 0.01 mM, isoform II

N,N-diisobutyl-4-(4'-carboxyphenoxy)benzamide

-

37°C, pH 6.6, 18% inhibition at 0.01 mM, isoform I, 37°C, pH 5.5, 22% inhibition at 0.01 mM, isoform II

N,N-diisopropyl-4-(4'-carboxyphenoxy)benzamide

-

37°C, pH 6.6, 4% inhibition at 0.01 mM, isoform I

N,N-diphenyl-4-(4'-carboxyphenoxy)benzamide

-

37°C, pH 6.6, 50% inhibition at 0.0045 mM, isoform I, 37°C, pH 5.5, 26% inhibition at 0.001 mM, isoform II

N-(1-adamantanoyl)piperdine-4-(2-methoxybenzyliden-4-carboxylic acid)

-

isoform 1, pH 6.6, 37°C, 50% inhibition at 0.0011 mM, isoform 2, pH 5.5, 37°C, 50% inhibition at 0.0011 mM

N-(1-adamantanoyl)piperidine-4-(2-fluorobenzylidene-4-carboxylic acid)

-

isoform 1, pH 6.6, 37°C, 52% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 51% inhibition at 0.01 mM

N-(3,3-diphenyl)propanoylpiperidine-4-(benzylidene-4-carboxylic acid)

-

isoform 1, pH 6.6, 37°C, 50% inhibition at 0.0016 mM, isoform 2, pH 5.5, 37°C, 50% inhibition at 0.00088 mM

N-(dicyclohexyl)acetylpiperidine-4-(2-fluorobenzylidene-4-carboxylic acid)

-

isoform 1, pH 6.6, 37°C, 50% inhibition at 0.0018 mM, isoform 2, pH 5.5, 37°C, 50% inhibition at 0.003 mM

N-(dicyclohexyl)acetylpiperidine-4-(benzylidene-3-carboxylic acid)

-

isoform 1, pH 6.6, 37°C, 35% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 25% inhibition at 0.01 mM

N-(dicyclohexyl)acetylpiperidine-4-(benzylidene-4-acetic acid)

-

isoform 1, pH 6.6, 37°C, 66% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 56% inhibition at 0.01 mM

N-(dicyclohexyl)acetylpiperidine-4-(benzylidene-4-carboxylic acid)

-

isoform 1, pH 6.6, 37°C, 51% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 50% inhibition at 0.00008 mM

N-(diphenyl)acetylpiperidine-4-(2-fluorobenzylidene-4-carboxylic acid)

-

isoform 1, pH 6.6, 37°C, 50% inhibition at 0.0011 mM, isoform 2, pH 5.5, 37°C, 50% inhibition at 0.0011 mM

N-(diphenyl)acetylpiperidine-4-(2-methoxybenzylidene-4-carboxylic acid)

-

isoform 1, pH 6.6, 37°C, 50% inhibition at 0.0019 mM, isoform 2, pH 5.5, 37°C, 50% inhibition at 0.00094 mM

N-(diphenyl)acetylpiperidine-4-(benzylidene-3-carboxylic acid)

-

isoform 1, pH 6.6, 37°C, 49% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 43% inhibition at 0.01 mM

N-(diphenyl)acetylpiperidine-4-(benzylidene-4-acetic acid)

-

isoform 1, pH 6.6, 37°C, 50% inhibition at 0.0045 mM, isoform 2, pH 5.5, 37°C, 63% inhibition at 0.01 mM

N-adamantyl-4-(4'-carboxyphenoxy)benzamide

-

37°C, pH 6.6, 50% inhibition at 0.0082 mM, isoform I, 37°C, pH 5.5, 50% inhibition at 0.008 mM, isoform II

N-cyclohexyl-4-(4'-carboxyphenoxy)benzamide

-

37°C, pH 6.6, 17% inhibition at 0.01 mM, isoform I, 37°C, pH 5.5, 35% inhibition at 0.01 mM, isoform II

N-phenyl-4-(4'-carboxyphenoxy)benzamide

-

37°C, pH 6.6, 22% inhibition at 0.01 mM, isoform I, 37°C, pH 5.5, 39% inhibition at 0.01 mM, isoform II

N-tert-butyl-4-(4'-carboxyphenoxy)benzamide

-

37°C, pH 6.6, 5% inhibition at 0.01 mM, isoform I, 37°C, pH 5.5, 26% inhibition at 0.01 mM, isoform II

NADP+

oleic acid

-

50% inhibition at 0.44 mM

654925

p-chloromercuribenzoate

palmitic acid

-

50% inhibition at 1.35 mM

654925

penta-O-galloyl-beta-D-glucose

-

i.e. 5GG, from Thea sativa, inhibits the liver microsomal enzyme

Piper betle ethanolic whole plant extract

-

42.3% inhibition at 2 mg/ml

-

Piper cueba ethanolic fruit extract

-

28.0% inhibition at 2 mg/ml

-

Piper kadsura ethanolic leaf extract

-

19.0% inhibition at 2 mg/ml

-

Piper kadsura ethanolic rhizome extract

-

36.5% inhibition at 2 mg/ml

-

Piper kadsura ethanolic root extract

-

39.2% inhibition at 2 mg/ml

-

Piper kadsura ethanolic stem extract

-

16.9% inhibition at 2 mg/ml

-

Piper longum ethanolic whole plant extract

-

12.3% inhibition at 2 mg/ml

-

Piper methysticum ethanolic leaf extract

-

28.4% inhibition at 2 mg/ml

-

Piper methysticum ethanolic rhizome extract

-

42.5% inhibition at 2 mg/ml

-

Piper methysticum ethanolic stem extract

-

21.9% inhibition at 2 mg/ml

-

Piper nigrum ethanolic fruit extract

-

63% inhibition at 2 mg/ml

-

Piper nigrum ethanolic leaf extract

-

53.0% inhibition at 2 mg/ml

-

Piper nigrum ethanolic stem extract

-

40.8% inhibition at 2 mg/ml

-

piperine

-

progesterone

riboflavin

-

soyasaponin I

-

0.1 mM, 66.8% inhibition

725765

testosterone

theaflavin-3'-gallate

-

i.e. TF2b, from Thea sativa, inhibits the liver microsomal enzyme

theaflavin-3,3'-digallate

-

i.e. TF3, from Thea sativa, inhibits the liver microsomal enzyme

theaflavin-3-gallate

-

i.e. TF2a, from Thea sativa, inhibits the liver microsomal enzyme

Unsaturated 3-carboxysteroids

-

390655

-

yangonin

-

Zn2+

additional information

5 entries

-

sulpiride

40 mg/kg doses induce mRNA expression of 5alphaR1 and 5alpha-R2

3beta-acetoxy-16alpha-17alpha-epoxy-4-pregnen-20-one

-

3beta-acetoxy-5,16-pregnadien-20-one

-

4-pregnen-17-ol-3-one

-

dihydrotestosterone

-

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

676162

dilauroylphosphatidylcholine

-

marked stimulatory effect on activity

390661

dithiothreitol

-

no influence on microsomal enzyme, but slightly stimulating the solubilized enzyme

390652

iodoacetamide

-

stimulatory on solubilized enzyme from microsomes

morphine

-

morphine significantly reduces the testosterone concentration after acute and chronic exposure in the spinal cord. In contrast, the 5alpha-reductase 1 expression and of course dihydrotestosterone levels increase tfollowing chronic morphine administration

726046

N-ethylmaleimide

-

stimulatory on solubilized enzyme from microsomes

phosphatidylserine

-

4fold increase in activity

390661

Phospholipids

-

stimulate

390652

sulpiride

40 mg/kg doses induce mRNA expression of 5alphaR1 and 5alpha-R2

0.0014

dihydrotestosterone

37°C, pH not specified in the publication

0.001568

testosterone

37°C, pH not specified in the publication

0.00057 - 0.00078

17-epitestosterone

0.00086

20alpha-hydroxypregn-4-en-3-one

-

0.14

cortisone

-

0.00102 - 0.53

NADPH

0.000095 - 0.12

progesterone

6 entries

0.0002 - 0.032

testosterone

6 entries

additional information

-

0.000035

(5alpha,20-R)-4-Diazo-21-hydroxy-20-methylpregnan-3-one

-

at 25°C formation of the reversible EI complex is not rate-limiting for enzyme inactivation, and this is expressed as saturation kinetics for the inhibition reaction

396204

0.026 - 0.036

17beta-estradiol

0.146

17beta-hydroxyandrosta-1,4-diene-3-one

-

0.00006

20alpha-hydroxypregn-4-en-3-one

-

0.0000062 - 0.0000118

4-Aza-4-methyl-5alpha-pregnane-3,20-dione

0.000003 - 0.000008

4-methyl-azasteroid

0.000004 - 0.00002

acylate episteride

-

0.000004 - 0.000006

finasteride

0.0043 - 0.0319

NADP+

0.00048 - 0.0027

penta-O-galloyl-beta-D-glucose

0.0026 - 0.0065

theaflavin-3'-gallate

0.00036 - 0.0056

theaflavin-3,3'-digallate

additional information

-

inhibition kinetics

-

0.1

apigenin

Rattus norvegicus

37°C, pH not specified in the publication

0.0047

tert-butyl-4-hydroxyanisole

Rattus norvegicus

37°C, pH not specified in the publication

0.00076

(2E,4E,6E,8E)-((2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoate

Rattus norvegicus

-

pH not specified in the publication, temperature not specified in the publication

0.00053

(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl palmitoate

Rattus norvegicus

-

pH not specified in the publication, temperature not specified in the publication

0.44

(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(1,3,5-benzotrioxepin-6-ylmethyl)tetrahydrofuran-2-ol

Rattus norvegicus

-

0.44

(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(1,3,5-benzotrioxepin-7-ylmethyl)tetrahydrofuran-2-ol

Rattus norvegicus

-

1.03

(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(2,3-dimethoxybenzyl)tetrahydrofuran-2-ol

Rattus norvegicus

-

1.03

(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(3,4-dimethoxybenzyl)tetrahydrofuran-2-ol

Rattus norvegicus

-

0.00072

(5'S)-17beta-(2-chlorophenyl-4,5-dihydrooxazol-5-yl)androst-5-en-3-one

Rattus norvegicus

-

pH 7.3, 37°C

0.00105

(5'S)-17beta-(4-bromophenyl-4,5-dihydrooxazol-5-yl)androst-5-en-3-one

Rattus norvegicus

-

pH 7.3, 37°C

0.00048

(Z)-((2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl) hexadec-9-enoate

Rattus norvegicus

-

pH not specified in the publication, temperature not specified in the publication

0.14

Biochanin A

Rattus norvegicus

-

pH not specified in the publication, temperature not specified in the publication

0.37

equol

Rattus norvegicus

-

pH not specified in the publication, temperature not specified in the publication

0.81

ethinylestradiol

Rattus norvegicus

-

0.000008

finasteride

Rattus norvegicus

-

pH 7.3, 37°C

0.71

genistein

Rattus norvegicus

-

pH not specified in the publication, temperature not specified in the publication

0.086

ginsenoside Rg3

Rattus norvegicus

-

pH 7.2, 37°C

0.259

ginsenoside Ro

Rattus norvegicus

-

pH 7.2, 37°C

0.48

piperine

Rattus norvegicus

-

0.017

riboflavin

Rattus norvegicus

-

pH not specified in the publication, temperature not specified in the publication

0.03413

-

female

396199

1090

additional information

4 entries

5

-

isozyme 2, high substrate concentration

396220

5.5

-

isozyme 2, low substrate concentration, efficiency optimum Vmax/Km

5.5 - 7.5

-

5.8 - 7.5

-

6 - 7.2

-

6.5

-

assay at

6.6

-

6.9

-

7

-

7.2

-

male

7.3 - 7.6

-

4.5 - 9

-

pH .5: about 30% of activity maximum, pH 9.0: about 20% of activity maximum

5 - 8

-

pH 5.0: about 20% of activity maximum, pH 8.0: about 20% of activity maximum

5 - 8.5

-

at pH 5 and 8.5: about 50% of activity maximum

32

-

37

-

assay at

15 - 42

-

15°C: about 50% of activity maximum, 42°C: about 30% of activity maximum

-

prefrontal cortex

-

prefrontal cortex

central nervous system

-

-

external

-

-

389558, 389559, 389561, 390653, 390659, 390662

-

-

similar 5alpha-R1 mRNA expression in female and male rats, 5alpha-R2 mRNA expression significantly higher in females than in males

-

prostate carcinoma cell

-

-

-

-

additional information

-

389557, 389558, 389559

cytosol

-

5829

389557, 389558, 389559

endoplasmic reticulum

-

-

-

396192, 396193, 396209

-

additional information

-

nuclear and cell-debris fraction

-

390660

P24008 pBLAST

S5A1_RAT

259

3

29780

Swiss-Prot

Show Sequence

Secretory Pathway (Reliability: 2)

27000

SDS-PAGE

25000 - 35000

-

gel filtration

396209

26000

-

10% SDS-PAGE

27000

SDS-PAGE

5.7 - 8.4

-

in the cold

396209

6.6 - 7.8

-

4 days, in the cold, presence of KCl and NADH

396209

25

-

1 h stable

37

-

rapid loss of activity

4

-

2 days, 50% loss of activity

dialysis at 4°C, 22 h, n-octylglycoside-KCl extracted enzyme without loss of activity

-

glycerol stabilizes

-

NADPH stabilizes

-

-20°C, 1 week, solubilized enzyme

-

-20°C, 6 months

-

4°C, 2 days, 50% loss of activity

-

-

-

partial

-

three-step purification of a photolabeled tryptic peptide corresponding to the NADP(H) binding domain of 5alpha-reductase

-

396214

expressed in COS1 cells

expression in Cos-1 cells

transcription and expression levels of both 5alpha-reductase isozymes were significantly higher in environmentally stressed rats than in unstressed rats

726043

morphine significantly reduces the testosterone concentration after acute and chronic exposure in the spinal cord. In contrast, the 5alpha-reductase 1 expression and of course dihydrotestosterone levels increase the following chronic morphine administration

-

726046

transcription and expression levels of both 5alpha-reductase isozymes were significantly higher in environmentally stressed rats than in unstressed rats

medicine

transcription and expression levels of both 5alpha-reductase isozymes were significantly higher in environmentally stressed rats than in unstressed rats. Increased 5alpha-reductase isozyme levels may play a role in the development or maintenance of prostate disease

analysis

medicine

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

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

J. Steroid Biochem. Mol. Biol.

60

311-318

1997

Rattus norvegicus

9219922

389558

Krause, J.E.; Karavolas, H.J.

Subcellular location of hypothalamic progesterone metabolizing enzymes and evidence for distinct NADH- and NADPH-linked 3alpha-hydroxysteroid oxidoreductase activities

J. Steroid Biochem.

13

271-280

1980

Rattus norvegicus

6930523

389559

Karavolas, H.J.; Hodges, D.R.

Changes in pituitary, hypothalamic and brain progestin-metabolizing enzyme activities during lactation

J. Steroid Biochem. Mol. Biol.

44

299-303

1993

Rattus norvegicus

8461262

389561

Bertics, P.J.; Edman, C.F.; Karavolas, H.J.

Potent inhibition of the hypothalamic progesterone 5alpha-reductase by a 5alpha-dihydroprogesterone analog

J. Biol. Chem.

259

107-111

1984

Rattus norvegicus

6706922

390592

Wilton, D.C.

Is a Schiff base involved in the mechanism of the DELTA4-3-oxo steroid 5alpha- or 5beta-reductases from mammalian liver?

Biochem. J.

155

487-491

1976

Rattus norvegicus

949314

390652

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

Pituitary progesterone 5alpha-reductase: solubilization and partial characterization

J. Steroid Biochem.

22

795-802

1985

Rattus norvegicus

4021482

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

Partial characterization of the microsomal and solubilized hypothalamic progesterone 5alpha-reductase

J. Steroid Biochem.

21

305-314

1984

Rattus norvegicus

6593506

390655

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

Inhibition of steroid 5alpha-reductase by unsaturated 3-carboxysteroids

J. Med. Chem.

33

943-950

1990

Homo sapiens, Rattus norvegicus

2308145

390656

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

Steroidal A ring aryl carboxylic acids: a new class of steroid 5alpha-reductase inhibitors

J. Med. Chem.

33

937-942

1990

Homo sapiens, Rattus norvegicus

2308144

390659

Campbell, J.S.; Karavolas, H.J.

The kinetic mechanism of the hypothalamic progesterone 5alpha-reductase

J. Steroid Biochem.

32

283-289

1989

Rattus norvegicus

2921870

390660

Cheng, Y.J.; Karavolas, H.J.

Properties and subcellular distribution of DELTA4-steroid (progesterone) 5alpha-reductase in rat anterior pituitary

Steroids

26

57-71

1975

Rattus norvegicus

1166484

390661

Ichihara, K.; Tanaka, C.

Specific stimulation of steroid 5alpha-reductase solubilized from rat liver microsomes by endogenous phosphatidylserine

Biochem. Biophys. Res. Commun.

149

482-487

1987

Rattus norvegicus

3426586

Cheng, Y.J.; Karavolas, H.J.

Subcellular distribution and properties of progesterone (delta4-steroid) 5alpha-reductase in rat medial basal hypothalamus

J. Biol. Chem.

250

7997-8003

1975

Rattus norvegicus

240847

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

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

J. Biol. Chem.

235

3112-3117

1960

Rattus norvegicus

-

390766

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

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

Hoppe-Seyler's Z. Physiol. Chem.

355

1499-1507

1974

Rattus norvegicus

4156680

390767

Robaire, B.; Ewing, L.L.; Zirkin, B.R.; Irby, D.C.

Steroid DELTA4-5alpha-reductase and 3alpha-hydroxysteroid dehydrogenase in the rat epididymis

Endocrinology

101

1379-1390

1977

Rattus norvegicus

913319

Enderle-Schmitt, U.; Neuhaus, C.; Aumuller, G.

Solubilization of nuclear steroid 5alpha-reductase from rat ventral prostate

Biochim. Biophys. Acta

987

21-28

1989

Rattus norvegicus

2597683

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

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

Methods Enzymol.

36A

466-474

1975

Rattus norvegicus

234171

396196

Frederiksen, D.W.; Wilson, J.D.

Partial characterization of the nuclear reduced nicotinamide adenine dinucleotide phosphate: DELTA 4-3-ketosteroid 5alpha-oxidoreductase of rat prostate

J. Biol. Chem.

246

2584-2593

1971

Rattus norvegicus

4396507

396199

Graef, V.; Golf, S.W.; Tuschen, M.

NADPH: 4-ene-3-oxosteroid-5alpha-reductase and NADH: 4-ene-3-oxosteroid-5alpha-reductase in liver microsomes of different species of animals

J. Steroid Biochem.

14

883-887

1981

Gallus gallus, Chinchilla chinchilla, Oryctolagus cuniculus, Homo sapiens, Mesocricetus auratus, Mus musculus, Rattus norvegicus, Sus scrofa

7300356

396200

Lotz, W.

Importance of 5alpha-reduction for the trophic effects of androgens on rat accessory sex organs and LH control

J. Steroid Biochem.

13

1261-1264

1980

Rattus norvegicus

7453171

396201

Sholiton, L.J.; Grossman, C.J.; Taylor, B.B.

Rat thymic homogenates convert testosterone to androgenic metabolites

J. Steroid Biochem.

13

1365-1367

1980

Rattus norvegicus

7453178

396203

Kondo, K.; Aono, T.; Furubayashi, Y.; Terada, N.; Matsumoto, K.

Hormonal regulation of activities of 4-ene-5alpha-reductase and 17beta-ol-dehydrogenase in adult androgene-sterilized rat ovaries

J. Steroid Biochem.

13

703-705

1986

Rattus norvegicus

6247578

396204

Blohm, T.R.; Metcalf, B.W.; Laughlin, M.E.; Sjoerdsma, A.; Schatzman, G.L.

Inhibition of testosterone 5alpha-reductase by a proposed enzyme-activated, active site-directed inhibitor

Biochem. Biophys. Res. Commun.

95

273-280

1980

Rattus norvegicus

7417256

Koninckx, P.; Verhoeven, G.; Heyns, W.; De Moore, P.

Biochemical characterization of the NADPH: 4-ene-3-ketosteroid 5alpha-oxidoreductase in rat ovarian suspension cultures

J. Steroid Biochem.

10

325-333

1979

Rattus norvegicus

459495

396209

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

Extraction of the reduced nicotinamide adenine dinucleotide phosphate:delta 4-3-ketosteroid-5-alpha oxidoreductase of rat prostate with digitonin and potassium chloride

Biochemistry

13

450-456

1974

Rattus norvegicus

4810062

396210

Scheer, H.; Robaire, B.

Solubilization and partial characterization of rat epididymal delta 4-steroid 5alpha-reductase (cholestenone 5alpha-reductase)

Biochem. J.

211

65-74

1983

Rattus norvegicus

6870829

Shefer, S.; Hauser, S.; Mosbach, E.H.

Studies on the biosynthesis of 5alpha-cholestan-3beta-ol 1.Cholestenone of rat liver

J. Biol. Chem.

241

946-952

1965

Rattus norvegicus

5907469

396214

Bhattacharyya, A.K.; Chavan, A.J.; Haley, B.E.; Taylor, M.F.; Collins, D.C.

Identification of the NADP(H) binding site of rat liver microsomal 5alpha-reductase (isoenzyme-1): purification of a photolabeled peptide corresponding to the adenine binding domain

Biochemistry

34

3663-3669

1995

Rattus norvegicus

7893662

396219

Levy, M.A.; Brandt, M.; Sheedy, K.M.; Holt, D.A.; Heaslip, J.I.; Trill, J.J.; Ryan, P.J.; Morris, R.A.; Garrison, L.M.; Bergsma, D.J.

Cloning, expression and functional characterization of type 1 and type 2 steroid 5alpha-reductase from cynomolgus monkey: comparison with human and rat isoenzymes

J. Steroid Biochem. Mol. Biol.

52

307-319

1995

Homo sapiens, Macaca fascicularis, Rattus norvegicus

7734398

396220

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

Rat steroid 5alpha-reductase kinetic characteristics: extreme pH-dependancy of the type II isozyme in prostate and epididymis homogenates

J. Steroid Biochem. Mol. Biol.

54

185-192

1995

Rattus norvegicus

7662592

654925

Matsuda, H.; Yamazaki, M.; Naruo, S.; Asanuma, Y.; Kubo, M.

Anti-androgenic and hair growth promoting activities of Lygodii spora (spore of Lygodium japonicum) I. Active constituents inhibiting testosterone 5alpha-reductase

Biol. Pharm. Bull.

25

622-626

2002

Rattus norvegicus

12033503

654933

Killian, J.; Pratis, K.; Clifton, R.J.; Stanton, P.G.; Robertson, D.M.; O'Donnell, L.

5alpha-reductase isoenzymes 1 and 2 in the rat testis during postnatal development

Biol. Reprod.

68

1711-1718

2003

Rattus norvegicus

12606426

Lee, H.H.; Ho, C.T.; Lin, J.K.

Theaflavin-3,3'-digallate and penta-O-galloyl-beta-D-glucose inhibit rat liver microsomal 5alpha-reductase activity and the expression of androgen receptor in LNCaP prostate cancer cells

Carcinogenesis

25

1109-1118

2004

Homo sapiens, Rattus norvegicus

14963012

655351

Assinder, S.J.; Johnson, C.; King, K.; Nicholson, H.D.

Regulation of 5alpha-reductase isoforms by oxytocin in the rat ventral prostate

Endocrinology

145

5767-5773

2004

Rattus norvegicus

15358676

656373

Pratis, K.; O'Donnell, L.; Ooi, G.T.; Stanton, P.G.; McLachlan, R.I.; Robertson, D.M.

Differential regulation of rat testicular 5alpha-reductase type 1 and 2 isoforms by testosterone and FSH

J. Endocrinol.

176

393-403

2003

Rattus norvegicus

12630924

Picard, F.; Hartmann, R.W.

N-Substituted 4-(4-carboxyphenoxy)benzamides.: Synthesis and evaluation as inhibitors of steroid 5alpha-reductase type 1 and 2

J. Enzyme Inhib. Med. Chem.

17

187-196

2002

Homo sapiens, Rattus norvegicus

12443045

Picard, F.; Barassin, S.; Mokhtarian, A.; Hartmann, R.W.

Synthesis and evaluation of 2'-substituted 4-(4'-carboxy- or 4'-carboxymethylbenzylidene)-N-acylpiperidines: highly potent and in vivo active steroid 5alpha-reductase type 2 inhibitors

J. Med. Chem.

45

3406-3417

2002

Homo sapiens, Rattus norvegicus

12139451

Guzman, D.C.; Mejia, G.B.; Vazquez, I.E.; Garcia, E.H.; del Angel, D.S.; Olguin, H.J.

Effect of testosterone and steroids homologues on indolamines and lipid peroxidation in rat brain

J. Steroid Biochem. Mol. Biol.

94

369-373

2005

Rattus norvegicus

15857756

676162

Sanchez, P.; Torres, J.M.; Ortega, E.

Effects of dihydrotestosterone on brain mRNA levels of steroid 5alpha-reductase isozymes in early postnatal life of rat

Neurochem. Res.

30

577-581

2005

Rattus norvegicus

16076027

684335

Borst, S.E.; Conover, C.F.; Carter, C.S.; Gregory, C.M.; Marzetti, E.; Leeuwenburgh, C.; Vandenborne, K.; Wronski, T.J.

Anabolic effects of testosterone are preserved during inhibition of 5alpha-reductase

Am. J. Physiol. Endocrinol. Metab.

293

E507-E514

2007

Rattus norvegicus

17488806

Hirata, N.; Tokunaga, M.; Naruto, S.; Iinuma, M.; Matsuda, H.

Testosterone 5alpha-reductase inhibitory active constituents of Piper nigrum leaf

Biol. Pharm. Bull.

30

2402-2405

2007

Rattus norvegicus

18057734

Sanchez, P.; Torres, J.M.; Vilchez, P.; Del Moral, R.G.; Ortega, E.

Effects of sulpiride on mRNA levels of steroid 5alpha-reductase isozymes in prostate of adult rats

IUBMB Life

60

68-72

2008

Rattus norvegicus (P24008), Rattus norvegicus (P31214)

18379994

688719

Tindall, D.J.; Rittmaster, R.S.

The rationale for inhibiting 5alpha-reductase isoenzymes in the prevention and treatment of prostate cancer

J. Urol.

179

1235-1242

2008

Homo sapiens, Rattus norvegicus

18280514

689176

Sanchez, P.; Torres, J.M.; Gavete, P.; Ortega, E.

Effects of swim stress on mRNA and protein levels of steroid 5alpha-reductase isozymes in prefrontal cortex of adult male rats

Neurochem. Int.

52

426-431

2008

Rattus norvegicus (P24008), Rattus norvegicus (P31214)

17826869

Sz�csi, M.; Ondr�, D.; T�th, I.; Magony, S.; W�lfling, J.; Schneider, G.; Julesz, J.

Determination of rat 5alpha-reductase type 1 isozyme activity and its inhibition by novel steroidal oxazolines

Acta Biol. Hung.

61

274-281

2010

Rattus norvegicus

20724274

Lin, S.F.; Lin, Y.H.; Lin, M.; Kao, Y.F.; Wang, R.W.; Teng, L.W.; Chuang, S.H.; Chang, J.M.; Yuan, T.T.; Fu, K.C.; Huang, K.P.; Lee, Y.S.; Chiang, C.C.; Yang, S.C.; Lai, C.L.; Liao, C.B.; Chen, P.; Lin, Y.S.; Lai, K.T.; Huang, H.J.; Yang, J.Y.; Liu, C.W.; Wei, W.Y.; Chen, C.K.; Hiipakka, R.A.; Liao, S.; Huang, J.J.

Synthesis and structure-activity relationship of 3-O-acylated (-)-epigallocatechins as 5?-reductase inhibitors

Eur. J. Med. Chem.

45

6068-6076

2010

Rattus norvegicus

21044810

725171

Sanchez, P.; Torres, J.M.; del Moral, R.G.; de Dios Luna, J.; Ortega, E.

Steroid 5alpha-reductase in adult rat brain after neonatal testosterone administration

IUBMB Life

64

81-86

2012

Rattus norvegicus

22131296

Bae, M.; Woo, M.; Kusuma, I.W.; Arung, E.T.; Yang, C.H.; Kim, Y.U.

Inhibitory effects of isoflavonoids on rat prostate testosterone 5alpha-reductase

J. Acupunct. Meridian Stud.

5

319-322

2012

Rattus norvegicus

23265084

725765

Murata, K.; Noguchi, K.; Kondo, M.; Onishi, M.; Watanabe, N.; Okamura, K.; Matsuda, H.

Inhibitory activities of Puerariae Flos against testosterone 5alpha-reductase and its hair growth promotion activities

J. Nat. Med.

66

158-165

2012

Rattus norvegicus

21822606

725859

Lee, S.; Lee, D.; Lee, J.; Lee, W.; Chung, B.; Choi, M.

Comparative GC-MS based in vitro assays of 5alpha-reductase activity using rat liver S9 fraction

Mass Spectrom. Lett.

3

21-24

2012

Rattus norvegicus

-

726043

Sanchez, P.; Torres, J.M.; Castro, B.; Del Moral, R.G.; de Dios Luna, J.; Ortega, E.

Steroid 5alpha-reductase in adult rat brain after neonatal dihydrotestosterone administration

Neurochem. Res.

38

557-563

2013

Rattus norvegicus (P24008), Rattus norvegicus (P31214)

23229791

726046

Sharif, A.; Shoae-Hassani, A.; Sharif, S.; Banafshe, H.R.; Mortazavi-Tabatabaei, S.A.; Verdi, J.

5alpha-reductase 1 regulates spinal cord testosterone after morphine administration

Neurol. Sci.

34

19-23

2013

Rattus norvegicus

22258359

Murata, K.; Takeshita, F.; Samukawa, K.; Tani, T.; Matsuda, H.

Effects of ginseng rhizome and ginsenoside Ro on testosterone 5alpha-reductase and hair re-growth in testosterone-treated mice

Phytother. Res.

26

48-53

2012

Mus musculus, Rattus norvegicus

21538628

Wu, Y.; Li, L.; Zhou, S.; Shen, Q.; Lin, H.; Zhu, Q.; Sun, J.; Ge, R.S.

Apigenin inhibits rat neurosteroidogenic 5alpha-reductase 1 and 3alpha-hydroxysteroid dehydrogenase

Neurochem. Int.

110

84-90

2017

Rattus norvegicus (P24008)

28947342