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progesterone + NADPH + H+
5alpha-pregnan-3,20-dione + NADP+
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
-
?
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
-
-
?
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+
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+ + H+
-
-
-
-
?
testosterone + NADPH + H+
androstan-3alpha,17beta-diol + androstan-3beta,17beta-diol + 5alpha-dihydrotestosterone
testosterone + NADPH + H+
dihydrotestosterone + NADP+
-
-
-
?
additional information
?
-
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
-
-
-
-
?
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
-
-
-
-
ir
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
-
-
390592, 396192, 396196, 396199, 396200, 396201, 396203, 396204, 396205, 396209, 396210 -
-
?
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
-
-
-
?
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
-
mammalian enzymes: no reverse reaction, first step in reverse direction (enolization) occurs, but energy barrier for hydride abstraction is extremely high
-
-
ir
deoxycorticosterone + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione
-
-
-
-
?
deoxycorticosterone + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione
-
-
-
-
ir
progesterone + NADPH + H+
5alpha-pregnan-3,20-dione + NADP+
-
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3,20-dione + NADP+
-
-
-
-
ir
progesterone + NADPH + H+
5alpha-pregnan-3,20-dione + NADP+
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
r
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
r
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
r
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
activity is higher in hypothalamus of non-lactating female rats than in lactating
-
r
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
riboflavin-deficient diet decreases the enzyme activity, after 5 weeks no activity is remaining
-
-
?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
-
-
-
-
?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
-
-
-
-
ir
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
-
-
-
ir
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
5alpha-dihydrotestosterone is a more potent androgen, regulatory function, overview
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
very low activity
-
-
?
testosterone + NADPH + H+
androstan-3alpha,17beta-diol + androstan-3beta,17beta-diol + 5alpha-dihydrotestosterone
-
-
-
r
testosterone + NADPH + H+
androstan-3alpha,17beta-diol + androstan-3beta,17beta-diol + 5alpha-dihydrotestosterone
-
reversible in the presence of coenzyme Q10 as electron-acceptor, electrons are transferred from NADPH to coenzyme Q10 via the enzyme NADPH:coenzyme Q10-oxidoreductase and then to testosterone
-
r
additional information
?
-
-
testosterone and 20alpha-hydroxy-4-pregnen-3-one can act in place of progesterone
-
-
?
additional information
?
-
-
testosterone is less effective
-
-
?
additional information
?
-
-
testosterone is less effective
-
-
?
additional information
?
-
-
role of enzyme in initiation of spermatogenensis
-
-
?
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(-)-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
(Z)-((2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl) hexadec-9-enoate
-
-
11-ketoprogesterone
-
complete inhibition
17alpha-hydroxyprogesterone
-
-
17alpha-methyltestosterone
-
-
17beta-Carbamoyl-1,3,5(10)-estratriene-3-carboxylic acids
-
formation of enzyme-NADP+-inhibitor complex
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%
3-Androstene-3-carboxylic acids
-
uncompetitive
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
-
5alpha-androstane-3,17-dione
-
30% inhibition
5beta-cholestan-3-one
-
-
6alpha-methyl-11-ketoprogesterone
-
25% inhibition
6beta-methyl-11-ketoprogesterone
-
50% inhibition
androst-1-ene-3,17dione
-
55% inhibition
androst-4-en-3,17-dione
-
-
androst-4-ene-3,17-dione
-
complete inhibition
asclepic acid
-
50% inhibition at 0.50 mM
Ca2+
-
1 mM: less than 20% inhibition
Cd2+
-
1 mM: less than 20% inhibition
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
dutasteride
-
dual 5alpha-reductase inhibitor
EDTA
-
slightly inhibitory
estradiol-17beta
-
high concentration
flavins
-
and flavin analogs, high concentration
-
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
linoleic acid
-
50% inhibition at 0.37 mM
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
oleic acid
-
50% inhibition at 0.44 mM
palmitic acid
-
50% inhibition at 1.35 mM
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
-
soyasaponin I
-
0.1 mM, 66.8% inhibition
tert-butyl-4-hydroxyanisole
a mixture of two isomers of tert-butyl-4-hydroxyanisole. Competitive inhibitor
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
-
-
-
17beta-estradiol
-
-
17beta-estradiol
-
noncompetitive inhibition
4-Aza-4-methyl-5alpha-pregnane-3,20-dione
-
-
4-Aza-4-methyl-5alpha-pregnane-3,20-dione
-
competitive against progesterone, reversible, transition state analog
Cu2+
-
-
ethinylestradiol
-
-
ethinylestradiol
-
50% inhibition at 0.81 mM
ethinylestradiol
-
63.3% inhibition at 1 mM
finasteride
-
-
finasteride
-
37°C, pH 6.6, 50% inhibition at 0.00001 mM, isoform I, 37°C, pH 5.5, 50% inhibition at 0.00001 mM, isoform II
finasteride
-
type 2 5alpha-reductase inhibitor
finasteride
-
0.025 mM, 78.3% inhibition
NADP+
-
-
NADP+
-
product inhibition
p-chloromercuribenzoate
-
-
p-chloromercuribenzoate
-
complete inhibition
progesterone
-
competitive
progesterone
-
complete inhibition
testosterone
-
-
testosterone
-
poor competitive inhibitor
Zn2+
-
-
additional information
-
not inhibitory: stearic acid
-
additional information
-
theaflavin, gallic acid, and n-propyl gallate are poor inhibitors, physiological effects of inhibitors in vivo, overview
-
additional information
-
no inhibitory activity of yangonin, (+)-methysticin, (+)-kawain, 5,6-dehydrokawain, and 7,8-epoxyyangonin against 5alpha reductase
-
additional information
-
yangonin, (+)-methysticin, (+)-kawain, 5,6-dehydrokawain, and 7,8-epoxyyangonin show no significant 5alpha-reductase inhibitory activity
-
additional information
-
flowers of Pueraria thomsonii, 50% ethanolic extract shows inhibitory activity of 60.2%
-
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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
brenda
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
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