1.1.1.149: 20alpha-hydroxysteroid dehydrogenase

This is an abbreviated version, for detailed information about 20alpha-hydroxysteroid dehydrogenase, go to the full flat file.

Reaction

17alpha,20alpha-dihydroxypregn-4-en-3-one
+
NAD(P)+
=
17alpha-hydroxyprogesterone
+
NAD(P)H
+
H+

Synonyms

20-alpha-HSD, 20-alpha-hydroxysteroid dehydrogenase, 20alpha-HSD, 20alpha-HSDH, 20alpha-hydroxy steroid dehydrogenase, 20alpha-hydroxysteroid dehydrogenase, 20alpha-hydroxysteroid oxidoreductase, 20alpha-OH-SDH, AKR1C1, AKR1C23, AKR1C3, aldo-keto reductase family 1 member C1, HSD1

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.149 20alpha-hydroxysteroid dehydrogenase

Inhibitors

Inhibitors on EC 1.1.1.149 - 20alpha-hydroxysteroid dehydrogenase

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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
-
50% inhibition at 0.065 mM
1,2-naphthoquinone
-
0.01 mM, 55% inhibition of enzyme in liver, 10% in kidney, 10% in lung cytosolic fraction, respectively
1-phenylcyclopentanecarboxylic acid
-
-
16alpha-Bromoacetoxyprogesterone
-
-
17alpha-hydroxyprogesterone
-
most inhibitory at pH 8.0, significant at pH 6.8
17beta-estradiol
-
20alpha-hydroxyprogesterone analog, competitive or noncompetitive depending on variable substrate
2',5'-adenosine bisphosphate
-
competitive inhibition versus NADP+
2',5'-ADP
-
coenzyme-competitive inhibitor
2'-adenylic acid
-
; coenzyme-competitive inhibitor
2'-phosphoadenosine diphosphoribose
2,4-Pentanedione
-
; pH profile for the inactivation, overview
2-(4-chlorobenzylidene)cyclopentanone
-
-
2-(4-chlorobenzylidene)cyclopentyl ethyl ether
-
-
2-acetylbenzofuran
-
50% inhibition at 0.033 mM
20beta-hydroxypregn-4-en-3-one
-
marginally inhibitory at pH 8.0
3',3'',5',5''-tetrabromophenolphthalein
-
50% inhibition at 33 nM
3',3'',5',5''-tetrabromophenolphthalein diacetate
-
50% inhibition at 350 nM
3',3'',5',5''-tetraiodophenolphthalein
-
50% inhibition at 120 nM
3',5'-cyclic AMP
-
coenzyme-competitive inhibitor
3,5-dibromo-4-hydroxybenzoic acid methyl ester
-
50% inhibition at 0.099 mM
3,5-dibromosalicylic acid
-
-
3,5-dichlorosalicylic acid
3,5-diiodosalicylic acid
-
competitive
3-Aminopyridine 1,N6-ethenoadenine dinucleotide phosphate
-
NADP analog, competitive inhibitor
3-Aminopyridine adenine dinucleotide phosphate
3-bromo-5-phenylsalicylic acid
-
-
3-chloro-5-phenylsalicylic acid
-
-
3-phenyl-5-bromosalicylic acid
-
-
3-phenylcyclopentanecarboxylic acid
-
-
4'-butyl-5-chloro-4-hydroxybiphenyl-3-carboxylic acid
-
7fold selectivity relative to 3alpha-hydroxysteroid dehydrogenase AKR1C2
5'-adenosine diphosphate
-
-
5'-Adenosine triphosphate
-
-
5'-adenylic acid
-
; coenzyme-competitive inhibitor
5'-ADP
-
coenzyme-competitive inhibitor
5'-ATP
-
coenzyme-competitive inhibitor
5-chloro-4-hydroxy-3'-methylbiphenyl-3-carboxylic acid
-
13fold selectivity relative to 3alpha-hydroxysteroid dehydrogenase AKR1C2
5-chloro-4-hydroxy-4'-methylbiphenyl-3-carboxylic acid
-
24fold selectivity relative to 3alpha-hydroxysteroid dehydrogenase AKR1C2
5-chloro-4-hydroxybiphenyl-3-carboxylic acid
-
24fold selectivity relative to 3alpha-hydroxysteroid dehydrogenase AKR1C2
5-fluoro-4-hydroxybiphenyl-3-carboxylic acid
-
1.2fold selectivity relative to 3alpha-hydroxysteroid dehydrogenase AKR1C2
5alpha-dihydrotestosterone
-
-
5beta-dihydrotestosterone
-
-
9,10-phenanthrenequinone
-
0.01 mM, 70% inhibition of enzyme in liver, 5% in kidney, 60% in lung cytosolic fraction, respectively
Acetylsalicylate
-
-
adenosine 2'-monophospho- 5'-diphosphoribose
-
strong inhibition
adenosine diphosphoribose
-
; coenzyme-competitive inhibitor
Ag+
-
very powerful
aminopyridine 1,N6-ethenoadenine dinucleotide phosphate
-
-
aminopyridine adenine dinucleotide phosphate
-
-
androstendione
-
most inhibitory at pH 8.0
apigenin
Barbiturates
-
-
-
benzbromarone
-
50% inhibition at 48 nM
benzbromarone acetate
-
50% inhibition at 430 nM
benzofuran
-
50% inhibition at 1.45 mM
benzofuran-2-carboxylic acid
-
50% inhibition at 0.16 mM
Bethamethasone
-
0.1 mM, 10% inhibition
Bile acids
Bromophenol blue
carboxylic acid
-
competitive for acetic and propionic acid, mixed-type from pentanoic to undecanoic acid with exception of heptanoic acid
cibacron
cloxazolam
-
0.01 mM, 38% inhibition
diazepam
-
50% inhibition at 0.0056 mM
Diazotized 3-aminopyridine 1,N6-ethenoadenine dinucleotide phosphate
-
; NADP+ analog, competitive inhibitor
Diazotized 3-aminopyridine adenine dinucleotide phosphate
-
; NADP analog, competitive inhibitor
dibenzofuran
-
50% inhibition at 0.895 mM
Dienstrol
Diphenic acid
-
less than 17% inhibition
ethyl acetate
fatty acids
fisetin
Flufenamic acid
Fluorescein mercuric acetate
-
-
glycerol
-
inhibition partially reversed by cysteine
glycyrrhetinic acid
-
50% inhibition at 0.0022 mM
Hexestrol
-
50% inhibition at 0.0083 mM
indomethacin
kaempferol
linear monocarboxylic acids
-
slight inhibition, overview
-
linear N-alkylammonium chloride derivatives
-
slight inhibition, overview
-
lithocholic acid
-
50% inhibition at 0.022 mM
luteolin
Maleimide
-
pH profile for the inactivation, overview
Meclofenamic acid
-
20alpha-hydroxyprogesterone oxidation
medazepam
-
50% inhibition at 0.0047 mM
Medroxyprogesterone acetate
-
50% inhibition at 700 nM
Metal ions
-
strong
-
myricetin
-
0.02 mM, 60% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 10% inhibition in kidney cytosolic fraction
N-1-butylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-decylnicotinamide chloride
-
inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-1-dodecylnicotinamide chloride
-
inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-1-ethylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-heptylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-hexylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-methylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-nonylnicotinamide chloride
-
inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-1-octylnicotinamide chloride
-
inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-1-pentylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-propylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-undecylnicotinamide chloride
-
inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-alkylammonium chloride
-
competitive from pentyl to heptyl, mixed type from nonyl to dodecyl
N-Alkylmaleimide
-
N-ethylmaleimide and N-butylmaleimide to N-octylmaleimide at 25°C, pH 7.7
N-alkylmaleimides
-
coenzyme-competitive inhibition, varying in chainlength from N-ethyl- to N-octylmaleimide, effectively inactivated the enzyme through pseudo-first-order rate processes, overview
-
N-Butylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-ethylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-Heptylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-Hexylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-Octylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-Pentylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N1-alkylnicotinamide chloride
-
competitive from methyl to heptyl, mixed-type from octyl to dodecyl with respect to NADP
NAD+
-
NADP analog, competitive inhibitor
NADH
-
concentrations above 0.1 mM
NADP+
NADPH
-
competitive and noncompetitive product inhibition with respect to NADP+ depending on substrate concentrations
naringenin
natural oestrogens
-
e.g. oestrone less than 15% inhibition
-
o-cresolphthalein
-
50% inhibition at 140 nM
p-chloromercuribenzoate
-
also other sufhydryl reagents like 5,5'-dithiobis-2-nitrobenzoic acid and iodoacetamide strong
phenazine methosulfate
-
0.01-0.3 mg/ml
Phenobarbital
Phenolphthalein
-
50% inhibition at 340 nM
progesterone
prolactin
-
down-regulating of gene-expression
-
pyridoxal 5'-phosphate
-
strong, 90% inactivation by 10 mM
quercetin
quercitrin
salicylate
-
-
sorbinil
Sulfobromophthalein
-
little effect on hepatic NADPH-dependent 20alpha-hydroxysteroid dehydrogenase, potent inhibitor of hepatic NADH-dependent 20alpha-hydroxysteroid dehydrogenase activity
synthetic non-steroidal oestrogens
-
hexoestrol most potent competitive inhibitor
-
synthetic oestrogens
-
e.g. hexestrol, silbestrol, dienstrol
-
Tolrestat
Ursodeoxycholic acid
-
50% inhibition at 0.34 mM
valporic acid
-
less than 17% inhibition
additional information
-