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.
Word Map on EC 1.1.1.149
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1.1.1.149
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progesterone
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androgen
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prostate
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reductases
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testosterone
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prostaglandin
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akr1cs
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steroidogenic
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luteal
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castration-resistant
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srd5a1
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androstenedione
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5alpha-reductase
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cyp17a1
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dihydrotestosterone
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progestin
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akr1b10
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17beta-hydroxysteroid
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3alpha-hsds
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abiraterone
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neurosteroids
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luteolysis
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hsd3b1
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5alpha-dihydrotestosterone
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17beta-hsds
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enzalutamide
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flufenamic
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17beta
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ketosteroid
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allopregnanolone
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3beta-hsd
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17alpha
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17alpha-hydroxyprogesterone
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hydrogenans
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pgf2alpha
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hsd17b3
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pre-receptor
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intracrine
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3-ketosteroids
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dihydrodiol
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scarb1
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analysis
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biotechnology
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food industry
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medicine
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environmental protection
- 1.1.1.149
- progesterone
- androgen
- prostate
- reductases
- testosterone
- prostaglandin
- akr1cs
-
steroidogenic
- luteal
-
castration-resistant
- srd5a1
- androstenedione
-
5alpha-reductase
- cyp17a1
- dihydrotestosterone
- progestin
- akr1b10
-
17beta-hydroxysteroid
- 3alpha-hsds
- abiraterone
-
neurosteroids
-
luteolysis
- hsd3b1
- 5alpha-dihydrotestosterone
- 17beta-hsds
-
enzalutamide
-
flufenamic
-
17beta
- ketosteroid
- allopregnanolone
- 3beta-hsd
-
17alpha
- 17alpha-hydroxyprogesterone
-
hydrogenans
-
pgf2alpha
- hsd17b3
-
pre-receptor
-
intracrine
- 3-ketosteroids
- dihydrodiol
-
scarb1
- analysis
- biotechnology
- food industry
- medicine
- environmental protection
Reaction
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, 20beta-HSDH, 20beta-hydroxysteroid dehydrogenase, 3alpha-HSOR, 3alpha-hydroxysteroid oxidoreductase, AKR1C1, AKR1C14, AKR1C23, AKR1C3, AKR1C5, AKR1C9, aldo-keto reductase family 1 member C1, HSD1, More
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Inhibitors
Inhibitors on EC 1.1.1.149 - 20alpha-hydroxysteroid dehydrogenase
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1,2-naphthoquinone
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0.01 mM, 55% inhibition of enzyme in liver, 10% in kidney, 10% in lung cytosolic fraction, respectively
17alpha-hydroxyprogesterone
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most inhibitory at pH 8.0, significant at pH 6.8
17beta-estradiol
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20alpha-hydroxyprogesterone analog, competitive or noncompetitive depending on variable substrate
3-Aminopyridine 1,N6-ethenoadenine dinucleotide phosphate
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NADP analog, competitive inhibitor
4'-butyl-5-chloro-4-hydroxybiphenyl-3-carboxylic acid
7fold selectivity relative to 3alpha-hydroxysteroid dehydrogenase AKR1C2
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
9,10-phenanthrenequinone
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0.01 mM, 70% inhibition of enzyme in liver, 5% in kidney, 60% in lung cytosolic fraction, respectively
carboxylic acid
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competitive for acetic and propionic acid, mixed-type from pentanoic to undecanoic acid with exception of heptanoic acid
Diazotized 3-aminopyridine 1,N6-ethenoadenine dinucleotide phosphate
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NADP+ analog, competitive inhibitor
Diazotized 3-aminopyridine adenine dinucleotide phosphate
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NADP analog, competitive inhibitor
linear N-alkylammonium chloride derivatives
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slight inhibition, overview
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N-1-butylnicotinamide chloride
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inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-decylnicotinamide chloride
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inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-1-dodecylnicotinamide chloride
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inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-1-ethylnicotinamide chloride
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inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-heptylnicotinamide chloride
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inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-hexylnicotinamide chloride
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inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-methylnicotinamide chloride
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inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-nonylnicotinamide chloride
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inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-1-octylnicotinamide chloride
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inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-1-pentylnicotinamide chloride
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inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-propylnicotinamide chloride
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inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-undecylnicotinamide chloride
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inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-alkylammonium chloride
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competitive from pentyl to heptyl, mixed type from nonyl to dodecyl
N-Alkylmaleimide
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N-ethylmaleimide and N-butylmaleimide to N-octylmaleimide at 25°C, pH 7.7
N-alkylmaleimides
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coenzyme-competitive inhibition, varying in chainlength from N-ethyl- to N-octylmaleimide, effectively inactivated the enzyme through pseudo-first-order rate processes, overview
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N-Butylmaleimide
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inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-ethylmaleimide
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inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-Heptylmaleimide
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inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-Hexylmaleimide
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inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-Octylmaleimide
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inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-Pentylmaleimide
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inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N1-alkylnicotinamide chloride
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competitive from methyl to heptyl, mixed-type from octyl to dodecyl with respect to NADP
NADPH
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competitive and noncompetitive product inhibition with respect to NADP+ depending on substrate concentrations
p-chloromercuribenzoate
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also other sufhydryl reagents like 5,5'-dithiobis-2-nitrobenzoic acid and iodoacetamide strong
synthetic non-steroidal oestrogens
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hexoestrol most potent competitive inhibitor
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2'-phosphoadenosine diphosphoribose
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NADP+ analog, competitive or noncompetitive depending on variable substrate
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NADP analog, competitive inhibitor
3-Aminopyridine adenine dinucleotide phosphate
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diazotized, coenzyme-competitive at 25°C, pH 7.4, reversible binding
apigenin
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0.02 mM, 90% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 45% inhibition in kidney cytosolic fraction
apigenin
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inhibitory effect on hepatic NADPH-dependent activity in decreasing order: fisetin > apigenin > naringenin > quercetin
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e.g. lithocholic acid, competitive with respect to (S)-ethyl 3-hydroxybutyrate
Bile acids
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e.g. lithocholic acid, competitive with respect to (S)-ethyl 3-hydroxybutyrate
Bromophenol blue
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little effect on hepatic NADPH-dependent 20alpha-hydroxysteroid dehydrogenase, moderate inhibitor of hepatic NADH-dependent 20alpha-hydroxysteroid dehydrogenase activity
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coenzyme analog, competitively with respect to both coenzymes
cibacron
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coenzyme analog, competitively with respect to both coenzymes
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noncompetitively with respect to NADP+ and (S)-ethyl 3-hydroxybutyrate at backward reaction
ethyl acetate
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noncompetitively with respect to NADP+ and (S)-ethyl 3-hydroxybutyrate at backward reaction
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e.g. myristic acid, competitive with respect to (S)-ethyl 3-hydroxybutyrate
fatty acids
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e.g. myristic acid, competitive with respect to (S)-ethyl 3-hydroxybutyrate
fisetin
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0.02 mM, 95% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 20% inhibition in kidney cytosolic fraction
fisetin
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inhibitory effect on hepatic NADPH-dependent activity in decreasing order: fisetin > apigenin > naringenin > quercetin
Flufenamic acid
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poor inhibition for 20alpha-hydroxyprogesterone oxidation
kaempferol
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0.02 mM, 80% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 15% inhibition in kidney cytosolic fraction
luteolin
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0.02 mM, 80% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 40% inhibition in kidney cytosolic fraction
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0.02 mM, 60% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 10% inhibition in kidney cytosolic fraction
NADP+
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(non)competitively with respect to NADPH and ethyl acetoacetate at forward reaction
NADP+
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(non)competitively with respect to NADPH and ethyl acetoacetate at forward reaction
naringenin
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0.02 mM, 85% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 3% inhibition in kidney cytosolic fraction
naringenin
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inhibitory effect on hepatic NADPH-dependent activity in decreasing order: fisetin > apigenin > naringenin > quercetin
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competitive with respect to (S)-ethyl 3-hydroxybutyrate
Phenobarbital
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competitive with respect to (S)-ethyl 3-hydroxybutyrate
progesterone
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1.5 mM marginally inhibitory at pH 8.0, 0.75-1.5 mM reduces activity at pH 6.8 by 46 and 60%, respectively; most inhibitory at pH 8.0, significant at pH 6.8
quercetin
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0.02 mM, 85% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 20% inhibition in kidney cytosolic fraction
quercetin
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inhibitory effect on hepatic NADPH-dependent activity in decreasing order: fisetin > apigenin > naringenin > quercetin
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little effect on hepatic NADPH-dependent 20alpha-hydroxysteroid dehydrogenase, potent inhibitor of hepatic NADH-dependent 20alpha-hydroxysteroid dehydrogenase activity
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pregnancy induces X-zone regression and abolishes 20alphaHSD expression, which is partially restored in animals that are kept from nursing their pups
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additional information
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adenosine: no inhibition, important features of coenzyme structure binding to coenzyme-binding site are 2'-phosphate, diphosphate and the positively charged ring nitrogen, hydrophobic region nearby the NADP-binding site might be responsible for nonpolar faciliation of the rates of maleimide inactivation; no inhibition by ATP, 3,5-cyclic AMP, and by adenosine up to 7.5 mM
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additional information
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apparent second-order rate constants for inactivation are observed to increase with increasing chain length of the N-alkylmaleimide used, NADP-and coenzyme-competitive inhibitors such as 3-aminopyridine adenine dinucleotide phosphate and various adenosine derivatives protect the enzyme against maleimide inactivation, whereas no protection is observed with the steroid substrate, overview; NADP+, 3-aminopyridine adenine dinucleotide phosphate and three adenosine derivatives protect enzyme against inactivation by N-ethylmaleimide, 20alpha-hydroxyprogesterone does not and N1-ethylnicotinamide chloride not significantly; sulfhydryl groups are modified during inactivation
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additional information
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no inhibition by NADPH with saturating concentration of NADP+
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additional information
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not inhibited by indomethacin, tolmetin and steroidal anti-inflammatory drugs
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additional information
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no inhibition but increase at preincubation with antiserum
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additional information
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Ca2+, Fe2+, Mg2+, Mn2+, Cd2+ and Zn2+ no significant effect
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additional information
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no inhibition with thiol reagents, reducing or chelating agents, ADH inhibitors
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