Information on EC 1.1.1.53 - 3alpha(or 20beta)-hydroxysteroid dehydrogenase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.1.1.53
-
RECOMMENDED NAME
GeneOntology No.
3alpha(or 20beta)-hydroxysteroid dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
androstan-3alpha,17beta-diol + NAD+ = 17beta-hydroxyandrostan-3-one + NADH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Metabolic pathways
-
-
Steroid hormone biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
3alpha(or 20beta)-hydroxysteroid:NAD+ oxidoreductase
The 3alpha-hydroxy group or 20beta-hydroxy group of pregnane and androstane steroids can act as donor.
CAS REGISTRY NUMBER
COMMENTARY hide
9028-42-6
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
japanese eel
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
snake head murrel
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
able to use steroids as sole carbon source
-
-
Manually annotated by BRENDA team
down regulation in the period from January to July
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Rv2002
Uniprot
Manually annotated by BRENDA team
amago salmon
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
-
isoform 20beta-HSD type 2 is involved in cortisol catabolism and stress response. The morpholino-induced knock-down of gene expression in zebrafish embryos reveals no developmental phenotype under normal culture conditions, but prominent effects are observed after a cortisol challenge. 20beta-Hydroxycortisone is not a physiological ligand for the zebrafish glucocorticoid or mineralocorticoid receptor but is excreted into the fish holding water
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
11alpha-hemisuccinyloxyprogesterone + NADH
?
show the reaction diagram
-
-
-
-
?
17-hydroxy-3,11,20-trioxo-4-pregnen-21-oate + NADH
17,20-dihydroxy-3,11-dioxo-4-pregnen-21-oate + NAD+
show the reaction diagram
-
-
-
-
?
17-hydroxy-3,20-dioxo-4-pregnen-21-oate + NADH
17,20-dihydroxy-4-pregnen-3-one-21-oate + NAD+
show the reaction diagram
-
-
-
-
?
17-hydroxyprogesterone + NADH
?
show the reaction diagram
-
-
-
-
?
17-hydroxyprogesterone + NADPH
17,20-beta-dihydroxy-4-pregnene-3-one
show the reaction diagram
-
-
-
-
?
17alpha,20beta-dihydroxypregn-4-ene-3-one + NADP+
17alpha-hydroxypregn-4-en-3,20-dione + NADPH
show the reaction diagram
-
-
-
-
?
17alpha-hydroxy-3,20-dioxo-4-pregnen-21-oate + NADH
17,20alpha-dihydroxy-4-pregnen-3-one-21-oate + NAD+
show the reaction diagram
17alpha-hydroxypregnenolone + NADPH
3beta,17alpha,20beta-trihydroxypregn-5-ene + NADP+
show the reaction diagram
-
i.e. 3beta,17alpha-dihydroxypregn-5-ene-20-one
-
-
?
17alpha-hydroxyprogesterone + NADPH
17alpha,20beta-dihydroxy-4-pregnen-3-one
show the reaction diagram
17alpha-hydroxyprogesterone + NADPH
17alpha,20beta-dihydroxy-4-pregnene-3-one + NADP+
show the reaction diagram
17alpha-hydroxyprogesterone + NADPH
17alpha,20beta-dihydroxy-pregn-4-ene-3-one (4-pregnene-17alpha,20beta-diol-3-one) + NADP+
show the reaction diagram
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20beta-dihydroxy-4-pregnene-3-one + NADP+
show the reaction diagram
-
-
-
-
?
17beta-estradiol + NAD+
estrone + NADH
show the reaction diagram
4% of the activity with androsterone
-
-
?
17beta-[(1S)-1-hydroxy-2-propynyl]-androst-4-ene-3-one + NAD+
17beta-[1-oxo-2-propynyl]-androst-4-ene-3-one + NADH
show the reaction diagram
-
-
-
?
20alpha-hydroxyprogesterone + NAD+
? + NADH
show the reaction diagram
2% of the activity with androsterone
-
-
?
20beta-hydroxypregn-4-ene-3-one + NADP+
pregn-4-ene-3,20-dione + NADPH
show the reaction diagram
-
-
-
-
?
20beta-hydroxyprogesterone + NAD+
? + NADH
show the reaction diagram
69% of the activity with androsterone
-
-
?
21-acetoxyprogesterone + NADH
?
show the reaction diagram
-
-
-
-
?
21-hemisuccinyloxyprogesterone + NADH
?
show the reaction diagram
-
-
-
-
?
3,20-dioxo-4-pregnen-21-oic acid + NADH
20beta-hydroxy-3-oxo-4-pregnen-21-oic acid + NAD+
show the reaction diagram
3alpha,20beta-hydroxysteroid androstanes or pregnane derivatives + NAD(P)H
?
show the reaction diagram
3beta,17alpha,20alpha-trihydroxypregn-5-ene + NADP+
3beta,17alpha-dihydroxypregn-5-en-20-one + NADPH
show the reaction diagram
-
-
-
-
?
3beta,20alpha-dihydroxypregn-5-ene + NADP+
3beta-hydroxypregn-5-en-20-one + NADPH
show the reaction diagram
-
-
-
-
?
4-acetyl-N-(cyclohexylcarbamoyl)benzenesulfonamide + NADPH
hydroxyhexamide + NADP+
show the reaction diagram
4-nitrobenzaldehyde + NADPH
?
show the reaction diagram
-
-
-
-
?
4-pregnen-11beta,21-diol-3,20-dione + NADPH
4-pregnen-11beta,20alpha,21-triol-3-one + NADP+
show the reaction diagram
-
-
-
-
?
5alpha-androstan-17beta-ol-3-one + NAD(P)H + H+
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
show the reaction diagram
5alpha-androstane-3,17-dione + NADPH
?
show the reaction diagram
-
-
-
-
?
5alpha-dihydrotestosterone + NADP+
5alpha-androstan-3alpha17beta-diol + NADPH + H+
show the reaction diagram
-
-
-
-
?
5alpha-dihydrotestosterone + NADPH
5alpha-androstan-3alpha,17beta-diol + NADP+
show the reaction diagram
14.4% of the activity with p-nitrobenzaldehyde
-
-
?
5alpha-pregnane-3,20-dione + NADH
?
show the reaction diagram
-
-
-
-
?
5alpha-pregnane-3,20-dione + NADPH
?
show the reaction diagram
-
-
-
-
?
5beta-androstan-17beta-ol-3-one + NAD(P)H
?
show the reaction diagram
-
i.e. 5beta-dihydrotestosterone
-
-
?
5beta-dihydrotestosterone + NADPH
5beta-androstan-3alpha,17beta-diol + NADP+
show the reaction diagram
9.2% of the activity with p-nitrobenzaldehyde
-
-
?
6beta-(bromoacetoxy)-progesterone + NADH
?
show the reaction diagram
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
show the reaction diagram
-
-
-
-
?
androsterone + NAD+
? + NADH
show the reaction diagram
-
-
-
?
camphorquinone + NADPH + H+
camphorquinol + NADP+
show the reaction diagram
-
-
-
-
?
cortisone + NAD(P)H
17alpha,20beta,21-trihydroxy-pregn-4-ene-3,11-dione + NAD(P)+
show the reaction diagram
cortisone + NADPH + H+
20beta-hydroxycortisone + NADP+
show the reaction diagram
-
-
i.e. 4-pregnen-17alpha,20beta,21-triol-3,11-dione
-
?
cyclohexanone + NADPH
cyclohexanol + NADP+
show the reaction diagram
-
-
-
-
?
deoxycorticosterone + NADPH
20,21-dihydroxypregn-4-ene-3-one + NADP+
show the reaction diagram
deoxycortisol + NADPH
?
show the reaction diagram
-
-
-
-
?
epiandrosterone + NAD+
? + NADH
show the reaction diagram
3% of the activity with androsterone
-
-
?
hydrindantin + NADPH
?
show the reaction diagram
-
-
-
-
?
menadione + NADPH
?
show the reaction diagram
75% of the activity with p-nitrobenzaldehyde
-
-
?
methylglyoxal + NADPH
?
show the reaction diagram
-
-
-
-
?
p-nitrobenzaldehyde + NADPH
p-nitrobenzyl alcohol + NADP+
show the reaction diagram
-
-
-
?
phenylglyoxal + NADPH
?
show the reaction diagram
-
-
-
-
?
pregnenolone + NADPH
3beta,20beta-Dihydroxypregn-5-ene + NADP+
show the reaction diagram
-
i.e. 3-hydroxypregn-5-en-20-one
-
-
?
progesterone + NAD(P)H
20beta-hydroxy-pregn-4-ene-3-one + NAD(P)+
show the reaction diagram
progesterone + NADH
20beta-hydroxy-pregn-4-ene-3-one + NAD+
show the reaction diagram
22% of the activity with androsterone
-
-
?
progesterone + NADP+
20beta-hydroxy-pregn-4-ene-3-one + NADPH + H+
show the reaction diagram
-
-
-
-
?
progesterone + NADPH
20beta-hydroxy-pregn-4-ene-3-one + NADP+
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
17alpha-hydroxyprogesterone + NADPH
17alpha,20beta-dihydroxy-4-pregnene-3-one + NADP+
show the reaction diagram
3alpha,20beta-hydroxysteroid androstanes or pregnane derivatives + NAD(P)H
?
show the reaction diagram
progesterone + NADPH
20beta-hydroxy-pregn-4-ene-3-one + NADP+
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
beta-3'-NADP+
-
-
NADP+
NADPH
additional information
-
not active: NADH
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
16alpha-Bromoacetoxyprogesterone
-
-
17-Acetoxyprogesterone
-
-
17-Bromoacetoxyprogesterone
-
-
17beta-Bromoacetoxyandrostan-3-one
-
-
20beta-Hydroxycortisol
-
-
20beta-hydroxyprogesterone
-
-
5alpha-Dihydrotestosterone bromoacetate
-
-
amiloride
carbenoxolone
-
-
Cd2+
-
-
Cortisone 21-iodoacetate
-
in absence of NADH, slight
cycloheximide
cysteine
-
slight
diclofenac
-
100 microM reduces carbonyl reductase activity by 66%
dithiothreitol
-
slight
Fe2+
-
-
glycyrrhizic acid
-
-
indomethacin
-
10 microM reduces carbonyl reductase activity by 69%
Phenylbutazone
-
50 microM reduces carbonyl reductase activity by 51%
pyridoxal 5'-phosphate
-
slightly
Tetranitromethane
-
other Tyr-selective reagents, Tyr residues are labeled with nitro-group by inhibitor
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
dibutyryl cAMP
estrogen
-
stimulation of the enzyme found in tissues from kidney, intestine and ovary
forskolin
salmon gonadotropin
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.19
11alpha-Hemisuccinyloxyprogesterone
-
-
0.49
17-Hydroxy-3,11,20-trioxo-4-pregnen-21-oate
-
-
0.64
17-Hydroxy-3,20-dioxo-4-pregnen-21-oate
-
-
0.0105
17-hydroxyprogesterone
-
-
0.00094
17alpha-hydroxyprogesterone
-
reduction
0.46
17beta-hydroxyandrostan-2-one
-
-
0.017
20beta-hydroxyprogesterone
pH 6.0, 30C, reaction with NAD+, mutant enzyme I6T/V47M/T69K
2.23
21-Acetoxyprogesterone
-
-
1.43
21-Hemisuccinyloxyprogesterone
-
-
0.0251
21-hydroxyprogesterone
-
-
0.14
3,20-Dioxo-4-pregnen-21-oic acid
0.00018
5alpha-androstan-17beta-ol-3-one
-
reduction
0.00032
5alpha-Androstan-3alpha-ol-17-one
-
oxidation
0.00218 - 0.07103
5alpha-dihydrotestosterone
0.00016 - 0.0045
5alpha-pregnane-3,20-dione
0.02
6beta-[bromoacetoxy]-progesterone
-
-
126.1
alpha-NADH
-
-
328
alpha-NADPH
-
-
0.024
androsterone
pH 6.0, 30C, reaction with NAD+, mutant enzyme I6T/V47M/T69K
88.2
beta-NAD+
-
-
294.8
beta-NADH
-
-
14.8
beta-NADP+
-
-
7.2
beta-NADPH
-
-
0.024 - 0.318
cortisone
0.0086
deoxycorticosterone
-
-
0.0035 - 0.029
NADH
0.004
pregnonolone
-
-
-
0.00015 - 0.0061
progesterone
additional information
additional information
-
-
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
258
20beta-hydroxyprogesterone
Mycobacterium tuberculosis
P9WGT1
pH 6.0, 30C, reaction with NAD+
0.061 - 0.115
5alpha-dihydrotestosterone
456
androsterone
Mycobacterium tuberculosis
P9WGT1
pH 6.0, 30C, reaction with NAD+
0.333
cortisone
Streptomyces exfoliatus
-
NADH
0.004 - 72
progesterone
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
100 - 1680
5alpha-dihydrotestosterone
737
250 - 1100
progesterone
286
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.003
-
purified enzyme, NADPH, progesterone
0.004
-
-
0.019
-
purified enzyme, NADPH, 5beta-androstan-3alpha,17beta-diol oxidation
0.023
-
purified enzyme, NADPH, dehydroisoandrosterone
0.025
-
purified enzyme, NADPH, 5alpha-androstan-3alpha-ol-17-one oxidation
0.038
-
NADPH, phenylglyoxal
0.039
-
NADPH, 5alpha-dihydrotestosterone; NADPH, 5beta-dihydrotestosterone
0.042
-
NADPH, cyclohexanone
0.043
-
NADPH, 4-nitrobenzaldehyde
0.045
-
NADPH, camphorquinone
0.046
-
purified enzyme, NADPH, 5alpha-androstan-17beta-ol-3-one
0.051
-
purified enzyme, NADPH, 5alpha-pregnane-3,20-dione
0.052
-
purified enzyme, NADPH, 5alpha-androstan-3alpha,17beta-diol oxidation
0.091
-
purified enzyme, NADPH, 17alpha-methyl-5alpha-androstan-17beta-ol-3-one
0.123
-
NADPH, methylglyoxal
0.157
-
NADPH, phenanthrenequinone
0.167
-
NADPH, hydrindantin
0.27
-
enzyme type B mutant Q27K, 17alpha-hydroxyprogesterone
1.57
-
enzyme type A, 17alpha-hydroxyprogesterone
1.64
-
enzyme type B mutant T15I, 17alpha-hydroxyprogesterone
additional information
-
specific activity about 3.8 pmol/min/mg in ovulated oocyte microsomes and 6.9 pmol/min/mg in ovulated oocyte mitochondria, 11.2 pmol/min/mg in ovarian tissue mitochondria after ovulation
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5
-
reduction of 5alpha-androstan-17beta-ol-3-one with beta-NADPH
5.1
-
reduction of oxo-steroids
5.5
-
reduction of oxosteroid
5.8
-
reduction of progesterone in aqueous solution
6 - 6.5
oxidation of androsterone shows a dual pH-optimum, one at pH 6.0-6.5 and the other at pH 10, mutant enzyme I6T/V47M/T69K/E142A
6
progesterone + NADH, mutant enzyme I6T/V47M/T69K
6.4
-
reduction of progesterone in reversed micelles
6.5
progesterone + NADH, mutant enzyme I6T/V47M/T69K/E142A
9.2
-
oxidation of hydroxysteroid
10
oxidation of androsterone shows a dual pH-optimum, one at pH 6.0-6.5 and the other at pH 10, mutant enzyme I6T/V47M/T69K/E142A
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5 - 5.5
-
-
4.5 - 9
-
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
35 - 60
-
50% of maximal activity at 35C, 10.4% of maximal activity at 60C
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.11
isoform A, calculated from the deduced amino acid sequence
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
PDB
SCOP
CATH
ORGANISM
UNIPROT
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
23380
-
x * 23380, insertion protein, calculated from the deduced amino acid sequence, confirmed by SDS-PAGE
27000
-
4 * 27000, SDS-PAGE
28000
-
4 * 28000, about, crystal structure and sequence analysis
30000
-
SDS-PAGE
30140
x * 30140, isoform A, calculated from the deduced amino acid sequence
30500
-
gel filtration
106000 - 111000
-
agarose gel filtration, density gradient centrifugation
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
crystal structure analysis, in silico data
monomer
-
1 * 30500, SDS-PAGE with and without 2-mercaptoethanol
tetramer
additional information
-
tetrameric, monomers with beta-alpha-beta-motif
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
no glycoprotein
-
-
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
in complex with NADP+ and progesterone, sitting drop vapor diffusion method, using 100 mM sodiumcacodylate buffer (pH 6.0), 200 mM ammonium sulfate, 24-26% (w/v) polyethylene glycol 3350
-
crystal structure of the mutant enzyme I6T/V47M/T69K in binary complex with NAD+ at 1.8 A resolution and as a ternary complex with androsterone and NADH at 2.4 A
crystallized with bound inhibitor carbenoxolone, asymmetric tetramer, Tyr152, Lys156 and Ser139 are conserved as the catalytic triade
-
refined model, also with bound cortisone molecule
-
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 10
-
-
287084
9
-
in Tris-buffer, best value for stability
287090
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45
-
up to
55
-
inactivation at
additional information
-
low stability
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
presence of octyl glucoside, 40.5% of enzyme activity from sonicated mitochondria retained, 20% glycerol
-
sensitive to proteolysis with Glu-C protease and trypsin, which can be nearly completly hindered by presence of NADH or cortisone
-
several detergents tested for solubilization
-
urea: investigation of denaturation process
-
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
deoxycholate
-
40.1% of enzyme activity from sonicated mitochondria retained, 20% glycerol
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, 5 mM phosphate buffer, pH 7.6
-
-20C, 50 mM potassium phosphate buffer, pH 7.4
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
glutathione agarose column chromatography and Q-Sepharose column chromatography
-
recombinant from Escherichia coli
-
recombinant protein using His-tag
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
85% amino acid sequence homology with human carbonyl reductase
-
expressed in Escherichia coli BL21(DE3)pLysS cells
-
expression in Escherichia coli
native and insertion protein, expressed as His-tag fusion protein in Escherichia coli XL1-blue and BL21
-
selenomethionine-substituted mutant enzyme I6T/V47M/T69K, expression in inclusion bodies in Escherichia coli B834(DE3)
subcloned in Escherichia coli strain BL21
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expressed during embryonic development
-
transcripts are up-regulated upon cortisol treatment. A cortisol-independent, short-term physical stressor leads to the up-regulation of isoforms 11beta-HSD2 and 20beta-HSD2 expression along with several hypothalamus-pituitary-interrenal axis genes
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
V54L
-
the mutation restricts the steroid alternative binding and enhances the 20alpha-hydroxysteroid dehydrogenase activity of the enzyme
I6T/V47M/T69K
mutant enzyme with a maximal improvement in solubility, high catalytic activity as a NADP-dependent 3alpha,20beta-hydroxysteroid dehydrogenase
I6T/V47M/T69K/E142A
pH optimum for reduction of progesterone shifts slightly from pH 6.0 to pH 6.5 compared to for mutant enzyme I6T/V47M/T69K, the oxidation of androsterone shows a dual pH optimum, one at pH 6.0-6.5 and the other at pH 10
I6T/V47M/T69K/S140A
both oxidation of androsterone and reduction of progesterone are completely lost
I6T/V47M/T69K/Y153F
both oxidation of androsterone and reduction of progesterone are completely lost
I15T
-
in 20beta-HSD type A, cofactor binding is abolished
Q27K
-
in 20beta-HSD type B, cofactor binding is reduced
T15I
-
in 20beta-HSD type B, enzyme activity is restored
Renatured/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Show AA Sequence (424 entries)
Please use the Sequence Search for a specific query.