Information on EC 1.3.99.4 - 3-oxosteroid 1-dehydrogenase

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

EC NUMBER
COMMENTARY hide
1.3.99.4
-
RECOMMENDED NAME
GeneOntology No.
3-oxosteroid 1-dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a 3-oxosteroid + acceptor = a 3-oxo-DELTA1-steroid + reduced acceptor
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
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redox reaction
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-
-
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reduction
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-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
androstenedione degradation
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Steroid degradation
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Metabolic pathways
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
3-oxosteroid:acceptor DELTA1-oxidoreductase
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CAS REGISTRY NUMBER
COMMENTARY hide
9029-04-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene kstDF
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-
Manually annotated by BRENDA team
3-oxo-5beta-steroid DELTA1-dehydrogenase is active only on 5-beta-steroids
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-
Manually annotated by BRENDA team
strain TA441
Uniprot
Manually annotated by BRENDA team
gene ksdD
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-
Manually annotated by BRENDA team
strain mc2155
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Manually annotated by BRENDA team
strain mc2155
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Manually annotated by BRENDA team
Nocardia erythropolis
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-
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
11-deoxy-17alpha-hydroxycorticosterone + acceptor
11-deoxy-17alpha,21-diol-1,4-pregnene-3,20-dione + reduced acceptor
show the reaction diagram
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4-pregnene-17alpha,21-diol-3,20-dione
-
-
?
11alpha-hydroxy-testosterone + acceptor
11alpha,17beta-dihydroxyandrost-1,4-diene-3-one + reduced acceptor
show the reaction diagram
-
-
-
-
?
11alpha-hydroxyprogesterone + acceptor
11alpha-hydroxy-1,4-pregnene-3,20-dione + reduced acceptor
show the reaction diagram
-
4-pregnene-11alpha-ol-3,20-dione
-
-
?
11beta-cortisol + 2,6-dichlorophenol-indophenol
(11beta)-11,17,21-trihydroxypregna-1,4-diene-3,20-dione + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
11beta-hydroxy-4-androstene-3,17-dione + acceptor
11beta-hydroxy-1,4-androstene-3,17-dione + reduced acceptor
show the reaction diagram
11beta-hydroxytestosterone + acceptor
11beta,17beta-dihydroxyandrost-1,4-diene-3-one + reduced acceptor
show the reaction diagram
-
4-androstene-11beta,17beta-diol-3-one
-
-
?
17alpha-hydroxy-progesterone + acceptor
1,4-pregnene-17alpha-ol-3,20-dione + reduced acceptor
show the reaction diagram
-
4-pregnene-17alpha-ol-3,20-dione
-
-
?
17alpha-methyltestosterone + acceptor
17alpha-methylandrost-1,4-diene-3-one + reduced acceptor
show the reaction diagram
-
-
-
-
?
19-nor-4-androstene-3,17-dione + acceptor
19-nor-1,4-androstene-3,17-dione + reduced acceptor
show the reaction diagram
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4-estren-3,17-dione
-
-
?
19-nortestosterone + acceptor
17beta-hydroxy-1,4-estrene-3-one + reduced acceptor
show the reaction diagram
-
4-estren-17beta-ol-3-one
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-
?
23,24-bis-nor-5alpha-cholestan-3-one acid + 2,6-dichlorophenol-indophenol
?
show the reaction diagram
3-oxo-5beta-cholan-24-oic acid + acceptor
? + reduced acceptor
show the reaction diagram
-
-
-
-
?
3-oxosteroid + acceptor
3-oxo-DELTA1-steroid + reduced acceptor
show the reaction diagram
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key catalyst in microbial steroid metabolism
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-
-
4-androstene-3,11,17-trione + acceptor
1,4-androstene-3,11,17-trione + reduced acceptor
show the reaction diagram
-
-
-
-
?
4-androstene-3,17-dione + 2,6-dichlorophenol-indophenol
1,4-androstene-3,17-dione + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
4-androstene-3,17-dione + acceptor
1,4-androstadiene-3,17-dione + reduced acceptor
show the reaction diagram
4-androstene-3,17-dione + acceptor
1,4-androstene-3,17-dione + reduced acceptor
show the reaction diagram
4-androstene-3,17-dione + FAD
1,4-androstadiene-3,17-dione + FADH2
show the reaction diagram
4-androstene-3,17-dione + phenazine methosulfate
1,4-androstene-3,17-dione + reduced phenazine methosulfate
show the reaction diagram
-
-
-
-
?
4-pregnene-3,20-dione + acceptor
1,4-pregnene-3,20 dione + reduced acceptor
show the reaction diagram
5alpha-androst-1-en-3-one + acceptor
5alpha-androstan-3-one + reduced acceptor
show the reaction diagram
-
-
-
-
?
5alpha-androstan-3-one-17beta-ol + 2,6-dichlorophenol-indophenol
(5alpha,17beta)-17-hydroxyandrost-1-en-3-one + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
5alpha-androstane-3,17-dione + 2,6-dichlorophenol-indophenol
5beta-androst-1-en-3,17-dione + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
5alpha-pregnane-3,20-dione + 2,6-dichlorophenol-indophenol
5alpha-pregn-1-en-3,20-dione + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
5beta-androstan-3,17-dione + acceptor
5beta-androst-1-en-3,17-dione + reduced acceptor
show the reaction diagram
-
-
-
-
?
9alpha-hydroxy-4-androstene-3,17-dione + 2,6-dichlorophenol-indophenol
9alpha-hydroxy-1,4-androstadiene 3,17-dione + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
9alpha-hydroxy-4-androstene-3,17-dione + 2,6-dichlorophenol-indophenol
9alpha-hydroxy-androst-1,4-diene-3,17-dione + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
-
-
-
?
9alpha-hydroxy-4-androstene-3,17-dione + acceptor
9alpha-hydroxy-1,4-androstadiene 3,17-dione + reduced acceptor
show the reaction diagram
9alpha-hydroxy-4-androstene-3,17-dione + FAD
9alpha-hydroxy-1,4-androstadiene-3,17-dione + FADH2
show the reaction diagram
androsterone + acceptor
3-alpha-hydroxy-1-androstene-17-one + reduced acceptor
show the reaction diagram
-
4-androstene-3,11,17-trione
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-
?
cholesterol + acceptor
?
show the reaction diagram
corticosterone + acceptor
1,4-pregnene-17alpha,21-diol-3,20-dione + reduced acceptor
show the reaction diagram
-
4-pregnene-11beta,21-diol-3,20-dione
-
-
?
cortisol + acceptor
prednisolone + reduced acceptor
show the reaction diagram
-
optimal concentration is 0.1 mg/ml, increase of concentration to 1 mg/ml reduces prednisolone yield
-
-
?
cortisone + acceptor
1,4-pregnene-17alpha,21-diol-3,11,20-trione + reduced acceptor
show the reaction diagram
deoxycorticosterone + acceptor
1,4-pregnene-21-ol-3,20-dione + reduced acceptor
show the reaction diagram
-
4-pregnene-21-ol-3,20-dione
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-
?
hydrocorticosterone + acceptor
1,4-pregnene-11beta,17alpha,21-triol-3,20-dione + reduced acceptor
show the reaction diagram
-
4-pregnene-11beta,17alpha,21triol-3,20-dione
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-
?
progesterone + 2,6-dichlorophenol-indophenol
pregna-1,4-diene-3,20-dione + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
testololactone + acceptor
D-homo-17alpha-oxoandrosta-1,4-diene-3,17-one + reduced acceptor
show the reaction diagram
-
D-homo-17a-oxoandrost-4-ene-3,17-dione
-
-
?
testosterone + acceptor
17beta-hydroxyandrost-1,4-diene-3-one + reduced acceptor
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
3-oxosteroid + acceptor
3-oxo-DELTA1-steroid + reduced acceptor
show the reaction diagram
-
key catalyst in microbial steroid metabolism
-
-
-
4-androstene-3,17-dione + acceptor
1,4-androstadiene-3,17-dione + reduced acceptor
show the reaction diagram
4-androstene-3,17-dione + FAD
1,4-androstadiene-3,17-dione + FADH2
show the reaction diagram
9alpha-hydroxy-4-androstene-3,17-dione + acceptor
9alpha-hydroxy-1,4-androstadiene 3,17-dione + reduced acceptor
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
flavin
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absorption maxima at 276, 362, 458 nm
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
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stimulates production of prednisolone, optimal activity in presence of 0.4 g/L
FeCl3
-
optimal concentration 0.06 g/l, 1.2-1.3fold increase of activity
K+
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stimulates production of prednisolone, optimal activity in presence of 0.4 g/L
Mg2+
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stimulates production of prednisolone, optimal activity in presence of 0.4 g/L
MnSO4
-
optimal concentration 0.06 g/l, 1.2-1.3fold increase of activity
Na+
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stimulates production of prednisolone, optimal activity in presence of 0.6 g/L
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-Androstene-3,17-dione
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Acriflavin
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cortisol
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optimal concentration is 0.1 mg/ml, increase of concentration to 1 mg/ml reduces prednisolone yield
estrone
HgCl2
hydrocortisone
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-
o-Iodosobenzoate
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p-chloromercuribenzoate
p-Chloromercuriphenylsulfonate
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Sodium acetate
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inhibits reaction with cortisol
sodium oxalate
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inhibits reaction with cortisol
Tetranitromethane
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modifies Y-116
additional information
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not sensitive to carbonyl reagents and little sensitivity to metal chelating agents
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
EDTA
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enhances activity 1.3fold
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0064
11-deoxy-17alpha-hydroxycorticosterone
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i.e. 4-pregnene-17alpha,21-diol-3,20-dione
0.0196
11alpha-hydroxyprogesterone
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i.e. 4-pregnene-11alpha-ol-3,20-dione, 11beta-hydroxy-4-androstene-3,17-dione, 4-estren-3,17-dione
0.064 - 0.557
11beta-cortisol
0.0063
11beta-hydroxytestosterone
-
i.e. 4-androstene-11beta,17beta-diol-3-one
0.0089
19-Nor-4-androstene-3,17-dione
-
i.e. 4-estren-3,17-dione
0.0083
19-nortestosterone
-
4-estren-17beta-ol-3one
0.026 - 0.074
23,24-bis-nor-5alpha-cholestan-3-one acid
0.005 - 0.104
4-androstene-3,17-dione
0.006 - 0.166
5alpha-androstan-3-one-17beta-ol
0.013 - 0.059
5alpha-androstane-3,17-dione
0.007 - 0.021
5alpha-pregnane-3,20-dione
0.058 - 0.165
9alpha-Hydroxy-4-androstene-3,17-dione
0.045
androstenedione
-
-
0.0066
androsterone
-
i.e. 4-androstene-3,11,17-trione
0.0204
corticosterone
-
i.e. 4-pregnene-11beta,21-diol-3,20-dione
0.0256
cortisone
-
i.e. 4-pregnene-17alpha,21diol-3,11,20-trione
0.000075
FAD
-
-
0.0385
hydrocorticosterone
-
i.e. 4-pregnene-11beta,17alpha,21-triol-3,20-dione
0.003 - 0.065
progesterone
0.0143
testololactone
-
i.e. 17alpha-oxo-D-homo-1,4-androstadiene-3,17-dione
additional information
additional information
-
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.000015
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intracellular, soluble, recombinant enzyme, in 0.86 M Tris-HCl (pH9.0), 150 mM phenazine methosulfate, at 25C, using 4-androstene-3,17-dione as substrate
0.000111
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exracellular, soluble, recombinant enzyme, in 0.86 M Tris-HCl (pH9.0), 150 mM phenazine methosulfate, at 25C, using 4-androstene-3,17-dione as substrate
0.8
soluble recombinant His-tagged enzyme, cell extract, pH 7.0, 30C
1.75
-
recombinant enzyme expressed in Bacillus subtilis, pH 7.0, 30C
additional information
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 8
30C, reaction with 4-androstene-3,17-dione
8 - 9
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3-oxo-5beta-steroid DELTA1-dehydrogenase is active only on 5beta-steroids
8.5 - 10
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oxidase reaction
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 10.5
-
pH 7: about 60% of activity maximum, pH 10.5: about 85% of activity maximum, phenazine methosulfate dehydrogenation
8 - 11
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pH 8: about 35% of activity maximum, pH 11: about 25% of activity maximum, oxidase reaction
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45
-
activity increases linearly up to 45C
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
15 - 40
-
maximum at 40C, enzyme stable below 40C
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.81
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sequence calculation
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
partly, recombinant protein in Escherichia coli
Manually annotated by BRENDA team
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associated with fine particulate structures
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Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60500
-
SDS-PAGE, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
sitting drop vapour diffusion method, mixing of 15 mg/ml protein in 25 mM bicine, pH 9.0, 100 mM NaCl, 10% v/v glycerol with 2% v/v PEG 400, 0.1 M, HEPES, pH 7.5, 2.0 M ammonium sulfate, 20C, 5-7 days, method optimization, X-ray diffraction structure determination and analysis at 2.0 A resolution, multiwavelength anomalous dispersion analysis
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 9
below pH 6.0 no apparent Tm is observed, indicating that DELTA1-KSTD1 is destabilized at low pH. The higher the pH value, within the range of pH 6.0-9.0, the higher the apparent Tm of DELTA1-KSTD1. At pH 9.0 the apparent Tm of DELTA1-KSTD1 is about 7 K higher than at pH 7.0
723868
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
52
-
20 min, 75% loss of activity
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
immobilized enzyme, adsorption on DEAE cellulose, half-life: 13-15 days
KSTD3 activity is lost upon purification using Ni-NTA column chromatography
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Glycerol
-
10%, stabilization
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4C, 1 week, stable
-
4C, 10% glycerol, at least 3 months stable
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
KSTD3 activity is lost upon purification using Ni-NTA column chromatography
recombinant enzyme from Pichia pastoris GS115 by hydrophobic interaction chromatography, recombinant His-tagged enzyme from Escherichia coli strain BL21(lambdaDE3) by nickel affinity chromatography
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recombinant His-tagged DELTA1-KSTD1 from Escherichia coli strain BL21(DE3) by nickel affinity chromatography and gel filtration
recombinant His-tagged enzyme by nickel affinity chromatography
recombinant protein expressed in Escherichia coli
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Bacillus subtilis strain WB600
-
expressed in Escherichia coli BL21(DE3) cells; expressed in Escherichia coli BL21(DE3) cells; expressed in Escherichia coli BL21(DE3) cells
expression in Escherichia coli
expression in Streptomyces lividans
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gene ksdD, phylogenetic analysis, expression in Bacillus subtilis strain 168 with 18fold higher activity compared to wild-type Mycobacterium neoaurum strain JC-12
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gene kstD, DNA and amino acid sequence determination and analysis, phylogenetic tree, heterologous expression of the His-tagged enzyme, by low-temperature induction at 22C, the recombinant protein appears partly as soluble protein
gene kstD1, heterologous expression of the His-tagged DELTA1-KSTD1 protein in Escherichia coli strain BL21(DE3)
gene kstDF, DNA and amino acid sequence determination, analysis, and comparison, expression in Escherichia coli strain BL21(lambdaDE3) and in Pichia pastoris strains KM71 and GS115 cytoplasm, both intracellularly and extracelluarly, the latter is inactive, method optimization
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into the pJam2 expression vector under the acetamidase promoter and introduced into the deltaksdD-1 mutant
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site directed mutagenesis of steroid binding site, Y-121 involved in catalytic function, Y-116, Y-104 involved in substrate binding
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under control of the Phsp promoter and introduced into mutant cells of Mycobacterium smegmatis
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unmarked gene deletion, biochemical evidence for a second 3-ketosteroid-DELTA1-dehydrogenase
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
construction of a mutant Mtb H37Rv strain containing an inactivated kstD gene, DELTAkstD, which encodes 3-ketosteroid 1(2)-dehydrogenase by homologous recombination-based gene-replacement technique. Replication of mutant Mycobacterium tuberculosis is attenuated in resting human macrophages compared to the wild-type or complemented strains. The mutant is unable to inhibit the NO and reactive oxygen species production induced through Toll-like receptor 2 signaling in infected resting macrophages. But mutant and wild-type Mycobacterium tuberculosis behave similarly in macrophages activated with IFN-gamma before and during infection. The mutant is unable to use cholesterol as a source of carbon and energy and has a limited ability to multiply
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
S325F
mutant enzyme has no detectable KSTD enzyme activity
T503I
mutant enzyme has no detectable KSTD enzyme activity
S325F
-
mutant enzyme has no detectable KSTD enzyme activity
-
T503I
-
mutant enzyme has no detectable KSTD enzyme activity
-
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
additional information
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