BRENDA - Enzyme Database show
show all sequences of 1.1.1.213

Structure and function of 3alpha-hydroxysteroid dehydrogenase

Penning, T.M.; Bennett, M.J.; Smith-Hoog, S.; Schlegel, B.P.; Jez, J.M.; Lewis, M.; Steroids 62, 101-111 (1997)

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
full-length cDNA gene is expressed in Escherichia coli DH5alpha
Rattus norvegicus
Crystallization (Commentary)
Crystallization
Organism
vapor diffusion techniques using ammonium sulfate as precipitant
Rattus norvegicus
Engineering
Amino acid exchange
Commentary
Organism
C217A
resistant to inactivation by secosteroids, therefore Cys217 is the point of covalent attachment of acetylenic ketones
Rattus norvegicus
D50E
1/30th catalytic efficiency of wild type, unlikely to be the general amino acid for catalysis
Rattus norvegicus
D50N
1/30th catalytic efficiency of wild type, unlikely to be the general amino acid for catalysis
Rattus norvegicus
H117A
1/500th catalytic efficiency of wild type, unlikely to be the general amino acid for catalysis
Rattus norvegicus
K84M
inactive, unable to bind steroids
Rattus norvegicus
K84R
inactive, unable to bind steroids
Rattus norvegicus
additional information
positions of Tyr/Lys pair are conserved across the aldo-keto reductase and short-chain dehydrogenase/reductase family. Tyr retains ability to form ternary complex and acts as general acid
Rattus norvegicus
W148Y
can catalyse steroid oxidoreduction similar to wild type, plays no role in steroid binding or catalysis
Rattus norvegicus
W227Y
mainly influenced in steroid binding
Rattus norvegicus
W86Y
plays role in cofactor and steroid binding
Rattus norvegicus
Y205F
kinetically indistinguishable from the wild type, no general amino acid for catalysis in 3alpha-hydroxysteroid dehydrogenase
Rattus norvegicus
Y55F
inactive, unable to perform steroid oxidoreduction, strongest candidate for the general amino acid
Rattus norvegicus
Y55S
inactive, strongest candidate for the general amino acid
Rattus norvegicus
Inhibitors
Inhibitors
Commentary
Organism
Structure
acetylenic ketones
inactivation by forming Michael adducts with enzyme nucleophiles
Rattus norvegicus
cacodylate
-
Rattus norvegicus
citrate
-
Rattus norvegicus
D-glucose 6-phosphate
-
Rattus norvegicus
zopolrestat
-
Rattus norvegicus
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.0012
-
17beta-hydroxy-5alpha-androstan-3-one
cloned human liver enzyme type I
Rattus norvegicus
0.0041
-
5alpha-Androstan-3,17-dione
recombinant wild type enzyme
Rattus norvegicus
0.0042
-
5alpha-Androstan-3,17-dione
Y205F
Rattus norvegicus
0.0192
-
17beta-hydroxy-5alpha-androstan-3-one
cloned human liver enzyme type II
Rattus norvegicus
0.027
-
NADH
recombinant wild type enzyme
Rattus norvegicus
0.029
-
3alpha-hydroxy-5alpha-androstan-17-one
Y205F
Rattus norvegicus
0.03
-
NADH
Y205F
Rattus norvegicus
0.042
0.408
3alpha-hydroxy-5alpha-androstan-17-one
-
Rattus norvegicus
0.046
-
3alpha-hydroxy-5alpha-androstan-17-one
recombinant wild type enzyme
Rattus norvegicus
0.83
-
NAD+
Y205F
Rattus norvegicus
0.94
-
NAD+
recombinant wild type enzyme
Rattus norvegicus
Localization
Localization
Commentary
Organism
GeneOntology No.
Textmining
cytosol
-
Rattus norvegicus
5829
-
Metals/Ions
Metals/Ions
Commentary
Organism
Structure
additional information
non-metallo enzyme
Rattus norvegicus
Molecular Weight [Da]
Molecular Weight [Da]
Molecular Weight Maximum [Da]
Commentary
Organism
37029
-
1 * 37029
Rattus norvegicus
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
Rattus norvegicus
regulation of the amount of androgen in prostate, high levels of substrate are required for normal and abnormal growth of prostate
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
Rattus norvegicus
r
5alpha-pregnan-3,20-dione + NAD(P)H + H+
Rattus norvegicus
regulation of the amount of allosteric agonists that can bind to the GABA receptor in brain
5alpha-pregnan-3alpha-ol-20-one + NAD(P)+
-
Rattus norvegicus
r
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Rattus norvegicus
-
-
-
Reaction
Reaction
Commentary
Organism
a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
aldoketoreductase superfamily; bi bi mechanism, pyridine nucleotide binds first and leaves last
Rattus norvegicus
Source Tissue
Source Tissue
Commentary
Organism
Textmining
liver
-
Rattus norvegicus
-
Specific Activity [micromol/min/mg]
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
additional information
-
enzyme contains conserved catalytic tetrad of Asp50, Tyr55, Lys84 and His117
Rattus norvegicus
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
regulation of the amount of androgen in prostate, high levels of substrate are required for normal and abnormal growth of prostate
347989
Rattus norvegicus
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
347989
Rattus norvegicus
r
3alpha-hydroxy-5alpha-androstan-17-one + NAD+
-
347989
Rattus norvegicus
5alpha-androstan-3,17-dione + NADH
-
347989
Rattus norvegicus
r
5alpha-pregnan-3,20-dione + NAD(P)H + H+
regulation of the amount of allosteric agonists that can bind to the GABA receptor in brain
347989
Rattus norvegicus
5alpha-pregnan-3alpha-ol-20-one + NAD(P)+
-
347989
Rattus norvegicus
r
Subunits
Subunits
Commentary
Organism
monomer
1 * 37029
Rattus norvegicus
More
(alpha/beta)8-barrel fold
Rattus norvegicus
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.267
-
5alpha-Androstan-3,17-dione
Y205F
Rattus norvegicus
0.283
-
5alpha-Androstan-3,17-dione
recombinant wild type enzyme
Rattus norvegicus
0.283
-
NADH
recombinant wild type enzyme
Rattus norvegicus
0.367
-
NADH
Y205F
Rattus norvegicus
1.13
-
3alpha-hydroxy-5alpha-androstan-17-one
Y205F
Rattus norvegicus
1.13
-
NAD+
recombinant wild type enzyme
Rattus norvegicus
1.25
-
3alpha-hydroxy-5alpha-androstan-17-one
recombinant wild type enzyme
Rattus norvegicus
1.43
-
NAD+
Y205F
Rattus norvegicus
Cofactor
Cofactor
Commentary
Organism
Structure
additional information
4-pro-(R) hydrogen is transferred from the A-face of the cofactor to the B-face of the steroid
Rattus norvegicus
NAD+
-
Rattus norvegicus
NADH
-
Rattus norvegicus
NADP+
-
Rattus norvegicus
NADPH
preferred
Rattus norvegicus
Cloned(Commentary) (protein specific)
Commentary
Organism
full-length cDNA gene is expressed in Escherichia coli DH5alpha
Rattus norvegicus
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
additional information
4-pro-(R) hydrogen is transferred from the A-face of the cofactor to the B-face of the steroid
Rattus norvegicus
NAD+
-
Rattus norvegicus
NADH
-
Rattus norvegicus
NADP+
-
Rattus norvegicus
NADPH
preferred
Rattus norvegicus
Crystallization (Commentary) (protein specific)
Crystallization
Organism
vapor diffusion techniques using ammonium sulfate as precipitant
Rattus norvegicus
Engineering (protein specific)
Amino acid exchange
Commentary
Organism
C217A
resistant to inactivation by secosteroids, therefore Cys217 is the point of covalent attachment of acetylenic ketones
Rattus norvegicus
D50E
1/30th catalytic efficiency of wild type, unlikely to be the general amino acid for catalysis
Rattus norvegicus
D50N
1/30th catalytic efficiency of wild type, unlikely to be the general amino acid for catalysis
Rattus norvegicus
H117A
1/500th catalytic efficiency of wild type, unlikely to be the general amino acid for catalysis
Rattus norvegicus
K84M
inactive, unable to bind steroids
Rattus norvegicus
K84R
inactive, unable to bind steroids
Rattus norvegicus
additional information
positions of Tyr/Lys pair are conserved across the aldo-keto reductase and short-chain dehydrogenase/reductase family. Tyr retains ability to form ternary complex and acts as general acid
Rattus norvegicus
W148Y
can catalyse steroid oxidoreduction similar to wild type, plays no role in steroid binding or catalysis
Rattus norvegicus
W227Y
mainly influenced in steroid binding
Rattus norvegicus
W86Y
plays role in cofactor and steroid binding
Rattus norvegicus
Y205F
kinetically indistinguishable from the wild type, no general amino acid for catalysis in 3alpha-hydroxysteroid dehydrogenase
Rattus norvegicus
Y55F
inactive, unable to perform steroid oxidoreduction, strongest candidate for the general amino acid
Rattus norvegicus
Y55S
inactive, strongest candidate for the general amino acid
Rattus norvegicus
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
acetylenic ketones
inactivation by forming Michael adducts with enzyme nucleophiles
Rattus norvegicus
cacodylate
-
Rattus norvegicus
citrate
-
Rattus norvegicus
D-glucose 6-phosphate
-
Rattus norvegicus
zopolrestat
-
Rattus norvegicus
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.0012
-
17beta-hydroxy-5alpha-androstan-3-one
cloned human liver enzyme type I
Rattus norvegicus
0.0041
-
5alpha-Androstan-3,17-dione
recombinant wild type enzyme
Rattus norvegicus
0.0042
-
5alpha-Androstan-3,17-dione
Y205F
Rattus norvegicus
0.0192
-
17beta-hydroxy-5alpha-androstan-3-one
cloned human liver enzyme type II
Rattus norvegicus
0.027
-
NADH
recombinant wild type enzyme
Rattus norvegicus
0.029
-
3alpha-hydroxy-5alpha-androstan-17-one
Y205F
Rattus norvegicus
0.03
-
NADH
Y205F
Rattus norvegicus
0.042
0.408
3alpha-hydroxy-5alpha-androstan-17-one
-
Rattus norvegicus
0.046
-
3alpha-hydroxy-5alpha-androstan-17-one
recombinant wild type enzyme
Rattus norvegicus
0.83
-
NAD+
Y205F
Rattus norvegicus
0.94
-
NAD+
recombinant wild type enzyme
Rattus norvegicus
Localization (protein specific)
Localization
Commentary
Organism
GeneOntology No.
Textmining
cytosol
-
Rattus norvegicus
5829
-
Metals/Ions (protein specific)
Metals/Ions
Commentary
Organism
Structure
additional information
non-metallo enzyme
Rattus norvegicus
Molecular Weight [Da] (protein specific)
Molecular Weight [Da]
Molecular Weight Maximum [Da]
Commentary
Organism
37029
-
1 * 37029
Rattus norvegicus
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
Rattus norvegicus
regulation of the amount of androgen in prostate, high levels of substrate are required for normal and abnormal growth of prostate
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
Rattus norvegicus
r
5alpha-pregnan-3,20-dione + NAD(P)H + H+
Rattus norvegicus
regulation of the amount of allosteric agonists that can bind to the GABA receptor in brain
5alpha-pregnan-3alpha-ol-20-one + NAD(P)+
-
Rattus norvegicus
r
Source Tissue (protein specific)
Source Tissue
Commentary
Organism
Textmining
liver
-
Rattus norvegicus
-
Specific Activity [micromol/min/mg] (protein specific)
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
additional information
-
enzyme contains conserved catalytic tetrad of Asp50, Tyr55, Lys84 and His117
Rattus norvegicus
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
regulation of the amount of androgen in prostate, high levels of substrate are required for normal and abnormal growth of prostate
347989
Rattus norvegicus
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
347989
Rattus norvegicus
r
3alpha-hydroxy-5alpha-androstan-17-one + NAD+
-
347989
Rattus norvegicus
5alpha-androstan-3,17-dione + NADH
-
347989
Rattus norvegicus
r
5alpha-pregnan-3,20-dione + NAD(P)H + H+
regulation of the amount of allosteric agonists that can bind to the GABA receptor in brain
347989
Rattus norvegicus
5alpha-pregnan-3alpha-ol-20-one + NAD(P)+
-
347989
Rattus norvegicus
r
Subunits (protein specific)
Subunits
Commentary
Organism
monomer
1 * 37029
Rattus norvegicus
More
(alpha/beta)8-barrel fold
Rattus norvegicus
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.267
-
5alpha-Androstan-3,17-dione
Y205F
Rattus norvegicus
0.283
-
5alpha-Androstan-3,17-dione
recombinant wild type enzyme
Rattus norvegicus
0.283
-
NADH
recombinant wild type enzyme
Rattus norvegicus
0.367
-
NADH
Y205F
Rattus norvegicus
1.13
-
3alpha-hydroxy-5alpha-androstan-17-one
Y205F
Rattus norvegicus
1.13
-
NAD+
recombinant wild type enzyme
Rattus norvegicus
1.25
-
3alpha-hydroxy-5alpha-androstan-17-one
recombinant wild type enzyme
Rattus norvegicus
1.43
-
NAD+
Y205F
Rattus norvegicus
Other publictions for EC 1.1.1.213
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
724719
Matsunaga
Pathophysiological roles of al ...
Homo sapiens
Chem. Biol. Interact.
202
234-242
2013
-
1
-
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1
-
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1
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2
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1
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1
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1
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1
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2
-
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1
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1
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1
1
1
1
1
1
724915
Heinrich
Synthesis and structure-activi ...
Homo sapiens
Eur. J. Med. Chem.
62
738-744
2013
-
-
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1
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3
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-
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1
-
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3
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1
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3
3
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724916
Gazvoda
2,3-diarylpropenoic acids as s ...
Homo sapiens
Eur. J. Med. Chem.
62
89-97
2013
-
-
-
1
-
-
4
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1
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723866
Jackson
Structure of AKR1C3 with 3-phe ...
Homo sapiens
Acta Crystallogr. Sect. F
68
409-413
2012
-
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1
1
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1
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1
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724533
Chen
Crystal structures of AKR1C3 c ...
Homo sapiens
Bioorg. Med. Chem. Lett.
22
3492-3497
2012
-
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1
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2
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1
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724538
Sinreih
N-Benzoyl anthranilic acid der ...
Homo sapiens
Bioorg. Med. Chem. Lett.
22
5948-5951
2012
-
-
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4
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1
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4
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4
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725153
Miller
Aldo-keto reductase family 1 m ...
Homo sapiens
Int. J. Clin. Exp. Pathol.
5
278-289
2012
-
1
-
-
-
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2
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8
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1
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8
-
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725671
Brozic
Selective inhibitors of aldo-k ...
Homo sapiens
J. Med. Chem.
55
7417-7424
2012
-
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1
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2
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1
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1
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2
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2
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1
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2
2
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1
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725825
Byrns
Overexpression of aldo-keto re ...
Homo sapiens
J. Steroid Biochem. Mol. Biol.
130
7-15
2012
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1
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2
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-
-
-
-
-
-
-
-
-
-
-
-
-
1
1
-
-
-
724517
Adeniji
Discovery of substituted 3-(ph ...
Homo sapiens
Bioorg. Med. Chem. Lett.
21
1464-1468
2011
-
-
-
-
-
-
3
-
-
-
-
-
-
1
-
-
-
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1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
725152
Zakharov
Suppressed expression of type ...
Homo sapiens
Int. J. Clin. Exp. Pathol.
3
608-617
2010
-
1
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
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-
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-
-
-
-
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-
-
-
-
-
-
1
-
-
1
-
-
697265
Skarydova
AKR1C3 as a potential target f ...
Homo sapiens
Chem. Biol. Interact.
178
138-144
2009
-
1
1
-
-
-
15
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
1
-
-
-
-
-
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-
-
1
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-
7
-
1
1
1
-
-
-
7
15
-
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-
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-
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-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
685529
Uwai
Electronic effects of para-sub ...
Rattus norvegicus
Bioorg. Med. Chem.
16
1084-1089
2008
-
-
-
-
-
-
-
1
-
-
-
-
-
2
-
-
-
-
-
2
-
-
8
-
1
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-
1
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1
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-
2
-
-
8
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
688137
Azzarello
Tissue distribution of human A ...
Homo sapiens, Rattus norvegicus
J. Histochem. Cytochem.
56
853-861
2008
-
-
1
-
-
-
-
-
6
-
2
2
-
7
-
-
-
-
-
14
-
-
2
1
-
-
-
-
-
-
-
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-
-
-
-
-
1
-
-
-
-
-
-
-
-
6
-
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2
-
-
-
-
-
14
-
-
2
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
689169
Meyer
The biological activity of 3al ...
Rattus norvegicus
Neurobiol. Dis.
30
30-41
2008
-
1
-
-
-
-
-
-
-
-
1
1
-
3
-
-
-
-
-
2
-
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1
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-
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-
-
2
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
697310
Shultz
Fjord-region benzo[g]chrysene- ...
Rattus norvegicus
Chem. Res. Toxicol.
21
668-677
2008
-
-
1
-
8
-
2
2
-
-
-
-
-
3
-
-
1
-
-
2
1
-
2
-
1
-
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-
1
-
-
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-
-
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-
-
1
1
-
8
-
-
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-
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-
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-
-
-
-
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1
-
2
1
-
2
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
684676
Sanai
Rat NAD+-dependent 3alpha-hydr ...
Rattus norvegicus
Arch. Biochem. Biophys.
464
122-129
2007
-
-
1
-
3
-
3
9
3
-
2
-
-
2
-
-
1
1
-
3
2
-
31
1
1
-
-
9
1
1
-
4
3
-
-
-
-
1
4
-
3
-
-
3
3
9
3
-
2
-
-
-
-
1
-
3
2
-
31
1
1
-
-
9
1
1
-
-
-
-
-
-
-
-
687635
Cooper
Elucidation of a complete kine ...
Rattus norvegicus
J. Biol. Chem.
282
33484-33493
2007
-
-
-
-
-
-
-
3
-
-
-
1
-
2
-
-
-
1
-
2
-
-
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-
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-
-
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1
-
-
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-
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-
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-
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-
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-
-
3
-
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-
1
-
-
-
-
-
2
-
-
1
-
1
-
-
2
1
-
-
-
-
-
-
-
-
-
687639
McCarthy
3-ketosteroid reductase activi ...
Rattus norvegicus
J. Biol. Chem.
282
34003-34012
2007
1
-
1
-
-
-
-
-
-
-
-
2
-
2
-
-
-
-
-
2
-
-
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-
-
-
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-
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-
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-
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2
-
-
3
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
687642
Chang
Mechanism of proton transfer i ...
Comamonas testosteroni
J. Biol. Chem.
282
34306-34314
2007
-
-
1
-
2
-
-
3
-
-
-
1
-
1
-
-
1
1
-
-
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-
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-
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-
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-
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2
-
2
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-
3
-
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-
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-
-
1
-
2
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
687870
Hoffmann
Understanding oligomerization ...
Comamonas testosteroni
J. Biotechnol.
129
131-139
2007
-
-
1
-
1
-
-
-
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
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-
-
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-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
668392
Matsunaga
Multiplicity of mammalian redu ...
Homo sapiens
Drug Metab. Pharmacokinet.
21
1-18
2006
-
-
1
-
-
-
-
-
1
-
-
16
-
4
-
-
-
-
-
4
-
-
30
-
-
-
-
-
-
-
-
1
-
-
-
-
-
1
1
-
-
-
-
-
-
-
1
-
-
16
-
-
-
-
-
4
-
-
30
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
672088
Jin
Multiple steps determine the o ...
Homo sapiens
Biochemistry
45
13054-13063
2006
-
-
1
-
-
-
-
3
-
-
-
1
-
1
-
-
1
-
-
1
-
-
3
-
1
-
-
2
1
-
-
2
-
-
-
-
-
1
2
-
-
-
-
-
-
3
-
-
-
1
-
-
-
1
-
1
-
-
3
-
1
-
-
2
1
-
-
-
-
-
-
-
-
-
673349
Papari-Zareei
Arginine 276 controls the dire ...
Rattus norvegicus
Endocrinology
147
1591-1597
2006
-
-
1
-
3
-
-
1
-
-
-
1
-
3
-
-
-
1
-
4
1
-
2
-
-
-
-
-
-
-
-
1
-
-
-
-
-
1
1
-
3
-
-
-
-
1
-
-
-
1
-
-
-
-
-
4
1
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
673967
Rani
Discrete analysis of bile acid ...
Comamonas testosteroni
Indian J. Biochem. Biophys.
43
98-104
2006
-
1
-
-
1
-
-
-
-
-
-
-
-
3
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
-
-
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-
1
-
1
-
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-
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-
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-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
674674
Nakamura
Apo- and holo-structures of 3a ...
Pseudomonas sp., Pseudomonas sp. B-0831
J. Biol. Chem.
281
31876-31884
2006
-
-
-
1
-
-
-
-
-
-
1
2
-
8
-
-
-
-
-
-
-
-
2
2
-
-
-
-
-
-
-
1
-
-
-
-
-
-
1
1
-
-
-
-
-
-
-
-
1
2
-
-
-
-
-
-
-
-
2
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
674981
Okochi
Enhanced activity of 3alpha-hy ...
Comamonas testosteroni
J. Biotechnol.
128
376-382
2006
3
1
-
-
-
-
-
1
-
-
-
1
-
1
-
-
-
-
-
1
-
-
1
-
1
-
-
-
-
-
-
2
-
-
-
3
1
-
2
-
-
-
-
-
-
1
-
-
-
1
-
-
-
-
-
1
-
-
1
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
675595
Steckelbroeck
Tibolone metabolism in human l ...
Homo sapiens
J. Pharmacol. Exp. Ther.
316
1300-1309
2006
-
-
-
-
-
-
3
-
2
-
-
1
-
2
-
-
-
-
-
3
1
-
2
-
1
-
-
-
1
-
-
1
-
-
2
-
-
-
1
-
-
-
2
3
-
-
2
-
-
1
-
-
-
-
-
3
1
-
2
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
675678
Wiebe
Dutasteride affects progestero ...
Homo sapiens
J. Steroid Biochem. Mol. Biol.
100
129-140
2006
-
-
-
-
-
-
1
-
-
-
-
-
-
2
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
675687
Bellemare
Isolation and characterization ...
Mus musculus
J. Steroid Biochem. Mol. Biol.
98
18-24
2006
-
-
1
-
-
-
-
-
-
-
-
1
-
4
-
-
-
-
-
3
-
-
5
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
3
-
-
5
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
676002
Bauman
Identification of the major ox ...
Homo sapiens
Mol. Endocrinol.
20
444-458
2006
-
-
1
-
-
-
-
-
1
-
-
2
-
3
-
-
-
-
-
3
-
-
3
-
-
-
-
-
-
-
-
2
-
-
-
-
-
1
2
-
-
-
-
-
-
-
1
-
-
2
-
-
-
-
-
3
-
-
3
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
676812
Yee
Fluorogenic metabolic probes f ...
Homo sapiens
Proc. Natl. Acad. Sci. USA
103
13304-13309
2006
-
-
1
-
-
-
6
2
-
-
-
2
-
1
-
-
-
-
-
1
-
-
4
-
-
-
-
-
-
-
-
1
-
-
5
-
-
1
1
-
-
-
5
6
-
2
-
-
-
2
-
-
-
-
-
1
-
-
4
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
669389
Hwang
Mechanistic roles of Ser-114, ...
Comamonas testosteroni
J. Biol. Chem.
280
3522-3528
2005
-
-
1
-
5
-
-
7
-
-
1
1
-
1
-
-
1
1
-
-
-
-
3
1
1
-
-
6
1
1
-
2
-
-
-
-
-
1
2
-
5
-
-
-
-
7
-
-
1
1
-
-
-
1
-
-
-
-
3
1
1
-
-
6
1
1
-
-
-
-
-
-
-
-
673101
Uwai
Purification and characterizat ...
Rattus norvegicus
Chirality
17
494-500
2005
-
-
-
-
-
-
-
1
1
-
2
2
-
3
-
-
1
-
-
1
1
-
6
1
1
-
-
-
1
-
-
1
-
-
-
-
-
-
1
-
-
-
-
-
-
1
1
-
2
2
-
-
-
1
-
1
1
-
6
1
1
-
-
-
1
-
-
-
-
-
-
-
-
-
677001
Couture
Comparison of crystal structur ...
Homo sapiens
Protein Sci.
14
1485-1497
2005
-
-
1
1
2
-
-
3
-
1
-
1
-
2
-
-
1
1
-
-
1
-
5
1
-
-
-
3
1
-
-
2
-
-
-
-
-
1
2
1
2
-
-
-
-
3
-
1
-
1
-
-
-
1
-
-
1
-
5
1
-
-
-
3
1
-
-
-
-
-
-
-
-
-
654726
Heredia
Dissection of the physiologica ...
Rattus norvegicus
Biochemistry
43
12028-12037
2004
-
-
-
-
2
-
-
1
-
-
-
2
-
3
-
-
-
-
-
1
-
-
3
-
1
-
-
9
1
-
-
5
-
-
-
-
-
-
5
-
2
-
-
-
-
1
-
-
-
2
-
-
-
-
-
1
-
-
3
-
1
-
-
9
1
-
-
-
-
-
-
-
-
-
654756
Heredia
Alanine scanning mutagenesis o ...
Rattus norvegicus
Biochemistry
43
5832-5841
2004
-
-
1
-
8
-
2
-
-
-
-
-
-
2
-
-
1
1
-
-
9
-
5
-
-
-
-
5
1
-
-
2
-
-
-
-
-
1
2
-
8
-
-
2
-
-
-
-
-
-
-
-
-
1
-
-
9
-
5
-
-
-
-
5
1
-
-
-
-
-
-
-
-
-
347990
Ma
Mutation of nicotinamide pocke ...
Rattus norvegicus
Biochemistry
39
102-109
2000
-
-
-
-
5
-
-
8
-
-
1
2
-
2
-
-
1
1
-
2
4
1
3
1
1
-
-
-
-
-
-
5
-
-
-
-
-
-
5
-
5
-
-
-
-
8
-
-
1
2
-
-
-
1
-
2
4
1
3
1
1
-
-
-
-
-
-
-
-
-
-
-
-
-
347989
Penning
Structure and function of 3alp ...
Rattus norvegicus
Steroids
62
101-111
1997
-
-
1
1
13
-
5
11
1
1
1
2
-
1
-
-
-
1
-
1
1
-
3
2
-
-
-
8
-
-
-
5
-
-
-
-
-
1
5
1
13
-
-
5
-
11
1
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8
-
-
-
-
-
-
-
-
-
-
347987
Span
3alpha-Hydroxysteroid oxidored ...
Rattus norvegicus
J. Steroid Biochem. Mol. Biol.
58
319-324
1996
-
-
-
-
-
-
-
8
2
-
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1
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347988
Jez
Characterization of the substr ...
Rattus norvegicus
J. Biol. Chem.
271
30190-30198
1996
-
-
1
-
3
-
11
4
-
-
-
2
-
2
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347986
Mallonee
Expression in Escherichia coli ...
Eubacterium sp., Eubacterium sp. VPI 12708
Curr. Microbiol.
30
259-263
1995
1
-
1
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1
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-
286355
Sawada
Kinetic and stereochemical cha ...
Mesocricetus auratus
J. Biochem.
109
770-775
1991
-
-
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2
4
1
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347979
Askonas
The kinetic mechanism catalyse ...
Rattus norvegicus
Biochem. J.
278
835-841
1991
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2
4
1
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1
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-
347981
Pawlowski
Cloning and sequencing of the ...
Rattus norvegicus, Rattus norvegicus Sprangue-Dawley
J. Biol. Chem.
266
8820-8825
1991
-
-
1
-
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1
-
2
4
-
7
-
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1
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1
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286354
Ohmura
Demonstration of 3alpha(17beta ...
Mesocricetus auratus
Biochem. J.
266
583-589
1990
-
-
-
-
-
-
9
2
1
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1
-
-
1
-
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1
5
1
13
1
1
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1
17
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9
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5
1
13
1
1
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1
17
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347985
Ricigliano
Evidence that enzyme-generated ...
Rattus norvegicus, Rattus norvegicus Sprangue-Dawley
Biochem. J.
269
749-755
1990
-
-
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-
-
-
5
-
-
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-
-
-
4
-
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347980
Penning
Prostaglandin dehydrogenase ac ...
Rattus norvegicus
Biochem. Biophys. Res. Commun.
148
646-652
1987
-
-
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-
-
-
5
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3
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3
1
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-
-
-
-
347982
Penning
Purification and properties of ...
Rattus norvegicus, Rattus norvegicus Sprangue-Dawley
Biochem. J.
222
601-611
1984
-
-
-
-
-
-
25
-
1
-
2
2
-
5
-
-
1
-
-
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2
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15
1
1
-
-
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17
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5
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25
17
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1
15
1
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-
722157
Björkhem
Stereochemistry of hydrogen tr ...
Rattus norvegicus
Eur. J. Biochem.
12
80-4
1970
-
-
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-
347984
Tomkins
A mammalian 3alpha-hydroxyster ...
Rattus norvegicus
J. Biol. Chem.
218
437-447
1956
-
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4
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