BRENDA - Enzyme Database show
show all sequences of 1.1.1.213

Characterization of the substrate binding site in rat liver 3alpha-hydroxysteroid/dihydrodiol dehydrogenase. The roles of tryptophans in ligand binding and protein fluorescence

Jez, J.M.; Schlegel, B.P.; Penning, T.M.; J. Biol. Chem. 271, 30190-30198 (1996)

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
wild-type enzyme and mutants are overexpressed in Escherichia coli DH5alpha
Rattus norvegicus
Engineering
Amino acid exchange
Commentary
Organism
W148Y
site-directed mutagenesis, kinetically similar to wild type enzyme, no function in ligand binding
Rattus norvegicus
W227Y
site-directed mutagenesis, important role in binding steroid hormones, but not small substrates or inhibitors, interacts with the C and/or D-rings of steroid ligand
Rattus norvegicus
W86Y
site-directed mutagenesis, important in binding steroids and non-steroidal anti-inflamatory drugs, region in which it resides is part of the substrate/inhibitor binding pocket, near the A-, and B-rings of bound steroid
Rattus norvegicus
Inhibitors
Inhibitors
Commentary
Organism
Structure
(E/Z)-sulfindac
wild-type, W86Y and W227Y
Rattus norvegicus
1,10-phenanthroline
wild-type, W86Y and W227Y
Rattus norvegicus
1,7-phenanthroline
wild-type, W86Y and W227Y
Rattus norvegicus
Flufenamic acid
wild-type, W86Y and W227Y
Rattus norvegicus
Hexestrol
-
Rattus norvegicus
indomethacin
wild-type, W86Y and W227Y
Rattus norvegicus
Meclofenamic acid
wild-type, W86Y and W227Y
Rattus norvegicus
Mefenamic acid
wild-type, W86Y and W227Y
Rattus norvegicus
non-steroidal anti-inflamatory drug
-
Rattus norvegicus
ponalrestat
wild-type, W86Y and W227Y, weak inhibitor
Rattus norvegicus
zopolrestat
wild-type, W86Y and W227Y, weak inhibitor
Rattus norvegicus
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.00122
0.0051
9,10-phenanthrenequinone
-
Rattus norvegicus
0.042
0.408
3alpha-hydroxy-5alpha-androstan-17-one
-
Rattus norvegicus
0.163
0.211
4-nitrobenzyldehyde
-
Rattus norvegicus
3.54
33.7
2-decalone
-
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
-
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
Rattus norvegicus
?
additional information
Rattus norvegicus
inactivating circulating androgens, progestins and glucocorticoids. Regulation of hormone levels in endocrine target tissues and in carcinogen actibation
?
-
-
-
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Rattus norvegicus
-
-
-
Purification (Commentary)
Commentary
Organism
anion exchange and Blue Sepharose column
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 before substrate
Rattus norvegicus
Source Tissue
Source Tissue
Commentary
Organism
Textmining
liver
-
Rattus norvegicus
-
Specific Activity [micromol/min/mg]
Specific Activity Minimum [Ámol/min/mg]
Specific Activity Maximum [Ámol/min/mg]
Commentary
Organism
0.059
-
W86Y mutant
Rattus norvegicus
0.08
-
W227Y mutant
Rattus norvegicus
0.674
-
W148Y mutant
Rattus norvegicus
1.5
-
native enzyme
Rattus norvegicus
Storage Stability
Storage Stability
Organism
-70░C, 20 mM potassium phosphate buffer, pH 7.0, 1 mM EDTA, 1 mM beta-mercaptoethanol, 30% glycerol
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+
-
347988
Rattus norvegicus
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
347988
Rattus norvegicus
?
2-decalone + NADH
pH 6.0
347988
Rattus norvegicus
? + NAD+
-
347988
Rattus norvegicus
?
3alpha-hydroxy-5alpha-androstan-17-one + NAD+
-
347988
Rattus norvegicus
5alpha-androstan-3,17-dione + NADH
-
347988
Rattus norvegicus
r
4-nitrobenzaldehyde + NAD(P)H
pH 6.0
347988
Rattus norvegicus
(4-nitrophenyl)methanol + NAD(P)+
-
347988
Rattus norvegicus
-
4-nitrobenzaldehyde + NAD(P)H
NADH as cofactor
347988
Rattus norvegicus
(4-nitrophenyl)methanol + NAD(P)+
-
347988
Rattus norvegicus
-
9,10-phenanthrenequinone + NAD(P)H
NADPH
347988
Rattus norvegicus
? + NAD(P)+
-
347988
Rattus norvegicus
?
9,10-phenanthrenequinone + NAD(P)H
pH 6.0
347988
Rattus norvegicus
? + NAD(P)+
-
347988
Rattus norvegicus
?
additional information
inactivating circulating androgens, progestins and glucocorticoids. Regulation of hormone levels in endocrine target tissues and in carcinogen actibation
347988
Rattus norvegicus
?
-
-
-
-
Subunits
Subunits
Commentary
Organism
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
1.17
3.93
9,10-phenanthrenequinone
-
Rattus norvegicus
Cofactor
Cofactor
Commentary
Organism
Structure
additional information
4-pro-R-hydride transfer of the nicotinamide cofactor
Rattus norvegicus
NAD+
-
Rattus norvegicus
NADH
-
Rattus norvegicus
NADPH
-
Rattus norvegicus
Cloned(Commentary) (protein specific)
Commentary
Organism
wild-type enzyme and mutants are overexpressed in Escherichia coli DH5alpha
Rattus norvegicus
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
additional information
4-pro-R-hydride transfer of the nicotinamide cofactor
Rattus norvegicus
NAD+
-
Rattus norvegicus
NADH
-
Rattus norvegicus
NADPH
-
Rattus norvegicus
Engineering (protein specific)
Amino acid exchange
Commentary
Organism
W148Y
site-directed mutagenesis, kinetically similar to wild type enzyme, no function in ligand binding
Rattus norvegicus
W227Y
site-directed mutagenesis, important role in binding steroid hormones, but not small substrates or inhibitors, interacts with the C and/or D-rings of steroid ligand
Rattus norvegicus
W86Y
site-directed mutagenesis, important in binding steroids and non-steroidal anti-inflamatory drugs, region in which it resides is part of the substrate/inhibitor binding pocket, near the A-, and B-rings of bound steroid
Rattus norvegicus
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
(E/Z)-sulfindac
wild-type, W86Y and W227Y
Rattus norvegicus
1,10-phenanthroline
wild-type, W86Y and W227Y
Rattus norvegicus
1,7-phenanthroline
wild-type, W86Y and W227Y
Rattus norvegicus
Flufenamic acid
wild-type, W86Y and W227Y
Rattus norvegicus
Hexestrol
-
Rattus norvegicus
indomethacin
wild-type, W86Y and W227Y
Rattus norvegicus
Meclofenamic acid
wild-type, W86Y and W227Y
Rattus norvegicus
Mefenamic acid
wild-type, W86Y and W227Y
Rattus norvegicus
non-steroidal anti-inflamatory drug
-
Rattus norvegicus
ponalrestat
wild-type, W86Y and W227Y, weak inhibitor
Rattus norvegicus
zopolrestat
wild-type, W86Y and W227Y, weak inhibitor
Rattus norvegicus
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.00122
0.0051
9,10-phenanthrenequinone
-
Rattus norvegicus
0.042
0.408
3alpha-hydroxy-5alpha-androstan-17-one
-
Rattus norvegicus
0.163
0.211
4-nitrobenzyldehyde
-
Rattus norvegicus
3.54
33.7
2-decalone
-
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
-
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
Rattus norvegicus
?
additional information
Rattus norvegicus
inactivating circulating androgens, progestins and glucocorticoids. Regulation of hormone levels in endocrine target tissues and in carcinogen actibation
?
-
-
-
Purification (Commentary) (protein specific)
Commentary
Organism
anion exchange and Blue Sepharose column
Rattus norvegicus
Source Tissue (protein specific)
Source Tissue
Commentary
Organism
Textmining
liver
-
Rattus norvegicus
-
Specific Activity [micromol/min/mg] (protein specific)
Specific Activity Minimum [Ámol/min/mg]
Specific Activity Maximum [Ámol/min/mg]
Commentary
Organism
0.059
-
W86Y mutant
Rattus norvegicus
0.08
-
W227Y mutant
Rattus norvegicus
0.674
-
W148Y mutant
Rattus norvegicus
1.5
-
native enzyme
Rattus norvegicus
Storage Stability (protein specific)
Storage Stability
Organism
-70░C, 20 mM potassium phosphate buffer, pH 7.0, 1 mM EDTA, 1 mM beta-mercaptoethanol, 30% glycerol
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+
-
347988
Rattus norvegicus
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
347988
Rattus norvegicus
?
2-decalone + NADH
pH 6.0
347988
Rattus norvegicus
? + NAD+
-
347988
Rattus norvegicus
?
3alpha-hydroxy-5alpha-androstan-17-one + NAD+
-
347988
Rattus norvegicus
5alpha-androstan-3,17-dione + NADH
-
347988
Rattus norvegicus
r
4-nitrobenzaldehyde + NAD(P)H
pH 6.0
347988
Rattus norvegicus
(4-nitrophenyl)methanol + NAD(P)+
-
347988
Rattus norvegicus
-
4-nitrobenzaldehyde + NAD(P)H
NADH as cofactor
347988
Rattus norvegicus
(4-nitrophenyl)methanol + NAD(P)+
-
347988
Rattus norvegicus
-
9,10-phenanthrenequinone + NAD(P)H
NADPH
347988
Rattus norvegicus
? + NAD(P)+
-
347988
Rattus norvegicus
?
9,10-phenanthrenequinone + NAD(P)H
pH 6.0
347988
Rattus norvegicus
? + NAD(P)+
-
347988
Rattus norvegicus
?
additional information
inactivating circulating androgens, progestins and glucocorticoids. Regulation of hormone levels in endocrine target tissues and in carcinogen actibation
347988
Rattus norvegicus
?
-
-
-
-
Subunits (protein specific)
Subunits
Commentary
Organism
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
1.17
3.93
9,10-phenanthrenequinone
-
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
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724915
Heinrich
Synthesis and structure-activi ...
Homo sapiens
Eur. J. Med. Chem.
62
738-744
2013
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724916
Gazvoda
2,3-diarylpropenoic acids as s ...
Homo sapiens
Eur. J. Med. Chem.
62
89-97
2013
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4
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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
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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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724538
Sinreih
N-Benzoyl anthranilic acid der ...
Homo sapiens
Bioorg. Med. Chem. Lett.
22
5948-5951
2012
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725153
Miller
Aldo-keto reductase family 1 m ...
Homo sapiens
Int. J. Clin. Exp. Pathol.
5
278-289
2012
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725671
Brozic
Selective inhibitors of aldo-k ...
Homo sapiens
J. Med. Chem.
55
7417-7424
2012
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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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724517
Adeniji
Discovery of substituted 3-(ph ...
Homo sapiens
Bioorg. Med. Chem. Lett.
21
1464-1468
2011
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725152
Zakharov
Suppressed expression of type ...
Homo sapiens
Int. J. Clin. Exp. Pathol.
3
608-617
2010
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697265
Skarydova
AKR1C3 as a potential target f ...
Homo sapiens
Chem. Biol. Interact.
178
138-144
2009
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15
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7
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1
1
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7
15
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1
-
-
-
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-
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685529
Uwai
Electronic effects of para-sub ...
Rattus norvegicus
Bioorg. Med. Chem.
16
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2008
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1
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2
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2
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8
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1
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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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8
-
1
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1
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Azzarello
Tissue distribution of human A ...
Homo sapiens, Rattus norvegicus
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14
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2
1
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1
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6
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2
2
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14
-
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2
1
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689169
Meyer
The biological activity of 3al ...
Rattus norvegicus
Neurobiol. Dis.
30
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2008
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1
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1
1
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3
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2
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1
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2
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1
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2
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2
1
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697310
Shultz
Fjord-region benzo[g]chrysene- ...
Rattus norvegicus
Chem. Res. Toxicol.
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668-677
2008
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1
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8
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2
2
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3
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1
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2
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
1
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8
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2
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2
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1
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2
1
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2
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1
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1
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684676
Sanai
Rat NAD+-dependent 3alpha-hydr ...
Rattus norvegicus
Arch. Biochem. Biophys.
464
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1
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3
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3
9
3
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2
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2
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1
1
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3
2
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31
1
1
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9
1
1
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4
3
-
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-
1
4
-
3
-
-
3
3
9
3
-
2
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1
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3
2
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31
1
1
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9
1
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687635
Cooper
Elucidation of a complete kine ...
Rattus norvegicus
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1
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3
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1
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2
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1
-
1
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2
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687639
McCarthy
3-ketosteroid reductase activi ...
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2
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3
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687642
Chang
Mechanism of proton transfer i ...
Comamonas testosteroni
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2
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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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687870
Hoffmann
Understanding oligomerization ...
Comamonas testosteroni
J. Biotechnol.
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2
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668392
Matsunaga
Multiplicity of mammalian redu ...
Homo sapiens
Drug Metab. Pharmacokinet.
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30
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1
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1
1
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1
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16
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4
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30
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672088
Jin
Multiple steps determine the o ...
Homo sapiens
Biochemistry
45
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2006
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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
1
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2
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1
2
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3
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1
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1
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3
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1
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2
1
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673349
Papari-Zareei
Arginine 276 controls the dire ...
Rattus norvegicus
Endocrinology
147
1591-1597
2006
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3
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1
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3
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4
1
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2
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1
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1
1
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3
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1
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4
1
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2
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673967
Rani
Discrete analysis of bile acid ...
Comamonas testosteroni
Indian J. Biochem. Biophys.
43
98-104
2006
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1
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1
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1
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Nakamura
Apo- and holo-structures of 3a ...
Pseudomonas sp., Pseudomonas sp. B-0831
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1
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1
1
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2
2
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674981
Okochi
Enhanced activity of 3alpha-hy ...
Comamonas testosteroni
J. Biotechnol.
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376-382
2006
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1
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1
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1
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2
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3
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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1
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675595
Steckelbroeck
Tibolone metabolism in human l ...
Homo sapiens
J. Pharmacol. Exp. Ther.
316
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2006
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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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2
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1
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2
3
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2
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1
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3
1
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2
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1
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1
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675678
Wiebe
Dutasteride affects progestero ...
Homo sapiens
J. Steroid Biochem. Mol. Biol.
100
129-140
2006
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1
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675687
Bellemare
Isolation and characterization ...
Mus musculus
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18-24
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1
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1
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3
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5
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676002
Bauman
Identification of the major ox ...
Homo sapiens
Mol. Endocrinol.
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444-458
2006
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1
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3
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1
2
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1
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3
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3
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676812
Yee
Fluorogenic metabolic probes f ...
Homo sapiens
Proc. Natl. Acad. Sci. USA
103
13304-13309
2006
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1
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1
1
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6
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2
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2
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1
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4
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Hwang
Mechanistic roles of Ser-114, ...
Comamonas testosteroni
J. Biol. Chem.
280
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2005
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1
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6
1
1
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2
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1
2
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5
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7
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1
1
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3
1
1
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6
1
1
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673101
Uwai
Purification and characterizat ...
Rattus norvegicus
Chirality
17
494-500
2005
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6
1
1
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1
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1
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1
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1
1
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2
2
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1
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1
1
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6
1
1
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-
-
1
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-
677001
Couture
Comparison of crystal structur ...
Homo sapiens
Protein Sci.
14
1485-1497
2005
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1
1
2
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3
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1
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5
1
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3
1
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2
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1
2
1
2
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3
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1
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1
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1
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1
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5
1
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3
1
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654726
Heredia
Dissection of the physiologica ...
Rattus norvegicus
Biochemistry
43
12028-12037
2004
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2
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3
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9
1
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5
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5
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2
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1
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2
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1
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3
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1
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9
1
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654756
Heredia
Alanine scanning mutagenesis o ...
Rattus norvegicus
Biochemistry
43
5832-5841
2004
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1
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8
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347990
Ma
Mutation of nicotinamide pocke ...
Rattus norvegicus
Biochemistry
39
102-109
2000
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5
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5
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2
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1
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2
4
1
3
1
1
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347989
Penning
Structure and function of 3alp ...
Rattus norvegicus
Steroids
62
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11
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1
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2
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Span
3alpha-Hydroxysteroid oxidored ...
Rattus norvegicus
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1996
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1
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Jez
Characterization of the substr ...
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1
4
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1
8
1
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1
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Mallonee
Expression in Escherichia coli ...
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1
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1
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1
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1
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8
1
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Kinetic and stereochemical cha ...
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4
1
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5
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5
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1
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347979
Askonas
The kinetic mechanism catalyse ...
Rattus norvegicus
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2
4
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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347981
Pawlowski
Cloning and sequencing of the ...
Rattus norvegicus, Rattus norvegicus Sprangue-Dawley
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7
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1
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1
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6
1
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286354
Ohmura
Demonstration of 3alpha(17beta ...
Mesocricetus auratus
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1990
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9
2
1
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1
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1
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1
5
1
13
1
1
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1
17
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2
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2
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9
-
2
1
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1
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1
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
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1990
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5
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1
1
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1
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4
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1
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5
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1
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1
4
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1
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347980
Penning
Prostaglandin dehydrogenase ac ...
Rattus norvegicus
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1987
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5
1
1
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1
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3
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3
1
1
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1
3
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1
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5
3
1
1
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1
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1
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1
3
-
3
1
1
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347982
Penning
Purification and properties of ...
Rattus norvegicus, Rattus norvegicus Sprangue-Dawley
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222
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1984
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25
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1
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2
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1
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1
2
1
15
1
1
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5
17
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2
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5
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2
25
17
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1
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2
2
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1
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1
2
1
15
1
1
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722157
Bj÷rkhem
Stereochemistry of hydrogen tr ...
Rattus norvegicus
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1970
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347984
Tomkins
A mammalian 3alpha-hydroxyster ...
Rattus norvegicus
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1956
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3
4
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