Information on EC 1.1.1.50 - 3alpha-hydroxysteroid 3-dehydrogenase (Si-specific)

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

EC NUMBER
COMMENTARY hide
1.1.1.50
-
RECOMMENDED NAME
GeneOntology No.
3alpha-hydroxysteroid 3-dehydrogenase (Si-specific)
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + 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
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-
Primary bile acid biosynthesis
-
-
Steroid hormone biosynthesis
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testosterone and androsterone degradation to androstendione
-
-
SYSTEMATIC NAME
IUBMB Comments
3alpha-hydroxysteroid:NAD(P)+ 3-oxidoreductase (Si-specific)
The enzyme acts on androsterone and other 3alpha-hydroxysteroids and on 9-, 11- and 15-hydroxyprostaglandin. Si-specific with respect to NAD+ or NADP+. cf. EC 1.1.1.213, 3alpha-hydroxysteroid 3-dehydrogenase (Re-specific).
CAS REGISTRY NUMBER
COMMENTARY hide
9028-56-2
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
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Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
strain VPI 12708
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Manually annotated by BRENDA team
strain VPI 12708
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-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
-
replacement of hsdA gene by the green fluorescent protein gene inserted downstream from the hsdA regulatory region and use of the resulting strain as fluorescence based biosensor system for steroid determination. With this cell-based system testosterone can be determined in a range between 57 and 450 ng/ml, estradiol between 1.6 and 12.8 ng/ml, and cholesterol between 19.3 and 154.4 ng/nl. The sensitivity of this bioassay can be further increased by using only the cytosol of the mutant. With the resulting cell-free system testosterone is determined in a range between 28 and 219 pg/ml, estradiol between 0.029 and 0.430 fg/ml, and cholesterol between 9.7 and 77.2 fg/ml. The recovery ratio of the extraction is around 95% and the maximum fluorescence signals are obtained as early as after 30 min. Limitations of the established steroid biosensor system are quenching at higher steroid concentrations and the relatively high background of fluorescence
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1-acenaphthenol + NADP+
?
show the reaction diagram
-
isozymes AKR1C1-AKR1C4
-
-
r
1-acenaphthenol + NADPH
?
show the reaction diagram
-
-
-
-
?
1-acetophenone + NADPH
1-phenylethanol + NADP+
show the reaction diagram
-
-
-
-
?
1-indanol + NADP+
?
show the reaction diagram
-
isozymes AKR1C1-AKR1C4
-
-
r
17beta-estradiol + NADP+
estrone + NADPH
show the reaction diagram
-
-
-
-
r
17beta-hydroxy-dihydrotestosterone + NAD+
5alpha-androstan-3,17-dione + NADH
show the reaction diagram
-
-
-
r
3-hydroxysteroid + NAD(P)+
3-ketosteroid + NAD(P)H
show the reaction diagram
-
-
-
?
3-oxocholic acid + NADPH
3alpha-hydroxycholic acid + NADP+
show the reaction diagram
-
reverse reaction rate negligible
-
ir
3alpha,12alpha-dihydroxy-5beta-cholanoyl glycine + NAD+
12alpha-hydroxy-3-oxo-5beta-cholanoyl glycine + NADH
show the reaction diagram
-
-
-
-
?
3alpha,17alpha,21-trihydroxy-5beta-pregnan-11,20-dione + NADP+
17alpha,21-dihydroxy-5beta-pregnan-3,11,20-trione + NADPH
show the reaction diagram
-
-
-
r
3alpha,17beta-androstene-3,17-diol + NAD(P)+
dihydrotestosterone + NAD(P)H + H+
show the reaction diagram
-
-
-
?
3alpha,21-dihydroxy-5beta-pregnan-20-one + NADP+
21-hydroxy-5beta-pregnan-3,20-dione + NADPH
show the reaction diagram
-
-
-
-
r
3alpha,5alpha, 20alpha-trihydroxyprogesterone + NADP+
5alpha, 20alphy-dihydroxyprogesterone-3-one + NADPH
show the reaction diagram
-
-
-
-
r
3alpha,5alpha-allopregnenolone + NAD(P)+
5alpha-dihydroprogesterone + NAD(P)H
show the reaction diagram
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl glycine + NAD+
7alpha,12alpha-dihydroxy-5beta-cholan-3-one-24-oyl glycine + NADH
show the reaction diagram
3alpha,7alpha-dihydroxy-5beta-cholanoyl glycine + NAD+
7alpha-hydroxy-3-oxo-5beta-cholanoyl glycine + NADH
show the reaction diagram
-
-
-
-
?
3alpha-adiol + NAD(P)+
dihydrotestosterone + NAD(P)H
show the reaction diagram
3alpha-androstanediol + NAD+
5alpha-dihydrotestosterone + NADH
show the reaction diagram
-
oxidation utilizing NAD+ as a cofactor is the preferred reaction in vitro
-
-
r
3alpha-hydroxy-12-oxo-9,11-cholenic acid + NADP+
3,12-dioxo-9,11-cholenic acid + NADPH
show the reaction diagram
-
-
-
-
?
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
5alpha-pregnan-3,20-dione + NADPH
show the reaction diagram
-
-
-
-
?
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
5alpha-pregnan-3,20-dione + NADPH + H+
show the reaction diagram
-
-
-
-
r
3alpha-hydroxy-5beta-androstan-17-one + NADP+
5beta-androstan-3,17-dione + NADPH
show the reaction diagram
3alpha-hydroxy-5beta-pregnan-20-one + NADP+
5beta-pregnan-3,20-dione + NADPH
show the reaction diagram
3alpha-hydroxypregn-4-en-20-one + NADP+
pregn-4-en-3,20-dione + NADPH + H+
show the reaction diagram
-
-
-
-
?
3alpha-hydroxytibolone + NAD+
tibolone + NADH
show the reaction diagram
-
isozymes AKR1C2 and AKR1C4, no activity with isozyme AKR1C1
-
-
r
3alpha-tetrahydroprogesterone + NADH
5alpha-dihydroprogesterone + NAD+
show the reaction diagram
-
-
-
r
3beta-hydroxytibolone + NAD+
tibolone + NADH
show the reaction diagram
-
isozymes AKR1C2, AKR1C1, and AKR1C4
-
-
r
4'-methoxyacetophenone + NADPH + H+
1-(4-methoxyphenyl)ethanol + NADP+
show the reaction diagram
-
-
R,S-enantiomeric product
-
?
4-androsten-3alpha-ol-17-one + NADH + H+
4-androsten-3alpha,17beta-diol + NAD+
show the reaction diagram
-
AKR1C17
-
-
r
4-androstene-3,17-dione + NADH + H+
4-androsten-3alpha-ol-17-one + NAD+
show the reaction diagram
-
low activity
-
-
r
4-bromoacetophenone + NADPH + H+
1-(4-bromophenyl)ethanol + NADP+
show the reaction diagram
-
-
-
-
?
4-cyanoacetophenone + NADPH + H+
1-(4-cyanophenyl)ethanol + NADP+
show the reaction diagram
-
-
-
-
?
4-methylacetophenone + NADPH + H+
1-(4-methylphenyl)ethanol + NADP+
show the reaction diagram
-
-
R,S-enantiomeric product
-
?
4-nitroacetophenone + NADPH + H+
1-(4-nitrophenyl)ethanol + NADP+
show the reaction diagram
4-pregnen-3alpha,20beta-diol + NAD+
(20beta)-20-hydroxypregn-4-en-3-one + NADH + H+
show the reaction diagram
-
-
-
?, ir
5alpha-androstan-3,17-dione + NADH + H+
androsterone + NAD+
show the reaction diagram
-
-
-
-
?
5alpha-androstan-3,17-dione + NADPH + H+
3alpha-hydroxy-5alpha-androstan-17-one + NADP+
show the reaction diagram
-
-
-
r
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
17beta-hydroxy-5alpha-androstan-3-one + NADPH
show the reaction diagram
5alpha-androstan-3alpha,17beta-diol + NAD(P)H
5alpha-dihydrotestosterone + NAD(P)+
show the reaction diagram
5alpha-androstan-3alpha-ol-17-one + NADH + H+
5beta-androstan-3alpha,17beta-diol + NAD+
show the reaction diagram
-
-
-
-
r
5alpha-androstane-3,17-dione + NADH
5alpha-androstan-3alpha-ol-17-one + NAD+
show the reaction diagram
-
low activity
AKR1C9
-
r
5alpha-androstane-3,17-dione + NADH + H+
androsterone + NAD+
show the reaction diagram
-
-
-
-
?
5alpha-dihydrocortisol + NADPH
3alpha,5alpha-tetrahydrocortisol + NADP+
show the reaction diagram
-
-
-
?
5alpha-dihydroprogesterone + 2 NADPH + 2 H+
4-pregnen-3alpha,20beta-diol + 2 NADP+
show the reaction diagram
5alpha-dihydroprogesterone + NAD(P)H
4-pregnen-3alpha,20beta-diol + NAD(P)+
show the reaction diagram
-
-
-
-
?
5alpha-dihydroprogesterone + NADPH
3alpha,17beta-dihydroxyandrostane + NADP+
show the reaction diagram
-
type 2 isozyme AKR1C3 catalyzes the forward reaction, type 3 isozyme AKR1C2 catalyzes the reverse reaction
-
-
ir
5alpha-dihydroprogesterone + NADPH
4-pregnen-3alpha,20beta-diol + NADP+
show the reaction diagram
5alpha-dihydroprogesterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
show the reaction diagram
-
isozymes AKR1C1-AKR1C4
-
-
r
5alpha-dihydroprogesterone + NADPH
5alpha-hydroxy-pregnan-20-one + NADP+
show the reaction diagram
-
isozyme AKR1C2
-
-
?
5alpha-dihydroprogesterone + NADPH + H*
3alpha,5alpha-3-hydroxypregnan-20-one + 5alpha,20alpha-tetrahydroprogesterone + NADP+
show the reaction diagram
-
-
-
-
?
5alpha-dihydroprogesterone + NADPH + H+
3alpha,5alpha-3-hydroxypregnan-20-one + NADP+
show the reaction diagram
5alpha-dihydroprogesterone + NADPH + H+
4-pregnen-3alpha,20beta-diol + NADP+
show the reaction diagram
5alpha-dihydrotestosterone + NAD(P)H
3beta-adiol + NAD(P)+
show the reaction diagram
5alpha-dihydrotestosterone + NAD(P)H
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
show the reaction diagram
5alpha-dihydrotestosterone + NAD(P)H
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
show the reaction diagram
5alpha-dihydrotestosterone + NADH
3alpha-androstanediol + NAD+
show the reaction diagram
-
reaction direction is regulated by the NAD+:NADPH relation in the cell
-
-
r
5alpha-dihydrotestosterone + NADH
?
show the reaction diagram
-
low activity
-
-
?
5alpha-dihydrotestosterone + NADPH
3alpha-androstanediol + NADP+
show the reaction diagram
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
show the reaction diagram
5alpha-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5alpha-pregnan-20-one + NAD(P)+
show the reaction diagram
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnane-3alpha-ol-20-one + NAD(P)+
show the reaction diagram
5alpha-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
show the reaction diagram
5alpha-pregnane-20alpha-ol-3-one + NADH
5alpha-pregnane-3,20alpha-diol + NAD+
show the reaction diagram
-
-
-
-
?
5alpha-pregnane-3,20-dione + NADH
5alpha-pregnan-3alpha-ol-20-one + NAD+
show the reaction diagram
-
low activity
-
-
r
5beta-androstan-3,17-dione + NAD(P)H
5beta-androstan-17one-3-ol + NAD(P)+
show the reaction diagram
5beta-androstan-3,17-dione + NADPH
5beta-androstan-3alpha,17alpha-diol + NADP+
show the reaction diagram
-
-
-
r
5beta-androstan-3alpha,17beta-diol + NADP+
17beta-hydroxy-5beta-androstan-3-one + NADPH
show the reaction diagram
5beta-androstan-3alpha-ol-17-one + NADH
5beta-androstane-3alpha,17beta-diol + NAD+
show the reaction diagram
-
-
-
-
r
5beta-androstan-3alpha-ol-17-one + NADPH
5beta-androstan-3alpha,17alpha-diol + NADP+
show the reaction diagram
-
-
-
r
5beta-androstane-3,17-dione + NADH
5beta-androstan-3alpha-ol-17-one + NAD+
show the reaction diagram
-
-
-
-
r
5beta-androstane-3,17-dione + NADH + H+
5beta-androstan-3alpha-ol-17-one + NAD+
show the reaction diagram
-
-
-
-
?
5beta-dihydrocortisol + NADPH
3alpha,5beta-tetrahydrocortisol + NADP+
show the reaction diagram
-
-
-
?
5beta-dihydroprogesterone + NADPH
?
show the reaction diagram
-
isozyme AKR1C1 and AKR1C2
-
-
?
5beta-dihydroprogesterone + NADPH + H+
3alpha,5beta-3-hydroxypregnan-20-one + NADP+
show the reaction diagram
-
preferred substrate
-
-
?
5beta-dihydrotestosterone + NAD(P)H
5beta-androstan-3alpha,17beta-diol + NAD(P)+
show the reaction diagram
5beta-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5beta-pregnan-20-one + NAD(P)+
show the reaction diagram
5beta-pregnane-20alpha-ol-3-one + NADH + H+
5beta-pregnane-3,20alpha-diol + NAD+
show the reaction diagram
-
-
-
-
?
5beta-pregnane-3,20-dione + NADH + H+
5beta-pregnan-3alpha-ol-20-one + NAD+
show the reaction diagram
-
-
-
-
r
6-ketolithocholate + NAD+
5beta-cholan-3,6-dione-24-oic acid + NADH
show the reaction diagram
-
-
-
-
r
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one + NADH
?
show the reaction diagram
-
the enzyme produces both R- and S-form products in a ratio of 2.3 : 1
-
-
?
9,10-phenanthrenequinone + NADH
?
show the reaction diagram
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
show the reaction diagram
9-(phenylcarbonyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADPH
9-[hydroxy(phenyl)methyl]-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADP+
show the reaction diagram
androsterone + NAD(P)+
5alpha-androstan-3,17-dione + NAD(P)H
show the reaction diagram
androsterone + NAD+
5alpha-androstan-3,17-dione + NADH + H+
show the reaction diagram
-
-
-
-
?
androsterone + NAD+
5alpha-androstane-3,17-dione + NADH
show the reaction diagram
androsterone + NAD+
5alpha-androstane-3,17-dione + NADH + H+
show the reaction diagram
-
-
-
-
?
androsterone + NAD+
androstanedione + NADH
show the reaction diagram
androsterone + NADP+
5alpha-androstane-3,17-dione + NADPH
show the reaction diagram
-
-
-
-
r
androsterone + NADP+
androstane-3,17-dione + NADPH
show the reaction diagram
benzenedihydrodiol + NADP+
?
show the reaction diagram
-
isozymes AKR1C1-AKR1C4
-
-
r
benzoylpyridine + NADPH
?
show the reaction diagram
-
-
-
-
?
beta-muricholic acid + NADH
?
show the reaction diagram
-
low activity
-
-
?
camphorquinone + NADPH
?
show the reaction diagram
chenodeoxycholic acid + NAD(P)+
7alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid + NAD(P)H
show the reaction diagram
chenodeoxycholic acid + NAD+
7alpha,12alpha-dihydroxy-5beta-cholan-3-one-24-oic acid + NADH
show the reaction diagram
chenodeoxycholic acid + NADH
?
show the reaction diagram
-
-
-
-
?
cholic acid + NAD(P)+
7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic acid + NAD(P)H
show the reaction diagram
cholic acid + NAD+
7alpha,12alpha-dihydroxy-5beta-cholan-3-one-24-oic acid + NADH
show the reaction diagram
cholic acid + NADH
?
show the reaction diagram
-
low activity
-
-
?
cholic acid + thio-NAD+
7alpha,12alpha-dihydroxy-5beta-cholan-3-one-24-oic acid + thio-NADH
show the reaction diagram
-
-
-
-
?
dehydrolithocholic acid + NADH + H+
?
show the reaction diagram
-
-
-
-
?
deoxycholic acid + NAD(P)+
12alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid + NAD(P)H + H+
show the reaction diagram
deoxycholic acid + NADH
?
show the reaction diagram
-
low activity
-
-
?
diacetyl + NADH
?
show the reaction diagram
-
-
-
-
?
estradiol + NAD(P)H
estrone + NAD(P)+
show the reaction diagram
etiocholan-3alpha-ol-17-one + NADP+
etiocholan-3,17-dione + NADPH
show the reaction diagram
-
-
-
-
?
fusidic acid + NAD+
3-oxofusidic acid + NADH
show the reaction diagram
-
antibiotic steroid substrate
-
-
?
fusidic acid + NAD+
?
show the reaction diagram
-
-
-
-
r
glycochenodeoxycholic acid + NADH
?
show the reaction diagram
-
-
-
-
?
glycocholic acid + NAD+
7alpha,12alpha-dihydroxy-5beta-cholan-3-one-24-oyl-glycine + NADH
show the reaction diagram
-
-
-
-
?
glycolithocholic acid + NADH
?
show the reaction diagram
-
-
-
-
?
glycolithocholic acid + NADP+
3-oxo-glycocholanoic acid + NADPH
show the reaction diagram
glycoursodeoxycholic acid + NADH
?
show the reaction diagram
-
-
-
-
?
hydroxybutyrate + NADP+
oxobutanoate + NADPH
show the reaction diagram
-
-
-
-
?
hyodeoxycholic acid + NADH
?
show the reaction diagram
-
low activity
-
-
?
isatin + NADH
?
show the reaction diagram
-
-
-
-
?
lithocholic acid + NAD+
5beta-cholan-3-one-24-oic acid + NADH
show the reaction diagram
lithocholic acid + NADH
?
show the reaction diagram
-
-
-
-
?
lithocholic acid + NADP+
3-oxo-5beta-cholan-24-oic acid + NADPH
show the reaction diagram
menadione + NADPH
?
show the reaction diagram
-
-
-
-
?
metapyrone + NADH
?
show the reaction diagram
-
-
-
-
?
murocholic acid + NADH
?
show the reaction diagram
-
low activity
-
-
?
oxidized 8-acetyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-azabenzo[de]anthracen-10-one + NAD(P)H
reduced 8-acetyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-azabenzo[de]anthracen-10-one + NAD(P)+
show the reaction diagram
p-nitrobenzaldehyde + NAD(P)H
p-nitrobenzylalcohol + NAD(P)+
show the reaction diagram
p-nitrobenzylalcohol + NAD+
p-nitrobenzaldehyde + NADH
show the reaction diagram
-
-
-
r
progesterone + NADH
?
show the reaction diagram
-
-
-
-
r
progesterone + NADPH
?
show the reaction diagram
-
-
-
-
?
taurocholic acid + NAD(P)+
2[[7alpha,12alpha-dihydroxy-3,24-dioxo-5beta-cholan-24-yl]amino]ethane sulfonic acid + NADPH
show the reaction diagram
taurocholic acid + NAD+
7alpha,12alpha-dihydroxy-5beta-cholan-3-one-24-oyl-taurine + NADH
show the reaction diagram
-
-
-
-
?
taurolithocholic acid + NADH
?
show the reaction diagram
-
-
-
-
?
tauroursodeoxycholic acid + NADH
?
show the reaction diagram
-
-
-
-
?
testosterone + NAD(P)+
androstenedione + NAD(P)H + H+
show the reaction diagram
testosterone + NADH
?
show the reaction diagram
-
low activity
-
-
?
testosterone + NADP+
4-androstene-3,17-dione + NADPH + H+
show the reaction diagram
-
isozymes AKR1C1-AKR1C4
-
-
r
testosterone + NADPH
4-androstene-3alpha,17beta-diol + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH
?
show the reaction diagram
tibolone + NADPH
3-hydroxytibolone + NADP+
show the reaction diagram
tibolone + NADPH
3alpha-hydroxytibolone + NADP+
show the reaction diagram
-
isozyme AKR1C4 acts predominantly 3alpha-specific, isozyme AKR1C3 performs both 3alpha- and 3beta-reduction, tibolone is [7alpha,17alpha]-17-hydroxy-7-methyl-19-nor-pregn-5(10)-en-20-yn-3-one, or livial, a DELTA5(10)-ene-ketosteroid and a hormone replacement therapeutic used in the treatment of climacteric complaints and the prevention of osteoporosis, binding mode
-
-
r
tibolone + NADPH
3beta-hydroxytibolone + NADP+
show the reaction diagram
-
isozyme AKR1C1 is stereospecific forming exclusively the beta-isomer, isozyme AKR1C2 is 3beta-specific with substrate tibolone, isozyme AKR1C3 performs both 3alpha- and 3 beta-reduction, tibolbone is [7alpha,17alpha]-17-hydroxy-7-methyl-19-nor-pregn-5(10)-en-20-yn-3-one, or livial, a DELTA5(10)-ene-ketosteroid and a hormone replacement therapeutic used in the treatment of climacteric complaints and the prevention of osteoporosis
-
-
r
ursodeoxycholate + NAD+
7beta-hydroxy-3-oxo-5beta-cholan-24-oic acid + NADH
show the reaction diagram
-
-
-
-
r
ursodeoxycholic acid + NAD+
7alpha,12alpha-dihydroxy-5beta-cholan-3-one-24-oic acid + NADH
show the reaction diagram
-
-
-
-
?
ursodeoxycholic acid + NADH
?
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-hydroxysteroid + NAD(P)+
3-ketosteroid + NAD(P)H
show the reaction diagram
-
-
-
?
3alpha,5alpha-allopregnenolone + NAD(P)+
5alpha-dihydroprogesterone + NAD(P)H
show the reaction diagram
-
i.e. 3alpha,5alpha-tetrahydroprogesterone or 3alpha,5alpha-THP, the enzyme catalyzes the biosynthesis and oxidation of 3alpha,5alpha-reduced neurosteroids as allopregnanolone, which stimulates GABAA receptors, sciatic nerves-induced analgesia results in increased enzyme levels in neuropathic rats, overview
-
-
r
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
5alpha-pregnan-3,20-dione + NADPH + H+
show the reaction diagram
-
-
-
-
r
3alpha-hydroxypregn-4-en-20-one + NADP+
pregn-4-en-3,20-dione + NADPH + H+
show the reaction diagram
-
-
-
-
?
4-pregnen-3alpha,20beta-diol + NAD+
(20beta)-20-hydroxypregn-4-en-3-one + NADH + H+
show the reaction diagram
Q04828
-
-
-
ir
5alpha-dihydroprogesterone + 2 NADPH + 2 H+
4-pregnen-3alpha,20beta-diol + 2 NADP+
show the reaction diagram
5alpha-dihydroprogesterone + NAD(P)H
4-pregnen-3alpha,20beta-diol + NAD(P)+
show the reaction diagram
-
-
-
-
?
5alpha-dihydroprogesterone + NADPH
4-pregnen-3alpha,20beta-diol + NADP+
show the reaction diagram
Q04828
-
-
-
?
5alpha-dihydroprogesterone + NADPH + H+
3alpha,5alpha-3-hydroxypregnan-20-one + NADP+
show the reaction diagram
5alpha-dihydroprogesterone + NADPH + H+
4-pregnen-3alpha,20beta-diol + NADP+
show the reaction diagram
-
in the prostate: forward reaction by type 2 isozyme AKR1C3, reverse reaction by type 3 isozyme AKR1C2
-
-
ir
5alpha-dihydrotestosterone + NAD(P)H
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
show the reaction diagram
5alpha-dihydrotestosterone + NADH
3alpha-androstanediol + NAD+
show the reaction diagram
-
reaction direction is regulated by the NAD+:NADPH relation in the cell
-
-
r
5alpha-dihydrotestosterone + NADPH
3alpha-androstanediol + NADP+
show the reaction diagram
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
show the reaction diagram
-
-
-
-
?
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnane-3alpha-ol-20-one + NAD(P)+
show the reaction diagram
5alpha-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
show the reaction diagram
5beta-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5beta-pregnan-20-one + NAD(P)+
show the reaction diagram
9-(phenylcarbonyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADPH
9-[hydroxy(phenyl)methyl]-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADP+
show the reaction diagram
-
competitive substrate, fluorometric activity measurement in intact cells, overview
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-
?
androsterone + NAD+
5alpha-androstane-3,17-dione + NADH
show the reaction diagram
-
-
-
-
r
androsterone + NAD+
androstanedione + NADH
show the reaction diagram
P80702
-
-
-
r
androsterone + NADP+
5alpha-androstane-3,17-dione + NADPH
show the reaction diagram
-
-
-
-
r
tibolone + NADPH
3-hydroxytibolone + NADP+
show the reaction diagram
-
tibolone is used to treat climacteric symptoms and prevent osteoporosis, it exerts tissue-selective effects via site-specific metabolism into 3alpha- and 3beta-hydroxymetabolites and a DELTA4-isomer
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-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3-acetylpyridine adenine dinucleotide
-
i.e. APAD+, 42% of the activity with NAD+ when cholic acid is utilized as substrate
NAD(P)+
NAD(P)H
NADP+
nicotinamide hypoxanthine dinucleotide
-
i.e. deamino-NAD+, 36% of the activity with NAD+ when cholic acid is utilized as substrate
thio-NAD+
additional information
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-Methylpyrrole acetic acid
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-
11beta,17alpha,21-trihydroxy-4-pregnen-3,20-dione
-
-
11beta,21-dihydroxy-4-pregnen-3,20-dione
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-
17,21-Dihydroxy-5alpha-pregnan-3,20-dione
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-
17alpha,21-Dihydroxy-1,4-pregnadien-3,11,20-trione
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-
17alpha,21-dihydroxy-4-pregnen-3,11,20-trione
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-
17alpha-Hydroxy-4-androsten-3-one
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-
17alpha-hydroxy-4-pregnen-3,20-dione
-
-
17alpha-Methyl-5alpha-dihydrotestosterone
-
-
17alpha-methyltestosterone
-
competitive inhibition
17beta-hydroxy-4-androsten-3-one
-
-
21-Hydroxy-5alpha-pregnan-3,20-dione
-
-
2alpha-Bromo-17beta-hydroxy-5alpha-androstan-3-one
2alpha-Bromo-5alpha-androstan-3,17-dione
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-
2alpha-Cyano-17beta-methoxy-4-androsten-3-one
-
-
2alpha-Cyano-17beta-methoxy-5alpha-androstan-3-one
-
-
2alpha-Cyano-5alpha-dihydrotestosterone
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-
2alpha-Fluoro-5alpha-androstan-3,17-dione
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-
2alpha-Iodo-5alpha-androstan-3,17-dione
-
-
4-androsten-3,17-dione
-
-
4-Aza-4-methyl-5alpha-pregnane-3,20-dione
-
only slight inhibition
4-pregnen-3,20-dione
-
-
5,5'-dithiobis(2-nitrobenzoic acid)
-
-
5alpha-Androstan-3,16-dione
-
-
5alpha-Androstan-3,17-dione
-
-
5alpha-Androstan-3-one
-
-
5alpha-Dihydrotestosterone hemisuccinate
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-
5alpha-pregnan-3,20-dione
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-
5beta-dihydrotestosterone
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-
5beta-pregnan-3,20-dione
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-
6alpha-Methylprednisolone
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-
9-(phenylcarbonyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one
-
competitive
acetaminophen
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-
Arylpropionic acid
-
-
-
Bethamethasone
-
-
bromazepam
-
competitive inhibition of isozymes AKR1C1, AKR1C4, and AKR1C2
celecoxib
-
synthetic, nonsteroidal anti-inflammatory inhibitor, in vivo IC50: 0.050 mM in fluorometric assay, in vitro IC50: 0.050 mM in fluorometric assay
cholic acid
-
complete inhibition
cloxazolam
-
potent and specific, competitive inhibition of isozymes AKR1C1, AKR1C4, and AKR1C2
deoxycorticosterone
-
-
dexamethasone
dexamethasone 21-acetate
-
-
dexamethasone 21-hemisuccinate
-
-
diazepam
-
competitive inhibition of isozymes AKR1C1, AKR1C4, and AKR1C2
Dienstrol
-
-
estazolam
-
competitive inhibition of isozymes AKR1C1, AKR1C4, and AKR1C2
ethacrynate
-
-
ethynylestradiol
-
competitive inhibition
Fenamates
-
-
Flufenamic acid
flunitrazepam
-
competitive inhibition of isozymes AKR1C1 and AKR1C2
fluoxetine
-
allosteric interaction
Heavy metal ions
-
-
-
Hexestrol
-
-
Hg2+
-
-
Ibuprofen
-
synthetic, nonsteroidal anti-inflammatory inhibitor, in vivo IC50: 0.017 mM in fluorometric assay, in vitro IC50: 0.009 mM in fluorometric assay
indomethacin
Ketamine
-
inhibition of AKR1C17
medazepam
-
competitive inhibition of isozymes AKR1C1, AKR1C4, and AKR1C2
Medroxyprogesterone acetate
megestrol
-
competitive inhibition
Mg2+
-
strong inhibition of oxidation of 3alpha-hydroxysteroids
NADPH
naproxen
-
synthetic, nonsteroidal anti-inflammatory inhibitor, in vivo IC50: 0.0094 mM in fluorometric assay, 0.016 mM in radiometric assay, in vitro IC50: 0.0027 mM in fluorometric assay
nitrazepam
-
competitive inhibition of isozymes AKR1C1, AKR1C4, and AKR1C2
Norethindrone
-
-
p-chloromercuribenzoate
Phenolphthalein
-
AKR1C4-selective inhibitor, in vitro and in vivo inhibition, IC50: 0.0004 mM
Prednisolone
-
-
progesterone
-
-
prostaglandin A1
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-
Prostaglandin D2
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-
prostaglandin E2
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-
prostaglandin F2alpha
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-
Salicylates
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-
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Stilbestrol
-
-
sulfhydryl oxidizing reagents
-
-
-
testosterone
-
at concentration 0.001 mM 75% inhibition
tibolone
-
strong substrate inhibition of isozyme AKR1C2
Triamcinolone
-
-
ursodeoxycholate
Zomepirac
-
-
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-butyl-3-methylimidazolium L-lactate
-
activates the enzyme as 5% co-solvent in Tris-HCl buffer, overview; enhanced activity of 3alpha-hydroxysteroid dehydrogenase by addition of the co-solvent to 50 mM Tris-HCl buffer in aqueous phase of biphasic systems for reductive production of steroids. In a coupled-enzyme system comprising HSDH and formate dehydrogenase, a twofold increase in production rate of androsterone is obtained when utilizing 1-butyl-3-methylimidazolium L-lactate with NADH regeneration, overview
1-ethyl-3-methylimidazolium trifluoromethanesulfonate
-
addition of the co-solvent leads to slightly enhanced enzyme activity n an aqueous-organic solvent system with Tris-HCl buffer, overview
fluoxetine
-
activates allopregnanolone formation in vivo, not in vitro at a concentration up to 0.05 mM, therefore in vivo activation is probably not realized by enzyme activation but a different mechanism
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.017 - 0.042
(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide
0.069
(3alpha,5beta,7beta)-3,7-dihydroxycholan-24-oic acid
-
pH 8.5, 37C, with cofactor NAD+
0.0027
(5beta,20R)-20-hydroxypregnan-3-one
-
pH 7.4, 25C, recombinant wild-type AKR1C17
0.022 - 0.14
1-Acenaphthenol
0.048 - 1.4
1-Indanol
0.002 - 0.0024
17beta-hydroxy-5alpha-androstan-3-one
0.0007 - 0.0017
17beta-hydroxy-5beta-androstan-3-one
0.0007 - 0.00075
3-oxo-5beta-cholan-24-oic acid
-
-
0.0001
3alpha-adiol
-
-
-
0.0031
3alpha-androstanediol
-
pH 7.0, 25C, recombinant enzyme
0.0014
3alpha-hydroxy-5alpha-pregnan-20-one
-
oxidation
0.005
3alpha-tetrahydroprogesterone
-
-
0.2 - 0.8
4-Nitroacetophenone
-
also in this range: 2,3-hexanedione, 1-phenyl-1,2-propanedione, 2,3-pentanedione, pyridine-4-aldehyde, 2,3-butanedione
0.087
4-Nitrobenzaldehyde
-
NADPH, detection spectrophotometrically
0.0012 - 0.007
5alpha-Androstan-3,17-dione
0.00065 - 0.0031
5alpha-androstane-3,17-dione
0.0006 - 0.026
5alpha-dihydroprogesterone
0.0001 - 0.026
5alpha-dihydrotestosterone
0.000082
5alpha-pregnan-3,20-dione
-
reduction
0.00016 - 0.0016
5beta-androstan-3,17-dione
0.0012 - 0.007
5beta-androstane-3,17-dione
0.018
5beta-Dihydrocortisol
-
-
0.00051 - 0.0012
5beta-dihydroprogesterone
0.235
5beta-Pregnan-3alpha-ol-20-one
-
cytosolic NADH-linked 5beta-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase
0.0024
5beta-pregnane-3,20-dione
-
pH 7.4, 25C, recombinant wild-type AKR1C17
0.023
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one
-
pH 7.4, 25C, recombinant wild-type AKR1C17
0.021 - 0.038
9,10-phenanthrenequinone
0.003
9-(phenylcarbonyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one
-
recombinant enzyme in intact COS-1 cells
0.0015
allopregnanolone
-
pH 7.0, 25C
0.004 - 0.0422
androstanedione
0.0001 - 0.21
androsterone
0.017 - 1.8
benzenedihydrodiol
0.03 - 0.077
Camphorquinone
-
4-nitrobenzaldehyde, 2,3-heptanedione
0.063
chenodeoxycholic acid
-
pH 8.5, 37C, with cofactor NAD+
0.015
cholate
-
-
0.01 - 0.084
cholic acid
0.004
Dehydrolithocholic acid
-
pH 7.4, 25C, recombinant wild-type AKR1C17
0.0136
deoxycholate
-
-
0.42
diacetyl
-
pH 7.4, 25C, recombinant wild-type AKR1C17
0.0061 - 0.037
Fusidic acid
0.038
glycocholic acid
-
pH 8.5, 37C, with cofactor NAD+
0.0052 - 0.0059
glycolithocholic acid
0.022
isatin
-
pH 7.4, 25C, recombinant wild-type AKR1C17
0.068
lithocholic acid
-
pH 8.5, 37C, with cofactor NAD+
0.00305 - 0.87
NAD+
0.004 - 0.4
NADH
0.00023 - 0.0016
NADP+
0.00007 - 1.33
NADPH
0.0025
oxidized 8-acetyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-azabenzo[de]anthracen-10-one
-
isozyme AKR1C3
0.043
taurocholic acid
-
pH 8.5, 37C, with cofactor NAD+
0.0028 - 0.119
testosterone
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.004 - 0.507
(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide
82
(3alpha,5beta,7beta)-3,7-dihydroxycholan-24-oic acid
Pseudomonas sp.
-
pH 8.5, 37C, with cofactor NAD+
0.115
(5beta,20R)-20-hydroxypregnan-3-one
Rattus norvegicus
-
pH 7.4, 25C, recombinant wild-type AKR1C17
0.13 - 0.59
1-Acenaphthenol
0.09 - 0.21
1-Indanol
0.0833 - 0.183
3alpha-adiol
-
0.008
3alpha-androstanediol
Homo sapiens
-
pH 7.0, 25C, recombinant enzyme
0.000016 - 0.012
3alpha-hydroxytibolone
0.000016 - 0.016
3beta-hydroxytibolone
1.08
4-Nitrobenzaldehyde
Homo sapiens
-
-
0.0023 - 0.0735
4-pregnen-3alpha,20beta-diol
0.42
5alpha-androstane-3,17-dione
Rattus norvegicus
-
pH 7.0, 25, reduction reaction
0.003 - 0.04
5alpha-dihydroprogesterone
0.0038 - 1
5alpha-dihydrotestosterone
0.047
5beta-androstane-3,17-dione
Rattus norvegicus
-
pH 7.4, 25C, recombinant wild-type AKR1C17
0.0167 - 0.05
5beta-dihydroprogesterone
0.105
5beta-pregnane-3,20-dione
Rattus norvegicus
-
pH 7.4, 25C, recombinant wild-type AKR1C17
0.1
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one
Rattus norvegicus
-
pH 7.4, 25C, recombinant wild-type AKR1C17
0.183 - 18.9
9,10-phenanthrenequinone
0.00017
allopregnanolone
Homo sapiens
-
pH 7.0, 25C
1.9
androstanedione
Homo sapiens
-
detection spectrophotometrically
0.0018 - 318
androsterone
0.015 - 0.05
benzenedihydrodiol
76
chenodeoxycholic acid
Pseudomonas sp.
-
pH 8.5, 37C, with cofactor NAD+
35 - 75
cholic acid
0.022
Dehydrolithocholic acid
Rattus norvegicus
-
pH 7.4, 25C, recombinant wild-type AKR1C17
0.167
diacetyl
Rattus norvegicus
-
pH 7.4, 25C, recombinant wild-type AKR1C17
23 - 25
Fusidic acid
77
glycocholic acid
Pseudomonas sp.
-
pH 8.5, 37C, with cofactor NAD+
0.283
isatin
Rattus norvegicus
-
pH 7.4, 25C, recombinant wild-type AKR1C17
72
lithocholic acid
Pseudomonas sp.
-
pH 8.5, 37C, with cofactor NAD+
0.02 - 63
NADH
0.00017
NADP+
Homo sapiens
-
pH 7.0, 25C
0.003
NADPH
Homo sapiens
-
pH 7.0, 25C
0.14
oxidized 8-acetyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-azabenzo[de]anthracen-10-one
Homo sapiens
-
isozyme AKR1C3
0.0167
stanolone
Homo sapiens
-
-
74
taurocholic acid
Pseudomonas sp.
-
pH 8.5, 37C, with cofactor NAD+
0.0757
testosterone
Homo sapiens
-
-
additional information
additional information
-
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
6.5 - 54000
5alpha-androstane-3,17-dione
1493
3.8 - 15000
NADH
8
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0003 - 0.0029
diazepam
0.0008 - 0.001
estazolam
0.0011 - 0.0086
medazepam
0.0034 - 0.585
NADH
0.011 - 0.027
nitrazepam
0.000027 - 0.00055
ursodeoxycholate
additional information
additional information
-