1.1.1.50: 3alpha-hydroxysteroid 3-dehydrogenase (Si-specific)

This is an abbreviated version, for detailed information about 3alpha-hydroxysteroid 3-dehydrogenase (Si-specific), go to the full flat file.

Reaction

a 3alpha-hydroxysteroid
+
NAD(P)+
=
a 3-oxosteroid
+
NAD(P)H
+
H+

Synonyms

3 alpha-hydroxysteroid dehydrogenase, 3 alphaHD, 3-alpha-HSD, 3alpha-HSD, 3alpha-HSD/CR, 3alpha-HSOR, 3alpha-hydroxysteroid dehydrogenase, 3alpha-hydroxysteroid dehydrogenase/carbonyl reductase, 3alpha-hydroxysteroid oxido-reductase, 3alpha-hydroxysteroid oxidoreductase, 3alpha-hydroxysteroid-5beta-oxidoreductase activity, 3alpha-OR, 3alpha-oxidoreductase, 3alpha/3beta-hydroxysteroid dehydrogenase, 3alphaHSD, 3HSD, 5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase, AKR1C, AKR1C1-4, AKR1C17, AKR1C2, AKR1C3, AKR1C4, AKR1C9, aldo-keto reductase 1C2, bile-acid binding protein, chlordecone reductase, DD2, DD21, dihydrodiol dehydrogenase, HSD, HSD28, HSD29, hsdA, HSDH, hydroxyprostaglandin dehydrogenase, More, NAD(P)+-3alpha-hydroxysteroid dehydrogenase, NAD+-dependent 3alpha-HSD, NADP(H)-dependent 3alpha-HSD, NADPH:5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase, prostaglandin F2alpha-synthase, PT3HSD, sterognost 3alpha dehydrogenase, 3alpha-hydroxy steroid, type 2 3alpha-hydroxysteroid dehydrogenase/type 5 17beta-hydroxysteroid dehydrogenase, type 3 3alpha-hydroxysteroid dehydrogenase, type 5 17beta-hydroxysteroid dehydrogenase, type I 3alpha-HSD

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.50 3alpha-hydroxysteroid 3-dehydrogenase (Si-specific)

Substrates Products

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

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
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
?
-