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Information on EC 1.3.1.22 - 3-oxo-5alpha-steroid 4-dehydrogenase (NADP+)
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1.3.1.22 3-oxo-5alpha-steroid 4-dehydrogenase (NADP+)IUBMB Comments
The enzyme catalyses the conversion of assorted 3-oxo-Delta4 steroids into their corresponding 5alpha form. Substrates for the mammalian enzyme include testosterone, progesterone, and corticosterone. Substrates for the plant enzyme are brassinosteroids such as campest-4-en-3-one and (22alpha)-hydroxy-campest-4-en-3-one. cf. EC 1.3.99.5, 3-oxo-5alpha-steroid 4-dehydrogenase (acceptor).
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Word Map
- 1.3.1.22
- androgen
- prostate
- dihydrotestosterone
- srd5a2
- finasteride
- genitalia
-
5alpha-reduced
- hypospadias
-
3alpha-hydroxysteroid
- pseudohermaphroditism
- 5alpha-r1
- medicine
-
5alpha-reduction
- 17beta-hsds
-
1.3.99.5
- hirsutism
-
17beta-hydroxysteroid
-
virilization
- pharmacology
- analysis
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
5alphar, 5 alpha-reductase type 2, 5alpha-reductase 1, 5alpha-r2, steroid 5-alpha reductase, steroid 5-alpha-reductase, 5-alpha-reductase type 2, 5 alpha-r2, 5-alpha-reductase type 1, steroid 5alpha-reductase type ii, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
3-oxosteroid 5alpha-reductase
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3-oxosteroid DELTA4-dehydrogenase
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4-ene-3-oxosteroid 5alpha-reductase
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4-ene-5alpha-reductase
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5-alpha-reductase type 2
5alpha-R1
5alpha-R2
5alpha-reductase type 1
5alpha-reductase type 2
5alphaR
5alphaR1
5alphaR2
cholest-4-en-3-one 5alpha-reductase
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cortisone alpha-reductase
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cortisone DELTA 4-5alphareductase
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DELTA4-3-ketosteroid 5alpha-oxidoreductase
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DELTA4-3-ketosteroid reductase (5alpha)
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DELTA4-3-oxosteroid-5 alpha-reductase
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DELTA4-5alpha-reductase
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DELTA4-steroid 5alpha-reductase (progesterone)
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EC 1.3.1.30
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formerly
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EC 1.3.1.4
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formerly
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microsomal steroid reductase (5alpha)
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NADPH:DELTA4-3-oxosteroid-5alpha-oxidoreductase
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progesterone 5alpha-reductase
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reduced nicotinamide adenine dinucleotide phosphate:DELTA4-3-ketosteroid 5alpha-oxidoreductase
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reductase, cholestenone 5alpha-
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reductase, cortisone DELTA: 4-5alpha-
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reductase, progesterone 5alpha-
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S5alphaR
SRD5A1
SRD5A2
steroid 5-alpha reductase
steroid 5-alpha-reductase
steroid 5alpha-hydrogenase
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steroid 5alpha-reductase
testosterone 5alpha-reductase
testosterone delta4-5alpha-reductase
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testosterone delta4-hydrogenase
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type 1 5alpha-reductase
type 1 5alphaR
type 2 5alpha-reductase
type 2 5alphaR
additional information
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microsomal cholest-4-en-3-one 5alpha-reductase is not identical with microsomal DELTA4-3-ketosteroid 5alpha-reductase
5alpha-reductase type 1
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the isoenzyme predominates in the reproductive tissues, genital skin, and epididymis
5alpha-reductase type 2
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the isoenzyme is predominantly found in the skin, liver, and testes
steroid 5-alpha-reductase
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steroid 5alpha-reductase
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testosterone 5alpha-reductase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a 3-oxo-5alpha-steroid + NADP+ = a 3-oxo-DELTA4-steroid + NADPH + H+
mechanism
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a 3-oxo-5alpha-steroid + NADP+ = a 3-oxo-DELTA4-steroid + NADPH + H+
mechanism
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a 3-oxo-5alpha-steroid + NADP+ = a 3-oxo-DELTA4-steroid + NADPH + H+
sequential mechanism
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a 3-oxo-5alpha-steroid + NADP+ = a 3-oxo-DELTA4-steroid + NADPH + H+
reaction mechanism
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a 3-oxo-5alpha-steroid + NADP+ = a 3-oxo-DELTA4-steroid + NADPH + H+
kinetic mechanism
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a 3-oxo-5alpha-steroid + NADP+ = a 3-oxo-DELTA4-steroid + NADPH + H+
structure-activity relationship
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a 3-oxo-5alpha-steroid + NADP+ = a 3-oxo-DELTA4-steroid + NADPH + H+
structure-activity relationship
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a 3-oxo-5alpha-steroid + NADP+ = a 3-oxo-DELTA4-steroid + NADPH + H+
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY SOURCE
PATHWAYS
KEGG
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SYSTEMATIC NAME
IUBMB Comments
3-oxo-5alpha-steroid:NADP+ DELTA4-oxidoreductase
The enzyme catalyses the conversion of assorted 3-oxo-Delta4 steroids into their corresponding 5alpha form. Substrates for the mammalian enzyme include testosterone, progesterone, and corticosterone. Substrates for the plant enzyme are brassinosteroids such as campest-4-en-3-one and (22alpha)-hydroxy-campest-4-en-3-one. cf. EC 1.3.99.5, 3-oxo-5alpha-steroid 4-dehydrogenase (acceptor).
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CAS REGISTRY NUMBER
COMMENTARY
37255-34-8
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72412-84-1
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9029-09-8
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
11alpha-hydroxyprogesterone + NADPH + H+
11alpha-hydroxydihydroprogesterone + NADP+
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-
-
?
11beta,17alpha-dihydroxyprogesterone + NADPH + H+
11beta,17alpha-hydroxydihydroprogesterone + NADP+
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-
-
?
11beta-hydroxyprogesterone + NADPH + H+
11beta-hydroxydihydroprogesterone + NADP+
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-
-
?
17alpha,21-dihydroxypregn-4-ene-3,11,20-trione + NADPH
17alpha,21-dihydroxy-5alpha-pregnan-3,11,20-trione + NADP+
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trivial name cortisone
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ir
17alpha,21-dihydroxypregn-4-ene-3,20-dione + NADPH
17alpha,21-dihydroxy-5alpha-pregnane-3,20-dione
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-
-
?
17alpha-hydroxyprogesterone + NADPH
17alpha-hydroxy-5alpha-pregnan-3,20-dione + NADP+
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-
-
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ir
17alpha-hydroxyprogesterone + NADPH + H+
17alpha-hydroxy-5alpha-pregnan-3,20-dione + NADP+
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-
-
?
17beta-methyl-androsta-4,9-dien-3-one + NADPH
17beta-methyl-5alpha-androst-9-en-3-one + NADP+
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-
-
?
20alpha-hydroxy-4-pregnen-3-one + NADPH
20alpha-hydroxy-5-beta-pregnan-3-one + NADP+
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more reactive than progesterone
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-
?
21-hydroxypregn-4-ene-3,20-dione + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione + NADP+
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-
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?
androstenediol + NADPH
5alpha-androstan-3beta,17beta-diol + NADP+
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-
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ir
campestenone + NADPH
5alpha-campestan-3-one + NADP+
reduction at very low levels
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-
?
cortexolone + NADPH
17alpha,21-dihydroxy-5alpha-pregnan-3,20-dione + NADP+
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-
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ir
testosterone + NADPH + H+
androstan-3alpha,17beta-diol + androstan-3beta,17beta-diol + 5alpha-dihydrotestosterone
testosterone + NADPH + H+
dihydrotestosterone + NADP+
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-
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?
20-alpha-hydroxypregn-4-ene-3one + NADPH
20-alpha-hydroxy-5alpha-pregnan-3-one + NADP+
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?
20-alpha-hydroxypregn-4-ene-3one + NADPH
20-alpha-hydroxy-5alpha-pregnan-3-one + NADP+
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-
-
-
?
20-alpha-hydroxypregn-4-ene-3one + NADPH
20-alpha-hydroxy-5alpha-pregnan-3-one + NADP+
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-
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ir
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
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-
-
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?
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
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-
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?
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
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-
-
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?
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
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-
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ir
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
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-
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?
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
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?
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
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?
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
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mammalian enzymes: no reverse reaction, first step in reverse direction (enolization) occurs, but energy barrier for hydride abstraction is extremely high
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ir
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
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-
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?
corticosterone + NADPH + H+
5alpha-dihydrocorticosterone + NADP+
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-
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r
deoxycorticosterone + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione
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?
deoxycorticosterone + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione
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?
deoxycorticosterone + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione
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ir
progesterone + NADPH + H+
5alpha-pregnan-3,20-dione + NADP+
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-
-
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?
progesterone + NADPH + H+
5alpha-pregnan-3,20-dione + NADP+
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-
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?
progesterone + NADPH + H+
5alpha-pregnan-3,20-dione + NADP+
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-
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?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
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biosynthesis of cardenolides
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?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
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?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
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-
-
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?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
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?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
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activity is higher in hypothalamus of non-lactating female rats than in lactating
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r
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
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riboflavin-deficient diet decreases the enzyme activity, after 5 weeks no activity is remaining
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?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
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-
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?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
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-
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?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
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-
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?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
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-
-
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?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
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-
-
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?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
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-
-
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?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
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-
-
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?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
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-
-
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ir
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
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-
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ir
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
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-
-
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?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
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-
-
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?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
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-
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?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
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-
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?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
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5alpha-dihydrotestosterone is a potent androgen, abnormal overproduction is associated with pathologies of mainly prostate and skin, e.g. benign prostatic hyperplasia, prostate cancer, acne, androgenetic alopecia in men, and hirsutism in women, with different involvement of the isozymes
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?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
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dihydrotestosterone is a more potent androgen, regulatory function, overview
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?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
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reaction mechanism
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?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
the enzyme performs conversion of testosterone to dihydrotestosterone
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r
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
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-
-
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?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
5alpha-dihydrotestosterone is a more potent androgen, regulatory function, overview
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?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
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very low activity
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-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+ + H+
-
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+ + H+
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-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+ + H+
-
-
-
-
?
testosterone + NADPH + H+
androstan-3alpha,17beta-diol + androstan-3beta,17beta-diol + 5alpha-dihydrotestosterone
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-
-
r
testosterone + NADPH + H+
androstan-3alpha,17beta-diol + androstan-3beta,17beta-diol + 5alpha-dihydrotestosterone
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reversible in the presence of coenzyme Q10 as electron-acceptor, electrons are transferred from NADPH to coenzyme Q10 via the enzyme NADPH:coenzyme Q10-oxidoreductase and then to testosterone
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r
additional information
?
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testosterone and 20alpha-hydroxy-4-pregnen-3-one can act in place of progesterone
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?
additional information
?
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role of enzyme in initiation of spermatogenensis
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-
?
additional information
?
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neither Km nor Vmax for both corticosterone and testosterone are significantly different among reproductive periods
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-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
testosterone + NADPH + H+
dihydrotestosterone + NADP+
-
-
-
?
additional information
?
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-
role of enzyme in initiation of spermatogenensis
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
biosynthesis of cardenolides
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
activity is higher in hypothalamus of non-lactating female rats than in lactating
-
r
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
riboflavin-deficient diet decreases the enzyme activity, after 5 weeks no activity is remaining
-
-
?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
-
-
-
-
ir
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
5alpha-dihydrotestosterone is a potent androgen, abnormal overproduction is associated with pathologies of mainly prostate and skin, e.g. benign prostatic hyperplasia, prostate cancer, acne, androgenetic alopecia in men, and hirsutism in women, with different involvement of the isozymes
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
dihydrotestosterone is a more potent androgen, regulatory function, overview
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
the enzyme performs conversion of testosterone to dihydrotestosterone
-
-
r
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
5alpha-dihydrotestosterone is a more potent androgen, regulatory function, overview
-
?
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