Information on EC 1.3.1.22 - 3-oxo-5alpha-steroid 4-dehydrogenase (NADP+)

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The expected taxonomic range for this enzyme is: Eukaryota

EC NUMBER
COMMENTARY
1.3.1.22
-
RECOMMENDED NAME
GeneOntology No.
3-oxo-5alpha-steroid 4-dehydrogenase (NADP+)
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a 3-oxo-5alpha-steroid + NADP+ = a 3-oxo-DELTA4-steroid + NADPH + H+
show the reaction diagram
mechanism
-
a 3-oxo-5alpha-steroid + NADP+ = a 3-oxo-DELTA4-steroid + NADPH + H+
show the reaction diagram
sequential mechanism
-
a 3-oxo-5alpha-steroid + NADP+ = a 3-oxo-DELTA4-steroid + NADPH + H+
show the reaction diagram
reaction mechanism
-
a 3-oxo-5alpha-steroid + NADP+ = a 3-oxo-DELTA4-steroid + NADPH + H+
show the reaction diagram
kinetic mechanism
-
a 3-oxo-5alpha-steroid + NADP+ = a 3-oxo-DELTA4-steroid + NADPH + H+
show the reaction diagram
structure-activity relationship
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
allopregnanolone biosynthesis
-
-
androgen biosynthesis
-
-
Biosynthesis of secondary metabolites
-
-
Brassinosteroid biosynthesis
-
-
cardenolide biosynthesis
-
-
Metabolic pathways
-
-
Steroid hormone biosynthesis
-
-
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).
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
3-oxosteroid 5alpha-reductase
-
-
-
-
3-oxosteroid DELTA4-dehydrogenase
-
-
-
-
4-ene-3-oxosteroid 5alpha-reductase
-
-
-
-
4-ene-5alpha-reductase
-
-
-
-
5 alpha-R2
-
-
5 alpha-reductase type 2
-
-
5-alpha reductase I
-
isozyme
5-alpha reductase II
-
isozyme
5-alpha-reductase type 1
-
isozyme
5-alpha-reductase type 2
-
-
5-alpha-reductase type 2
-
isozyme
5a-reductase type 1
-
-
5a-reductase type 2
-
-
5alpha-R1
-
-
5alpha-R1
-
-
5alpha-R1
P24008
isozyme
5alpha-R1
P31214
isozyme
5alpha-R2
-
-
5alpha-R2
-
-
5alpha-R2
P24008
isozyme
5alpha-R2
P31214
isozyme
5alpha-reductase 1
-
-
5alpha-reductase II
-
-
5alpha-reductase type 1
-
-
5alpha-reductase type 1
-
the isoenzyme predominates in the reproductive tissues, genital skin, and epididymis
5alpha-reductase type 2
-
-
5alpha-reductase type 2
-
the isoenzyme is predominantly found in the skin, liver, and testes
5alpha-reductase type II
-
-
5alpha-SR2
P31213
-
5alphaR
-
-
5alphaR
Q5K2N1
-
5alphaR1
-
-
5alphaR2
-
-
cholest-4-en-3-one 5alpha-reductase
-
-
-
-
cortisone alpha-reductase
-
-
-
-
cortisone DELTA 4-5alphareductase
-
-
-
-
DELTA4-3-ketosteroid 5alpha-oxidoreductase
-
-
-
-
DELTA4-3-ketosteroid reductase (5alpha)
-
-
-
-
DELTA4-3-oxosteroid-5 alpha-reductase
-
-
-
-
DELTA4-5alpha-reductase
-
-
-
-
DELTA4-steroid 5alpha-reductase (progesterone)
-
-
-
-
LeDET2
Q5K2N1
-
NADPH:DELTA4-3-oxosteroid-5alpha-oxidoreductase
-
-
-
-
progesterone 5alpha-reductase
-
-
-
-
reduced nicotinamide adenine dinucleotide phosphate:DELTA4-3-ketosteroid 5alpha-oxidoreductase
-
-
-
-
reductase, cholestenone 5alpha-
-
-
-
-
reductase, cortisone DELTA: 4-5alpha-
-
-
-
-
reductase, progesterone 5alpha-
-
-
-
-
SRD5A2
-
-
SRD5A2
P31213
-
SRDA1
-
-
SRDA2
P31213
-
SRDA3
Q9H8P0
-
steroid 5-alpha reductase
-
-
steroid 5-alpha-reductase
-
-
-
-
steroid 5alpha-hydrogenase
-
-
-
-
steroid 5alpha-reductase
-
-
-
-
steroid 5alpha-reductase
-
-
steroid 5alpha-reductase
-
-
steroid 5alpha-reductase
-
-
steroid 5alpha-reductase
-
-
steroid 5alpha-reductase
P24008
-
steroid 5alpha-reductase
P31214
-
steroid 5alpha-reductase
Q5K2N1
-
testosterone 5alpha-reductase
-
-
-
-
testosterone 5alpha-reductase
-
-
testosterone delta4-5alpha-reductase
-
-
-
-
testosterone delta4-hydrogenase
-
-
-
-
type 1 5alpha-reductase
-
-
type 1 5alpha-reductase
-
isoenzyme
type 1 SR
-
-
type 1 steroid 5alpha reductase
-
-
type 1 steroid 5alpha-reductase
-
-
type 2 5alpha-reductase
-
-
type 2 5alpha-reductase
-
isoenzyme
type 2 SR
-
-
type 2 steroid 5alpha reductase
-
-
type 2 steroid 5alpha-reductase
-
-
type-1 5alpha-reductase
-
-
type-2 5alpha-reductase
-
-
microsomal steroid reductase (5alpha)
-
-
-
-
additional information
-
microsomal cholest-4-en-3-one 5alpha-reductase is not identical with microsomal DELTA4-3-ketosteroid 5alpha-reductase
CAS REGISTRY NUMBER
COMMENTARY
37255-34-8
-
72412-84-1
-
9029-09-8
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
floxglove
-
-
Manually annotated by BRENDA team
2 isozymes 5alpha-R1 and 5alpha-R2
-
-
Manually annotated by BRENDA team
; male and female, 2 isozymes 5alphaR-1 and 5alphaR-2
-
-
Manually annotated by BRENDA team
isoform 5alpha-SR2
UniProt
Manually annotated by BRENDA team
isoform I and II
-
-
Manually annotated by BRENDA team
isoform SRDA2
UniProt
Manually annotated by BRENDA team
isoform SRDA3
UniProt
Manually annotated by BRENDA team
isoform steroid 5-alpha-reductase 1
UniProt
Manually annotated by BRENDA team
isoform steroid 5-alpha-reductase 2
UniProt
Manually annotated by BRENDA team
patients, median age 70, range 55-86 years
-
-
Manually annotated by BRENDA team
recombinant isoforms 1 and 2, expressed in baculoviral system
-
-
Manually annotated by BRENDA team
golden Hamster
-
-
Manually annotated by BRENDA team
golden hamster, male
-
-
Manually annotated by BRENDA team
deficient in enzyme activity of isoform I or of isoform II
-
-
Manually annotated by BRENDA team
male withdrawal seizure-prone, WSP, and -resistant, WSR, mice
-
-
Manually annotated by BRENDA team
growth on fermented pistachos, lemons and corn tortillas
-
-
Manually annotated by BRENDA team
2 isozymes 5alpha-R1 and 5alpha-R2
-
-
Manually annotated by BRENDA team
isoform 5alpha reductase type 1
SwissProt
Manually annotated by BRENDA team
isoform 5alpha reductase type 2
UniProt
Manually annotated by BRENDA team
isoform I and II
-
-
Manually annotated by BRENDA team
isoforms I and II
-
-
Manually annotated by BRENDA team
isozyme 5alpha-R1
SwissProt
Manually annotated by BRENDA team
isozyme 5alpha-R2
UniProt
Manually annotated by BRENDA team
treatment with testosterone and estradiol
-
-
Manually annotated by BRENDA team
type 1 enzyme
-
-
Manually annotated by BRENDA team
Sf 9 cell-line
-
-
Manually annotated by BRENDA team
expressed in Arabidopsis thaliana
Swissprot
Manually annotated by BRENDA team
South African clawed frog
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
17-epitestosterone + NADPH
?
show the reaction diagram
-
-
-
-
?
17alpha,21-dihydroxypregn-4-ene-3,11,20-trione + NADPH
17alpha,21-dihydroxy-5alpha-pregnan-3,11,20-trione + NADP+
show the reaction diagram
-
trivial name cortisone
-
ir
17alpha,21-dihydroxypregn-4-ene-3,20-dione + NADPH
17alpha,21-dihydroxy-5alpha-pregnane-3,20-dione
show the reaction diagram
-
-
-
?
17alpha-hydroxyprogesterone + NADPH
17alpha-hydroxy-5alpha-pregnan-3,20-dione + NADP+
show the reaction diagram
-
-
-
-
ir
17beta-methyl-androsta-4,9-dien-3-one + NADPH
17beta-methyl-5alpha-androst-9-en-3-one + NADP+
show the reaction diagram
-
-
-
?
20-alpha-hydroxypregn-4-ene-3one + NADPH
20-alpha-hydroxy-5alpha-pregnan-3-one + NADP+
show the reaction diagram
-
-
-
-
-
20-alpha-hydroxypregn-4-ene-3one + NADPH
20-alpha-hydroxy-5alpha-pregnan-3-one + NADP+
show the reaction diagram
-
-
-
-
ir
20-alpha-hydroxypregn-4-ene-3one + NADPH
20-alpha-hydroxy-5alpha-pregnan-3-one + NADP+
show the reaction diagram
-
-
-
-
-
20alpha-hydroxy-4-pregnen-3-one + NADPH
20alpha-hydroxy-5-beta-pregnan-3-one + NADP+
show the reaction diagram
-
more reactive than progesterone
-
-
?
21-hydroxypregn-4-ene-3,20-dione + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione + NADP+
show the reaction diagram
-
-
-
?
5alpha-pregnan-3,20-dione + NADP+
progesterone + NADPH + H+
show the reaction diagram
-
-
-
-
r
androstenediol + NADPH
5alpha-androstan-3beta,17beta-diol + NADP+
show the reaction diagram
-
-
-
-
ir
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
show the reaction diagram
-
-
-
-
-
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
show the reaction diagram
-
-
-
-
-
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
show the reaction diagram
-
-
-
-
ir
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
show the reaction diagram
-
-
-
-
-
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
show the reaction diagram
Q5K2N1
-
-
-
?
campestenone + NADPH
5alpha-campestan-3-one + NADP+
show the reaction diagram
Q5K2N1
reduction at very low levels
-
-
?
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
show the reaction diagram
-
-
-
-
-
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
show the reaction diagram
-
-
-
-
-
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
show the reaction diagram
-
-
-
-
-
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
show the reaction diagram
-
-
-
-
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
show the reaction diagram
-
-
-
-
-
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
show the reaction diagram
-
-
-
-
-
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
show the reaction diagram
-
-
-
-
-
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
show the reaction diagram
-
-
-
-
-
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
show the reaction diagram
-
mammalian enzymes: no reverse reaction, first step in reverse direction (enolization) occurs, but energy barrier for hydride abstraction is extremely high
-
-
ir
cortexolone + NADPH
17alpha,21-dihydroxy-5alpha-pregnan-3,20-dione + NADP+
show the reaction diagram
-
-
-
-
ir
corticosterone + NADPH + H+
5alpha-dihydrocorticosterone + NADP+
show the reaction diagram
-
-
-
-
?
deoxycorticosterone + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione
show the reaction diagram
-
-
-
-
-
deoxycorticosterone + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione
show the reaction diagram
-
-
-
-
-
deoxycorticosterone + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione
show the reaction diagram
-
-
-
-
ir
deoxycorticosterone + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione
show the reaction diagram
-
-
-
-
-
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
-
-
-
?
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
-
-
-
?
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
-
-
-
?
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
-
-
r
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
-
-
r
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
-
-
r
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
-
-
-
?
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
-
-
?
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
-
-
?
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
-
-
ir
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
-
-
-
?
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
Q5K2N1
-
-
-
?
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
activity is higher in hypothalamus of non-lactating female rats than in lactating
-
r
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
biosynthesis of cardenolides
-
-
?
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
riboflavin-deficient diet decreases the enzyme activity, after 5 weeks no activity is remaining
-
-
?
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
Digitalis lanata VIII
-
-
-
?
progesterone + NADPH
5alpha-pregnan-3,20-dione + NADP+
show the reaction diagram
-
-
-
-
-
progesterone + NADPH
5alpha-pregnan-3,20-dione + NADP+
show the reaction diagram
-
-
-
-
?
progesterone + NADPH
5alpha-pregnan-3,20-dione + NADP+
show the reaction diagram
-
-
-
-
-
progesterone + NADPH
5alpha-pregnan-3,20-dione + NADP+
show the reaction diagram
-
-
-
-
ir
progesterone + NADPH
5alpha-pregnan-3,20-dione + NADP+
show the reaction diagram
-
-
-
-
-
progesterone + NADPH
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
?
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
Q5K2N1
-
-
-
?
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
P24008, P31214
-
-
-
?
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
-
5alpha-dihydrotestosterone is a more potent androgen, regulatory function, overview
-
?
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
-
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
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
-
dihydrotestosterone is a more potent androgen, regulatory function, overview
-
?
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
very low activity
-
-
?
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
reaction mechanism
-
-
?
testosterone + NADPH
androstan-3alpha,17beta-diol + androstan-3beta,17beta-diol + 5alpha-dihydrotestosterone
show the reaction diagram
-
-
-
r
testosterone + NADPH
androstan-3alpha,17beta-diol + androstan-3beta,17beta-diol + 5alpha-dihydrotestosterone
show the reaction diagram
-
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
-
r
testosterone + NADPH
17beta-hydroxy-5alpha-androstan-3-one + NADP+
show the reaction diagram
-
-
-
-
testosterone + NADPH
17beta-hydroxy-5alpha-androstan-3-one + NADP+
show the reaction diagram
-
-
-
-
testosterone + NADPH
17beta-hydroxy-5alpha-androstan-3-one + NADP+
show the reaction diagram
-
-
-
-
-
testosterone + NADPH
17beta-hydroxy-5alpha-androstan-3-one + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH
17beta-hydroxy-5alpha-androstan-3-one + NADP+
show the reaction diagram
-
-
-
-
-
testosterone + NADPH
17beta-hydroxy-5alpha-androstan-3-one + NADP+
show the reaction diagram
-
-
-
-
ir
testosterone + NADPH
17beta-hydroxy-5alpha-androstan-3-one + NADP+
show the reaction diagram
-
-
-
ir
testosterone + NADPH
17beta-hydroxy-5alpha-androstan-3-one + NADP+
show the reaction diagram
-
-
-
-
-
testosterone + NADPH
17beta-hydroxy-5alpha-androstan-3-one + NADP+
show the reaction diagram
-
-
-
-
-
testosterone + NADPH
17beta-hydroxy-5alpha-androstan-3-one + NADP+
show the reaction diagram
-
-
-
-
-
testosterone + NADPH
17beta-hydroxy-5alpha-androstan-3-one + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+ + H+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+ + H+
show the reaction diagram
-
-
-
-
ir
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+ + H+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+ + H+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
epitestosterone + NADPH
?
show the reaction diagram
-
-
-
-
ir
additional information
?
-
-
testosterone and 20alpha-hydroxy-4-pregnen-3-one can act in place of progesterone, testosterone is less effective
-
-
-
additional information
?
-
-
testosterone is less effective
-
-
-
additional information
?
-
-
role of enzyme in initiation of spermatogenensis
-
-
-
additional information
?
-
-
no activity for campestenone
-
-
-
additional information
?
-
-
neither Km nor Vmax for both corticosterone and testosterone are significantly different among reproductive periods
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
-
-
-
?
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
-
-
r
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
-
-
?
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
-
-
ir
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
-
-
-
?
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
activity is higher in hypothalamus of non-lactating female rats than in lactating
-
r
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
biosynthesis of cardenolides
-
-
?
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
riboflavin-deficient diet decreases the enzyme activity, after 5 weeks no activity is remaining
-
-
?
progesterone + NADPH
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
Digitalis lanata VIII
-
-
-
?
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
-
5alpha-dihydrotestosterone is a more potent androgen, regulatory function, overview
-
?
testosterone + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
-
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
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
-
dihydrotestosterone is a more potent androgen, regulatory function, overview
-
?
testosterone + NADPH
17beta-hydroxy-5alpha-androstan-3-one + NADP+
show the reaction diagram
-
-
-
-
ir
testosterone + NADPH
17beta-hydroxy-5alpha-androstan-3-one + NADP+
show the reaction diagram
-
-
-
-
-
5alpha-pregnan-3,20-dione + NADP+
progesterone + NADPH + H+
show the reaction diagram
-
-
-
-
r
additional information
?
-
-
role of enzyme in initiation of spermatogenensis
-
-
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADP+
-
-
NADPH
-
cannot be replaced by NADH
NADPH
-
cannot be replaced by NADH
NADPH
-
absolute requirement for NADPH
NADPH
-
absolute requirement for NADPH
NADPH
-
absolute requirement for NADPH; the NADPH following amino acids of 5alpha-reductase are identified as NADPH-binding site: NLRKPGETGYK
NADPH
Q5K2N1
-
NADPH
P24008, P31214
;
NADPH
-
dependent
coenzyme Q10
-
-
additional information
-
-
-
additional information
-
absolute requirement for NADPH in rat epididymis; NADH: low avtivity
-
additional information
-
absolute requirement for NADPH in rat epididymis; NADH: no activity
-
additional information
-
absolute requirement for NADPH in rat epididymis
-
additional information
-
absolute requirement for NADPH in rat epididymis; absolute requirement for NADPH in rat liver; NADH: no activity
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
EDTA
-
stimulatory at concentration 2 mM
K+
-
stimulate
Li+
-
stimulate
Mg2+
-
stimulatory at concentration 1 mM
additional information
-
not dependent on divalent cation
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(+)-methysticin
-
-
(+/-)-LY191704
-
i.e. (4aS,10aR)-7-chloro-1-methyl-3,4,4a,9,10,10a-hexahydrophenanthren-2(1H)-one, non-steroidal, most potent benzoquinoline mimicing 4-azasteroid inhibitors, and specific for isozyme 5alphaR-1, IC50 is 30 nM
(-)-epigallocatechin-3-gallate
-
i.e. EGCG, from Thea sativa, slightly inhibits the liver microsomal enzyme
(10bR)-8-chloro-4,10b-dimethyl-4a,5,6,10b-tetrahydrophenanthridin-2(1H)-one
-
isoform II, 49% inhibition at 0.02 mM
(10bR)-8-chloro-4,5,10b-trimethyl-4a,5,6,10b-tetrahydrophenanthridin-2(1H)-one
-
isoform II, 57% inhibition at 0.029 mM
(10bR)-8-chloro-5,10b-dimethyl-4a,5,6,10b-tetrahydrophenanthridin-2(1H)-one
-
isoform II, 42% inhibition at 0.03 mM
(2E,4E,6E,8E)-((2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoate
-
compound shows moderate anti-tumour activity in vivo
(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl palmitoate
-
activity of 3-O-acylated (e)-epigallocatechins increases with the increasing carbon numbers of the fatty acid moiety, reaching maximum for palmitoate
(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(1,3,5-benzotrioxepin-6-ylmethyl)tetrahydrofuran-2-ol
-
-
(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(1,3,5-benzotrioxepin-7-ylmethyl)tetrahydrofuran-2-ol
-
i.e. (-)-cubebin
(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(2,3-dimethoxybenzyl)tetrahydrofuran-2-ol
-
-
(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(3,4-dimethoxybenzyl)tetrahydrofuran-2-ol
-
i.e. (-)-3,4-dimethoxy-3,4-desmethylenedioxycubebin
(4aS)-7-chloro-4a-methyl-2,3,4,4a-tetrahydrophenanthrene-2-carboxylic acid
-
-
(4aS,10bS)-4,10b-dimethyl-8-[(E)-2-naphthylylvinyl]-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 6 nM, isoform II, 50% inhibition at 0.00134 mM
(4aS,10bS)-4,10b-dimethyl-8-[(E)-2-phenylvinyl]-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 6 nM, isoform II, 50% inhibition at 0.0014 mM
(4aS,10bS)-4,8-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 11 nM
(4aS,10bS)-8-(2-furyl)-4,10b-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 59 nM, isoform II, 50% inhibition above 10 nM
(4aS,10bS)-8-bromo-4-methyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 35 nM
(4aS,10bS)-8-chloro-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 60 nM
(4aS,10bS)-8-chloro-4,10b-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 17 nM
(4aS,10bS)-8-chloro-4-methyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 8 nM, isoform II, 50% inhibition above 0.01 mM
(4aS,10bS)-8-fluoro-4-methyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 35 nM
(4aS,10bS)-8-methoxy-4-methyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 120 nM
(4R)-4,8-dimethyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 312 nM
(4R)-8-chloro-4-methyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 141 nM
(4S)-4,8-dimethyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 137 nM
(5'S)-17beta-(2-chlorophenyl-4,5-dihydrooxazol-5-yl)androst-5-en-3-one
-
-
-
(5'S)-17beta-(4-bromophenyl-4,5-dihydrooxazol-5-yl)androst-5-en-3-one
-
-
-
(5alpha,20-R)-4-Diazo-21-hydroxy-20-methylpregnan-3-one
-
RMI18,341
(6R)-8-chloro-6-methyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 188 nM
(Z)-((2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl) hexadec-9-enoate
-
-
1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 298 nM
1-methyl-5-(4-(2-phenylacetyl)phenyl)pyridin-2(1H)-one
-
61% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
10-azasteroids
-
several
11-ketoprogesterone
-
complete inhibition
17-diisopropylcarbamoyl-2-androsten-3-carboxylate
-
-
17-diisopropylcarbamoyl-3,5-androstadien-3-carboxylate
-
-
17-diisopropylcarbamoyl-3-androsten-3-carboxyate
-
-
17-diisopropylcarbamoyl-androstan-3-carboxylate
-
-
17-tert-butylcarbamoyl-3,5-androstadien-3-carbaldehyde
-
-
17-tert-butylcarbamoyl-3,5-androstadien-3-carboxylate
-
dead-end inhibition versus testosterone
17-tert-butylcarbamoyl-3,5-androstadien-3-ol
-
-
17a-(2-propionoxyethyl)-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
P18405, P31213
0.01 mM, 100% inhibition; 0.01 mM, 8.5% inhibition
17a-allyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
P18405, P31213
0.01 mM, 0.4% inhibition; 0.01 mM, 99% inhibition
17a-ethyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
P18405, P31213
0.01 mM, 100% inhibition; 0.01 mM, 32.3% inhibition
17a-methyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
P18405, P31213
0.01 mM, 18.9% inhibition; 0.01 mM, 99% inhibition
17alpha-hydroxyprogesterone
-
-
17alpha-p-bromophenylcarbamoyloxy-4-pregnen-3 20-dione
-
-
17alpha-p-bromophenylcarbamoyloxy-4-pregnen-3,20-dione
-
-
17alpha-phenylcarbamoyloxy-4-pregnen-3,20-dione
-
-
17beta-(N-tert-butylcarbamoyl)androsta-3,5-diene-3-carboxylic acid
-
-
17beta-Carbamoyl-1,3,5(10)-estratriene-3-carboxylic acids
-
formation of enzyme-NADP+-inhibitor complex
17beta-estradiol
-
-
17beta-estradiol
-
noncompetitive inhibition
17beta-hydroxyandrosta-1,4-dien-3-one
-
50% inhibition
17beta[3-(N-4-bromophenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-chlorophenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-ethoxyphenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-ethylphenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-methoxyphenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-phenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-tolyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
slight inhibition
19-norandrost-4-ene-3,17-dione
-
complete inhibition
19-nortestosterone
-
complete inhibition
2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
-
-
2-(16-(acetylthio)hexadecanamido)ethyl 6-(2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamido)hex-4-enoate
-
43% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
2-(2-(16-(acetylthio)hexadecanamido)ethoxy)ethyl 6-(2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamido)hex-4-enoate
-
33% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
20alpha-hydroxypregn-4-en-3-one
-
competitive
21,21-pentamethylene-4-aza-5alpha-pregn-1-ene-3,20-dione
-
i.e. L685,273, suppresses testicular enzyme activity during puberty by 75-86%
3-Androstene-3-carboxylic acids
-
-
3-Androstene-3-carboxylic acids
-
uncompetitive
3beta-(3'-oxapentanoyloxy)-androst-5-en-17-one
-
good in vitro inhibitory activity, but compound does not bind to the androgen receptors
-
3beta-acetoxyandrost-5-en-17-one
-
good in vitro inhibitory activity, but compound does not bind to the androgen receptors
-
3beta-hexanoyloxyandrost-5-en-17-one
-
good in vitro inhibitory activity, but compound does not bind to the androgen receptors
-
4,16-androstadien-3-one
-
-
4,6,8-trimethyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 15.8 nM
4,8-dimethyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 20 nM
4-(1-[4-[acetyl(methyl)amino]-3-methylphenyl]-1-ethylpropyl)-2-methylphenyl diethylcarbamate
-
22% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]-3-methylphenyl]-1-ethylpropyl)phenyl diethylcarbamate
-
25% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)-2-methylphenyl diethylcarbamate
-
56% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl 4-methylpiperazine-1-carboxylate
-
17% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl azepane-1-carboxylate
-
70% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl azocane-1-carboxylate
-
20% inhibition at 0.001 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl bis(1-methylethyl)carbamate
-
72% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl bis(1-methylpropyl)carbamate
-
22% inhibition at 0.001 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl dibenzylcarbamate
-
51% inhibition at 0.001 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl dibutylcarbamate
-
32% inhibition at 0.001 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl diethylcarbamate
-
57% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl dimethylcarbamate
-
29% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl dipropylcarbamate
-
77% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl morpholine-4-carboxylate
-
15% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl piperidine-1-carboxylate
-
68% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl pyrrolidine-1-carboxylate
-
57% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-methylethyl)phenyl diethylcarbamate
-
16% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-propylbutyl)phenyl diethylcarbamate
-
27% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]cyclobutyl)phenyl diethylcarbamate
-
16% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]cycloheptyl)phenyl diethylcarbamate
-
25% inhibition at 0.01 mM; 46% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]cyclopentyl)phenyl diethylcarbamate
-
5% inhibition at 0.01 mM
4-(2-[5-[(diphenylmethyl)carbamoyl]-1-benzofuran-2-yl]phenoxy)butanoic acid
-
isoform I, 50% inhibition at 310 nM, isoform II, 50% inhibition above 0.1 mM
4-(2-[6-[(diphenylmethyl)carbamoyl]-1-benzofuran-2-yl]phenoxy)butanoic acid
-
isoform I, 50% inhibition at 62 nM, isoform II, 50% inhibition at 270 nM
4-(3-(4-(N-methylacetamido)phenyl)pentan-3-yl)phenyl dibenzylcarbamate
-
competitive inhibitor
4-(4'-formylphenoxy)benzoic acid
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.007 mM
4-(4'-formylphenoxy)benzoic acid
-
37C, pH 6.6, 7% inhibition at 0.01 mM, isoform I, 37C, pH 5.5, 16% inhibition at 0.01 mM, isoform II
4-(biphenyl-4'-yloxy)phenylacetic acid
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.00006 mM
4-(biphenyl-4'-yloxy)phenylacetic acid
-
37C, pH 6.6, 29% inhibition at 0.01 mM, isoform I, 37C, pH 5.5, 50% inhibition at 0.0096 mM, isoform II
4-(biphenyl-4'-yloxy)phenylformic acid
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.000006 mM
4-(biphenyl-4'-yloxy)phenylformic acid
-
37C, pH 6.6, 21% inhibition at 0.01 mM, isoform I, 37C, pH 5.5, 15% inhibition at 0.01 mM, isoform II
4-(N-(diphenyl)acetyl-4-piperidinyloxy)benzoic acid
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.0013 mM
4-(N-(diphenyl)acetyl-4-piperidinyloxy)benzoic acid
-
isoform 1, pH 6.6, 37C, 62% inhibition at 0.01 mM, isoform 2, pH 5.5, 37C, 58% inhibition at 0.01 mM
4-(N-(diphenyl)carbamoyl-4-piperidinyloxy)benzoic acid
-
pH 5.5, 37C, DU145 cells, 10% inhibition at 0.01 mM, BPH tissue, 68% inhibition at 0.01 mM
4-(N-(diphenyl)carbamoyl-4-piperidinyloxy)benzoic acid
-
isoform 1, pH 6.6, 37C, 53% inhibition at 0.01 mM, isoform 2, pH 5.5, 37C, 50% inhibition at 0.01 mM
4-(N-(tert-butyloxycarbonyl)-4-piperidinyloxy)benzoic acid
-
pH 5.5, 37C, DU145 cells, 2% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.0078 mM
4-(N-(tert-butyloxycarbonyl)-4-piperidinyloxy)benzoic acid
-
isoform 1, pH 6.6, 37C, 4% inhibition at 0.01 mM, isoform 2, pH 5.5, 37C, 12% inhibition at 0.01 mM
4-(N-adamantanoyl-4-piperidinyloxy)benzoic acid
-
pH 5.5, 37C, DU145 cells, 7% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.00043 mM
4-(N-adamantanoyl-4-piperidinyloxy)benzoic acid
-
isoform 1, pH 6.6, 37C, 18% inhibition at 0.01 mM, isoform 2, pH 5.5, 37C, 21% inhibition at 0.01 mM
4-Androsten-3-one-17beta-carboxylic acid
-
competitive
4-Aza-4-methyl-5alpha-pregnane-3,20-dione
-
competitive against progesterone, reversible, transition state analog
4-Aza-4-methyl-5alpha-pregnane-3,20-dione
-
-
4-azasteroids
-
competitive inhibition
4-azasteroids
-
-
4-bromo-17alpha-(p-fluorobenzoyloxy)-4-pregnene-3,20-dione
-
competitive
4-carboxy-4'-(N,N-dicyclohexyl)-aminobiphenyl
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.0047 mM, DU145 cells, 44% inhibition at 0.001 mM
4-carboxy-4'-(N,N-dicyclohexyl)-aminobiphenyl
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.0014 mM, DU145 cells, 44% inhibition at 0.003 mM
4-carboxy-4'-(N,N-diisobutyl)-aminobiphenyl
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.004 mM, DU145 cells, 16% inhibition at 0.001 mM
4-carboxy-4'-(N,N-diisobutyl)-aminobiphenyl
-
37C, pH 6.6, 24% inhibition at 0.001 mM, isoform I, 37C, pH 5.5, 37% inhibition at 0.001 mM, isoform II
4-carboxy-4'-(N,N-diisopropyl)-aminobiphenyl
-
pH 5.5, 37C, BPH tissue, 15% inhibition at 0.001 mM, DU145 cells, 9% inhibition at 0.001 mM
4-carboxy-4'-(N,N-diisopropyl)-aminobiphenyl
-
37C, pH 6.6, 4% inhibition at 0.01 mM, isoform I, 37C, pH 5.5, 10% inhibition at 0.01 mM, isoform II
4-carboxy-4'-(N,N-diphenyl)-aminobiphenyl
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.00233 mM, DU145 cells, 28% inhibition at 0.001 mM
4-carboxy-4'-(N,N-diphenyl)-aminobiphenyl
-
37C, pH 6.6, 50% inhibition at 0.00046 mM, isoform I, 37C, pH 5.5, 50% inhibition at 0.003 mM, isoform II
4-carboxy-4'-(N-adamantyl)-aminobiphenyl
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.0019 mM, DU145 cells, 16% inhibition at 0.001 mM
4-carboxy-4'-(N-adamantyl)-aminobiphenyl
-
37C, pH 6.6, 50% inhibition at 0.0056 mM, isoform I, 37C, pH 5.5, 50% inhibition at 0.01 mM, isoform II
4-Ene-3-keto-steroids
-
17beta-estradiol in high concentrations functions as an uncompetitive inhibitor
4-MA
Q5K2N1
active at 0.01 mM
4-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 185 nM
4-methyl-4-azasteroids
-
4-MA is a 90-fold more potent inhibitor than finasteride in the DU 145 cell-line; competitive
-
4-methyl-4-azasteroids
-
competitive
-
4-methyl-4-azasteroids
-
competitive
-
4-methyl-4-azasteroids
-
competitive
-
4-methyl-5,6-dihydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 1400 nM
4-methyl-azasteroid
-
-
4-[1-[4-(acetylamino)-3-methylphenyl]-1-ethylpropyl]-2-methylphenyl diethylcarbamate
-
17% inhibition at 0.01 mM
4-[2-(6-[[bis(4-fluorophenyl)methyl]carbamoyl]-1-benzofuran-2-yl)phenoxy]butanoic acid
-
isoform I, 50% inhibition at 50 nM, isoform II, 50% inhibition at 340 nM
4-[2-(6-[[bis(4-methoxyphenyl)methyl]amino]-1-benzofuran-2-yl)phenoxy]butanoic acid
-
isoform I, 50% inhibition at 42 nM, isoform II, 50% inhibition at 480 nM
4-[2-(6-[[bis(4-methoxyphenyl)methyl]carbamoyl]-1-benzofuran-2-yl)phenoxy]butanoic acid
-
isoform I, 50% inhibition at 130 nM, isoform II, 50% inhibition at 930 nM
4-[3-[(2,2-diphenyl-1,3-benzodioxol-5-yl)oxy]-2-methyl-1H-indol-1-yl]butanoic acid
-
isoform I, 50% inhibition at 10 nM, isoform II, 50% inhibition at 6300 nM
5alpha-androstane-3,17-dione
-
30% inhibition
6,8-dimethyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 14.3 nM
6-azasteroids
-
several
6-methylene-17alpha-(2-cyclohexylacetoxy)-pregn-4-ene-3,20-dione
-
-
6-methylene-17alpha-(3-cyclohexylpropionyloxy)-pregn-4-ene-3,20-dione
-
-
6-methylene-17alpha-(3-cyclopentylpropionyloxy)-pregn-4-ene-3,20-dione
-
-
6-methylene-17alpha-(4-cyclohexylbutyryloxy)-pregn-4-ene-3,20-dione
-
-
6alpha-methyl-11-ketoprogesterone
-
25% inhibition
6beta-methyl-11-ketoprogesterone
-
50% inhibition
7-bromo-2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
-
-
7-chloro-2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
-
-
8-bromo-4-methyl-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one
-
50% inhibition at 60 nM, isoform I
8-chloro-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 49 nM
8-chloro-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one
-
50% inhibition at 460 nM, isoform I
8-chloro-1-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 204 nM
8-chloro-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 459 nM
8-chloro-4,5-dimethyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 15.6 nM
8-chloro-4,6-dimethyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 8.5 nM
8-chloro-4-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 7.6 nM
8-chloro-4-methyl-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one
-
50% inhibition at 30 nM, isoform I
8-chloro-5-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 346 nM
8-chloro-6-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 14.4 nM
8-fluoro-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one
-
50% inhibition at 600 nM, isoform I
8-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 376 nM
8-methyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 176 nM
AFA131
Q5K2N1
active at 0.01 mM
AFA192
Q5K2N1
active at 0.01 mM
AFA27
Q5K2N1
active at 0.01 mM
AFA76
Q5K2N1
active at 0.01 mM, most potent inhibitor among non-steroid compounds tested
alpha-4-azasteroids
-
substitution of finasteride N-group by 6-azasteroids increased the rate of inhibition of type-1 5-alpha-reductases
androst-1-ene-3,17dione
-
55% inhibition
androst-4-ene-3,17-dione
-
complete inhibition
androst-4-enedione
-
-
AS601811
Q5K2N1
active at 0.01 mM
asclepic acid
-
50% inhibition at 0.50 mM
benzoquilizin-3-ones
-
diverse, mimics of 10-azasteroids, overview, structure-activity relationships
benzoquinolines
-
compounds as mimics of 4-azasteroid inhibitors, diverse, overview, compounds derived from 6-azasteroids, overview
beta-sitosterol
-
-
Biochanin A
-
-
Ca2+
-
1 mM: less than 20% inhibition
Cd2+
-
1 mM: less than 20% inhibition
cholest-5-en-3-one
-
-
dehydroepiandrosterone
-
good in vitro inhibitory activity, but compound does not bind to the androgen receptors
deoxycorticosterone acetate
-
competitive
Detergents
-
e.g.: Lubrol WX, Nonidet P-40, octyl D-glucopyranoside, L-alpha-lysophosphatidylcholine, CHAPS, concentration-dependent inhibition
dihydrotestosterone
-
significantly decreases 5alpha-R1 mRNA and 5alpha-R2 mRNA expression in female rats
docosanol
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
dutasteride
-
inhibits both isozymes, used in treatment of benign protstate hyperplasia, reduction of serum dihydrotestosterone levels
dutasteride
-
slow, time-dependent inhibitor, more efficient than finasteride
dutasteride
-
90% inhibition of type-2 and type-1 5alpha-reductases at clinical dosage of 0.5 mg/day
dutasteride
-
inhibitor of isoenzymes 5-alpha-reductase type 1 and type 2
dutasteride
-
0.5 mg/day, dual 5alpha-reductase inhibitor
dutasteride
-
-
dutasteride
-
-
dutasteride
-
dual 5alpha-reductase inhibitor, 45fold more effective in inhibiting type 1 5alpha-reductase and 2fold more effective in inhibiting type 2 5alpha-reductase than finasteride
dutasteride
-
dual 5alpha-reductase inhibitor
dutasteride
-
0.5 mg/day, inhibitor of type 1 and type 2 5alpha reductase; treatment with 0.5 mg daily for 1 year leads to reduced enzyme activity
EDTA
-
slightly inhibitory
epristeride
-
-
estradiol
-
in female genital skin fibroblasts
estradiol-17beta
-
-
estradiol-17beta
-
high concentration
ethinylestradiol
-
50% inhibition at 0.81 mM
ethinylestradiol
-
; 63.3% inhibition at 1 mM
finasteride
-
17-beta-N-tert-butylcarbonyl-4-aza-5alpha-androstan-1-en-3-one is a time-dependent, apparently irreversible inhibitor of 5alpha-reductases, but does not fully inhibit the activity of 5alpha-reductase in vivo
finasteride
-
-
finasteride
-
-
finasteride
-
replacement of residues 26-29 (AVFA) from isozyme 1 with residues 21-24 (GALA) from isozyme 2 increases the resistance to finasteride, what confirms that residues 26-29 from isozyme 1 are involved in the inhibitor/substrate binding but suggest residues 21-29 from isozyme 2 are not. More findings indicate that residues 15-17 of human 5 alpha-reductase 2 participate in inhibitor/substrate binding
finasteride
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.000003 mM, DU145 cells, 50% inhibition at 0.00041 mM
finasteride
-
37C, pH 6.6, 50% inhibition at 0.00001 mM, isoform I, 37C, pH 5.5, 50% inhibition at 0.00001 mM, isoform II
finasteride
-
; 4-azasteroid, specific for isozyme 5alphaR-2, used in treatment of benign protstate hyperplasia, reduction of serum dihydrotestosterone levels
finasteride
-
competitive
finasteride
-
i.e. 17beta-(N-tert-butylcarbamoyl)-4-aza-5alpha-androst-1-en-3-one
finasteride
-
slow, time-dependent inhibitor
finasteride
Q5K2N1
active at 0.01 mM
finasteride
-
70% inhibition of type-2 5alpha-reductase at clinical dosage of 5.0 mg/day
finasteride
-
5alphaR2 inhibitor
finasteride
-
5 mg/day, selective inhibitor of isoenzyme 5-alpha-reductase type 2
finasteride
-
5.0 mg/day, effective inhibitor of type 2 5alpha-reductase
finasteride
-
-
finasteride
-
type 2 5alpha-reductase inhibitor
finasteride
-
5.0 mg/day, inhibits type 2 5alpha-reductase; treatment with 5 mg daily for 1 year leads to reduced enzyme activity
finasteride
-
5 mg/day
finasteride
-
-
finasteride
-
0.025 mM, 78.3% inhibition
FK143
-
i.e. 4-[3-(3-[[bis-(4-isobutyl-phenyl)-methyl]amino]-benzoyl)-indol-1-yl]-butyric acid, a non-steroidal bi-substrate inhibitor
flavins
-
and flavin analogs, high concentration
-
genistein
-
-
ginsenoside Rg3
-
a unique ginsenoside in red ginseng
ginsenoside Ro
-
topical administration of ginsenoside Ro at 0.2 mg/mouse to shaved skin inhibits hair regrowth suppression after shaving in the testosterone-treated C57BL/6 mice
-
ginsenoside Ro
-
predominant ginsenoside in the rhizome of ginseng
-
kaikasaponin III
-
0.1 mM, 66.8% inhibition
lauric acid
-
isoform 1, 50% inhibition at 0.0167 mM, isoform 2, 50% inhibition at 0.0186 mM
lauric acid ethyl ester
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
linoleic acid
-
50% inhibition at 0.37 mM
linoleic acid
-
isoform 1, 50% inhibition at 0.013 mM, isoform 2, 50% inhibition at 0.035 mM
LY306089
-
a non steroid, non-competitive inhibitor of type I 5alpha-reductase in DU145 cells
MK386
-
steroidal inhibitor
MK386
-
potent inhibitory effect on 5alphaR1
MK434
-
-
myristic acid
-
isoform 2, 50% inhibition at 0.004 mM
N(dicyclohexyl)acetylpiperidine-4-(2-methoxybenzylidene-4-carboxylic acid)
-
isoform 1, pH 6.6, 37C, 55% inhibition at 0.01 mM, isoform 2, pH 5.5, 37C, 43% inhibition at 0.01 mM
N,N-bis(1-methylethyl)-4-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yl)benzamide
-
isoform I, 50% inhibition at 510 nM, isoform II, 9% inhibition at 0.01 mM
N,N-dicyclohexyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.0067 mM, DU145 cells, 4% inhibition at 0.001 mM
N,N-dicyclohexyl-4-(4'-carboxyphenoxy)benzamide
-
37C, pH 6.6, 50% inhibition at 0.0041 mM, isoform I, 37C, pH 5.5, 50% inhibition at 0.01 mM, isoform II
N,N-diisobutyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37C, BPH tissue, 46% inhibition at 0.01 mM
N,N-diisobutyl-4-(4'-carboxyphenoxy)benzamide
-
37C, pH 6.6, 18% inhibition at 0.01 mM, isoform I, 37C, pH 5.5, 22% inhibition at 0.01 mM, isoform II
N,N-diisopropyl-2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamide
-
8% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
N,N-diisopropyl-2-(4-(1-methyl-6-oxopiperidin-3-yl)phenoxy)acetamide
-
6% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
N,N-diisopropyl-2-(4-(2-methyl-4-oxo-3,4-dihydropyridin-1(2H)-yl)phenoxy)acetamide
-
3% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
N,N-diisopropyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37C, BPH tissue, 36% inhibition at 0.01 mM, DU145 cells, 4% inhibition at 0.001 mM
N,N-diisopropyl-4-(4'-carboxyphenoxy)benzamide
-
37C, pH 6.6, 4% inhibition at 0.01 mM, isoform I
N,N-diphenyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.00085 mM
N,N-diphenyl-4-(4'-carboxyphenoxy)benzamide
-
37C, pH 6.6, 50% inhibition at 0.0045 mM, isoform I, 37C, pH 5.5, 26% inhibition at 0.001 mM, isoform II
N-(1-adamantanoyl)piperdine-4-(2-methoxybenzyliden-4-carboxylic acid)
-
pH 5.5, 37C, DU145 cells, 10% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.0012 mM
N-(1-adamantanoyl)piperdine-4-(2-methoxybenzyliden-4-carboxylic acid)
-
isoform 1, pH 6.6, 37C, 50% inhibition at 0.0011 mM, isoform 2, pH 5.5, 37C, 50% inhibition at 0.0011 mM
N-(1-adamantanoyl)piperidine-4-(2-fluorobenzylidene-4-carboxylic acid)
-
pH 5.5, 37C, DU145 cells, 20% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.00021 mM
N-(1-adamantanoyl)piperidine-4-(2-fluorobenzylidene-4-carboxylic acid)
-
isoform 1, pH 6.6, 37C, 52% inhibition at 0.01 mM, isoform 2, pH 5.5, 37C, 51% inhibition at 0.01 mM
N-(3,3-diphenyl)propanoylpiperidine-4-(benzylidene-4-carboxylic acid)
-
pH 5.5, 37C, DU145 cells, 8% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.0011 mM
N-(3,3-diphenyl)propanoylpiperidine-4-(benzylidene-4-carboxylic acid)
-
isoform 1, pH 6.6, 37C, 50% inhibition at 0.0016 mM, isoform 2, pH 5.5, 37C, 50% inhibition at 0.00088 mM
N-(dicyclohexyl)acetylpiperidine-4-(2-fluorobenzylidene-4-carboxylic acid)
-
pH 5.5, 37C, DU145 cells, 12% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.000011 mM
N-(dicyclohexyl)acetylpiperidine-4-(2-fluorobenzylidene-4-carboxylic acid)
-
isoform 1, pH 6.6, 37C, 50% inhibition at 0.0018 mM, isoform 2, pH 5.5, 37C, 50% inhibition at 0.003 mM
N-(dicyclohexyl)acetylpiperidine-4-(2-methoxybenzylidene-4-carboxylic acid)
-
pH 5.5, 37C, DU145 cells, 5% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.00013 mM
N-(dicyclohexyl)acetylpiperidine-4-(benzylidene-3-carboxylic acid)
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.0007mM
N-(dicyclohexyl)acetylpiperidine-4-(benzylidene-3-carboxylic acid)
-
isoform 1, pH 6.6, 37C, 35% inhibition at 0.01 mM, isoform 2, pH 5.5, 37C, 25% inhibition at 0.01 mM
N-(dicyclohexyl)acetylpiperidine-4-(benzylidene-4-acetic acid)
-
pH 5.5, 37C, DU145 cells, 6% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.000006 mM
N-(dicyclohexyl)acetylpiperidine-4-(benzylidene-4-acetic acid)
-
isoform 1, pH 6.6, 37C, 66% inhibition at 0.01 mM, isoform 2, pH 5.5, 37C, 56% inhibition at 0.01 mM
N-(dicyclohexyl)acetylpiperidine-4-(benzylidene-4-carboxylic acid)
-
pH 5.5, 37C, DU145 cells, 46% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.00006 mM
N-(dicyclohexyl)acetylpiperidine-4-(benzylidene-4-carboxylic acid)
-
isoform 1, pH 6.6, 37C, 51% inhibition at 0.01 mM, isoform 2, pH 5.5, 37C, 50% inhibition at 0.00008 mM
N-(diphenyl)acetylpiperidine-4-(2-fluorobenzylidene-4-carboxylic acid)
-
pH 5.5, 37C, DU145 cells, 2% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.00041 mM
N-(diphenyl)acetylpiperidine-4-(2-fluorobenzylidene-4-carboxylic acid)
-
isoform 1, pH 6.6, 37C, 50% inhibition at 0.0011 mM, isoform 2, pH 5.5, 37C, 50% inhibition at 0.0011 mM
N-(diphenyl)acetylpiperidine-4-(2-methoxybenzylidene-4-carboxylic acid)
-
pH 5.5, 37C, DU145 cells, 8% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.0035 mM
N-(diphenyl)acetylpiperidine-4-(2-methoxybenzylidene-4-carboxylic acid)
-
isoform 1, pH 6.6, 37C, 50% inhibition at 0.0019 mM, isoform 2, pH 5.5, 37C, 50% inhibition at 0.00094 mM
N-(diphenyl)acetylpiperidine-4-(benzylidene-3-carboxylic acid)
-
pH 5.5, 37C, DU145 cells, 6% inhibition at 0.01 mM, BPH tissue, 57% inhibition at 0.01 mM
N-(diphenyl)acetylpiperidine-4-(benzylidene-3-carboxylic acid)
-
isoform 1, pH 6.6, 37C, 49% inhibition at 0.01 mM, isoform 2, pH 5.5, 37C, 43% inhibition at 0.01 mM
N-(diphenyl)acetylpiperidine-4-(benzylidene-4-acetic acid)
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.000075 mM
N-(diphenyl)acetylpiperidine-4-(benzylidene-4-acetic acid)
-
isoform 1, pH 6.6, 37C, 50% inhibition at 0.0045 mM, isoform 2, pH 5.5, 37C, 63% inhibition at 0.01 mM
N-adamantyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.00038 mM
N-adamantyl-4-(4'-carboxyphenoxy)benzamide
-
37C, pH 6.6, 50% inhibition at 0.0082 mM, isoform I, 37C, pH 5.5, 50% inhibition at 0.008 mM, isoform II
N-allyl-2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamide
-
6% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
N-allyl-2-(4-(2-methyl-4-oxo-3,4-dihydropyridin-1(2H)-yl)phenoxy)acetamide
-
8% inhibition of type 1 steroid 5alpha reductase at 0.01 mM and 12% inhibition of type 2 steroid 5alpha reductase at 0.01 mM
N-cyclohexyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.0023 mM
N-cyclohexyl-4-(4'-carboxyphenoxy)benzamide
-
37C, pH 6.6, 17% inhibition at 0.01 mM, isoform I, 37C, pH 5.5, 35% inhibition at 0.01 mM, isoform II
N-phenyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.001 mM
N-phenyl-4-(4'-carboxyphenoxy)benzamide
-
37C, pH 6.6, 22% inhibition at 0.01 mM, isoform I, 37C, pH 5.5, 39% inhibition at 0.01 mM, isoform II
N-tert-butyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37C, BPH tissue, 50% inhibition at 0.0028 mM
N-tert-butyl-4-(4'-carboxyphenoxy)benzamide
-
37C, pH 6.6, 5% inhibition at 0.01 mM, isoform I, 37C, pH 5.5, 26% inhibition at 0.01 mM, isoform II
NADP+
-
product inhibition
non-steroidal bi-substrate inhibitors
-
several, structures, overview
-
oleic acid
-
50% inhibition at 0.44 mM
oleic acid
-
isoform 1, 50% inhibition at 0.004 mM, isoform 2, 50% inhibition above 0.1 mM
oleic acid ethyl ester
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
ONO 3805
-
-
ONO-3805
-
a non-steroidal bi-substrate inhibitor
p-chloromercuribenzoate
-
complete inhibition
p-chloromercuribenzoate
-
-
palmitic acid
-
50% inhibition at 1.35 mM
palmitic acid
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
PD17
Q5K2N1
active at 0.01 mM
PD91
Q5K2N1
active at 0.01 mM
penta-O-galloyl-beta-D-glucose
-
from Thea sativa, inhibits the expression of androgen receptor and reduce secretion of prostate-specific antigen in LNCaP prostate cancer cells
penta-O-galloyl-beta-D-glucose
-
i.e. 5GG, from Thea sativa, inhibits the liver microsomal enzyme
Piper betle ethanolic whole plant extract
-
42.3% inhibition at 2 mg/ml
-
Piper cueba ethanolic fruit extract
-
28.0% inhibition at 2 mg/ml
-
Piper kadsura ethanolic leaf extract
-
19.0% inhibition at 2 mg/ml
-
Piper kadsura ethanolic rhizome extract
-
36.5% inhibition at 2 mg/ml
-
Piper kadsura ethanolic root extract
-
39.2% inhibition at 2 mg/ml
-
Piper kadsura ethanolic stem extract
-
16.9% inhibition at 2 mg/ml
-
Piper longum ethanolic whole plant extract
-
12.3% inhibition at 2 mg/ml
-
Piper methysticum ethanolic leaf extract
-
28.4% inhibition at 2 mg/ml
-
Piper methysticum ethanolic rhizome extract
-
42.5% inhibition at 2 mg/ml
-
Piper methysticum ethanolic stem extract
-
21.9% inhibition at 2 mg/ml
-
Piper nigrum ethanolic fruit extract
-
63% inhibition at 2 mg/ml
-
Piper nigrum ethanolic leaf extract
-
53.0% inhibition at 2 mg/ml
-
Piper nigrum ethanolic stem extract
-
40.8% inhibition at 2 mg/ml
-
piperine
-
-
progesterone
-
complete inhibition
progesterone
-
competitive
progesterone
-
competitive
progesterone
-
competitive
riboflavin
-
-
sitosterol
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
SKF105657
-
a steroidal type II 5alpha-reductase specific inhibitor
soyasaponin I
-
0.1 mM, 66.8% inhibition
stearic acid
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
steroid carboxylic acid compounds
-
diverse, tricyclic aryl acid mimics of, overview
Steroids
-
e.g.: androst-4-ene-3,17-dione
testosterone
-
poor competitive inhibitor
testosterone
-
-
theaflavin-3'-gallate
-
i.e. TF2b, from Thea sativa, inhibits the liver microsomal enzyme
theaflavin-3,3'-digallate
-
from Thea sativa, inhibits the expression of androgen receptor and reduce secretion of prostate-specific antigen in LNCaP prostate cancer cells
theaflavin-3,3'-digallate
-
i.e. TF3, from Thea sativa, inhibits the liver microsomal enzyme
theaflavin-3-gallate
-
i.e. TF2a, from Thea sativa, inhibits the liver microsomal enzyme
tocopherol
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
Unsaturated 3-carboxysteroids
-
-
-
VG106
Q5K2N1
active at 0.01 mM
yangonin
-
-
Zn2+
-
0.1 mM ZnCl2
Mn2+
-
1 mM: less than 20% inhibition
additional information
-
-
-
additional information
-
not inhibitory: stearic acid
-
additional information
-
theaflavin, gallic acid, and n-propyl gallate are poor inhibitors, physiological effects of inhibitors in vivo, overview
-
additional information
-
synthesis and inhibitory potency of compounds, IC50 values, and affinity for the androgen receptor in prostate, overview
-
additional information
-
kinetic inhibition mechanism of steroidal and non-steroidal inhibitors, competitive steroidal inhibitors, type A or type B, act with a substrate-like or a product-like transition state, type C uncompetitive steroidal inhibitors, overview
-
additional information
-
synthesis of diverse steroidal tetrahydrooxazin-2-ones as potential inhibitors of the enzyme, IC50 of inhibitory compounds, overview
-
additional information
-
no inhibitory activity of yangonin, (+)-methysticin, (+)-kawain, 5,6-dehydrokawain, and 7,8-epoxyyangonin against 5alpha reductase; yangonin, (+)-methysticin, (+)-kawain, 5,6-dehydrokawain, and 7,8-epoxyyangonin show no significant 5alpha-reductase inhibitory activity
-
additional information
-
no inhibition of type 2 steroid 5alpha reductase at 0.01 mM N,N-diisopropyl-2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamide, N-allyl-2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamide, N,N-diisopropyl-2-(4-(1-methyl-6-oxopiperidin-3-yl)phenoxy)acetamide, 1-methyl-5-(4-(2-phenylacetyl)phenyl)pyridin-2(1H)-one, N,N-diisopropyl-2-(4-(2-methyl-4-oxo-3,4-dihydropyridin-1(2H)-yl)phenoxy) acetamide, 2-(16-(acetylthio)hexadecanamido)ethyl 6-(2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamido)hex-4-enoate, and 2-(2-(16-(acetylthio)hexadecanamido)ethoxy)ethyl 6-(2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamido)hex-4-enoate
-
additional information
-
enzyme is not inhibited by finasteride
-
additional information
-
flowers of Pueraria thomsonii, 50% ethanolic extract shows inhibitory activity of 60.2%
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2-mercaptoethanol
-
3fold activity at 1 mM
3beta-acetoxy-16alpha-17alpha-epoxy-4-pregnen-20-one
-
-
3beta-acetoxy-5,16-pregnadien-20-one
-
-
4-pregnen-17-ol-3-one
-
-
androstandione
-
in male foreskin fibroblasts
androstenedione
-
in male foreskin fibroblasts
dihydrotestosterone
-
significantly increases 5alpha-R1 mRNA and 5alpha-R2 mRNA expression in male rats
dilauroylphosphatidylcholine
-
marked stimulatory effect on activity
dithiothreitol
-
3fold activity at 1 mM
dithiothreitol
-
no influence on microsomal enzyme, but slightly stimulating the solubilized enzyme
morphine
-
morphine significantly reduces the testosterone concentration after acute and chronic exposure in the spinal cord. In contrast, the 5alpha-reductase 1 expression and of course dihydrotestosterone levels increase tfollowing chronic morphine administration
N-ethylmaleimide
-
stimulatory on solubilized enzyme from microsomes
Oxytocin
-
increases activity in human prostate epithelial cells
phosphatidylserine
-
4fold increase in activity
Phospholipids
-
stimulate
sulpiride
-
40 mg/kg doses induce mRNA expression of 5alphaR1 and 5alpha-R2; 40 mg/kg doses induce mRNA expression of 5alphaR1 and 5alpha-R2
testosterone
-
in female genital skin fibroblasts
iodoacetamide
-
stimulatory on solubilized enzyme from microsomes
additional information
-
oxytocin does not stimulate enzyme activity or expression in human prostate epithelial cells
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00057
17-epitestosterone
-
in homogenates
0.00078
17-epitestosterone
-
in living cells
0.00086
20alpha-hydroxypregn-4-en-3-one
-
-
0.0002
20alpha-hydroxyprogesterone
-
isoenzyme 1
0.0004
20alpha-hydroxyprogesterone
-
isoenzyme 2
0.0005
20alpha-hydroxyprogesterone
-
isoenzyme 1
0.0004
androstenedione
-
isoenzyme 2
0.0006
androstenedione
-
isoenzyme 1
0.0008
androstenedione
-
isoenzyme 2
0.001
androstenedione
-
isoenzyme 1
0.02634
androstenedione
Q5K2N1
-
0.000569
corticosterone
-
pH 7.4, 28C
0.002
corticosterone
-
isoenzyme 2
0.004
corticosterone
-
isoenzyme 2
0.008
corticosterone
-
isoenzyme 1
0.018
corticosterone
-
isoenzyme 1
0.00102
NADPH
-
nuclear enzyme
0.015
NADPH
-
enzyme mutant G34R
0.02
NADPH
-
-
0.025
NADPH
-
enzyme mutant H231R
0.0376
NADPH
-
microsomal membrane-bound enzyme
0.13
NADPH
-
-
0.13
NADPH
-
-
0.18
NADPH
-
enzyme mutant G196S
0.316
NADPH
-
enzyme mutant G183S
0.325
NADPH
-
enzyme mutant N193S
0.34
NADPH
-
enzyme mutant R171S
0.401
NADPH
-
enzyme mutant R246Q
0.526
NADPH
-
enzyme mutant P181L
0.53
NADPH
-
-
0.584
NADPH
-
enzyme mutant R145W
0.65
NADPH
-
enzyme mutant R246W
0.000095
progesterone
-
-
0.000113
progesterone
-
-
0.00013
progesterone
-
-
0.0002
progesterone
-
isoenzyme 2
0.00027
progesterone
-
-
0.0003
progesterone
-
isoenzyme 1; isoenzyme 2
0.0003
progesterone
-
isoenzyme 1
0.00048
progesterone
-
-
0.00069
progesterone
-
-
0.00075
progesterone
Q5K2N1
-
0.028
progesterone
-
-
0.03
progesterone
-
-
0.03
progesterone
-
-
0.12
progesterone
-
-
0.0000013
testosterone
-
pH 7.0, 30C, low Km-isoform from prostate
0.000012
testosterone
-
pH 7.0, 30C, isoform from breast skin
0.0000196
testosterone
-
pH 7.0, 30C, high Km-isoform from prostate
0.0002
testosterone
-
nuclear and microsomal solubilized enzyme
0.0002
testosterone
-
isoenzyme 2
0.00022
testosterone
-
pH 6.0, 25C
0.0006
testosterone
-
-
0.0007
testosterone
-
isoenzyme 2
0.00073
testosterone
-
-
0.0009
testosterone
-
enzyme mutant R246Q
0.001
testosterone
-
; enzyme mutant G196S; enzyme mutant R246W
0.0011
testosterone
-
prostrate homogenate at pH 7
0.00119
testosterone
-
pH 7.4, 28C
0.0012
testosterone
-
enzyme mutant N193S; enzyme mutant R145W
0.0018
testosterone
-
enzyme mutant G183S
0.002
testosterone
-
-
0.002
testosterone
-
isoenzyme 1
0.0022
testosterone
-
enzyme mutant P181L
0.0023
testosterone
-
enzyme mutant R171S
0.00245
testosterone
-
pH 6.5, 37C
0.0025
testosterone
-
epidymis homogenate at pH 4.5
0.0035
testosterone
-
isoenzyme 1
0.0045
testosterone
-
-
0.0063
testosterone
-
-
0.008
testosterone
-
-
0.012
testosterone
-
enzyme mutant G34R
0.014
testosterone
-
enzyme mutant H231R
0.016
testosterone
-
-
0.032
testosterone
-
-
0.0446
testosterone
Q5K2N1
-
0.14
cortisone
-
-
additional information
additional information
-
-
-
additional information
additional information
-
variations of Km with various concentrations of zearaleone, zearalanol or estradiol-17beta
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000006
(+)-LY191704
-
-
0.000004
(-)-LY191704
-
-
0.00092
(10bR)-8-chloro-4,10b-dimethyl-4a,5,6,10b-tetrahydrophenanthridin-2(1H)-one
-
isoform I
0.0011
(10bR)-8-chloro-4,5,10b-trimethyl-4a,5,6,10b-tetrahydrophenanthridin-2(1H)-one
-
isoform I
0.00026
(4aS)-7-chloro-4a-methyl-2,3,4,4a-tetrahydrophenanthrene-2-carboxylic acid
-
isoform II, Ki,app-value
0.0012
(4aS)-7-chloro-4a-methyl-2,3,4,4a-tetrahydrophenanthrene-2-carboxylic acid
-
isoform I, Ki,app-value
0.000035
(5alpha,20-R)-4-Diazo-21-hydroxy-20-methylpregnan-3-one
-
at 25C formation of the reversible EI complex is not rate-limiting for enzyme inactivation, and this is expressed as saturation kinetics for the inhibition reaction
0.000085
17-diisopropylcarbamoyl-2-androsten-3-carboxylate
-
-
0.000007 - 0.000018
17-diisopropylcarbamoyl-3,5-androstadien-3-carboxylate
-
-
0.00003
17-diisopropylcarbamoyl-3-androsten-3-carboxyate
-
-
0.0022
17-diisopropylcarbamoyl-androstan-3-carboxylate
-
-
0.0045
17-tert-butylcarbamoyl-3,5-androstadien-3-carbaldehyde
-
-
0.000033
17-tert-butylcarbamoyl-3,5-androstadien-3-carboxylate
-
-
0.0042
17-tert-butylcarbamoyl-3,5-androstadien-3-ol
-
-
0.000036
17beta-(N-tert-butylcarbamoyl)androsta-3,5-diene-3-carboxylic acid
-
pH 7.0, 30C, low Km-isoform from prostate
0.0049
17beta-(N-tert-butylcarbamoyl)androsta-3,5-diene-3-carboxylic acid
-
pH 7.0, 30C, high Km-isoform from prostate
0.0093
17beta-(N-tert-butylcarbamoyl)androsta-3,5-diene-3-carboxylic acid
-
pH 7.0, 30C, isoform from breast skin
0.026
17beta-estradiol
-
intercept inhibition constant
0.036
17beta-estradiol
-
slope inhibition constant
0.146
17beta-hydroxyandrosta-1,4-diene-3-one
-
-
0.000315
2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
-
isoform I, Ki,app-value
0.01
2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
-
isoform II, Ki,app-value
0.00006
20alpha-hydroxypregn-4-en-3-one
-
-
0.0049
4,16-androstadien-3-one
-
-
0.0000058
4,8-dimethyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I
0.0000062
4-Aza-4-methyl-5alpha-pregnane-3,20-dione
-
versus progesterone
0.0000118
4-Aza-4-methyl-5alpha-pregnane-3,20-dione
-
versus NADPH
0.0126
4-bromo-17alpha-(p-fluorobenzoyloxy)-4-pregnene-3,20-dione
-
pH 6.0, 25C
0.000002
4-methyl-azasteroid
-
iosenzyme 2
0.000003
4-methyl-azasteroid
-
iosenzyme 1
0.000003
4-methyl-azasteroid
-
iosenzyme 2
0.000004
4-methyl-azasteroid
-
iosenzyme 2
0.000008
4-methyl-azasteroid
-
iosenzyme 1
0.0000084
4-methyl-azasteroid
-
-
0.000026
7-bromo-2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
-
isoform I, Ki,app-value
0.01
7-bromo-2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
-
isoform II, Ki,app-value
0.00032
7-chloro-2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
-
isoform I, Ki,app-value
0.0025
7-chloro-2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
-
isoform II, Ki,app-value
0.0000027
8-chloro-4-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I
0.0000003
acylate episteride
-
iosenzyme 2
-
0.0000005
acylate episteride
-
iosenzyme 2
-
0.000004
acylate episteride
-
iosenzyme 2
-
0.00002
acylate episteride
-
iosenzyme 1
-
0.0005
acylate episteride
-
iosenzyme 1
-
0.0041
acylate episteride
-
iosenzyme 1
-
0.0000043
dutasteride
-
wild-type, 30 min reaction time
0.000017
dutasteride
-
wild-type, 10 min reaction time
0.000001
finasteride
-
iosenzyme 2
0.000004
finasteride
-
iosenzyme 2
0.000005
finasteride
-
iosenzyme 2
0.000005
finasteride
-
isozyme 5alphaR-2
0.000006
finasteride
-
iosenzyme 1
0.000023
finasteride
-
wild-type, 30 min reaction time
0.00006
finasteride
-
wild-type, 10 min reaction time
0.00022
finasteride
-
iosenzyme 1
0.0003
finasteride
-
isozyme 5alphaR-1
0.00033
finasteride
-
-
0.00036
finasteride
-
-
0.001
finasteride
-
iosenzyme 1
0.0013
finasteride
-
pH 7.0, 30C, low Km-isoform from prostate
0.00154
finasteride
-
pH 6.0, 25C
0.0028
finasteride
-
pH 7.0, 30C, high Km-isoform from prostate
0.005
finasteride
-
pH 7.0, 30C, isoform from breast skin
0.000004
LY306089
-
-
0.0043
NADP+
-
versus NADPH
0.0319
NADP+
-
versus progesterone
0.00048
penta-O-galloyl-beta-D-glucose
-
pH 6.5, 37C, versus NADPH
0.0027
penta-O-galloyl-beta-D-glucose
-
pH 6.5, 37C, versus testosterone
0.00086
progesterone
-
-
0.0026
theaflavin-3'-gallate
-
pH 6.5, 37C, versus NADPH
0.0065
theaflavin-3'-gallate
-
pH 6.5, 37C, versus testosterone
0.00036
theaflavin-3,3'-digallate
-
pH 6.5, 37C, versus NADPH
0.0056
theaflavin-3,3'-digallate
-
pH 6.5, 37C, versus testosterone
0.0031
MK434
-
-
additional information
additional information
-
inhibition kinetics
-
additional information
additional information
-
isozyme-specific IC50-values of diverse inhibitors, overview
-
additional information
additional information
-
the majority of the enzyme variants result in a reduction of the apparent Ki for both finasteride and dutasteride from 10 min to the 30 min reaction like the wild-type enzyme, but several variants result in an increase of the apparent Ki for each inhibitor or no significant change between the 10 min and 30 min reactions, thus exhibiting time independent inhibition
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00003
(+/-)-LY191704
-
i.e. (4aS,10aR)-7-chloro-1-methyl-3,4,4a,9,10,10a-hexahydrophenanthren-2(1H)-one, non-steroidal, most potent benzoquinoline mimicing 4-azasteroid inhibitors, and specific for isozyme 5alphaR-1, IC50 is 30 nM
0.00076
(2E,4E,6E,8E)-((2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoate
-
pH not specified in the publication, temperature not specified in the publication
0.00053
(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl palmitoate
-
pH not specified in the publication, temperature not specified in the publication
0.44
(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(1,3,5-benzotrioxepin-6-ylmethyl)tetrahydrofuran-2-ol
-
-
0.44
(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(1,3,5-benzotrioxepin-7-ylmethyl)tetrahydrofuran-2-ol
-
-
1.03
(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(2,3-dimethoxybenzyl)tetrahydrofuran-2-ol
-
-
1.03
(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(3,4-dimethoxybenzyl)tetrahydrofuran-2-ol
-
-
0.00072
(5'S)-17beta-(2-chlorophenyl-4,5-dihydrooxazol-5-yl)androst-5-en-3-one
-
pH 7.3, 37C
-
0.00105
(5'S)-17beta-(4-bromophenyl-4,5-dihydrooxazol-5-yl)androst-5-en-3-one
-
pH 7.3, 37C
-
0.00048
(Z)-((2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl) hexadec-9-enoate
-
pH not specified in the publication, temperature not specified in the publication
0.000026
17a-(2-propionoxyethyl)-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
P18405, P31213
pH not specified in the publication, 37C
0.000073
17a-allyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
P18405, P31213
pH not specified in the publication, 37C
0.000022
17a-ethyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
P18405, P31213
pH not specified in the publication, 37C
0.000054
17a-methyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
P18405, P31213
pH not specified in the publication, 37C
0.00005
17alpha-p-bromophenylcarbamoyloxy-4-pregnen-3 20-dione
-
in the presence of 1 mM dithiothreitol, in 40 mM sodium phosphate buffer, at pH 6.5
0.00005
17alpha-p-bromophenylcarbamoyloxy-4-pregnen-3,20-dione
-
with 1 mM dithiothreitol in 40 mM sodium phosphate buffer, at pH 6.5 and 37C
0.00001
17alpha-phenylcarbamoyloxy-4-pregnen-3,20-dione
-
in the presence of 1 mM dithiothreitol, in 40 mM sodium phosphate buffer, at pH 6.5; with 1 mM dithiothreitol in 40 mM sodium phosphate buffer, at pH 6.5 and 37C
0.0000011
3beta-(3'-oxapentanoyloxy)-androst-5-en-17-one
-
pH 6.5, 37C
-
0.0000052
3beta-acetoxyandrost-5-en-17-one
-
pH 6.5, 37C
-
0.000000002
3beta-hexanoyloxyandrost-5-en-17-one
-
pH 6.5, 37C
-
0.00084
4-(3-(4-(N-methylacetamido)phenyl)pentan-3-yl)phenyl dibenzylcarbamate
-
-
0.14
Biochanin A
-
pH not specified in the publication, temperature not specified in the publication
0.000025
dehydroepiandrosterone
-
pH 6.5, 37C
0.37
equol
-
pH not specified in the publication, temperature not specified in the publication
0.81
ethinylestradiol
-
-
0.000008
finasteride
-
pH 7.3, 37C
0.0000085
finasteride
-
in the presence of 1 mM dithiothreitol, in 40 mM sodium phosphate buffer, at pH 6.5; with 1 mM dithiothreitol in 40 mM sodium phosphate buffer, at pH 6.5 and 37C
0.000025
finasteride
-
type 2 steroid 5alpha reductase inhibition
0.000453
finasteride
-
type 1 steroid 5alpha reductase inhibition
0.008
finasteride
-
-
0.71
genistein
-
pH not specified in the publication, temperature not specified in the publication
0.086
ginsenoside Rg3
-
pH 7.2, 37C
0.259
ginsenoside Ro
-
pH 7.2, 37C
-
0.0005
MK386
-
-
0.48
piperine
-
-
0.017
riboflavin
-
pH not specified in the publication, temperature not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.000000012
-
activity in dark grown cultures is slightly higher than in light grown cultures
0.00014
-
extract from shoot culture
0.00148
-
female
0.00234
-
male
0.03413
-
female
0.34
-
with NADPH
additional information
-
-
additional information
-
-
additional information
-
0.12 micromol/h/tissue, enzyme activity in cauda epididymis; 0.62 micromol/h/tissue, enzyme activity in caput-corpus epididymis
additional information
-
-
additional information
-
significant differences in 5 alpha-R2 activity levels between the cancerous and non-cancerous groups are observed
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5
-
recombinant human 5alpha-reductase isozyme 2
5
-
recombinant monkey 5alpha-reductase isozyme 2
5
-
isozyme 2, high substrate concentration
5
-
assay at, type 2 isoenzyme
5
-
assay at
5.2 - 5.6
-
mutant G34R
5.5 - 7.5
-
-
5.5
-
human: 2 forms, 1. pH-optimum 5.5 (only in fibroblasts derived from genital skin), 2. pH-optimum 7-9 (in both genital and nongenital skin regions and in fibroblast from all skin regions)
5.5
-
isozyme 2, low substrate concentration, efficiency optimum Vmax/Km
5.5
-
assay at, isoform 2
5.7
-
in testis microsomes of 5 month-old animals
5.8 - 7.5
-
-
6 - 6.5
-
mutant P181L
6.2
-
female
6.3
-
in testis microsomes of 6 month-old animals
6.5
-
assay at
7 - 9
-
human: 2 forms, 1. pH-optimum 5.5 (only in fibroblasts derived from genital skin), 2. pH-optimum 7-9 (in both genital and nongenital skin regions and in fibroblast from all skin regions)
7.3 - 7.6
-
-
7.4
-
assay at, isoform 1
7.5
-
recombinant human 5alpha-reductase isozyme 1
7.5
-
assay at, type 1 isoenzyme
8
-
recombinant monkey 5alpha-reductase isozyme 1
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4.5 - 7.5
-
recombinant monkey 5alpha-reductase isozyme 2
4.5 - 9
-
pH .5: about 30% of activity maximum, pH 9.0: about 20% of activity maximum
4.5 - 9
-
recombinant human 5alpha-reductase isozyme 1
4.5 - 9.5
-
recombinant human 5alpha-reductase isozyme 2
5 - 8
-
pH 5.0: about 20% of activity maximum, pH 8.0: about 20% of activity maximum
5 - 8.5
-
at pH 5 and 8.5: about 50% of activity maximum
5.5 - 9
-
recombinant monkey 5alpha-reductase isozyme 1
6.3 - 7.5
-
-
6.5 - 8.6
-
half maximal activity at pH 6.5 and 8.6
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
-
assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
15 - 42
-
15C: about 50% of activity maximum, 42C: about 30% of activity maximum
21 - 37
-
21C: about 50% of activity maximum, 37C: about 70% of activity maximum
additional information
-
-
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
adrenal 5alpha-reductase expression is decreased in male withdrawal seizure-prone mice
Manually annotated by BRENDA team
-
distribution in brain areas
Manually annotated by BRENDA team
-
testosterone concentrations during postnatal sexual differentiation of the rat Ccentral nervous system, among other sex-dependent factors, influence brain levels of 5alpha-reductase isozymes in adulthood and the pattern of their regulation by androgen hormones
Manually annotated by BRENDA team
-
from beard and axillary hair and frontal scalp hair
Manually annotated by BRENDA team
Digitalis lanata VIII
-
somatic
-
Manually annotated by BRENDA team
-
the enzyme is detected in biopsies of pelvic endometriosis
Manually annotated by BRENDA team
-
concentrated in caput corpus of epididymis
Manually annotated by BRENDA team
-
both type 1 and type 2 isoenzyme, copy number of mRNA and activity of type 1 isoenzyme is significantly higher than type 2
Manually annotated by BRENDA team
-
cultured female and male genital skin fibroblasts
Manually annotated by BRENDA team
-
foreskin, Hs68
Manually annotated by BRENDA team
-
not in young laeves, low activity
Manually annotated by BRENDA team
Q5K2N1
higher levels
Manually annotated by BRENDA team
Digitalis lanata VIII
-
-
-
Manually annotated by BRENDA team
-
only isozyme 5alpha-R1
Manually annotated by BRENDA team
-
prostate cancer cell line
Manually annotated by BRENDA team
-
similar 5alpha-R1 mRNA expression in female and male rats, 5alpha-R2 mRNA expression significantly higher in females than in males
Manually annotated by BRENDA team
-
prostate-specific
Manually annotated by BRENDA team
-
benign prostatic hyperplasia tissue, BPH
Manually annotated by BRENDA team
-
from gonadectomized male hamster
Manually annotated by BRENDA team
-
isozymes 5alphaR-1 and 5alphaR-2, only isozyme 5alphaR-1 is found in case of prostate cancer
Manually annotated by BRENDA team
-
prostate carcinoma DU145 cells or from benign prostatic hyperplasia patients, BPH
Manually annotated by BRENDA team
-
prostate carcinoma DU145 cells or from BPH patients
Manually annotated by BRENDA team
-
tissues with benign prostatic hyperplasia, primary prostate cancer, prostatic intraepithelial neoplasia, primary prostate cancer treated with neoadjuvant androgen ablation, locally recurrent prostate cancer specimens, and prostate cancer metastases
Manually annotated by BRENDA team
-
studies in DU 145 cells, a human cell-line of low androgen sensitivity derived from a cerebral metastasis of an ephithelial prostate cancer
Manually annotated by BRENDA team
-
ventral prostate, activity of both isoform I and II is increased after treatment with oxytocin
Manually annotated by BRENDA team
-
type-2 5alpha-reductase is only found in prostate and other genital tissues, enhancement of type-1 5alpha-reductase is enhanced in prostate cancer
Manually annotated by BRENDA team
-
culture, light grown
Manually annotated by BRENDA team
-
female breast skin
Manually annotated by BRENDA team
-
isozymes 5alphaR-1 and 5alphaR-2, dihydrotestosterone overproduction in skin pathologies, overview
Manually annotated by BRENDA team
-
type 2 isoenzyme
Manually annotated by BRENDA team
-
24-26 day old animals, no enzyme activity of isoform II
Manually annotated by BRENDA team
-
decrease in isoenzyme 1 activity and mRNA during testosterone treatment, but not isoenzyme 2. Active immunisation of animals against gonadotrophin-releasing hormone, increase in activity of both isoenzymes
Manually annotated by BRENDA team
-
postnatal animals, enzyme activity is low in 10-day old testis, peaks between days 20 and 40 during puberty and then declines
Manually annotated by BRENDA team
additional information
-
preembryogenic mass
Manually annotated by BRENDA team
additional information
-
highest activity in organs of acessory reproduction and in liver
Manually annotated by BRENDA team
additional information
-
isozymes show different tissue distribution in androgen target organs
Manually annotated by BRENDA team
additional information
-
not expressed in muscle or bone
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Q8NJV1
fusion protein of enzyme with green fluorescent protein
Manually annotated by BRENDA team
-
of endoplasmic reticulum
Manually annotated by BRENDA team
additional information
-
nuclear and cell-debris fraction
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
24000
-
5alphaR2, immunoblotting
676930
25000 - 35000
-
gel filtration
396209
26000
-
10% SDS-PAGE
396214
26000
-
5alphaR1, SDS-PAGE
684907
27000
-
SDS-PAGE; SDS-PAGE
689176
42000
-
5alpha-reductase isoenzyme 2, SDS-PAGE, after treatment with O-glycosidase and neuraminidase a protein of an apparent molecular weight of 30 kDa appears
396217
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
Q8NJV1
contains membrane-spanning domains
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5.7 - 8.4
-
in the cold
396209
6.6 - 7.8
-
4 days, in the cold, presence of KCl and NADH
396209
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4
-
2 days, 50% loss of activity
396192
25
-
1 h stable
396193
37
-
rapid loss of activity
396192
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
0.5% n-octyl beta-D-glucopyranoside stabilizes
-
dialysis at 4C, 22 h, n-octylglycoside-KCl extracted enzyme without loss of activity
-
glycerol stabilizes
-
NADPH stabilizes
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, 1 week, solubilized enzyme
-
-20C, 6 months
-
4C, 2 days, 50% loss of activity
-
-70C or storage in liquid nitrogen is necessary to preserve activity for more than a few days
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
5alpha-reductase 2 purified using a four-step chromatographic procedure
-
three-step purification of a photolabeled tryptic peptide corresponding to the NADP(H) binding domain of 5alpha-reductase
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
into vector pTarget and expressed in COS-7 cells
-
into pCMV7 and transfered to COS-1 cells
-
recombinant expression of isozymes 5alphaR-1 and 5alphaR-2 in e.g. human DU145 cells, in COS-1 cells, and in CHO 1827 and CHO 1829 cells, isozymes are chromosomal differently localized
-
transfection of HEK-293 cell; transfection of HEK-293 cell
P18405, P31213
monkey SR type 1 cDNA expression in CHO-cells
-
5alpha-reductase-1 transcript quantitative expression analysis by real-time quantitative reverse transcriptase PCR in brain tissues
-
into vector pTarget and expressed in COS-7 cells
Q5K2N1
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
androgen regulates the mRNA level of 5alpha reductase isoenzymes in a cell type-specific manner. Regulation occurs at the transcriptional level, and the androgen receptor is necessary for this regulation
-
androgen regulates the mRNA level of 5alpha reductase isoenzymes in a cell type-specific manner. Regulation occurs at the transcriptional level, and the androgen receptor is necessary for this regulation. The androgen receptor is recruited to a negative androgen response element on the promoter of isoform SRD5A3 in vivo and directly binds to the negative androgen response element in vitro
P31213, Q9H8P0
morphine significantly reduces the testosterone concentration after acute and chronic exposure in the spinal cord. In contrast, the 5alpha-reductase 1 expression and of course dihydrotestosterone levels increase the following chronic morphine administration
-
transcription and expression levels of both 5alpha-reductase isozymes were significantly higher in environmentally stressed rats than in unstressed rats
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
K204E
-
det2-1 mutant, substitution of lysine for Glu-204 totally inactivates the steroid 5alpha-reductase activity, residual activity for campestenone and progesterone
A248V
-
somatic variant, reduction of the apparent Ki for both finasteride and dutasteride
A49T
-
constitutional and somatic variant, time-independent inhibition, more than 100fold lower apparent Ki for dutasteride than for finasteride
A51T
-
constitutional variant, reduction of the apparent Ki for both finasteride and dutasteride
C5R
-
constitutional variant, reduction of the apparent Ki for both finasteride and dutasteride
F118L
-
somatic variant, no significant change of the apparent Ki for both finasteride and dutasteride
F194L
-
constitutional variant, time-independent inhibition, displays lower apparent Ki for finasteride than dutasteride
F234L
-
constitutional variant, reduction of the apparent Ki for finasteride but not for dutasteride
G183D
-
somatic variant, reduction of the apparent Ki for both finasteride and dutasteride
G183S
-
mutant of 5alpha-reductase isozyme type-2
G191E
-
somatic variant, reduction of the apparent Ki for both finasteride and dutasteride
G196S
-
mutant of 5alpha-reductase isozyme type-2
G34R
-
mutant of 5alpha-reductase isozyme type-2
H231R
-
mutant of 5alpha-reductase isozyme type-2
H264Q
-
mutant of 5alpha-reductase isozyme type-2
L221P
-
somatic variant, reduction of the apparent Ki for both finasteride and dutasteride
L226P
-
somatic variant, reduction of the apparent Ki for finasteride but not for dutasteride
N193S
-
mutant of 5alpha-reductase isozyme type-2
P181L
-
mutant of 5alpha-reductase isozyme type-2
P30L
-
constitutional variant, more than 100fold lower apparent Ki for dutasteride than for finasteride
P48R
-
constitutional variant, displays lower apparent Ki for finasteride than dutasteride in the 10 min reaction
R145W
-
mutant of 5alpha-reductase isozyme type-2
R171S
-
mutant of 5alpha-reductase isozyme type-2
R227Q
-
constitutional variant, reduction of the apparent Ki for both finasteride and dutasteride
R246W
-
mutant of 5alpha-reductase isozyme type-2
T187M
-
constitutional variant, reduction of the apparent Ki for both finasteride and dutasteride
V189A
-
somatic variant, reduction of the apparent Ki for both finasteride and dutasteride
V3I
-
somatic variant, reduction of the apparent Ki for both finasteride and dutasteride
V63M
-
somatic variant, reduction of the apparent Ki for both finasteride and dutasteride
V89L
-
constitutional variant, reduction of the apparent Ki for both finasteride and dutasteride
V89L
-
the mutant of low 5-alpha-reductase type 2 activity is associated with an increased risk of aggressive prostate cancer
V89L
P31213
a significant sex-dependent effect of genotype for the V89L variant in male but not female subjects on symptoms of post-traumatic stress disorder
additional information
Q8NJV1
Arabidopsis wild type and enzyme mutant strains carrying the enzyme gene controlled by cauliflower mosaic virus 35S promotor differed from wild type plants by accelerated stem growth, flower and seed development and a reducution in size and number of rosette leaves
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
-
30 min incubation with dutasteride results in the lowest apparent Ki values overall and the lowest variation, significant for designing protocols for treatment and/or chemoprevention of prostatic diseases
medicine
-
5alphaR1 is increased and 5alphaR2 is decreased during development of prostate cancer, increased expression of both isozymes in recurrent and metastatic cancer, both isozymes may be important in the development and progression of prostate cancer
medicine
-
5alpha reductase inhibitors decrease prostate volume and induce atrophy and apoptosis in benign prostatic epithelium
medicine
P31213
functional variation within isoform SRD5A2 influences, in a sex-specific way, the severity of post-traumatic stress symptoms and risk for diagnosis of post-traumatic stress disorder. There is a significant sex-dependent effect of genotype for the V89L variant in male but not female subjects on symptoms
pharmacology
-
enzyme is a target for drug developement
analysis
-
assay for evaluating 5alpha-reductase activity in large-scale clinical studies using the S9 fraction obtained by centrifugation of the homogenate supernatant at 9000 g for 30 min and gas chromatography-mass spectrometry
analysis
-
radiosubstrate in vitro incubation method for the determination of 5alpha-reductase type 1 activity using rat liver microsomes as an enzyme source
medicine
-
higher expression of 5alpha-R2, which is considered a masculinizing enzyme, in the female versus male central nervous system, sexual dimorphism in the regulation of 5alpha isozymes by dihydrotestosterone
medicine
-
assay for evaluating 5alpha-reductase activity in large-scale clinical studies using the S9 fraction obtained by centrifugation of the homogenate supernatant at 9000 g for 30 min and gas chromatography-mass spectrometry
medicine
-
morphine significantly reduces the testosterone concentration after acute and chronic exposure in the spinal cord. In contrast, the 5alpha-reductase 1 expression and of course dihydrotestosterone levels increase the following chronic morphine administration
medicine
-
testosterone concentrations during postnatal sexual differentiation of the rat Ccentral nervous system, among other sex-dependent factors, influence brain levels of 5alpha-reductase isozymes in adulthood and the pattern of their regulation by androgen hormones
medicine
-
transcription and expression levels of both 5alpha-reductase isozymes were significantly higher in environmentally stressed rats than in unstressed rats. Increased 5alpha-reductase isozyme levels may play a role in the development or maintenance of prostate disease
additional information
-
two isoenzymes of 5alphaR is probably characteristic of the whole plant kingdom