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Information on EC 1.1.1.51 - 3(or 17)beta-hydroxysteroid dehydrogenase
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EC Tree
1.1.1.51 3(or 17)beta-hydroxysteroid dehydrogenaseIUBMB Comments
Also acts on other 3beta- or 17beta-hydroxysteroids. cf. EC 1.1.1.209 3(or 17)alpha-hydroxysteroid dehydrogenase.
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Word Map
- 1.1.1.51
- testosterone
- progesterone
-
steroidogenic
- estradiol
- adrenal
- androstenedione
-
steroidogenesis
- testicular
- ovarian
- estrone
- aromatase
- pregnenolone
- 17beta-hsds
- testis
- leydig
- dehydroepiandrosterone
- gonad
-
gonadotropin
-
granulosa
- dheas
- fsh
- luteal
- cortisol
- p450scc
- progestin
-
alpha-hydroxylase
-
alpha-reductase
- dihydrotestosterone
- cyp11a1
-
alpha-hydroxyprogesterone
- androsterone
- hsd3b1
-
17-ketosteroids
- p450arom
-
alpha-dihydrotestosterone
- pseudohermaphroditism
- trilostane
- genitalia
- hirsutism
-
alpha-hydroxysteroid
-
beta-diol
-
virilization
- 17-hydroxyprogesterone
-
lhcgr
- environmental protection
-
pubarche
-
hcg-stimulated
- drug development
-
17-hydroxylase
- srd5a2
- medicine
- 11-deoxycortisol
-
adrenarche
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
3 beta-hydroxysteroid dehydrogenase, 17 beta-hydroxysteroid dehydrogenase, 17beta-hydroxysteroid dehydrogenase, 3betahsd, hsd17b3, 17beta-hydroxysteroid dehydrogenases, 17beta-hsd3, 17beta-hsd2, 17betahsd2, 17beta-hsd type 2, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
17-ketoreductase
-
-
-
-
17beta-HSD
17beta-HSD type 3
17beta-HSD3
17beta-hydroxy steroid dehydrogenase
-
-
-
-
17beta-hydroxysteroid dehydrogenase
17beta-hydroxysteroid dehydrogenase type 3
3,17beta-HSD
3,17beta-hydroxysteroid dehydrogenase
3beta,17beta-hydroxysteroid dehydrogenase
-
-
-
-
3beta-HSD
3beta-HSD/isomerase
3beta-hydroxy steroid dehydrogenase
-
-
-
-
3beta-hydroxy-steroid dehydrogenase/DELTA5-DELTA4 isomerase
3beta-hydroxysteroid dehydrogenase
3beta-hydroxysteroid dehydrogenase/isomerase
3beta-hydroxystroid oxidoreductase
-
-
-
-
3beta17betaHSDH
-
-
-
-
3betaHSD
beta-hydroxy steroid dehydrogenase
-
-
-
-
betahsd
dehydrogenase, 17beta-hydroxy steroid
-
-
-
-
dehydrogenase, 3beta-hydroxy steroid
-
-
-
-
dehydrogenase, beta-hydroxy steroid
-
-
-
-
DELTA5-3beta-HSD
DELTA5-3beta-hydroxysteroid dehydrogenase
HSD17B3
steroid 17beta-reductase
-
-
-
-
type 2 17beta-HSD
additional information
3beta-hydroxysteroid dehydrogenase
-
-
-
-
additional information
-
the enzyme is a member of the short-chain dehydrogenase/reductase, SDR, superfamily
additional information
-
the enzyme belongs to the short-chain alcohol dehydrogenase family
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
testosterone + NAD(P)+ = androstenedione + NAD(P)H + H+
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
redox reaction
reduction
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
KEGG
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SYSTEMATIC NAME
IUBMB Comments
3(or 17)beta-hydroxysteroid:NAD(P)+ oxidoreductase
Also acts on other 3beta- or 17beta-hydroxysteroids. cf. EC 1.1.1.209 3(or 17)alpha-hydroxysteroid dehydrogenase.
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CAS REGISTRY NUMBER
COMMENTARY
9015-81-0
-
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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
(R)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH + H+
i.e. R-tetralol
-
-
?
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH + H+
i.e. S-tetralol
-
-
?
(S)-1,2,3,4-tetrahydro-1-naphthol + NADP+
3,4-dihydronaphthalen-1(2H)-one + NADPH + H+
i.e. S-tetralol
-
-
?
(S)-1-indanol + NAD+
2,3-dihydro-1H-inden-1-one + NADH + H+
-
-
-
?
1-acenaphthenol + NAD+
acenaphthylen-1(2H)-one + NADH + H+
-
-
-
?
11beta-hydroxyandrost-5-ene-3,17-dione + NADPH
11beta,17beta-dihydroxyandrost-5-ene-3-one + NADP+
17-oxo steroids + NADPH
?
-
maintenance of balance between oxidized and reduced steroids in blood
-
-
-
17alpha-hydroxypregnenolone + NAD(P)+
17alpha-hydroxy-pregn-5-en-3,20-dione + NAD(P)H + H+
-
-
-
-
?
17beta-hydroxy-5beta-androstane-3-one + NAD(P)H + H+
testosterone + NAD(P)+
-
-
-
?
2-cyclohexen-1-ol + NAD+
2-cyclohexen-1-one + NADH + H+
-
-
-
?
20alpha-dihydroprogesterone + NAD+
4-pregnen-3alpha,20beta-diol + NADH
-
-
-
-
r
20alpha-dihydroprogesterone + NADP+
4-pregnen-3alpha,20beta-diol + NADPH
-
-
-
-
r
3beta-hydroxy-5alpha-androstan-17-one + NADP+
5alpha-androstane-3,17-dione + NADPH
-
-
-
?
4-androsten-17beta-ol-3-one + NAD(P)+
4-androstene-3,17-dione + NAD(P)H + H+
17keto function is reduced. NADP+ is 3-5times less effective than NAD+
-
-
?
4-estrene-17beta-ol-3-one + NADP+
4-estrene-3,17-dione + NADPH
-
-
-
-
r
5-androsten-3beta-ol-17-one + NAD(P)+
5-androstene-3,17-dione + NAD(P)H + H+
NADP+ is 3-5times less effective than NAD+
-
-
?
5-androstenedione + NADPH
5alpha-dihydrotestosterone + NADP+
-
isozyme 17beta-HSD3
-
-
r
5-pregnen-3beta-ol-20-one + NAD(P)+
5-pregnene-3,20-dione + NAD(P)H + H+
NADP+ is 3-5times less effective than NAD+
-
-
?
5alpha-androst-16-en-3-one + NADH
3beta-hydroxy-5alpha-androst-16-ene + NAD+
-
-
-
?
5alpha-androstan-3alpha-ol-17-one + NAD+
5alpha-androstan-3,20-dione + NADH + H+
-
-
-
?
5alpha-androstan-3beta-ol-17-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
-
-
-
?
5alpha-androstane-3beta,17beta-diol + NADP+
3beta-hydroxy-5alpha-androstan-17-one + NADPH
-
-
-
?
5alpha-dihydrotestosterone + NAD(P)H
5alpha-androstane-3beta,17beta-diol + NADP+
-
-
-
?
5alpha-pregnan-3alpha-ol-20-one + NAD+
5alpha-pregnan-3,20-dione + NADH + H+
-
-
-
?
5alpha-pregnan-3beta-ol-20-one + NAD(P)+
5alpha-pregnan-3,20-dione + NAD(P)H + H+
NADP+ and NADPH are 3-5times less effective than NAD+ and NADH
-
-
r
5alpha-pregnan-3beta-ol-20-one + NAD+
5alpha-pregnan-3,20-dione + NADH + H+
-
-
-
?
5beta-androstan-17beta-ol-3-one + NAD+
5beta-androstan-3,17-dione + NADH + H+
-
-
-
?
5beta-androstan-3alpha-ol-17-one + NAD+
5beta-androstan-3,17-dione + NADH + H+
-
-
-
?
5beta-pregnan-20alpha-ol-3-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
-
-
-
?
5beta-pregnan-3,20-dione + NAD(P)H + H+
3beta-hydroxy-5beta-pregnan-20-one + NAD(P)+
NADP+ is 3-5times less effective than NAD+
-
-
?
5beta-pregnan-3,20-dione + NADH
3beta-hydroxy-5beta-pregnan-20-one + NAD+
-
-
-
?
5beta-pregnan-3beta,21-diol-20-one + NADH + H+
? + NAD+
-
-
-
?
5beta-pregnan-3beta-ol-20-one + NAD(P)+
5-pregnan-3,20-dione + NAD(P)H + H+
NADP+ and NADPH are 3-5times less effective than NAD+ and NADH
-
-
r
5beta-pregnan-3beta-ol-20-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
-
-
-
?
androstenediol + NAD(P)H + H+
testosterone + NAD(P)+
-
reaction catalysed by 3beta-HSD (type 1)
-
-
?
androstenedione + NAD(P)H + H+
testosterone + NAD(P)+
-
reaction catalysed by 17beta-HSD (type 1 and 3)
-
-
?
androsterone + NADPH
androstane-3beta,17beta-diol + NADP+
-
reduction at C17
-
-
?
beta-ionol + NAD+
(3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one + NADH + H+
-
-
-
?
dehydroepiandrosterone + NAD(P)H + H+
androstenediol + NAD(P)+
-
reaction catalysed by 17beta-HSD (type 1 and 3)
-
-
?
dehydroepiandrosterone + NADPH
5-androstene-3beta,17beta-diol + NADP+
-
reduction at C17
-
-
?
dehydroepiandrosterone + NADPH + H+
androst-5-ene-3beta,17beta-diol + NADP+
-
-
-
-
?
dihydrotestosterone + NADPH + H+
5alpha-androstane-3beta,17beta-diol + NADP+
-
androsterone inactivation
-
-
?
epiandrosterone + NADPH
5-androstane-3beta,17beta-diol + NADP+
-
reduction at C17
-
-
?
epiandrosterone + NADPH
androstane-3beta,17beta-diol + NADP+
reduction at C17
-
-
?
estrone + NAD(P)H + H+
estradiol + NAD(P)+
-
reaction catalysed by 17beta-HSD (type 1 and 3)
-
-
?
11beta-hydroxyandrost-5-ene-3,17-dione + NADPH
11beta,17beta-dihydroxyandrost-5-ene-3-one + NADP+
i.e. 11beta-hydroxy-androstenedione, reduction at C17
i.e. 11beta-testosterone
-
?
11beta-hydroxyandrost-5-ene-3,17-dione + NADPH
11beta,17beta-dihydroxyandrost-5-ene-3-one + NADP+
-
i.e. 11beta-hydroxy-androstenedione, reduction at C17
i.e. 11beta-testosterone
-
?
3beta-hydroxy-16alpha,17alpha-epoxypregn-5-en-20-one + NAD(P)+
?
-
-
-
-
?
3beta-hydroxy-16alpha,17alpha-epoxypregn-5-en-20-one + NAD(P)+
?
-
-
-
-
?
4-androstene-3,17-dione + NADPH + H+
testosterone + NADP+
-
isozymes 17beta-HSD3 and 17beta-HSD5
-
-
r
4-androstene-3,17-dione + NADPH + H+
testosterone + NADP+
-
selective reduction at C17
-
-
?
5alpha-dihydrotestosterone + NADP+
5alpha-androstane-3,17-dione + NADPH
-
-
-
?
5alpha-dihydrotestosterone + NADP+
5alpha-androstane-3,17-dione + NADPH
-
-
-
?
5beta-pregnan-3,20-dione + NADPH + H+
5beta-pregnane-3beta-ol-20-one + NADP+
-
-
-
-
?
5beta-pregnan-3,20-dione + NADPH + H+
5beta-pregnane-3beta-ol-20-one + NADP+
-
-
-
-
?
androst-5-ene-3,11,17-trione + NADPH
17beta-hydroxyandrost-5-ene-3,11-dione + NADP+
i.e. 11-keto-androstenedione, reduction at C17
i.e. 11-keto-testosterone
-
?
androst-5-ene-3,11,17-trione + NADPH
17beta-hydroxyandrost-5-ene-3,11-dione + NADP+
-
i.e. 11-ketoandrostenedione, reduction at C17
i.e. 11-keto-testosterone
-
?
androst-5-ene-3beta,17beta-diol + NADP+
dehydroepiandrosterone + NADPH
-
-
-
r
androst-5-ene-3beta,17beta-diol + NADP+
dehydroepiandrosterone + NADPH
-
-
-
r
androst-5-ene-3beta,17beta-diol + NADP+
dehydroepiandrosterone + NADPH
-
-
-
r
androstenedione + NADPH + H+
testosterone + NADP+
the forward reaction is preferred, no activity with NADH in the forward reaction, poor activity with NAD+ in the reverse raection, overview
-
-
r
androstenedione + NADPH + H+
testosterone + NADP+
-
the equilibrium state is 2% testosterone to 95% androstenedione
-
-
r
androstenedione + NADPH + H+
testosterone + NADP+
-
the forward reaction is preferred, no activity with NADH in the forward reaction, poor activity with NAD+ in the reverse raection, overview
-
-
r
androstenedione + NADPH + H+
testosterone + NADP+
-
isozymes 17beta-HSD1 and 17beta-HSD8
-
-
r
androsterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
-
-
-
?
androsterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
-
-
-
?
dehydroepiandrosterone + NAD(P)+
androst-5-en-3,17-dione + NAD(P)H + H+
-
-
-
-
?
dehydroepiandrosterone + NAD(P)+
androst-5-en-3,17-dione + NAD(P)H + H+
-
-
-
-
?
dehydroepiandrosterone + NAD(P)+
androst-5-en-3,17-dione + NAD(P)H + H+
-
-
-
-
?
dehydroepiandrosterone + NAD+
4-androstene-3,17-dione + NADH + H+
-
-
-
-
?
dehydroepiandrosterone + NAD+
4-androstene-3,17-dione + NADH + H+
-
-
-
-
?
dehydroepiandrosterone + NADPH
androstene-3beta,17beta-diol + NADP+
-
reduction at C17
-
-
?
dehydroepiandrosterone + NADPH
androstene-3beta,17beta-diol + NADP+
reduction at C17
-
-
?
estradiol + NADP+
estrone + NADPH
-
the equilibrium state is 3% estradiol and 97% estrone
-
-
r
pregnenolone + NAD(P)+
progesterone + NAD(P)H + H+
-
-
-
?
pregnenolone + NAD+
progesterone + NADH + H+
-
the mitochondrial enzyme is essential for the synthesis of progesterone by corpora lutea, overview
-
-
?
testosterone + NAD(P)+
androst-4-en-3,17-dione + NAD(P)H + H+
-
-
-
?
testosterone + NAD(P)+
androst-4-en-3,17-dione + NAD(P)H + H+
-
-
-
?
testosterone + NAD(P)+
androst-4-en-3,17-dione + NAD(P)H + H+
-
-
-
?
testosterone + NAD(P)+
androst-4-en-3,17-dione + NAD(P)H + H+
-
-
-
?
testosterone + NAD(P)+
androst-4-en-3,17-dione + NAD(P)H + H+
-
-
-
?
testosterone + NADP+
androstenedione + NADPH + H+
-
-
-
r
testosterone + NADP+
androstenedione + NADPH + H+
-
-
-
?
additional information
?
-
-
the wild-type strain ATCC 119960 degrades steroids, such as testosterone, estradiol, or cholesterol, differences in the enzyme mutant strains, overview
-
-
-
additional information
?
-
the wild-type strain ATCC 119960 degrades steroids, such as testosterone, estradiol, or cholesterol, differences in the enzyme mutant strains, overview
-
-
-
additional information
?
-
-
no activity with androstanedione and androsterone
-
-
-
additional information
?
-
no activity with androstanedione and androsterone
-
-
-
additional information
?
-
-
activity of the enzyme is associated with the mechanism of prostatic regulation by androgens after castration, which is important in prostate cancer
-
-
-
additional information
?
-
-
the enzyme is an important therapeutic target for androgen-sensitive diseases, overview
-
-
-
additional information
?
-
-
the isozyme 17beta-HSD3 is a critical determinant in steroid hormone biosynthesis
-
-
-
additional information
?
-
-
the isozyme might play an imporant role in modulation of active hormone levels in estrogen-sensitive cells or tissues
-
-
-
additional information
?
-
-
isozyme 17beta-HSD5 also shows 3alpha- and 20alpha-hydroxysteroid dehydrogenase, dihydrodiol dehydrogenase, and prostaglandin synthase activities
-
-
-
additional information
?
-
-
AKR1C3 physically interacts with the androgen receptor
-
-
-
additional information
?
-
the enzyme AKR1C35 efficiently oxidizes various 3beta- and 17beta-hydroxysteroids, including biologically active 3beta-hydroxy-5alpha/beta-dihydro-C19/C21-steroids, dehydroepiandrosterone, and 17beta-estradiol, substrate specificity, detailed overview. Val54 plays a critical role in non-/recognition of the steroidal substrates. Reaction products identification by thin-layer chromatography (TLC) and liquid chromatography/mass spectrometry (LC/MS). No activity with 5beta-pregnan-3alpha-ol-20-one, 3alpha-hydroxyprogesterone, 5beta-androstan-3alpha-ol-17-one, 20alpha-hydroxyprogesterone, and 5alpha-pregnan-20alpha-ol-3-one
-
-
-
additional information
?
-
-
the enzyme AKR1C35 efficiently oxidizes various 3beta- and 17beta-hydroxysteroids, including biologically active 3beta-hydroxy-5alpha/beta-dihydro-C19/C21-steroids, dehydroepiandrosterone, and 17beta-estradiol, substrate specificity, detailed overview. Val54 plays a critical role in non-/recognition of the steroidal substrates. Reaction products identification by thin-layer chromatography (TLC) and liquid chromatography/mass spectrometry (LC/MS). No activity with 5beta-pregnan-3alpha-ol-20-one, 3alpha-hydroxyprogesterone, 5beta-androstan-3alpha-ol-17-one, 20alpha-hydroxyprogesterone, and 5alpha-pregnan-20alpha-ol-3-one
-
-
-
additional information
?
-
-
the enzyme plays a role in gonadal steroidogenesis
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
17-oxo steroids + NADPH
?
-
maintenance of balance between oxidized and reduced steroids in blood
-
-
-
4-androstene-3,17-dione + NADPH + H+
testosterone + NADP+
-
isozymes 17beta-HSD3 and 17beta-HSD5
-
-
r
5-androstenedione + NADPH
5alpha-dihydrotestosterone + NADP+
-
isozyme 17beta-HSD3
-
-
r
dihydrotestosterone + NADPH + H+
5alpha-androstane-3beta,17beta-diol + NADP+
-
androsterone inactivation
-
-
?
pregnenolone + NAD+
progesterone + NADH + H+
-
the mitochondrial enzyme is essential for the synthesis of progesterone by corpora lutea, overview
-
-
?
5beta-pregnan-3,20-dione + NADPH + H+
5beta-pregnane-3beta-ol-20-one + NADP+
-
-
-
-
?
5beta-pregnan-3,20-dione + NADPH + H+
5beta-pregnane-3beta-ol-20-one + NADP+
-
-
-
-
?
testosterone + NADP+
androstenedione + NADPH + H+
P19871
-
-
-
r
testosterone + NADP+
androstenedione + NADPH + H+
O54939
-
-
-
?
additional information
?
-
-
the wild-type strain ATCC 119960 degrades steroids, such as testosterone, estradiol, or cholesterol, differences in the enzyme mutant strains, overview
-
-
-
additional information
?
-
P19871
the wild-type strain ATCC 119960 degrades steroids, such as testosterone, estradiol, or cholesterol, differences in the enzyme mutant strains, overview
-
-
-
additional information
?
-
-
activity of the enzyme is associated with the mechanism of prostatic regulation by androgens after castration, which is important in prostate cancer
-
-
-
additional information
?
-
-
the enzyme is an important therapeutic target for androgen-sensitive diseases, overview
-
-
-
additional information
?
-
-
the isozyme 17beta-HSD3 is a critical determinant in steroid hormone biosynthesis
-
-
-
additional information
?
-
-
the isozyme might play an imporant role in modulation of active hormone levels in estrogen-sensitive cells or tissues
-
-
-
additional information
?
-
-
AKR1C3 physically interacts with the androgen receptor
-
-
-
additional information
?
-
-
the enzyme plays a role in gonadal steroidogenesis
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NAD+
conserved residues Gln270 and Glu276 are critical residues for the NAD+ specificity
NADPH
-
binding of the coenzyme NADPH to the enzyme causes local structural changes that do not significantly affect the thermal stability of this protein
NADPH
-
-
657673, 658489, 659176, 669784, 669905, 670033, 670259, 670273, 672586, 672862, 700188, 740156, 740161, 740329, 740916
additional information
-
no activity with NADH in the forward reaction, poor activity with NAD+ in the reverse raection, overview
-
additional information
no activity with NADH in the forward reaction, poor activity with NAD+ in the reverse raection, overview
-
additional information
-
no activity with NADH in the forward reaction, poor activity with NAD+ in the reverse raection, overview
-
additional information
the enzyme shows high preference for NAD+ compared with NADP+
-
additional information
-
the enzyme shows high preference for NAD+ compared with NADP+
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
NaCl
-
addition of a neutral electrolyte, such as NaCl, shields repulsion interactions in the highly positively charged enzyme at pH 2.0, effects on the secondary structure by increasing NaCl concentrations at pH 2.0 and 25°C, overview
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(3a,5a)-3-[[(2R,5S)-4-[[5-(dimethylamino)naphthalen-1-yl]sulfonyl]-2,5-dimethylpiperazin-1-yl]methyl]-17-methylideneandrostan-3-ol
-
-
(3alpha,5alpha)-3-([(2R,5S)-2,5-dimethyl-4-[2-(trifluoromethyl)benzene-1-sulfonyl]piperazin-1-yl]methyl)-3-hydroxyandrostan-17-one
-
i.e. RM-532-105
(3alpha,5alpha)-3-[(2,5-dimethyl-4-{[2-(trifluoromethyl)phenyl]sulfonyl}piperazin-1-yl)methyl]-3-hydroxyandrostan-17-one
the inhibitor RM-532-105 seems to have difficulties in penetrating inside the testis and is concentrated in the testicular capsule. Therefore it is unable to inhibit the 17bets-HSD3 located inside the testis. At a higher concentration, RM-532-105 significantly decreases the level of testosterone and dihydrotestosterone in rat plasma, in vivo effects of the inhibitor in testis and plasma, detailed overview
(4-(4-chlorophenyl)piperazin-1-yl)(3,4-dihydroisoquinolin-2(1H)-yl)methanone
-
-
(4-(4-chlorophenyl)piperazin-1-yl)(4-(2-hydroxyethyl)piperazin-1-yl)methanone
-
-
(5-(4-chlorophenyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl)(morpholino)methanone
-
-
1-(4-(4-(4-chlorophenyl)piperazine-1-carbonyl)piperazin-1-yl)-2-hydroxyethanone
-
-
1-[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl]-3-(morpholin-4-yl)propan-2-yl cyclohexanecarboxylate
1-[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]ethanone
-
IC50: 0.02 nM
1-[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]methanamine
-
IC50: 0.00024 mM; IC50: 0.00029 mM
11-[3-hydroxy-17-beta-hydroxyestr-5(10)-en-17alpha-yl-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl]-undecanoic acid butyl-methyl-amide
-
selective inhibition of type 2 17beta-HSD
12-acetyl-1-chloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.0115 mM
12-acetyl-2,3-dichloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00001 mM
12-acetyl-2-(trifluoromethyl)-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00281 mM
12-acetyl-2-chloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00003 mM
12-acetyl-3,4-dichloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00076 mM
12-acetyl-3-bromo-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00025 mM
12-acetyl-3-chloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00010 mM
12-acetyl-3-fluoro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00009 mM
12-acetyl-3-methoxy-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.0021 mM
12-acetyl-3-methyl-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.001 mM
17-hydroxy-7alpha-thioethyl-3-oxo-4-androstene-17alpha-propionic acid, gamma-lactone
-
IC50 for reduction of androst-4-en-3,17-dione: 0.0009 mM
17alpha-ethynyl-estradiol
-
0.01 mM, 54% inhibition, reaction with 0.002 mM estradiol; inhibits oxidation of testosterone
17beta-dihydroequilin
-
0.01 mM, 88% inhibition, reaction with 0.002 mM estradiol
2,5-dioxo-3-(2-propyn-1-yl)-3-pyrrolidinecarboxylic acid 2,3,3-triphenyl-2-propen-1-yl-ester
-
-
2-((3-chloro-4-hydroxybenzoyl)amino)-N-(2-(2-methoxyphenyl)ethyl)-5-phenoxy-benzamide
-
-
2-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo(b,f)azocin-8-yl)-benzoic acid methyl ester
-
-
2-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzonitrile
-
IC50: 3 nM
20alpha-dihydroprogesterone
-
0.01 mM, 71% inhibition, reaction with 0.002 mM estradiol, inhibits oxidation of testosterone
3,4-dihydrobenzoic acid
-
0.001 mM, 40% inhibition, reduction of androst-4-en-3,17-dione
3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzonitrile
-
IC50: 3 nM
3-hydroxy-1,3,5(10)-estratriene-17beta-O,17alpha-butanolactone
-
selective for type 2 17beta-HSD versus types 1, 3, and 7 but not versus type 5 17beta-HSD
3-oxo-17alpha-pregna-4-ene-7alpha-(benzylthia)-21,17-carbolactone
-
IC50 for reduction of androst-4-en-3,17-dione: 0.00042 mM,IC50 for oxidation of testosterone: 0.001 mM
3-oxo-17alpha-pregna-4-ene-7alpha-(phenylthia)-21,17-carbolactone
-
IC50 for reduction of androst-4-en-3,17-dione: 0.001 mM
3-oxo-17alpha-pregna-4-ene-7alpha-(propylthia)-21,17-carbolactone
-
IC50 for reduction of androst-4-en-3,17-dione: 0.0011 mM; IC50 for reduction of androst-4-en-3,17-dione: 0.0014 mM
3-oxo-17alpha-pregna-4-ene-7alpha-[4-[2-(1-piperidinyl)-ethoxy]benzylthia]-21,17-carbolactone
-
IC50 for oxidation of testosterone: 0.0007 mM, no inhibition of type 1, 3 and 5 17beta-HSD, nor against P450 aromatase
3alpha-alkylated androsterone derivatives
-
17-88% inhibition at 0.003 mM, overview
-
3alpha-ether-3beta-substituted androsterone derivatives
-
diverse derivatives, IC50: 70-760 nM, overview
-
3beta-phenyl-androsterone
-
mixed-type inhibition, shows some proliferative activity on AR+ and Er+ cell lines not mediated through androgen or estrogen receptors
4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)-N-methylbenzamide
-
IC50: 25 nM
4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzonitrile
-
IC50: 5 nM
5-acetyl-2-chloro-8-(2-methoxyphenyl)-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 3 nM
5-acetyl-2-chloro-8-(3-methoxyphenyl)-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 8 nM
5-acetyl-2-chloro-8-(4-methoxyphenyl)-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 2 nM
5-acetyl-N-cyclohexyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-amine
-
IC50: 8 nM
5alpha-androstane-3alpha,17beta-diol
-
0.01 mM, 87% inhibition, reaction with 0.002 mM estradiol
5beta-androstane-3alpha,17beta-diol
-
0.01 mM, 83% inhibition, reaction with 0.002 mM estradiol
GTx-560
-
competitively and selectively inhibits AKR1C3-dependent androgen receptor transactivation. GTx-560 completely blocks the formation of testosterone from androstenedione, indicating the ability of AKR1C3 inhibitors, unlike 5alpha-reductase inhibitors, to reduce testosterone levels
methyl 12-acetyl-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine-3-sulfinate
-
IC50: 0.01 mM
methyl 3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzoate
-
IC50: 0.00004 mM
methyl 4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzoate
-
IC50: 0.00004 mM; IC50: 0.7 nM
methyl [3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]amidosulfite
-
IC50: 0.00014 mM
methyl [4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]amidosulfite
-
IC50: 2 nM
N-(((3,5)-3-hydroxy-17-oxoandrostan-3-yl)methyl)-N-(tricyclo(3.3.1.13.7)dec-2-ylmethyl)butanamide
-
-
N-(5-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-yl)benzamide
-
IC50: 0.00016 mM
oleuropein glycoside
-
0.001 mM, 40% inhibition, reduction of androst-4-en-3,17-dione
spiro-gamma-lactone-estradiol
-
inhibits the reduction of androst-4-en-3,17-dione, reversible, IC50: 0.00025 mM
[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]methanol
-
IC50: 0.9 nM
(2,4-dihydroxyphenyl)-phenylmethanone
-
(2,4-dihydroxyphenyl)-phenylmethanone leads to inhibition of testosterone synthesis in freshly isolated mouse and rat testis tissue
(2,4-dihydroxyphenyl)-phenylmethanone
-
(2,4-dihydroxyphenyl)-phenylmethanone leads to inhibition of testosterone synthesis in freshly isolated mouse and rat testis tissue
1-[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl]-3-(morpholin-4-yl)propan-2-yl cyclohexanecarboxylate
-
-
1-[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl]-3-(morpholin-4-yl)propan-2-yl cyclohexanecarboxylate
-
D-5-2
3beta-phenylmethyl-androsterone
-
mixed-type inhibition, shows some proliferative activity on AR+ and Er+ cell lines not mediated through androgen or estrogen receptors
RM-532-105
-
3beta-(o-trifluoromethylphenyl-sulfonyl-dimethylpipera-zino)-androsterone, a 3 beta-dimethylpiperazino-ADT sulfonamide derivative. RM-532-105 is a better competitor of labeled enzyme substrate [14C]-4-dione than the unlabeled natural substrate 4-dione (IC50 = 341 and 337 nM) used itself as an inhibitor
Strogen forte
-
standardized extract of the plant Sabalis serrulata, 0.212 mg/ml result in 50% enzyme inhibition
-
Strogen forte
-
standardized extract of the plant Sabalis serrulata, 0.4 mg/ml result in 50% enzyme inhibition
-
additional information
-
synthesis, inhibitory potency, and in vivo effects of the diverse inhibitor derivatives, detailed overview
-
additional information
-
design, synthesis and in vitro evaluation of 4-androstene-3,17-dione/adenosine hybrid compounds as bisubstrate inhibitors of type 3 17beta-HSD, the bisubstrate inhibitors are less potent in intact cells than in homogenated cells, overview, the best inhibitors of that series are those bearing an alkyl side-chain spacer of 11 or 12 methylenes with inhibition of 69% and 78% at 1 mM
-
additional information
-
high-throughput screening, a series of non-carboxylate morpholino(phenylpiperazin-1-yl)methanones are prepared by palladium-catalysed coupling of substituted phenyl or pyridyl bromides with morpholino(piperazin-1-yl)methanone, and are shown to be potent and very isoform-selective inhibitors of AKR1C3, competitive fluorescence assay, structure-activity relationships, overview
-
additional information
-
small-molecule inhibitors inhibit both the enzymatic and coactivator functions of AKR1C3 resulting in androgen-dependent prostate cancer and CRPC regression. No inhibition by indomethacin
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
R1881
-
requires amino acids 1-282 of AKR1C3 to elicit its coactivation, inhibitor GTx-560 requires the full-length AKR1C3 to bind and inhibit R1881-induced activity
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.028
(R)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C, recombinant enzyme
0.0015
(S)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C, recombinant enzyme
0.685
3-acetylpyridine adenine dinucleotide
-
testosterone as substrate
0.063
3-pyridinealdehyde adenine dinucleotide
-
testosterone as substrate
0.0009
3beta-hydroxyprogesterone
pH 7.4, 25°C, recombinant enzyme
0.0081
4-androstene-3alpha,17beta-diol
pH 7.4, 25°C, recombinant enzyme
0.0033
5-androstene-3beta,17beta-diol
pH 7.4, 25°C, recombinant enzyme
0.0025
5alpha-Androstan-3beta-ol-17-one
pH 7.4, 25°C, recombinant enzyme
0.046
5beta-androstan-3beta-ol-17-one
pH 7.4, 25°C, recombinant enzyme
0.0039
5beta-androstane-3alpha,17beta-diol
pH 7.4, 25°C, recombinant enzyme
0.015
5beta-androstane-3beta,17beta-diol
pH 7.4, 25°C, recombinant enzyme
0.013
5beta-dihydrotestosterone
pH 7.4, 25°C, recombinant enzyme
0.015
5beta-pregnan-3beta,21-diol-20-one
pH 7.4, 25°C, recombinant enzyme
0.014
alpha-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
0.04
beta-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
0.0097
cis-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
0.083
Thionicotinamide adenine dinucleotide
-
testosterone as substrate
0.011
trans-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
0.0076
5alpha-dihydrotestosterone
pH 7.4, 25°C, recombinant enzyme
0.0039
5alpha-pregnan-3beta-ol-20-one
pH 7.4, 25°C, recombinant enzyme
0.0068
5beta-Pregnan-3beta-ol-20-one
pH 7.4, 25°C, recombinant enzyme
0.0043
dehydroepiandrosterone
pH 7.4, 25°C, recombinant enzyme
0.0082
NADP+
-
testosterone as substrate, 17beta-hydroxysteroid dehydrogenase activity
0.009
NADP+
-
3beta-hydroxy-5alpha-androstan-17-one as substrate, 3beta-hydroxysteroid dehydrogenase activity
0.0018
NADPH
-
5alpha-dihydrotestosterone as substrate, 3-beta-hydroxysteroid dehydrogenase activity
0.0021
NADPH
-
estrone as substrate, 17beta-hydroxysteroid dehydrogenase activity
additional information
additional information
Michaelis-Menten kinetics
-
additional information
additional information
-
Michaelis-Menten kinetics
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.022
(R)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C, recombinant enzyme
0.025
(S)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C, recombinant enzyme
0.056
3beta-hydroxyprogesterone
pH 7.4, 25°C, recombinant enzyme
0.043
4-androstene-3alpha,17beta-diol
pH 7.4, 25°C, recombinant enzyme
0.043
5-androstene-3beta,17beta-diol
pH 7.4, 25°C, recombinant enzyme
0.027
5alpha-Androstan-3beta-ol-17-one
pH 7.4, 25°C, recombinant enzyme
0.057
5alpha-dihydrotestosterone
pH 7.4, 25°C, recombinant enzyme
0.013
5alpha-pregnan-3beta-ol-20-one
pH 7.4, 25°C, recombinant enzyme
0.022
5beta-androstan-3beta-ol-17-one
pH 7.4, 25°C, recombinant enzyme
0.012
5beta-androstane-3alpha,17beta-diol
pH 7.4, 25°C, recombinant enzyme
0.036
5beta-androstane-3beta,17beta-diol
pH 7.4, 25°C, recombinant enzyme
0.032
5beta-dihydrotestosterone
pH 7.4, 25°C, recombinant enzyme
0.0043
5beta-pregnan-3beta,21-diol-20-one
pH 7.4, 25°C, recombinant enzyme
0.0028
5beta-Pregnan-3beta-ol-20-one
pH 7.4, 25°C, recombinant enzyme
0.018
alpha-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
0.025
beta-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
0.025
cis-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
0.033
trans-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.78
(R)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C, recombinant enzyme
16.67
(S)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C, recombinant enzyme
63.33
3beta-hydroxyprogesterone
pH 7.4, 25°C, recombinant enzyme
5.5
4-androstene-3alpha,17beta-diol
pH 7.4, 25°C, recombinant enzyme
9.67
5-androstene-3beta,17beta-diol
pH 7.4, 25°C, recombinant enzyme
10.67
5alpha-Androstan-3beta-ol-17-one
pH 7.4, 25°C, recombinant enzyme
2.83
5alpha-dihydrotestosterone
pH 7.4, 25°C, recombinant enzyme
3.33
5alpha-pregnan-3beta-ol-20-one
pH 7.4, 25°C, recombinant enzyme
0.47
5beta-androstan-3beta-ol-17-one
pH 7.4, 25°C, recombinant enzyme
3
5beta-androstane-3alpha,17beta-diol
pH 7.4, 25°C, recombinant enzyme
2.5
5beta-androstane-3beta,17beta-diol
pH 7.4, 25°C, recombinant enzyme
0.6
5beta-dihydrotestosterone
pH 7.4, 25°C, recombinant enzyme
0.28
5beta-pregnan-3beta,21-diol-20-one
pH 7.4, 25°C, recombinant enzyme
0.42
5beta-Pregnan-3beta-ol-20-one
pH 7.4, 25°C, recombinant enzyme
1.3
alpha-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
0.63
beta-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0153
Perfluorooctanoic acid
-
testicular microsome, inhibition of 17beta-hydroxysteroid dehydrogenase, pH and temperature not specified in the publication
0.0213
Perfluorooctanoic acid
-
testicular microsome, pH and temperature not specified in the publication, inhibition of 3beta-hydroxysteroid dehydrogenase
0.0586
Perfluorooctanoic acid
-
intact Leydig cells, pH and temperature not specified in the publication, inhibition of 3beta-hydroxysteroid dehydrogenase
0.181
Perfluorooctanoic acid
-
intact Leydig cells, inhibition of 17beta-hydroxysteroid dehydrogenase, pH and temperature not specified in the publication
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000262
(3a,5a)-3-[[(2R,5S)-4-[[5-(dimethylamino)naphthalen-1-yl]sulfonyl]-2,5-dimethylpiperazin-1-yl]methyl]-17-methylideneandrostan-3-ol
Homo sapiens
-
pH and temperature not specified in the publication
0.000085
(3alpha,5alpha)-3-([(2R,5S)-2,5-dimethyl-4-[2-(trifluoromethyl)benzene-1-sulfonyl]piperazin-1-yl]methyl)-3-hydroxyandrostan-17-one
Homo sapiens
-
pH and temperature not specified in the publication
0.00297
1-(11,12-dihydro-6H-dibenzo[b,f]oxocin-12-yl)ethanone
Homo sapiens
-
IC50: 0.00297 mM
0.00474
1-(5,6,11,12-tetrahydrodibenzo[b,f]azocin-12-yl)ethanone
Homo sapiens
-
IC50: 0.00474 mM
0.000037 - 0.000051
1-[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl]-3-(morpholin-4-yl)propan-2-yl cyclohexanecarboxylate
Rattus norvegicus
-
pH 7.4, 37°C
0.00000002
1-[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]ethanone
Homo sapiens
-
IC50: 0.02 nM
0.00024 - 0.00029
1-[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]methanamine
0.0115
12-acetyl-1-chloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.0115 mM
0.00281
12-acetyl-11,12-dihydro-2-(trifluoromethyl)-6H-dibenzo(b,f)(1,4)thiazocine
Homo sapiens
-
pH and temperature not specified in the publication
0.0004
12-acetyl-11,12-dihydro-6H-dibenzo(b,f)(1,4)thiazocine
Homo sapiens
-
pH and temperature not specified in the publication
0.0049
12-acetyl-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocin-3-ol
Homo sapiens
-
IC50: 0.0049 mM
0.00001
12-acetyl-2,3-dichloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.00001 mM
0.00281
12-acetyl-2-(trifluoromethyl)-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.00281 mM
0.00003
12-acetyl-2-chloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.00003 mM
0.00076
12-acetyl-3,4-dichloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.00076 mM
0.00025
12-acetyl-3-bromo-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.00025 mM
0.0001
12-acetyl-3-chloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.00010 mM
0.00009
12-acetyl-3-fluoro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.00009 mM
0.0021
12-acetyl-3-methoxy-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.0021 mM
0.001
12-acetyl-3-methyl-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.001 mM
0.0009
17-hydroxy-7alpha-thioethyl-3-oxo-4-androstene-17alpha-propionic acid, gamma-lactone
Homo sapiens
-
IC50 for reduction of androst-4-en-3,17-dione: 0.0009 mM
0.00915
2,5-dioxo-3-(2-propyn-1-yl)-3-pyrrolidinecarboxylic acid 2,3,3-triphenyl-2-propen-1-yl-ester
Homo sapiens
-
pH and temperature not specified in the publication
0.00006
2-((3-chloro-4-hydroxybenzoyl)amino)-N-(2-(2-methoxyphenyl)ethyl)-5-phenoxy-benzamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00000002
2-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo(b,f)azocin-8-yl)-benzoic acid methyl ester
Homo sapiens
-
pH and temperature not specified in the publication
0.000003
2-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzonitrile
Homo sapiens
-
IC50: 3 nM
0.000003
3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzonitrile
Homo sapiens
-
IC50: 3 nM
0.001
3-oxo-17alpha-pregna-4-ene-7alpha-(benzylthia)-21,17-carbolactone
Homo sapiens
-
IC50 for reduction of androst-4-en-3,17-dione: 0.00042 mM,IC50 for oxidation of testosterone: 0.001 mM
0.001
3-oxo-17alpha-pregna-4-ene-7alpha-(phenylthia)-21,17-carbolactone
Homo sapiens
-
IC50 for reduction of androst-4-en-3,17-dione: 0.001 mM
0.0007
3-oxo-17alpha-pregna-4-ene-7alpha-[4-[2-(1-piperidinyl)-ethoxy]benzylthia]-21,17-carbolactone
Homo sapiens
-
IC50 for oxidation of testosterone: 0.0007 mM, no inhibition of type 1, 3 and 5 17beta-HSD, nor against P450 aromatase
0.000116
3alpha-butyl-3-hydroxy-5alpha-androstan-17-one
Homo sapiens
-
pH and temperature not specified in the publication
0.00007 - 0.00076
3alpha-ether-3beta-substituted androsterone derivatives
Homo sapiens
-
diverse derivatives, IC50: 70-760 nM, overview
-
0.000057 - 0.000147
3beta-alkylated androsterone derivatives
Homo sapiens
-
IC50: 57-147 nM
-
0.000057 - 0.000147
3beta-substituted androsterone derivatives
Homo sapiens
-
IC50: 57-147 nM
-
0.000025
4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)-N-methylbenzamide
Homo sapiens
-
IC50: 25 nM
0.000005
4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzonitrile
Homo sapiens
-
IC50: 5 nM
0.00007
5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 0.00007 mM
0.00024
5-acetyl-2-chloro-5,6-dihydro-dibenzo(b,f)azocine
Homo sapiens
-
pH and temperature not specified in the publication
0.000003
5-acetyl-2-chloro-8-(2-methoxyphenyl)-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 3 nM
0.000008
5-acetyl-2-chloro-8-(3-methoxyphenyl)-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 8 nM
0.000002
5-acetyl-2-chloro-8-(4-methoxyphenyl)-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 2 nM
0.000004
5-acetyl-2-chloro-8-phenyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 4 nM
0.00005
5-acetyl-3-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 0.00005 mM
0.00474
5-acetyl-5,6,11,12-tetrahydro-dibenzo(b,f)(1,4)diazocine
Homo sapiens
-
pH and temperature not specified in the publication
0.00049
5-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-amine
Homo sapiens
-
IC50: 0.00049 mM
0.001
5-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine-9-carboxamide
Homo sapiens
-
IC50: 0.001 mM
0.00000002
5-acetyl-8-phenyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 0.02 nM
0.000008
5-acetyl-N-cyclohexyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-amine
Homo sapiens
-
IC50: 8 nM
0.00028
9-bromo-11,12-dihydrodibenzo[b,f]azocine-5(6H)-carboxamide
Homo sapiens
-
IC50: 0.00028 mM
0.00032
9-bromo-5-butanoyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 0.00032 mM
0.01
methyl 12-acetyl-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine-3-sulfinate
Homo sapiens
-
IC50: 0.01 mM
0.00004
methyl 3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzoate
Homo sapiens
-
IC50: 0.00004 mM
0.0000007 - 0.00004
methyl 4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzoate
0.00014
methyl [3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]amidosulfite
Homo sapiens
-
IC50: 0.00014 mM
0.000002
methyl [4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]amidosulfite
Homo sapiens
-
IC50: 2 nM
0.000035
N-(((3,5)-3-hydroxy-17-oxoandrostan-3-yl)methyl)-N-(tricyclo(3.3.1.13.7)dec-2-ylmethyl)butanamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00016
N-(5-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-yl)benzamide
Homo sapiens
-
IC50: 0.00016 mM
0.00025
spiro-gamma-lactone-estradiol
Homo sapiens
-
inhibits the reduction of androst-4-en-3,17-dione, reversible, IC50: 0.00025 mM
0.0000009
[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]methanol
Homo sapiens
-
IC50: 0.9 nM
0.00024
1-[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]methanamine
Homo sapiens
-
IC50: 0.00024 mM
0.00029
1-[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]methanamine
Homo sapiens
-
IC50: 0.00029 mM
0.0011
3-oxo-17alpha-pregna-4-ene-7alpha-(propylthia)-21,17-carbolactone
Homo sapiens
-
IC50 for reduction of androst-4-en-3,17-dione: 0.0011 mM
0.0014
3-oxo-17alpha-pregna-4-ene-7alpha-(propylthia)-21,17-carbolactone
Homo sapiens
-
IC50 for reduction of androst-4-en-3,17-dione: 0.0014 mM
0.0000007
methyl 4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzoate
Homo sapiens
-
IC50: 0.7 nM
0.00004
methyl 4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzoate
Homo sapiens
-
IC50: 0.00004 mM
0.0177
Perfluorooctanoic acid
Rattus norvegicus
-
testicular microsome, inhibition of 17beta-hydroxysteroid dehydrogenase, pH and temperature not specified in the publication
0.0532
Perfluorooctanoic acid
Rattus norvegicus
-
testicular microsome, pH and temperature not specified in the publication, inhibition of 3beta-hydroxysteroid dehydrogenase
0.146
Perfluorooctanoic acid
Rattus norvegicus
-
intact Leydig cells, pH and temperature not specified in the publication, inhibition of 3beta-hydroxysteroid dehydrogenase
0.194
Perfluorooctanoic acid
Rattus norvegicus
-
intact Leydig cells, inhibition of 17beta-hydroxysteroid dehydrogenase, pH and temperature not specified in the publication
0.000026
RM-532-105
Rattus norvegicus
-
pH 7.4, 37°C, inhibition in recombinant HEK-293 cells overexpressing 17 beta-HSD3, overview
0.0001
RM-532-105
Rattus norvegicus
-
pH 7.4, 37°C, inhibition in wild-type rat testis, overview
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.0000000002255
-
male, 24 hours old, 37°C, pH not specified in the publication
0.0000000003795
-
female, 24 hours old, 37°C, pH not specified in the publication
0.000000000483
-
female, 48 hours old, 37°C, pH not specified in the publication
0.000000000499
-
male, 48 hours old, 37°C, pH not specified in the publication
0.000000001085
-
female, 0 hours old, 37°C, pH not specified in the publication
0.000000002165
-
male, 0 hours old, 37°C, pH not specified in the publication
0.00000000935
-
female abdominal skin, mean value, n=4, 37°C, pH not specified in the publication
0.0000000122
-
male inguinal skin, mean value, n=8, 37°C, pH not specified in the publication
0.0000000213
-
female perineal skin, mean value, n=4, 37°C, pH not specified in the publication
additional information
additional information
-
determination of serum and tumor tissue concentrations of steroids in prostate cancer patients, overview
additional information
-
activities of the two key enzymes for testosterone biosynthesis, 3-beta-HSD and 17-beta-HSD, are significantly affected by rats subjected to semi-synthetic diet. Both enzyme activities are significantly decreased in interstitial cell homogenates from rats fed with a soybean diet and a grape seed diet compared with the levels observed in the group fed a olive or coconut diet
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.4
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
37
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
287072, 657673, 658489, 659176, 669784, 669905, 670033, 670259, 670273, 672586, 672862, 688683, 700188, 712201, 713515, 740156, 741000
-
-
brenda
Nile tilapia, tissue-specific isozymes 17beta-HSD1 and 17beta-HSD8
-
-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
male abdominal, 17beta-HSD type 2 is localized in the vasculature of the adipose compartment, real-time RT-PCR expression analysis
brenda
exposure of the fish to water-soluble fraction of crude oil produces an apparent concentration-specific increase of 3beta-hydroxysteroid dehydrogenase
brenda
enzyme expression during embryogenesis from sphere to 84 h post-fertilization
brenda
-
EpiskinTM is a cultured human epidermis. 17beta-hydroxysteroid dehydrogenase and 3alpha-hydroxysteroid dehdyrogenase activities are present at moderate levels in EpiskinTM, while 3beta-hydroxysteroid dehdyrogenase activity is low
brenda
-
the relative expression level of 17beta- or 3beta-hydroxysteroid dehydrogenase is approximately 1.3-1.5fold higher at the neonatal than at the adult stage
brenda
-
taken from 10-20 days pregnant mice for enzyme extraction including the embryo
brenda
additional information
-
3beta- and 17beta-hydroxysteroid dehydrogenase are not altered in metyrapone-treated cells
brenda
-
male pigs with high androstenone concentrations in fat have low 3betaHSD gene expression in liver and testis. Immunocastrated and surgically castrated male pigs shows significant increase of 3betaHSD expression. Fat androstenone is negatively correlated with liver 3betaHSD gene expression. The mRNA expression is generally much greater from the 3betaHSD than from the 17betaHSD gene
brenda
-
cancer and bening hyperplasia, protstaic intraepithelial neoplasia, enzyme distribution, overview
brenda
-
male pigs with high androstenone concentrations in fat have low 3betaHSD gene expression in liver and testis. Immunocastrated and surgically castrated male pigs shows significant increase of 3betaHSD expression. The mRNA expression is generally much greater from the 3betaHSD than from the 17betaHSD gene
brenda
additional information
-
expression in female and male tissues, sexual dimorphism, no activity in zf4 cells
brenda
additional information
expression in female and male tissues, sexual dimorphism, no activity in zf4 cells
brenda
additional information
-
the enzyme is also expressed in cardenolide-free tissues of cardenolide-containing plants
brenda
additional information
-
the enzyme is also expressed in cardenolide-free tissues of cardenolide-containing plants
-
brenda
additional information
mRNA for AKR1C34 is expressed liver-specific in male hamsters and ubiquitously in female hamsters
brenda
additional information
-
mRNA for AKR1C34 is expressed liver-specific in male hamsters and ubiquitously in female hamsters
brenda
additional information
-
three tissue-specific isozymes, 17beta-HSD1 and 17beta-HSD8
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
additional information
-
the enzyme is distributed between microsomes and mitochondria, the HSD activity in microsomes is predominant throughout the follicular phase of the estrous cycle, the enzyme activity is increased in pregnant mice uteri including embryos, overview
-
brenda
-
the hydrophobic 17beta-HSD3 is membrane-bound through an N-terminal transmembrane domain
brenda