Information on EC 1.1.1.51 - 3(or 17)beta-hydroxysteroid dehydrogenase

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

EC NUMBER
COMMENTARY hide
1.1.1.51
-
RECOMMENDED NAME
GeneOntology No.
3(or 17)beta-hydroxysteroid dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
testosterone + NAD(P)+ = androstenedione + NAD(P)H + H+
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
redox reaction
reduction
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
androgen and estrogen metabolism
-
-
Steroid hormone biosynthesis
-
-
Steroid degradation
-
-
Metabolic pathways
-
-
Microbial metabolism in diverse environments
-
-
testosterone and androsterone degradation to androstendione
-
-
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.
CAS REGISTRY NUMBER
COMMENTARY hide
9015-81-0
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain KITA
-
-
Manually annotated by BRENDA team
strain KITA
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(R)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH + H+
show the reaction diagram
i.e. R-tetralol
-
-
?
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH + H+
show the reaction diagram
i.e. S-tetralol
-
-
?
(S)-1,2,3,4-tetrahydro-1-naphthol + NADP+
3,4-dihydronaphthalen-1(2H)-one + NADPH + H+
show the reaction diagram
i.e. S-tetralol
-
-
?
(S)-1-indanol + NAD+
2,3-dihydro-1H-inden-1-one + NADH + H+
show the reaction diagram
-
-
-
?
(S)-camphorquinone + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
(S)-camphorquinone + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
1-acenaphthenol + NAD+
acenaphthylen-1(2H)-one + NADH + H+
show the reaction diagram
-
-
-
?
11beta-hydroxyandrost-5-ene-3,17-dione + NADPH
11beta,17beta-dihydroxyandrost-5-ene-3-one + NADP+
show the reaction diagram
17-oxo steroids + NADPH
?
show the reaction diagram
-
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+
show the reaction diagram
-
-
-
-
?
17beta-estradiol + NAD+
estrone + NADH + H+
show the reaction diagram
-
-
-
?
17beta-hydroxy-5beta-androstane-3-one + NAD(P)H + H+
testosterone + NAD(P)+
show the reaction diagram
-
-
-
?
2-cyclohexen-1-ol + NAD+
2-cyclohexen-1-one + NADH + H+
show the reaction diagram
-
-
-
?
20alpha-dihydroprogesterone + NAD+
4-pregnen-3alpha,20beta-diol + NADH
show the reaction diagram
-
-
-
-
r
20alpha-dihydroprogesterone + NADP+
4-pregnen-3alpha,20beta-diol + NADPH
show the reaction diagram
-
-
-
-
r
20alpha-hydroxypregn-4-en-3-one + NADP+
progesterone + NADPH
show the reaction diagram
-
-
-
r
3beta-hydroxy-16alpha,17alpha-epoxypregn-5-en-20-one + NAD(P)+
?
show the reaction diagram
3beta-hydroxy-5alpha-androstan-17-one + NADP+
5alpha-androstane-3,17-dione + NADPH
show the reaction diagram
-
-
-
?
3beta-hydroxyprogesterone + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
4-androsten-17beta-ol-3-one + NAD(P)+
4-androstene-3,17-dione + NAD(P)H + H+
show the reaction diagram
17keto function is reduced. NADP+ is 3-5times less effective than NAD+
-
-
?
4-androsten-3,17-dione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
-
-
-
?
4-androstene-3,17-dione + NADPH + H+
testosterone + NADP+
show the reaction diagram
4-androstene-3alpha,17beta-diol + NAD+
? + NADH + H+
show the reaction diagram
-
-
-
?
4-estrene-17beta-ol-3-one + NADP+
4-estrene-3,17-dione + NADPH
show the reaction diagram
-
-
-
-
r
4-estrene-3,17-dione + NADPH
4-estrene-17beta-ol-3-one + NADP+
show the reaction diagram
-
-
-
-
r
5-androsten-3beta-ol-17-one + NAD(P)+
5-androstene-3,17-dione + NAD(P)H + H+
show the reaction diagram
NADP+ is 3-5times less effective than NAD+
-
-
?
5-androstene-3beta,17beta-diol + NAD+
? + NADH + H+
show the reaction diagram
-
-
-
?
5-androstenedione + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
isozyme 17beta-HSD3
-
-
r
5-pregnen-3beta-ol-20-one + NAD(P)+
5-pregnene-3,20-dione + NAD(P)H + H+
show the reaction diagram
NADP+ is 3-5times less effective than NAD+
-
-
?
5alpha-androst-16-en-3-one + NADH
3beta-hydroxy-5alpha-androst-16-ene + NAD+
show the reaction diagram
-
-
-
?
5alpha-androstan-3alpha-ol-17-one + NAD+
5alpha-androstan-3,20-dione + NADH + H+
show the reaction diagram
-
-
-
?
5alpha-androstan-3beta-ol-17-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
show the reaction diagram
-
-
-
?
5alpha-androstane-3alpha,17beta-diol + NAD+
?
show the reaction diagram
-
-
-
?
5alpha-androstane-3beta,17beta-diol + NADP+
3beta-hydroxy-5alpha-androstan-17-one + NADPH
show the reaction diagram
-
-
-
?
5alpha-dihydrotestosterone + NAD(P)H
5alpha-androstane-3beta,17beta-diol + NADP+
show the reaction diagram
-
-
-
?
5alpha-dihydrotestosterone + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
5alpha-dihydrotestosterone + NADP+
5alpha-androstane-3,17-dione + NADPH
show the reaction diagram
5alpha-pregnan-3alpha-ol-20-one + NAD+
5alpha-pregnan-3,20-dione + NADH + H+
show the reaction diagram
-
-
-
?
5alpha-pregnan-3beta-ol-20-one + NAD(P)+
5alpha-pregnan-3,20-dione + NAD(P)H + H+
show the reaction diagram
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+
show the reaction diagram
-
-
-
?
5beta-androstan-17beta-ol-3-one + NAD+
5beta-androstan-3,17-dione + NADH + H+
show the reaction diagram
-
-
-
?
5beta-androstan-3alpha-ol-17-one + NAD+
5beta-androstan-3,20-dione + NADH + H+
show the reaction diagram
-
-
-
?
5beta-androstan-3beta-ol-17-one + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
5beta-androstane-3alpha,17beta-diol + NAD+
? + NAD+
show the reaction diagram
-
-
-
?
5beta-androstane-3beta,17beta-diol + NAD+
? + NAD+
show the reaction diagram
-
-
-
?
5beta-dihydrotestosterone + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
5beta-pregnan-20alpha-ol-3-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
show the reaction diagram
-
-
-
?
5beta-pregnan-3,20-dione + NAD(P)H + H+
3beta-hydroxy-5beta-pregnan-20-one + NAD(P)+
show the reaction diagram
NADP+ is 3-5times less effective than NAD+
-
-
?
5beta-pregnan-3,20-dione + NADH
3beta-hydroxy-5beta-pregnan-20-one + NAD+
show the reaction diagram
-
-
-
?
5beta-pregnan-3,20-dione + NADPH + H+
5beta-pregnane-3beta-ol-20-one + NADP+
show the reaction diagram
5beta-pregnan-3beta,21-diol-20-one + NAD+
?
show the reaction diagram
-
-
-
?
5beta-pregnan-3beta,21-diol-20-one + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
5beta-pregnan-3beta-ol-20-one + NAD(P)+
5-pregnan-3,20-dione + NAD(P)H + H+
show the reaction diagram
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+
show the reaction diagram
-
-
-
?
alpha-3-hydroxyhexobarbital + NAD+
?
show the reaction diagram
-
-
-
?
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
show the reaction diagram
-
-
-
-
?
androst-5-ene-3,11,17-trione + NADPH
17beta-hydroxyandrost-5-ene-3,11-dione + NADP+
show the reaction diagram
androst-5-ene-3beta,17beta-diol + NADP+
dehydroepiandrosterone + NADPH
show the reaction diagram
androstane-3,17-dione + NADPH
dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
androstanedione + NADPH
dihydrotestosterone + NADP+
show the reaction diagram
-
reduction at C17
-
-
?
androstenediol + NAD(P)H + H+
testosterone + NAD(P)+
show the reaction diagram
-
reaction catalysed by 3beta-HSD (type 1)
-
-
?
androstenedione + NAD(P)H + H+
testosterone + NAD(P)+
show the reaction diagram
-
reaction catalysed by 17beta-HSD (type 1 and 3)
-
-
?
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
androsterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
show the reaction diagram
androsterone + NADPH
androstane-3beta,17beta-diol + NADP+
show the reaction diagram
-
reduction at C17
-
-
?
beta-3-hydroxyhexobarbital + NAD+
?
show the reaction diagram
-
-
-
?
beta-ionol + NAD+
(3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one + NADH + H+
show the reaction diagram
-
-
-
?
cis-benzene dihydrodiol + NAD+
?
show the reaction diagram
-
-
-
?
cyclohexanol + NAD+
?
show the reaction diagram
-
-
-
?
dehydroepiandrosterone + NAD(P)+
androst-5-en-3,17-dione + NAD(P)H + H+
show the reaction diagram
dehydroepiandrosterone + NAD(P)H + H+
androstenediol + NAD(P)+
show the reaction diagram
-
reaction catalysed by 17beta-HSD (type 1 and 3)
-
-
?
dehydroepiandrosterone + NAD+
4-androstene-3,17-dione + NADH + H+
show the reaction diagram
dehydroepiandrosterone + NAD+
androstene-3,17-dione + NADH + H+
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
dehydroepiandrosterone + NADPH
5-androstene-3beta,17beta-diol + NADP+
show the reaction diagram
-
reduction at C17
-
-
?
dehydroepiandrosterone + NADPH
androstene-3beta,17beta-diol + NADP+
show the reaction diagram
dehydroepiandrosterone + NADPH + H+
androst-5-ene-3beta,17beta-diol + NADP+
show the reaction diagram
-
-
-
-
?
dihydroepiandrostendione + NADPH
dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
dihydrotestosterone + NAD+
5alpha-androstan-3,17-dione + NADH
show the reaction diagram
-
-
-
-
r
dihydrotestosterone + NADP+
5alpha-androstan-3,17-dione + NADPH
show the reaction diagram
-
-
-
-
r
dihydrotestosterone + NADPH + H+
5alpha-androstane-3beta,17beta-diol + NADP+
show the reaction diagram
-
androsterone inactivation
-
-
?
epiandrosterone + NADPH
5-androstane-3beta,17beta-diol + NADP+
show the reaction diagram
-
reduction at C17
-
-
?
epiandrosterone + NADPH
androstane-3beta,17beta-diol + NADP+
show the reaction diagram
reduction at C17
-
-
?
estradiol + NAD(P)+
estrone + NAD(P)H
show the reaction diagram
estradiol + NAD+
estrone + NADH
show the reaction diagram
-
-
-
-
?
estradiol + NADP+
estrone + NADPH
show the reaction diagram
estradiol sulfate + NADP+
estrone sulfate + NADPH
show the reaction diagram
-
-
-
?
estrone + NAD(P)H + H+
estradiol + NAD(P)+
show the reaction diagram
-
reaction catalysed by 17beta-HSD (type 1 and 3)
-
-
?
estrone + NADPH
estradiol + NADP+
show the reaction diagram
-
estrogen activation
-
-
?
farnesol + NAD+
farnesal + NADH + H+
show the reaction diagram
-
-
-
?
geraniol + NAD+
geranial + NADH + H+
show the reaction diagram
-
-
-
?
geranylgeraniol + NAD+
geranylgeranial + NADH + H+
show the reaction diagram
-
-
-
?
nerol + NAD+
neral + NADH + H+
show the reaction diagram
-
-
-
?
pregnenolone + NAD(P)+
progesterone + NAD(P)H + H+
show the reaction diagram
pregnenolone + NAD+
progesterone + NADH + H+
show the reaction diagram
pregnenolone + NADP+
progesterone + NADPH + H+
show the reaction diagram
-
-
-
-
?
pregnenolone + NADPH
progesterone + NADP+
show the reaction diagram
-
-
-
-
?
pregnenolone + NADPH + H+
isoprogesterone + NADP+
show the reaction diagram
testosterone + 3-acetylpyridine adenine dinucleotide
?
show the reaction diagram
-
-
-
-
?
testosterone + 3-pyridinealdehyde adenine dinucleotide
?
show the reaction diagram
-
-
-
-
?
testosterone + NAD(P)+
androst-4-en-3,17-dione + NAD(P)H + H+
show the reaction diagram
testosterone + NAD(P)+
androstenedione + NAD(P)H + H+
show the reaction diagram
testosterone + NAD+
4-androstenedione + NADPH + H+
show the reaction diagram
-
-
-
?
testosterone + NAD+
androst-4-en-3,17-dione + NADH
show the reaction diagram
-
-
-
-
r
testosterone + NADP+
androst-4-en-3,17-dione + NADPH
show the reaction diagram
-
-
-
-
r
testosterone + NADP+
androstenedione + NADPH + H+
show the reaction diagram
testosterone + thionicotinamide adenine dinucleotide
?
show the reaction diagram
-
-
-
-
?
trans-benzene dihydrodiol + NAD+
?
show the reaction diagram
-
-
-
?
zymosterone + NADPH
zymosterol + NADP+
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
17-oxo steroids + NADPH
?
show the reaction diagram
-
maintenance of balance between oxidized and reduced steroids in blood
-
-
-
4-androstene-3,17-dione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
isozymes 17beta-HSD3 and 17beta-HSD5
-
-
r
5-androstenedione + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
isozyme 17beta-HSD3
-
-
r
5beta-pregnan-3,20-dione + NADPH + H+
5beta-pregnane-3beta-ol-20-one + NADP+
show the reaction diagram
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
show the reaction diagram
-
-
-
-
?
androstane-3,17-dione + NADPH
dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
dihydrotestosterone + NADPH + H+
5alpha-androstane-3beta,17beta-diol + NADP+
show the reaction diagram
-
androsterone inactivation
-
-
?
estrone + NADPH
estradiol + NADP+
show the reaction diagram
-
estrogen activation
-
-
?
pregnenolone + NAD+
progesterone + NADH + H+
show the reaction diagram
-
the mitochondrial enzyme is essential for the synthesis of progesterone by corpora lutea, overview
-
-
?
pregnenolone + NADPH + H+
isoprogesterone + NADP+
show the reaction diagram
testosterone + NAD(P)+
androstenedione + NAD(P)H + H+
show the reaction diagram
testosterone + NADP+
androstenedione + NADPH + H+
show the reaction diagram
zymosterone + NADPH
zymosterol + NADP+
show the reaction diagram
-
-
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3-acetylpyridine adenine dinucleotide
-
-
3-pyridinealdehyde adenine dinucleotide
-
-
NAD(P)H
additional information
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
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
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2,4-dihydroxyphenyl)-phenylmethanone
(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
(4-(2,4-dichlorophenyl)piperazin-1-yl)(morpholino)methanone
-
-
(4-(2-chlorophenyl)piperazin-1-yl)(morpholino)methanone
-
-
(4-(2-methoxyphenyl)piperazin-1-yl)(morpholino)methanone
-
-
(4-(3-chlorophenyl)piperazin-1-yl)(morpholino)methanone
-
-
(4-(4-(methylsulfonyl)phenyl)piperazin-1-yl)(morpholino)methanone
-
-
(4-(4-bromophenyl)piperazin-1-yl)(morpholino)methanone
-
-
(4-(4-chloro-2-(hydroxymethyl)phenyl)piperazin-1-yl)(morpholino)methanone
-
-
(4-(4-chloro-2-methylphenyl)piperazin-1-yl)(morpholino)methanone
-
-
(4-(4-chlorobenzoyl)piperazin-1-yl)(morpholino)methanone
-
-
(4-(4-chlorobenzyl)piperazin-1-yl)(morpholino)methanone
-
-
(4-(4-chlorophenyl)-1,4-diazepan-1-yl)(morpholino)methanone
-
-
(4-(4-chlorophenyl)piperazin-1-yl)(1-oxido-4-thiomorpholino)methanone
-
-
(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
-
-
(4-(4-chlorophenyl)piperazin-1-yl)(4-methylpiperazin-1-yl)methanone
-
-
(4-(4-chlorophenyl)piperazin-1-yl)(cyclohexyl)methanone
-
-
(4-(4-chlorophenyl)piperazin-1-yl)(morpholino)methanethione
-
-
(4-(4-chlorophenyl)piperazin-1-yl)(morpholino)methanone
-
-
(4-(4-chlorophenyl)piperazin-1-yl)(phenyl)methanone
-
-
(4-(4-chlorophenyl)piperazin-1-yl)(piperidin-1-yl)methanone
-
-
(4-(4-chlorophenyl)piperazin-1-yl)(pyridin-4-yl)methanone
-
-
(4-(4-chlorophenyl)piperazin-1-yl)(tetrahydro-2H-pyran-4-yl)methanone
-
-
(4-(4-chlorophenyl)piperazin-1-yl)(thiomorpholino)methanone
-
-
(4-(4-ethynylphenyl)piperazin-1-yl)(morpholino)methanone
-
-
(4-(4-fluorophenyl)piperazin-1-yl)(morpholino)methanone
-
-
(4-(4-iodophenyl)piperazin-1-yl)(morpholino)methanone
-
-
(4-(4-methoxyphenyl)piperazin-1-yl)(morpholino)methanone
-
-
(4-(6-bromopyridin-2-yl)piperazin-1-yl)(morpholino)methanone
-
-
(4-(6-chloropyridin-3-yl)piperazin-1-yl)(morpholino)methanone
-
-
(4-(biphenyl-4-yl)piperazin-1-yl)(morpholino)methanone
-
-
(5-(4-chlorophenyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl)(morpholino)methanone
-
-
(S)-ibuprofen
-
-
1-(11,12-dihydro-6H-dibenzo[b,f]oxocin-12-yl)ethanone
-
IC50: 0.00297 mM
1-(4-(4-(4-chlorophenyl)piperazine-1-carbonyl)piperazin-1-yl)-2-hydroxyethanone
-
-
1-(4-(4-chlorophenyl)piperazine-1-carbonyl)piperidine-4-carboxylic acid
-
-
1-(5,6,11,12-tetrahydrodibenzo[b,f]azocin-12-yl)ethanone
-
IC50: 0.00474 mM
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-11,12-dihydro-2-(trifluoromethyl)-6H-dibenzo(b,f)(1,4)thiazocine
-
-
12-acetyl-11,12-dihydro-6H-dibenzo(b,f)(1,4)thiazocine
-
-
12-acetyl-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocin-3-ol
-
IC50: 0.0049 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
13-cis-retinoic acid
-
-
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
2,2',4,4'-tetrahydroxybenzophenone
-
remaining 17beta HSD3 activity: 47%
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
2-hydroxy-estradiol
-
0.01 mM, 67% inhibition, reaction with 0.002 mM estradiol
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-(4-(morpholine-4-carbonyl)piperazin-1-yl)benzamide
-
-
3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzonitrile
-
IC50: 3 nM
3-benzylidene camphor
-
remaining 17beta HSD3 activity: 56%
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-butyl-3-hydroxy-5alpha-androstan-17-one
-
-
3alpha-ether-3beta-substituted androsterone derivatives
-
diverse derivatives, IC50: 70-760 nM, overview
-
3beta-alkylated androsterone derivatives
-
IC50: 57-147 nM
-
3beta-cyclohexylethyl-androsterone
-
-
3beta-hexyl-androsterone
-
-
3beta-phenyl-androsterone
-
mixed-type inhibition, shows some proliferative activity on AR+ and Er+ cell lines not mediated through androgen or estrogen receptors
3beta-phenylethyl-3alpha-methyl-O-androsterone
-
IC50: 73 nM
3beta-phenylethyl-androsterone
3beta-phenylmethyl-androsterone
3beta-substituted androsterone derivatives
-
IC50: 57-147 nM
-
4-((4-(4-chlorophenyl)piperazin-1-yl)sulfonyl)morpholine
-
-
4-((4-chlorophenyl)-4-piperazinylcarbonyl)-1,1-dioxide
-
-
-
4-(4-(morpholine-4-carbonyl)piperazin-1-yl)benzamide
-
-
4-(4-(morpholine-4-carbonyl)piperazin-1-yl)benzoic acid
-
-
4-(4-chlorophenyl)-N-cyclohexylpiperazine-1-carboxamide
-
-
4-(4-chlorophenyl)-N-phenylpiperazine-1-carboxamide
-
-
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
4-MA
-
-
4-methylbenzylidene camphor
-
remaining 17beta HSD3 activity: 33%
5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 0.00007 mM
5-acetyl-2-chloro-5,6-dihydro-dibenzo(b,f)azocine
-
-
5-acetyl-2-chloro-5,6-dihydrodibenzo[b,f]azocine
-
IC50: 0.00024 mM
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-2-chloro-8-phenyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 4 nM
5-acetyl-3-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 0.00005 mM
5-acetyl-5,6,11,12-tetrahydro-dibenzo(b,f)(1,4)diazocine
-
-
5-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-amine
-
IC50: 0.00049 mM
5-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine-9-carboxamide
-
IC50: 0.001 mM
5-acetyl-8-bromo-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 9 nM
5-acetyl-8-phenyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 0.02 nM
5-acetyl-9-bromo-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 7 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
5alpha-dihydrotestosterone
-
inhibits oxidation of testosterone
5beta-androstane-3alpha,17beta-diol
-
0.01 mM, 83% inhibition, reaction with 0.002 mM estradiol
5beta-dihydrotestosterone
-
inhibits oxidation of testosterone
9-bromo-11,12-dihydrodibenzo[b,f]azocine-5(6H)-carboxamide
-
IC50: 0.00028 mM
9-bromo-5-butanoyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 0.00032 mM
9-bromo-5-ethyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 0.001 mM
9-cis-retinoic acid
albumin
-
-
-
androstenedione
-
-
androsterone
-
-
beta-octylglucoside
-
strong
chloromercuribenzene-p-sulfonic acid
-
-
cyproterone acetate
-
-
danazol
-
inhibits oxidation of testosterone, 0.01 mM, 83% inhibition
dibenzothiazocine
-
IC50: 0.0004 mM
Dimethylsulfoxide
-
-
dodecyl-beta-D-maltoside
-
inhibition above 0.5%
EM-919
-
a 17beta-HSD type 2 inhibitor
-
epostane
-
-
estradiol
-
inhibits oxidation of testosterone
Flufenamic acid
-
-
flurbiprofen
-
-
gallic acid
-
0.001 mM, 50% inhibition, reduction of androst-4-en-3,17-dione
glycerol
-
-
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
-
indomethacin
-
-
Iodosobenzoate
-
-
Meclofenamic acid
-
-
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-(4-(morpholine-4-carbonyl)piperazin-1-yl)benzoate
-
-
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
morpholino(4-(2-(trifluoromethyl)phenyl)piperazin-1-yl)methanone
-
-
morpholino(4-(4-nitrophenyl)piperazin-1-yl)methanone
-
-
morpholino(4-(naphthalen-2-yl)piperazin-1-yl)methanone
-
-
morpholino(4-(o-tolyl)piperazin-1-yl)methanone
-
-
morpholino(4-(p-tolyl)piperazin-1-yl)methanone
-
-
morpholino(4-(quinolin-3-yl)piperazin-1-yl)methanone
-
-
morpholino(4-phenylpiperazin-1-yl)methanone
-
-
-
morpholino-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)methanone
-
-
N,N-dimethyl-4-(4-(morpholine-4-carbonyl)piperazin-1-yl)benzamide
-
-
N-(((3,5)-3-hydroxy-17-oxoandrostan-3-yl)methyl)-N-(tricyclo(3.3.1.13.7)dec-2-ylmethyl)butanamide
-
-
N-(4-(4-(morpholine-4-carbonyl)piperazin-1-yl)phenyl)acetamide
-
-
N-(4-(4-(morpholine-4-carbonyl)piperazin-1-yl)phenyl)methanesulfonamide
-
-
N-(5-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-yl)benzamide
-
IC50: 0.00016 mM
N-methyl-4-(4-(morpholine-4-carbonyl)piperazin-1-yl)benzamide
-
-
naproxen
-
-
oleuropein glycoside
-
0.001 mM, 40% inhibition, reduction of androst-4-en-3,17-dione
p-chloromercuribenzoate
Perfluorooctanoic acid
-
-
Propyleneglycol
-
-
RM-532-10
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
-
RM-532-105
-
spiro-gamma-lactone-estradiol
-
inhibits the reduction of androst-4-en-3,17-dione, reversible, IC50: 0.00025 mM
spironolactone
-
IC50 for oxidation of testosterone: 0.0011 mM
Strogen forte
-
testosterone
-
0.01 mM, 70% inhibition, reaction with 0.002 mM estradiol
tetrahydrodibenzazocine
-
IC50: 0.00009 mM
thiomorpholine
-
-
Triton X-100
Tween-80
-
-
[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]methanol
-
IC50: 0.9 nM
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
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
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
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
0.0012
(S)-1-indanol
pH 7.4, 25°C, recombinant enzyme
0.023
1-Acenaphthenol
pH 7.4, 25°C, recombinant enzyme
0.0004
17beta-estradiol
pH 7.4, 25°C, recombinant enzyme
0.026
2-Cyclohexen-1-ol
pH 7.4, 25°C, recombinant enzyme
0.00053
20alpha-dihydroprogesterone
-
pH 7.4, with NAD+ as cofactor
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
0.642
5-androsten-3beta-ol-17-one
-
50°C, pH 7.8
0.0033
5-androstene-3beta,17beta-diol
pH 7.4, 25°C, recombinant enzyme
0.09
5-pregnen-3beta-ol-20-one
-
50°C, pH 7.8
0.068 - 0.176
5alpha-Androst-16-en-3-one
0.0025
5alpha-Androstan-3beta-ol-17-one
pH 7.4, 25°C, recombinant enzyme
0.0076 - 0.2
5alpha-dihydrotestosterone
0.106
5alpha-pregnan-3,20-dione
-
50°C, pH 7.8
0.0039 - 0.116
5alpha-pregnan-3beta-ol-20-one
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
0.21 - 1.725
5beta-pregnan-3,20-dione
0.015
5beta-pregnan-3beta,21-diol-20-one
pH 7.4, 25°C, recombinant enzyme
-
0.0068 - 0.314
5beta-Pregnan-3beta-ol-20-one
0.014
alpha-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
-
0.04
beta-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
-
0.001
beta-ionol
pH 7.4, 25°C, recombinant enzyme
-
0.0097
cis-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
0.074
Cyclohexanol
pH 7.4, 25°C, recombinant enzyme
0.00001 - 0.0043
dehydroepiandrosterone
0.00025
dihydrotestosterone
-
pH 7.4, with NAD+ as cofactor
0.00035
estradiol
-
pH 7.4, with NAD+ as cofactor
0.0012
farnesol
pH 7.4, 25°C, recombinant enzyme
0.0041
geraniol
pH 7.4, 25°C, recombinant enzyme
0.001
geranylgeraniol
pH 7.4, 25°C, recombinant enzyme
0.023 - 0.26
NAD+
0.0053 - 0.642
NADH
0.0082 - 9.6
NADP+
0.0018 - 0.0021
NADPH
0.011
nerol
pH 7.4, 25°C, recombinant enzyme
0.00067
pregnenolone
-
pH and temperature not specified in the publication
0.00061 - 0.31
testosterone
0.083
Thionicotinamide adenine dinucleotide
-
testosterone as substrate
0.011
trans-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
additional information
additional information
Michaelis-Menten kinetics
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
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
0.028
(S)-1-indanol
pH 7.4, 25°C, recombinant enzyme
0.022
1-Acenaphthenol
pH 7.4, 25°C, recombinant enzyme
0.022
17beta-estradiol
pH 7.4, 25°C, recombinant enzyme
0.04
2-Cyclohexen-1-ol
pH 7.4, 25°C, recombinant enzyme
0.78
20alpha-dihydroprogesterone
-
pH 7.4, with NAD+ as cofactor
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
-
0.022
beta-ionol
pH 7.4, 25°C, recombinant enzyme
-
0.025
cis-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
0.009
Cyclohexanol
pH 7.4, 25°C, recombinant enzyme
0.01
dehydroepiandrosterone
pH 7.4, 25°C, recombinant enzyme
2.4
dihydrotestosterone
-
pH 7.4, with NAD+ as cofactor
3.9
estradiol
-
pH 7.4, with NAD+ as cofactor
0.018
farnesol
pH 7.4, 25°C, recombinant enzyme
0.023
geraniol
pH 7.4, 25°C, recombinant enzyme
0.008
geranylgeraniol
pH 7.4, 25°C, recombinant enzyme
0.11 - 4.7
NAD+
0.1 - 0.33
NADH
0.15 - 1.3
NADP+
0.023
nerol
pH 7.4, 25°C, recombinant enzyme
0.0078 - 3.4
testosterone
0.033
trans-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
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
23.3
(S)-1-indanol
pH 7.4, 25°C, recombinant enzyme
0.95
1-Acenaphthenol
pH 7.4, 25°C, recombinant enzyme
116.7
17beta-estradiol
pH 7.4, 25°C, recombinant enzyme
1.55
2-Cyclohexen-1-ol
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
-
21.67
beta-ionol
pH 7.4, 25°C, recombinant enzyme
-
2.5
cis-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
0.117
Cyclohexanol
pH 7.4, 25°C, recombinant enzyme
2.33
dehydroepiandrosterone
pH 7.4, 25°C, recombinant enzyme
14.17
farnesol
pH 7.4, 25°C, recombinant enzyme
5.67
geraniol
pH 7.4, 25°C, recombinant enzyme
7.67
geranylgeraniol
pH 7.4, 25°C, recombinant enzyme
5
NAD+
pH 7.4, 25°C, with substrate S-tetralol
6
NADH
pH 7.4, 25°C, with substrate S-camphorquinone
0.063
NADP+
pH 7.4, 25°C, with substrate S-camphorquinone
2.17
nerol
pH 7.4, 25°C, recombinant enzyme
3.5
testosterone
pH 7.4, 25°C, recombinant enzyme
3
trans-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0024
13-cis-retinoic acid
-
-
0.0003
17alpha-ethynyl-estradiol
-
-
0.00011
7-hydroxyflavone
pH 7.4, 25°C, recombinant enzyme
0.0041
9-cis-retinoic acid
-
-
0.00011
chrysin
pH 7.4, 25°C, recombinant enzyme
0.0006
danazol
-
-
0.0008
estradiol
-
-
0.00069
galangin
pH 7.4, 25°C, recombinant enzyme
0.00055
genistein
pH 7.4, 25°C, recombinant enzyme
0.00054
Hexestrol
pH 7.4, 25°C, recombinant enzyme
0.00039
lithocholic acid
pH 7.4, 25°C, recombinant enzyme
0.0153 - 0.181
Perfluorooctanoic acid
0.00046
quercetin
pH 7.4, 25°C, recombinant enzyme
0.0033
zearalenone
pH 7.4, 25°C, recombinant enzyme
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.001
(2,4-dihydroxyphenyl)-phenylmethanone
Homo sapiens
-
pH 7.4, 37°C
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
0.0181
2,2',4,4'-tetrahydroxybenzophenone
Homo sapiens
-
pH 7.4, 37°C
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
0.033
3-benzylidene camphor
Homo sapiens
-
pH 7.4, 37°C
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
0.0011 - 0.0014
3-oxo-17alpha-pregna-4-ene-7alpha-(propylthia)-21,17-carbolactone
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
-
0.000073
3beta-phenylethyl-3alpha-methyl-O-androsterone
Homo sapiens
-
IC50: 73 nM
0.000099
3beta-phenylethyl-androsterone
Homo sapiens
-
IC50: 99 nM
0.000057
3beta-phenylmethyl-androsterone
Homo sapiens
-
IC50: 57 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
0.00000145
4-MA
Homo sapiens
-
37°C, pH not specified in the publication
0.0107
4-methylbenzylidene camphor
Homo sapiens
-
pH 7.4, 37°C
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
0.00024
5-acetyl-2-chloro-5,6-dihydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 0.00024 mM
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
0.000009
5-acetyl-8-bromo-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 9 nM
0.00000002
5-acetyl-8-phenyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 0.02 nM
0.000007
5-acetyl-9-bromo-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 7 nM
0.000008
5-acetyl-N-cyclohexyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-amine
Homo sapiens
-
IC50: 8 nM
0.00092
7-hydroxyflavone
Mesocricetus auratus
A0A097ZMZ1
pH 7.4, 25°C, recombinant enzyme
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
0.001
9-bromo-5-ethyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 0.001 mM
0.000337 - 0.000341
androstenedione
Rattus norvegicus
-
pH 7.4, 37°C
0.000182
androsterone
Homo sapiens
-
pH and temperature not specified in the publication
0.001
chrysin
Mesocricetus auratus
A0A097ZMZ1
pH 7.4, 25°C, recombinant enzyme
0.00015
cyproterone acetate
Homo sapiens
-
37°C, pH not specified in the publication
0.0004
dibenzothiazocine
Homo sapiens
-
IC50: 0.0004 mM
0.0000062
epostane
Homo sapiens
-
37°C, pH not specified in the publication
0.005
galangin
Mesocricetus auratus
A0A097ZMZ1
pH 7.4, 25°C, recombinant enzyme
0.0042
genistein
Mesocricetus auratus
A0A097ZMZ1
pH 7.4, 25°C, recombinant enzyme
0.0065
Hexestrol
Mesocricetus auratus
A0A097ZMZ1
pH 7.4, 25°C, recombinant enzyme
0.05
hinokitiol
Mesocricetus auratus
A0A097ZMZ1
above, pH 7.4, 25°C, recombinant enzyme
0.0044
lithocholic acid
Mesocricetus auratus
A0A097ZMZ1
pH 7.4, 25°C, recombinant enzyme
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
0.0177 - 0.194
Perfluorooctanoic acid
0.05
Phenolphthalein
Mesocricetus auratus
A0A097ZMZ1
above, pH 7.4, 25°C, recombinant enzyme
0.0026
quercetin
Mesocricetus auratus
A0A097ZMZ1
pH 7.4, 25°C, recombinant enzyme
0.000026 - 0.0001
RM-532-105
-
0.00025
spiro-gamma-lactone-estradiol
Homo sapiens
-
inhibits the reduction of androst-4-en-3,17-dione, reversible, IC50: 0.00025 mM
0.0011
spironolactone
Homo sapiens
-
IC50 for oxidation of testosterone: 0.0011 mM
0.00009
tetrahydrodibenzazocine
Homo sapiens
-
IC50: 0.00009 mM
0.015
zearalenone
Mesocricetus auratus
A0A097ZMZ1
pH 7.4, 25°C, recombinant enzyme
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
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
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
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 7
-
reductase activity
7.2
-
assay at
8.2
-
dehydrogenase activity
8.5
-
20 mM Tris-HCl
8.7
-
testosterone oxidation
9
substrate oxidation
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5
-
isoelectric focusing, pH-range: 3-9
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
derived from an epidermoid carcinoma of the vulva
Manually annotated by BRENDA team
-
real-time RT-PCR expression 17beta-HSD type 2 analysis
Manually annotated by BRENDA team
-
male abdominal, 17beta-HSD type 2 is localized in the vasculature of the adipose compartment, real-time RT-PCR expression analysis
Manually annotated by BRENDA team
in female and male hamsters
Manually annotated by BRENDA team
exposure of the fish to water-soluble fraction of crude oil produces an apparent concentration-specific increase of 3beta-hydroxysteroid dehydrogenase
Manually annotated by BRENDA team
enzyme expression during embryogenesis from sphere to 84 h post-fertilization
Manually annotated by BRENDA team
-
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
Manually annotated by BRENDA team
-
isozyme 17beta-HSD8
Manually annotated by BRENDA team
-
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
Manually annotated by BRENDA team
-
isozyme 17beta-HSD8
Manually annotated by BRENDA team
in female hamsters
Manually annotated by BRENDA team
-
isozyme 17beta-HSD8
Manually annotated by BRENDA team
-
cultured muscle cell
Manually annotated by BRENDA team
-
real-time RT-PCR expression 17beta-HSD type 2 analysis
Manually annotated by BRENDA team
-
isozyme 17beta-HSD5
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
in female hamsters
Manually annotated by BRENDA team
-
taken from 10-20 days pregnant mice for enzyme extraction including the embryo
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
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
-
Manually annotated by BRENDA team