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Information on EC 1.1.1.62 - 17beta-estradiol 17-dehydrogenase
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1.1.1.62 17beta-estradiol 17-dehydrogenaseIUBMB Comments
The enzyme oxidizes or reduces the hydroxy/keto group on C17 of estrogens and androgens in mammals and regulates the biological potency of these steroids. The mammalian enzyme is bifunctional and also catalyses EC 1.1.1.270, 3beta-hydroxysteroid 3-dehydrogenase . The enzyme also acts on (S)-20-hydroxypregn-4-en-3-one and related compounds, oxidizing the (S)-20-group, but unlike EC 1.1.1.149, 20alpha-hydroxysteroid dehydrogenase, it is Si-specific with respect to NAD(P)+.
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Word Map
- 1.1.1.62
- estrone
- progesterone
- androgen
- breast
- testosterone
- 17beta-hsds
- ovarian
- aromatase
- women
-
steroidogenic
- endometrium
- androstenedione
-
steroidogenesis
-
granulosa
- progestin
-
aldo-keto
- akr1c1
-
sulfatase
- cyp19a1
-
alpha-hsd
- endometriosis
-
estrogen-dependent
-
hormone-dependent
- luteal
- hsd3b1
- medicine
-
3beta-hydroxysteroid
-
alpha-dihydroprogesterone
- pregnenolone
-
5alpha-reductase
- 5alpha-dihydrotestosterone
- cochliobolus
- 3betahsd
-
d-bifunctional
- hsd17b3
-
3alpha-hydroxysteroid
-
17-ketosteroids
- p450arom
-
fsh-stimulated
- sult1e1
-
17-keto
-
alpha-hydroxyprogesterone
- lunatus
- tibolone
- srd5a1
-
c19-steroids
- diagnostics
-
alpha-diol
- drug development
The enzyme appears in viruses and cellular organisms
Synonyms
(17beta-HSD) type 1, (17beta-HSD) type 2, 17-beta-HSD 2, 17-beta-hydroxysteroid dehydrogenase type 12, 17-beta-hydroxysteroid dehydrogenase type 2, 17-HOR, 17-HSD, 17beta HSD1, 17beta,20alpha-hydroxysteroid dehydrogenase, 17beta-estradiol dehydrogenase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
17-HOR
-
-
-
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17-HSD
-
-
-
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17beta,20alpha-hydroxysteroid dehydrogenase
-
-
-
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17beta-estradiol dehydrogenase
-
-
-
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17beta-HSD
17beta-HSD1
17beta-HSD12
17beta-HSD2
17beta-HSDcl
17beta-hydroxysteroid dehydrogenase
17beta-hydroxysteroid dehydrogenase type 1
17beta-hydroxysteroid dehydrogenase type 14
17beta-hydroxysteroid dehydrogenase type 2
17beta-hydroxysteroid dehydrogenase type I
17betaHSD1
20 alpha-hydroxysteroid dehydrogenase
-
-
-
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20-alpha-HSD
-
-
-
-
20alpha-hydroxysteroid dehydrogenase
dehydrogenase, estradiol 17beta-
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-
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E2DH
-
-
-
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EDH
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estradiol 17beta-dehydrogenase
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-
-
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estradiol dehydrogenase
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-
-
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estrogen 17-oxidoreductase
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-
-
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HSD17B1
HSD17B2
HSD17B4
Ke6 protein
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-
-
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microsomal 17-beta-hydroxysteroid dehydrogenase
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-
-
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oestradiol-17beta hydroxysteroid dehydrogenase
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placental 17-beta-hydroxysteroid dehydrogenase
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PRAP
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-
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PRL receptor associated protein
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testicular 17-beta-hydroxysteroid dehydrogenase
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additional information
17beta-HSD
-
-
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17beta-HSD1
-
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17beta-hydroxysteroid dehydrogenase
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-
-
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17beta-hydroxysteroid dehydrogenase type 1
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17beta-hydroxysteroid dehydrogenase type 1
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20alpha-hydroxysteroid dehydrogenase
-
-
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additional information
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the enzyme belongs to the cP1 subfamily of the short-chain dehydrogenase/reductase superfamily
additional information
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the enzyme belongs to the short-chain dehydrogenase/reductase superfamily
additional information
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17beta-HSDs belong to the aldo-keto reductase family or the short-chain dehydrogenase family, overview
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
17beta-estradiol + NAD(P)+ = estrone + NAD(P)H + H+
5 isoforms with different substrate specificities and tissue distribution, 17beta-HSD1 predominantly catalyzes the reaction of estrone to estradiol-17beta, 17beta-HSD2 catalyzes the reaction of estradiol-17beta to estrone and testosterone to androstenedione, 17beta-HSD3 and 5 catalyzes the reaction of androstenedione to testosterone, 17beta-HSD4 catalyzes the reaction of estradiol-17beta to estrone with low substrate affinty
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17beta-estradiol + NAD(P)+ = estrone + NAD(P)H + H+
17beta-HSD2 and 5 catalyzes the reaction of estradiol-17beta to estrone and testosterone to androstenedione, 17beta-HSD2 also has 20alpha-HSD activity
-
17beta-estradiol + NAD(P)+ = estrone + NAD(P)H + H+
isoforms differs in substrate specificity and tissue distribution, some enzyme forms displays also other activities such as type 4 that acts also as a short chain alcohol dehydrogenase and hydratase and type 10, that is identical to endoplasmic amyloid-beta-binding protein and mitochondrial short chain L-3-hydroxyacyl-CoA dehydrogenase
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17beta-estradiol + NAD(P)+ = estrone + NAD(P)H + H+
structure-function analysis, dimerization is crucial for catalytic activity
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17beta-estradiol + NAD(P)+ = estrone + NAD(P)H + H+
cofactor binding residues are Tyr49, Thr202, Ala50, and Asn51, Theorell-Chance reaction mechanism
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17beta-estradiol + NAD(P)+ = estrone + NAD(P)H + H+
active site structure of isozymes 17beta-HSD1 and 17beta-HSD14
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17beta-estradiol + NAD(P)+ = estrone + NAD(P)H + H+
a structural analysis of available crystal structures is performed and representative conformations are assigned to each step of the putative kinetic mechanism. An essential role played by the backbone and side chain motions, especially of the betaFalphaG’-loop, in cofactor and substrate binding is disclosed. A selected-fit mechanism is suggested for 17beta-HSD1, where ligand-binding induces concerted motions of the FG-segment and the C-terminal part guide the enzyme along its preferred catalytic pathway
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17beta-estradiol + NAD(P)+ = estrone + NAD(P)H + H+
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-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
17beta-estradiol:NAD(P)+ 17-oxidoreductase
The enzyme oxidizes or reduces the hydroxy/keto group on C17 of estrogens and androgens in mammals and regulates the biological potency of these steroids. The mammalian enzyme is bifunctional and also catalyses EC 1.1.1.270, 3beta-hydroxysteroid 3-dehydrogenase [3]. The enzyme also acts on (S)-20-hydroxypregn-4-en-3-one and related compounds, oxidizing the (S)-20-group, but unlike EC 1.1.1.149, 20alpha-hydroxysteroid dehydrogenase, it is Si-specific with respect to NAD(P)+.
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CAS REGISTRY NUMBER
COMMENTARY
9028-61-9
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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
1,2-dimethyl-6-dehydroestrone + NADH
1,2-dimethyl-6-dehydroestradiol + NAD+
-
-
-
-
?
1,3-dimethyl-6-dehydroestrone + NADH
1,3-dimethyl-6-dehydroestradiol + NAD+
-
-
-
-
?
1,4-diacetoxy-1,3,5(10)-estratrien-17-one + NADH
17beta-hydroxy-1,4-diacetoxy-1,3,5(10)-estratriene + NAD+
-
-
-
-
?
1,4-dihydroxy-1,3,5(10)-estratrien-17-one + NADH
1,4,17-trihydroxy-1,3,5(10)-estratrien + NAD+
-
-
-
-
?
11-ketoequilenin acetate + NADH
17beta-hydroxy-11-ketoequilenin acetate + NAD+
-
-
-
-
?
17beta-hydroxyestra-4-en-3-one + NADP+
estra-4-en-3,17-dione + NADPH + H+
-
-
-
-
r
18-nor-D-homoestrone 3-methyl ether + NADH
18-nor-D-homoestradiol 3-methyl ether + NAD+
-
-
-
-
?
19-nortestosterone + NAD+
4-estren-3,17-dione + NADH
-
2% of the activity with estradiol-17beta
-
-
?
2,4-dinitroestrone 3-oxyacetic acid ether + NADH
2,4-dinitroestradiol 3-oxyacetic acid ether + NAD+
-
-
-
-
?
2,5(10)-estradiene-1,4,17-trione + NADH
17beta-hydroxy-2,5(10)-estradiene-1,4-dione + NAD+
-
-
-
-
?
2-nitroestrone 3-oxyacetic acid ester + NADH + H+
2-nitroestradiol-17beta-3-oxyacetic acid ester + NAD+
-
-
-
-
?
3-hydroxy-2,5(10)-estradiene-1,4,17-trione + NADH
3,17beta-dihydroxy-2,5(10)-estradiene-1,4-dione + NAD+
-
-
-
-
?
3beta-hydroxyandrost-5-en-17-one + NADPH
3beta,17beta-dihydroxyandrost-5-ene + NADP+
-
i.e. dehydroepiandrosterone
-
-
?
4-aminoestrone 3,4-diacetate + NADH
4-aminoestradiol 3,4-diacetate + NAD+
-
-
-
-
?
4-estrene-3,17-dione + NADH + H+
4-estrene-17beta-ol-3-one + NAD+
-
-
-
r
4-estrene-3,17-dione + NADPH
4-estrene-17beta-ol-3-one + NADP+
-
-
-
-
r
4-estrene-3,17-dione + NADPH + H+
4-estrene-17beta-ol-3-one + NADP+
-
-
-
r
4-methyl-1,3,5(10)-estratriene-1,17beta-diol + NAD+
1-hydroxy-4-methyl-1,3,5(10)-estratriene-17-one + NADH
-
-
-
-
?
5,7,9-estratrien-3beta-ol-17-one + NADH
5,7,9-estratriene-3beta,17beta-diol + NAD+
-
-
-
-
?
5,7,9-estratriene-3beta,17beta-diol + NAD+
5,7,9-estratriene-3beta-ol-17-one + NADH
-
-
-
-
?
5-androstene-3beta,17beta-diol + NAD+
5-androstene-3-beta-ol-17-one + NADH
-
5.9% of the activity with estradiol
-
-
?
5-androstene-3beta-ol-17-one + NADPH
5-androstene-3beta,17beta-diol + NADP+
-
-
-
?
5alpha-adrostane-3alpha,17beta-diol + NAD+
androsterone + NADH + H+
-
-
-
?
5alpha-androstane-3,17-dione + NADH + H+
5alpha-androstane-17beta-ol-3-one + NAD+
-
-
-
r
5alpha-androstane-3alpha,17beta-diol + NAD+
androsterone + NADH + H+
-
-
-
?
5alpha-dihydrotestosterone + NAD+
5alpha-androstan-3,17-dione + NADH
-
3.2% of the activity with estradiol
-
-
?
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3,17-dione + NADP+
-
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstane-3beta,17beta-diol + 5alpha-androstane-3,17-dione + NADP+
-
-
-
?
5beta-pregnan-20alpha-ol-3-one + NADPH
5beta-pregnane-3,20-dione + NADP+
-
-
-
?
6-dehydroestrone 3-benzoate + NADH
6-dehydro-17beta-estradiol 3-benzoate + NAD+
-
-
-
-
?
6alpha,7alpha-dihydroxyestrone + NADH
6alpha,7alpha-dihydroxyestradiol + NAD+
-
-
-
-
?
androst-4-ene-3,17-dione + NADPH
androst-4-ene-17beta-ol-3-one + NADP+
-
-
-
-
-
androsterone + NAD(P)H
5alpha-androstane-3alpha,17beta-diol + NAD(P)+ + H+
-
-
-
?
androsterone + NADH + H+
5alpha-adrostane-3alpha,17beta-diol + NAD+
-
-
-
?
dehydroepiandrosterone + NAD(P)H
5-androstene-3beta,17beta-diol + NAD(P)+
-
-
-
?
dehydroepiandrosterone + NAD(P)H
androst-5-ene-3beta,17beta-diol + NAD(P)+
-
-
-
-
?
dehydroepiandrosterone + NADPH + H+
5-androstene-3beta,17beta-diol + NADP+
-
-
-
-
?
dihydrotestosterone + NAD(P)H + H+
androstane-3beta,17beta-diol + NAD(P)+
-
-
-
-
?
dihydrotestosterone + NADPH + H+
5alpha-androstane-3beta,17beta-diol + NADP+
-
-
-
-
?
DL-6-methoxy-3-deoxy-equilenin + NAD+
17beta-hydroxy-DL-6-methoxy-3-deoxyequilenin + NAD+
-
-
-
-
?
epitestosterone + NADP+
4-androsten-3,17-dione + NADPH + H+
-
poor substrate
-
-
?
estradiol + NADP+
estrone + NADPH
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the equilibrium state is 92% estradiol to 8% estrone
-
-
?
estradiol-17alpha + NADP+
estrone + NADPH
-
at about 3% of the activity with estradiol-17beta
-
-
?
estrone 3-oxyacetic acid ether + NADH
17beta-estradiol 3-O-oxyacetic acid ether + NAD+
-
-
-
-
?
testosterone + NAD(P)+
4-androstene-3,17-dione + NAD(P)H
-
17beta-HSD2 and 5, key role in regulating steroid receptor occupancy in normal and tumor tissues
-
-
?
17beta-estradiol + NAD(P)+
estrone + NAD(P)H + H+
-
-
-
-
r
20alpha-hydroxy-4-pregnen-3-one + NADP+
4-pregnen-3,20-dione + NADPH
-
low activity
-
-
?
3-O-methyl-17beta-estradiol + NAD+
3-O-methylestrone + NADH
-
85% of the activity with estradiol-17beta
-
-
?
4-androstene-3,17-dione + NADPH + H+
testosterone + NADP+
-
17beta-HSD3 and 5, formation of active androgens in testis and prostate
-
-
?
5alpha-dihydrotestosterone + NADP+
5alpha-androstan-3,17-dione + NADPH
-
-
-
-
?
5alpha-dihydrotestosterone + NADP+
5alpha-androstan-3,17-dione + NADPH
-
-
-
?
5alpha-dihydrotestosterone + NADP+
5alpha-androstan-3,17-dione + NADPH
the enzyme could play a critical role in estrogen-sensitive cells, since it inactivates 5alpha-dihydrotestosterone that generally shows antagonistic effect in the cells
-
-
?
androstenedione + NADPH + H+
testosterone + NADP+
-
50% of the activity with estradiol-17beta
-
-
?
estradiol-17beta + NAD(P)+
estrone + NAD(P)H
-
17beta-HSD2 and 5, key role in regulating steroid receptor occupancy in normal and tumor tissues
-
-
?
estradiol-17beta + NAD(P)+
estrone + NAD(P)H + H+
-
17beta-HSD4 is involved in etsrogen inactivation and may protect against an excessive accumulation of E2 in human ovarian epithelial cells
-
-
?
estradiol-17beta + NAD+
estrone + NADH
-
type 1 enzyme is a cytosolic isoform highly specific for estradiol. Type 2 is a membrane bound isoform reactive with both estradiol and testosterone
-
-
-
estradiol-17beta + NAD+
estrone + NADH
-
reversible at neutral pH, reduction of estrone at 5% of the activity of reduction of estradiol-17beta
-
-
r
estradiol-17beta + NAD+
estrone + NADH
-
reduction of estrone is 400fold slower than oxidation of 17beta-estradiol
-
-
r
estradiol-17beta + NAD+
estrone + NADH + H+
-
vitamin K2 binds 17beta-hydroxysteroid dehydrogenase 4 and modulates estrogen metabolism. Vitamin K2 decreases the estradiol-17beta/estrone ratio in cells by 25%
-
-
?
estradiol-17beta + NAD+
estrone + NADH + H+
-
enzyme catalyzes the reduction of estrone to estradiol, the rate is 2.3% of the activity with estradiol
-
-
?
estradiol-17beta + NAD+
estrone + NADH + H+
-
activity with NAD+ is barely detectable
-
-
?
estradiol-17beta + NAD+
estrone + NADH + H+
-
activity with NAD+ is 2.2-3.8fold lower than with NADP+, depending on sample
-
-
?
estradiol-17beta + NADP+
estrone + NADPH
-
rate of oxidation of estradiol-17beta at the optimum, pH 9.9, is three to four times faster than that of the reverse reaction at pH 7.4
-
-
r
estradiol-17beta + NADP+
estrone + NADPH
-
maximal activity with NADP+ is approximately 1/3 of that with NAD+
-
-
r
estradiol-17beta + NADP+
estrone + NADPH
-
17beta-HSD2, important role in peripheral inactivation of androgens and estrogens, 17beta-HSD4, low substrate affinity
-
-
?
estradiol-17beta + NADP+
estrone + NADPH
-
reverse reaction catalyzed by different isoforms of the enzyme
-
-
-
estradiol-17beta + NADP+
estrone + NADPH
-
reversible at neutral pH, reduction of estrone at 5% of the activity of reduction of estradiol-17beta
-
-
r
estradiol-17beta + NADP+
estrone + NADPH
-
activity with NADP+ is only 30% of the activity with NAD+
-
-
r
estradiol-17beta + NADP+
estrone + NADPH + H+
-
-
-
-
?
estrone + NAD(P)H
estradiol + NAD(P)+
-
normal and tubal pregancies possess identical expression of 17HSD1 in syncytiotrophoblast cells and therefore, similar estradiol production in the placenta. Association of 17HSD1 with extravillous cells indicates that the enzyme perhaps plays a role in trophoblast invasion.Increased expression of 17HSD1 in epithelial cells of fallopian tube may lead to a local estradiol supply sufficient for maintenance of tubal pregnancy
-
-
?
estrone + NAD(P)H
estradiol-17beta + NAD(P)+
-
final step in the synthesis of active estrogens
-
-
r
estrone + NAD(P)H
estradiol-17beta + NAD(P)+
the enzyme produces active estradiol for cell proliferation
-
-
?
estrone + NAD(P)H + H+
estradiol + NAD(P)+
-
17beta-hydroxysteroid dehydrogenase has a pivotal role in regulating the synthesis of estradiol within breast tumours. 17beta-hydroxysteroid dehydrogenase activity contributes to the high estradiol concentrations found in most breast tumours
-
-
?
estrone + NAD(P)H + H+
estradiol + NAD(P)+
-
the enzyme efficiently converts estrone to estradiol and enhances the estrogen-dependent growth of cultured MCF-7 cells in the presence of hormonally less active estrone. The reaction is reversible in vitro, but in cultured cells the production of estradiol is the predominant rection in physiological conditions
-
-
r
estrone + NAD(P)H + H+
estradiol + NAD(P)+
type 12 17beta-hydroxysteroid dehydrogenase plays a role in estrogen formation. Type 12 17beta-hydroxysteroid dehydrogenase is the major estrogenic 17beta-HSD responsible for the conversion of estrone to estradiol in women, especially in the ovary, the predominant source of estrogens before menopause
-
-
?
estrone + NAD(P)H + H+
estradiol-17beta + NAD(P)+
-
type 1 17beta-hydroxysteroid dehydrogenase plays a critical role in the biosynthesis of estradiol
-
-
?
estrone + NADH
estradiol-17beta + NAD+
key enzyme responsible for elevated levels of 17beta-estradiol in breast tumor tissues
-
-
?
estrone + NADH
estradiol-17beta + NAD+
-
exposure to epidermal growth factor slowly induces a cellular state in which enzyme activity is subject to modulation by both progesterone and estradiol
-
-
?
estrone + NADH
estradiol-17beta + NAD+
-
17beta-estradiol is a potent stimulator of certain endocrine-dependent forms of breast cancer. The enzyme catalyzes the last step in the biosynthesis of 17beta-estradiol from the less potent estrogen, estrone
-
-
?
estrone + NADH
estradiol-17beta + NAD+
-
type 1 enzyme, catalyzes the conversion of the low activity estrogen, estrone, into highly active estradiol, both in the gonads and in target tissues
-
?
estrone + NADH
estradiol-17beta + NAD+
-
the reductive activity predominates in hormone dependent breast tumors. This gives rise to high concentrations of estradiol in breast cancer
-
-
?
estrone + NADH
estradiol-17beta + NAD+
-
trans-retinoic acid increases expression of the enzyme in a dose-dependent and time-dependent manner in T47D breast cancer cells, the increased expression is associated with an increase in reductive activity of the enzyme
-
-
?
estrone + NADH
estradiol-17beta + NAD+
-
reversible at neutral pH, reduction of estrone at 5% of the activity of reduction of estradiol-17beta
-
-
r
estrone + NADH
estradiol-17beta + NAD+
-
reduction of estrone is 400fold slower than oxidation of 17beta-estradiol
-
-
r
estrone + NADH
estradiol-17beta + NAD+
-
progesterone treatment of ovariectomized gilts stimulates oxidative activity in uterus, anterior pituitary, skeletal muscle and kidney, constitutive levels of activity in adrenals, lung and liver
-
-
?
estrone + NADPH
17beta-estradiol + NADP+
-
convertion of the weak androgen estrone into the potent estrogen 17beta-estradiol
-
-
?
estrone + NADPH
17beta-estradiol + NADP+
-
the reversible reaction constitutes an important pre-receptor control mechanism for nuclear receptor ligands, since the conversion switches between the 17beta-hydroxy receptor ligands and their inactive 17-oxo metabolites
-
-
r
estrone + NADPH
17beta-estradiol + NADP+
-
substrate of e.g. isozyme 17beta-HSD3, 17beta-HSD8, and 17beta-HSD14
-
-
r
estrone + NADPH
17beta-estradiol + NADP+
-
type 8 17beta-HSD can downregulate 17beta-estradiol levels in a large variety of tissues
-
-
?
estrone + NADPH
17beta-estradiol + NADP+
-
type 8 17beta-HSD is substrate-specific
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
-
final step in the synthesis of active estrogens
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
final step in the synthesis of active estrogens, important in the maintenance of pregnancy
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
final step in the synthesis of active estrogens, important in the maintenance of pregnancy
-
-
r
estrone + NADPH + H+
estradiol-17beta + NADP+
reductive activity is 1.5-3fold higher than oxidative activity
-
-
r
estrone + NADPH + H+
estradiol-17beta + NADP+
-
rate of oxidation of estradiol-17beta at the optimum, pH 9.9, is three to four times faster than that of the reverse reaction at pH 7.4
-
-
r
estrone + NADPH + H+
estradiol-17beta + NADP+
-
-
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
-
type 1 enzyme is a cytosolic isoform highly specific for estradiol. Type 2 is a membrane bound isoform reactive with both estradiol and testosterone
-
-
-
estrone + NADPH + H+
estradiol-17beta + NADP+
-
17beta-HSD1, final step in the synthesis of active estrogens
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
final step in the synthesis of active estrogens
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
-
final step in the synthesis of active estrogens
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
-
final step in the synthesis of active estrogens, maintenance of a proper balance of inactive estrone and active estradiol-17beta in brain
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
-
reverse reaction catalyzed by different isoforms of the enzyme
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
-
final step in synthesis of estradiol
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
-
final step in the synthesis of active estrogens
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
-
reversible at neutral pH, reduction of estrone at 5% of the activity of oxidation of estradiol-17beta
-
-
r
estrone + NADPH + H+
estradiol-17beta + NADP+
-
related to nuclear maturation in oocytes
-
-
?
testosterone + NAD+
4-androstene-3,17-dione + NADH
-
2.4% of the activity with estradiol
-
-
?
testosterone + NADP+
4-androstene-3,17-dione + NADPH + H+
-
poor substrate
-
-
?
testosterone + NADP+
4-androstene-3,17-dione + NADPH + H+
-
-
androstenedione
r
testosterone + NADP+
4-androstene-3,17-dione + NADPH + H+
-
75% of the activity with estradiol-17beta
-
r
testosterone + NADP+
4-androstene-3,17-dione + NADPH + H+
-
17beta-HSD2, important role in peripheral inactivation of androgens and estrogens
-
-
?
testosterone + NADP+
4-androstene-3,17-dione + NADPH + H+
-
activity is 22fold lower than with estradiol-17beta
-
-
?
testosterone + NADP+
4-androstene-3,17-dione + NADPH + H+
-
lower activity than with estradiol 17beta
-
-
?
testosterone + NADP+
4-androstene-3,17-dione + NADPH + H+
-
activity is 2.3-2.8fold lower than with estradiol-17beta, depending on sample
-
-
?
additional information
?
-
-
type 1 enzyme is a cytosolic isoform highly specific for estradiol. Type 2 enzyme is a membrane bound isoform reactive with both estradiol and testosterone
-
-
-
additional information
?
-
-
the isozymes constitute by showing different properties a complex system ensuring cell-specific adaptation and regulation of sex steroid hormone levels, isozyme 17beta-HSD1 is the major determinant of peripheral and gonadal estradiol synthesis
-
-
-
additional information
?
-
-
17beta-HSD isozymes differ in their expression pattern, nucleotide cofactor preferences, steroid substrate specificity, and subcellular localization, detailed overview, substrate are androgens, estrogens, cholesterol, progestins, and eicosanoids, isozyme 17beta-HSD3 also shows 3beta-hydroxysteroid dehydrogenase, EC 1.1.1.51, isozyme 17beta-HSD8 also shows, to a lessser extent, NAD+-dependent testosterone oxidation to androstenedione, EC 1.1.1.63
-
-
-
additional information
?
-
-
human 17beta-hydroxysteroid dehydrogenases are multifunctional enzymes, isozyme 17beta-HSD4 also performs beta-oxidation of branched fatty acids, like pristanic acid, and in bile acid synthesis, e.g. of di- and trihydroxycholestanoic acids, overview
-
-
-
additional information
?
-
-
expression is stimulated 2fold by dexamethasone but is completly downregulated by phorbol ester
-
-
-
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
4-androstene-3,17-dione + NADPH + H+
testosterone + NADP+
-
17beta-HSD3 and 5, formation of active androgens in testis and prostate
-
-
?
4-estrene-3,17-dione + NADPH
4-estrene-17beta-ol-3-one + NADP+
-
-
-
-
r
5alpha-androstane-3alpha,17beta-diol + NAD+
androsterone + NADH + H+
C9JRZ8
-
-
-
?
5alpha-dihydrotestosterone + NADP+
5alpha-androstan-3,17-dione + NADPH
Q5MGS6
the enzyme could play a critical role in estrogen-sensitive cells, since it inactivates 5alpha-dihydrotestosterone that generally shows antagonistic effect in the cells
-
-
?
estradiol-17beta + NAD(P)+
estrone + NAD(P)H
-
17beta-HSD2 and 5, key role in regulating steroid receptor occupancy in normal and tumor tissues
-
-
?
estradiol-17beta + NAD(P)+
estrone + NAD(P)H + H+
-
17beta-HSD4 is involved in etsrogen inactivation and may protect against an excessive accumulation of E2 in human ovarian epithelial cells
-
-
?
estradiol-17beta + NAD+
estrone + NADH + H+
-
vitamin K2 binds 17beta-hydroxysteroid dehydrogenase 4 and modulates estrogen metabolism. Vitamin K2 decreases the estradiol-17beta/estrone ratio in cells by 25%
-
-
?
estradiol-17beta + NADP+
estrone + NADPH
-
17beta-HSD2, important role in peripheral inactivation of androgens and estrogens, 17beta-HSD4, low substrate affinity
-
-
?
estrone + NAD(P)H
estradiol + NAD(P)+
-
normal and tubal pregancies possess identical expression of 17HSD1 in syncytiotrophoblast cells and therefore, similar estradiol production in the placenta. Association of 17HSD1 with extravillous cells indicates that the enzyme perhaps plays a role in trophoblast invasion.Increased expression of 17HSD1 in epithelial cells of fallopian tube may lead to a local estradiol supply sufficient for maintenance of tubal pregnancy
-
-
?
estrone + NAD(P)H + H+
estradiol-17beta + NAD(P)+
-
type 1 17beta-hydroxysteroid dehydrogenase plays a critical role in the biosynthesis of estradiol
-
-
?
testosterone + NAD(P)+
4-androstene-3,17-dione + NAD(P)H
-
17beta-HSD2 and 5, key role in regulating steroid receptor occupancy in normal and tumor tissues
-
-
?
testosterone + NADP+
4-androstene-3,17-dione + NADPH + H+
-
17beta-HSD2, important role in peripheral inactivation of androgens and estrogens
-
-
?
17beta-estradiol + NAD(P)+
estrone + NAD(P)H + H+
-
-
-
-
r
estrone + NAD(P)H
estradiol-17beta + NAD(P)+
-
final step in the synthesis of active estrogens
-
-
r
estrone + NAD(P)H
estradiol-17beta + NAD(P)+
Q5MGS6
the enzyme produces active estradiol for cell proliferation
-
-
?
estrone + NAD(P)H + H+
estradiol + NAD(P)+
-
17beta-hydroxysteroid dehydrogenase has a pivotal role in regulating the synthesis of estradiol within breast tumours. 17beta-hydroxysteroid dehydrogenase activity contributes to the high estradiol concentrations found in most breast tumours
-
-
?
estrone + NAD(P)H + H+
estradiol + NAD(P)+
-
the enzyme efficiently converts estrone to estradiol and enhances the estrogen-dependent growth of cultured MCF-7 cells in the presence of hormonally less active estrone. The reaction is reversible in vitro, but in cultured cells the production of estradiol is the predominant rection in physiological conditions
-
-
r
estrone + NAD(P)H + H+
estradiol + NAD(P)+
Q53GQ0
type 12 17beta-hydroxysteroid dehydrogenase plays a role in estrogen formation. Type 12 17beta-hydroxysteroid dehydrogenase is the major estrogenic 17beta-HSD responsible for the conversion of estrone to estradiol in women, especially in the ovary, the predominant source of estrogens before menopause
-
-
?
estrone + NADH
estradiol-17beta + NAD+
P14061
key enzyme responsible for elevated levels of 17beta-estradiol in breast tumor tissues
-
-
?
estrone + NADH
estradiol-17beta + NAD+
-
exposure to epidermal growth factor slowly induces a cellular state in which enzyme activity is subject to modulation by both progesterone and estradiol
-
-
?
estrone + NADH
estradiol-17beta + NAD+
-
17beta-estradiol is a potent stimulator of certain endocrine-dependent forms of breast cancer. The enzyme catalyzes the last step in the biosynthesis of 17beta-estradiol from the less potent estrogen, estrone
-
-
?
estrone + NADH
estradiol-17beta + NAD+
-
type 1 enzyme, catalyzes the conversion of the low activity estrogen, estrone, into highly active estradiol, both in the gonads and in target tissues
-
?
estrone + NADH
estradiol-17beta + NAD+
-
the reductive activity predominates in hormone dependent breast tumors. This gives rise to high concentrations of estradiol in breast cancer
-
-
?
estrone + NADH
estradiol-17beta + NAD+
-
trans-retinoic acid increases expression of the enzyme in a dose-dependent and time-dependent manner in T47D breast cancer cells, the increased expression is associated with an increase in reductive activity of the enzyme
-
-
?
estrone + NADH
estradiol-17beta + NAD+
-
progesterone treatment of ovariectomized gilts stimulates oxidative activity in uterus, anterior pituitary, skeletal muscle and kidney, constitutive levels of activity in adrenals, lung and liver
-
-
?
estrone + NADPH
17beta-estradiol + NADP+
-
convertion of the weak androgen estrone into the potent estrogen 17beta-estradiol
-
-
?
estrone + NADPH
17beta-estradiol + NADP+
-
the reversible reaction constitutes an important pre-receptor control mechanism for nuclear receptor ligands, since the conversion switches between the 17beta-hydroxy receptor ligands and their inactive 17-oxo metabolites
-
-
r
estrone + NADPH
17beta-estradiol + NADP+
-
type 8 17beta-HSD can downregulate 17beta-estradiol levels in a large variety of tissues
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
-
final step in the synthesis of active estrogens
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
Q9GME2, Q9N0M8
final step in the synthesis of active estrogens, important in the maintenance of pregnancy
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
Q9GME2, Q9N0M8
final step in the synthesis of active estrogens, important in the maintenance of pregnancy
-
-
r
estrone + NADPH + H+
estradiol-17beta + NADP+
-
17beta-HSD1, final step in the synthesis of active estrogens
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
P14061
final step in the synthesis of active estrogens
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
-
final step in the synthesis of active estrogens
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
-
final step in the synthesis of active estrogens, maintenance of a proper balance of inactive estrone and active estradiol-17beta in brain
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
-
final step in synthesis of estradiol
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
-
final step in the synthesis of active estrogens
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
-
related to nuclear maturation in oocytes
-
-
?
additional information
?
-
-
the isozymes constitute by showing different properties a complex system ensuring cell-specific adaptation and regulation of sex steroid hormone levels, isozyme 17beta-HSD1 is the major determinant of peripheral and gonadal estradiol synthesis
-
-
-
additional information
?
-
-
expression is stimulated 2fold by dexamethasone but is completly downregulated by phorbol ester
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
cofactor binding mechanism and specificity involving residues Tyr49, Thr202, Ala50, and Asn51, overview
-
NAD+
-
cofactor; maximal activity with NADP+ is approximately 1/3 of that with NAD+
NAD+
-
cofactor
NAD+
-
activity with NAD+ is 2.2-3.8fold lower than with NADP+, depending on sample
NAD+
-
-
NADH
-
-
NADP+
-
cofactor; maximal activity with NADP+ is approximately 1/3 of that with NAD+
NADP+
mutant enzyme Y49D show activity with NADP+, wild-type enzyme shows no activity
NADP+
-
-
656644, 656645, 657673, 659810, 675982, 675983, 699435, 699843, 700184, 700186, 740136, 740409, 740542, 740743, 740839
NADPH
mutant enzyme Y49D show activity with NADPH, wild-type enzyme shows no activity
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(10R,13S,17R)-10,13-dimethyl-1,2,7,8,9,10,11,12,13,14,15,16-dodecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-3,5',6(4'H)-trione
-
0.003 mM, 45% inhibition, substrate: 4-androstene-3,17-dione
(10R,13S,17R)-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-3,5'(2H,4'H)-dione
-
0.003 mM, 61% inhibition, substrate: 4-androstene-3,17-dione; 0.003 mM, 63% inhibition, substrate: 4-androstene-3,17-dione
(13alpha)-3-hydroxyestra-1(10),2,4-trien-17-one
-
inhibits the enzyme activity effectively, enzyme affinity is similar to that of the natural estrone substrate
(13S,17R)-13-methyl-4',5',6,7,8,9,11,12,13,14,15,16-dodecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-3,5'-diol
-
0.003 mM, 61% inhibition, substrate: 4-androstene-3,17-dione
(13S,17R)-3-hydroxy-13-methyl-3',4',6,7,8,9,11,12,13,14,15,16-dodecahydro-5'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-5'-one
-
0.003 mM, 79% inhibition, substrate: 4-androstene-3,17-dione
(13S,17R)-3-hydroxy-13-methyl-5'-propyl-4',5',6,7,8,9,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,2'-pyran]-6'(3'H)-one
-
0.003 mM, 83% inhibition, substrate: 4-androstene-3,17-dione
(13S,17R)-3-hydroxy-5',13-dimethyl-4',5',6,7,8,9,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,2'-pyran]-6'(3'H)-one
-
0.003 mM, 94% inhibition, substrate: 4-androstene-3,17-dione
(13S,17R)-5',13-dimethyl-4',5',6,7,8,9,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,2'-pyran]-6'(3'H)-one
-
0.003 mM, 94% inhibition, substrate: 4-androstene-3,17-dione
(13S,17R)-5',5',13-trimethyl-4',5',6,7,8,9,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,2'-pyran]-6'(3'H)-one
-
0.003 mM, 95% inhibition, substrate: 4-androstene-3,17-dione
(13S,17S)-13-methyl-4',5',6,7,8,9,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,2'-pyran]-6'(3'H)-one
-
0.003 mM, 95% inhibition, substrate: 4-androstene-3,17-dione
(13S,17S)-3-hydroxy-13-methyl-3',4',6,7,8,9,11,12,13,14,15,16-dodecahydro-5'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-5'-one
-
0.003 mM, 45% inhibition, substrate: 4-androstene-3,17-dione
(13S,17S)-3-hydroxy-13-methyl-4',5',6,7,8,9,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,2'-pyran]-6'(3'H)-one
-
0.003 mM, 95% inhibition, substrate: 4-androstene-3,17-dione
(13S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-7'H-spiro[cyclopenta[a]phenanthrene-17,2'-oxepan]-7'-one
-
0.003 mM, 93% inhibition, substrate: 4-androstene-3,17-dione
(15alpha)-3-hydroxy-N-(5-methyl-1,3-thiazol-2-yl)-17-oxoestra-1(10),2,4-triene-15-carboxamide
-
-
(15beta)-15-(4-morpholin-4-yl-4-oxobutyl)-17-oxoestra-1(10),2,4-trien-3-yl sulfamate
-
0.0001 mM, 10% inhibition
(16Z)-3-hydroxy-16-(2,2,2-trifluoro-1-hydroxyethylidene)estra-1(10),2,4-trien-17-one
-
-
(17beta)-3,17-dihydroxy-N-(pyridin-3-ylmethyl)estra-1(10),2,4-triene-16-carboxamide
-
-
(1Z)-N'-[[(3,5-dimethylisoxazol-4-yl)carbonyl]oxy]-2-[4-(1,2,3-thiadiazol-4-yl)phenyl]ethanimidamide
-
-
(2'R,13S)-3-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2'-pyran]-6'(3'H)-one
-
0.003 mM, 92% inhibition, substrate: 4-androstene-3,17-dione
(2'R,13S)-3-hydroxy-4',13-dimethyl-4',5',6,7,8,9,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,2'-pyran]-6'(3'H)-one
-
0.003 mM, 94% inhibition, substrate: 4-androstene-3,17-dione
(2'R,13S)-3-hydroxy-5',5',13-trimethyl-4',5',6,7,8,9,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,2'-pyran]-6'(3'H)-one
-
0.003 mM, 94% inhibition, substrate: 4-androstene-3,17-dione
(2'R,13S)-5'-cyclopropyl-3-hydroxy-13-methyl-4',5',6,7,8,9,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,2'-pyran]-6'(3'H)-one
-
0.003 mM, 91% inhibition, substrate: 4-androstene-3,17-dione
(2'R,13S)-methyl 3-hydroxy-13-methyl-6'-oxo-3',4',5',6,6',7,8,9,11,12,13,14,15,16-tetradecahydrospiro[cyclopenta[a]phenanthrene-17,2'-pyran]-5'-carboxylate
-
0.003 mM, 92% inhibition, substrate: 4-androstene-3,17-dione
(2E)-3-[2-hydroxy-6-(3-hydroxyphenyl)-1-naphthyl]-N-methylacrylamide
-
58% inhibition at 0.001 mM
(2E)-3-[2-hydroxy-6-(3-hydroxyphenyl)-1-naphthyl]-N-phenylacrylamide
-
60% inhibition at 0.001 mM
(2R,4aS,4bR,10bS,12aS)-9-chloro-2-fluoro-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydrochrysen-1(2H)-one
-
-
(2S,4aS,4bR,10bS,12aS)-9-chloro-2-fluoro-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydrochrysen-1(2H)-one
-
-
(2Z,2'E)-N,N'-1H-1,5-benzodiazepine-2,4-diylbis(3-phenylprop-2-enamide)
-
30% inhibition at 0.006 mM
(3-amino-5-[13-[(16beta,17beta)-3,17-dihydroxyestra-1(10),2,4-trien-16-yl]tridecyl]phenyl)acetic acid
-
-
(3-[(4-aminophenyl)carbonyl]-5-[13-[(16beta,17beta)-3,17-dihydroxyestra-1(10),2,4-trien-16-yl]tridecyl]phenyl)acetic acid
-
-
(3-[13-[(16beta,17beta)-3,17-dihydroxyestra-1(10),2,4-trien-16-yl]tridecyl]phenyl)acetic acid
-
-
(4aS,4bR,10bS,12aS)-8-hydroxy-12a-methyl-9-(2-phenylethyl)-3,4,4a,4b,5,6,10b,11,12,12a-decahydrochrysen-1(2H)-one
-
-
(4aS,4bR,10bS,12aS)-8-hydroxy-12a-methyl-9-prop-2-en-1-yl-3,4,4a,4b,5,6,10b,11,12,12a-decahydrochrysen-1(2H)-one
-
-
(4aS,4bR,10bS,12aS)-8-hydroxy-9-iodo-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydrochrysen-1(2H)-one
-
-
(4aS,4bR,10bS,12aS)-8-hydroxy-9-methoxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydrochrysen-1(2H)-one
-
-
(4aS,4bR,10bS,12aS)-9-bromo-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydrochrysen-1(2H)-one
-
-
(4aS,4bR,10bS,12aS)-9-chloro-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydrochrysen-1(2H)-one
-
-
(4R,5R)-4-(2-fluorophenyl)-5-[hydroxy(5-phenylthiophen-2-yl)methyl]-1-methylpyrrolidin-2-one
-
-
(4R,5R)-5-[hydroxy[5-(pyridin-3-yl)thiophen-2-yl]methyl]-1-methyl-4-phenylpyrrolidin-2-one
-
-
(4S,5S)-5-[biphenyl-3-yl(hydroxy)methyl]-4-(2-fluorophenyl)-1-methylpyrrolidin-2-one
-
;
(4S,5S)-5-[biphenyl-4-yl(hydroxy)methyl]-4-(2-fluorophenyl)-1-methylpyrrolidin-2-one
-
;
(4S,5S)-5-[hydroxy[5-(pyridin-3-yl)thiophen-2-yl]methyl]-1-methyl-4-phenylpyrrolidin-2-one
-
;
(6-hydroxy-1,3-benzothiazol-2-yl)(3-hydroxyphenyl)methanone
-
modeling of binding to crystal structure shows five hydrogen bond interactions and a cation-pi-interaction
(6aS)-2-(benzyloxy)-6a-methyl-9-[(2E)-4-morpholin-4-yl-4-oxobut-2-en-1-yl]-5,6,6a,10,10a,10b,11,12-octahydro-4bH-naphtho[2',1':4,5]indeno[2,1-d]isoxazole
-
0.0001 mM, 21% inhibition
(6aS)-2-hydroxy-6a,8-dimethyl-5,6,6a,7,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazol-9(4bH)-one
-
0.01 mM, 32% inhibition
(6aS)-2-hydroxy-6a-methyl-5,6,6a,7,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazol-9(4bH)-one
-
0.01 mM, 86% inhibition
(6aS)-2-hydroxy-6a-methyl-N-(2-pyridin-3-ylethyl)-4b,5,6,6a,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazole-9-carboxamide
(6aS)-2-hydroxy-6a-methyl-N-(pyridin-2-ylmethyl)-4b,5,6,6a,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazole-9-carboxamide
(6aS)-2-hydroxy-6a-methyl-N-(pyridin-3-ylmethyl)-4b,5,6,6a,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazole-9-carboxamide
(6aS)-2-hydroxy-6a-methyl-N-[(1-methyl-1H-pyrrol-2-yl)methyl]-4b,5,6,6a,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazole-9-carboxamide
-
0.01 mM, 90% inhibition, IC50: 0.0023 mM
(6aS)-2-hydroxy-6a-methyl-N-[(5-methylpyrazin-2-yl)methyl]-4b,5,6,6a,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazole-9-carboxamide
-
0.01 mM, 80% inhibition
(6aS)-3-ethyl-2-hydroxy-6a-methyl-N-(2-pyridin-3-ylethyl)-4b,5,6,6a,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazole-9-carboxamide
-
-
(6aS)-6a-methyl-4b,5,6,6a,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazol-2-ol
-
-
(6aS)-6a-methyl-9-(4-morpholin-4-yl-4-oxobutyl)-4b,5,6,6a,7,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazol-2-ol
-
0.0001 mM, 53% inhibition
(6aS)-6a-methyl-9-(trifluoromethyl)-4b,6,6a,7,9a,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazole-2,6b(5H)-diol
-
-
(6aS)-8-(2-methoxyethyl)-6a-methyl-4b,5,6,6a,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazol-2-ol
-
-
(6aS)-9-(hydroxymethyl)-6a-methyl-4b,5,6,6a,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazol-2-ol
-
-
(6aS,6bR,10aR)-2-hydroxy-6a-methyl-5,6,6a,6b,9,10,10a,11,11a,11b,12,13-dodecahydronaphtho[2',1':4,5]indeno[1,2-b]pyran-8(4bH)-one
-
0.003 mM, 52% inhibition, substrate: 4-androstene-3,17-dione
(6aS,6bS,10aS)-2-hydroxy-6a-methyl-5,6,6a,6b,9,10,10a,11,11a,11b,12,13-dodecahydronaphtho[2',1':4,5]indeno[1,2-b]pyran-8(4bH)-one
-
0.003 mM, 85% inhibition, substrate: 4-androstene-3,17-dione
(6aS,6bS,11aS)-2-hydroxy-6a-methyl-4b,5,6,6a,6b,9,10,11,11a,12,12a,12b,13,14-tetradecahydro-8H-naphtho[2',1':4,5]indeno[1,2-b]oxepin-8-one
-
0.003 mM, 91% inhibition, substrate: 4-androstene-3,17-dione
(6aS,6bS,9aR)-2-hydroxy-6a-methyl-4b,5,6,6a,6b,9,9a,10,10a,10b,11,12-dodecahydro-8H-naphtho[2',1':4,5]indeno[1,2-b]furan-8-one
-
0.003 mM, 62% inhibition, substrate: 4-androstene-3,17-dione
(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-4',5',6,7,8,9,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,2'-pyran]-6'(3'H)-one
-
85% inhibition at 0.001 mM
(S)-2-Methoxy-6a-methyl-5,6,6a,10,10a,10b,11,12-octahydro-4bH-7-oxa-8-aza-pentaleno[2,1-a]phenanthrene
-
-
(S)-6a-Methyl-5,6,6a,10,10a,10b,11,12-octahydro-4bH-7-oxa-8-aza-pentaleno[2,1-a]phenanthren-2-ol
-
-
1-(4'-hydroxy-2'_methyl-biphenyl-4-yl)-ethanone
-
37°C, 0.01 mM, 89% inhibition, substrate: estrone, 7beta-HSD type 1
1-(4'-hydroxy-biphenyl-4-yl)-ethanone
-
37°C, 01 mM, 97% inhibition, substrate: estrone, 7beta-HSD type 1; 97% inhibition at 0.001 mM
1-(4-hydroxy-phenyl)-butan-1-one
-
weak inhibitor with 35.1% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-decan-1-one
-
weak inhibitor with 28.2% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-dodecan-1-one
-
weak inhibitor with 42.5% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-ethanone
-
weak inhibitor with 20.8% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-heptan-1-one
-
weak inhibitor with 47.6% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-hexan-1-one
-
weak inhibitor with 45.7% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-octan-1-one
-
weak inhibitor with 36.9% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-pentan-1-one
-
weak inhibitor with 39.8% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-propan-1-one
-
weak inhibitor with 17.5% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-undecan-1-one
-
weak inhibitor with 30.6% inhibition at 0.1 mM
1-(4-hydroxyphenyl)-nonan-1-one
-
weak inhibitor with 36.3% inhibition at 0.1 mM
1-(6-hydroxy-9H-fluoren-2-yl)-ethanone
-
37°C, 0.01 mM, 86% inhibition, substrate: estrone, 7beta-HSD type 1; 86% inhibition at 0.001 mM
1-Chloro-4-(2,2-dichloro-1-(5-Chloro-phenyl)-ethyl)-benzene
-
oxidation of estradiol
1-Chloro-4-(2,2-dichloro-1-(6-Chloro-phenyl)-ethyl)-benzene
-
oxidation of estradiol
1-[(3-hydroxyphenyl)sulfanyl]-5-oxo-4,5,7,8,9,10,11,13-octahydro-3H-indeno[2',1':4,5]pyrimido[1,2-a]azepine-2-carbaldehyde
-
-
1-[2-[4-(6-Methoxy-2-phenyl-3,4-dihydro-naphthalen-1-yl)-phenoxy]-ethyl]-pyrrolidine
-
oxidation of estradiol
1-[5-(3'-hydroxybiphenyl-3-yl)-2-thienyl]ethanone
-
0.001 mM, 10 min, 22% inhibition; 0.001 mM, 10 min, 23% inhibition
1-[5-(3'-Hydroxybiphenyl-4-yl)-2-thienyl]ethanone
-
0.001 mM, 10 min, 10% inhibition; 0.001 mM, 10 min, 38% inhibition
10-((13S,16S,17S)-3,17-Dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-16-yl)-decanoic acid 5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester
-
IC50: 140 nM
11-((13S,17R)-17-Ethynyl-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl)-undecanoic acid butyl-methyl-amide
-
-
13-oxo-4-(phenylsulfanyl)-1,2,7,8,9,10,11,13-octahydro[1]benzothieno[2',3':4,5]pyrimido[1,2-a]azepine-3-carbaldehyde
-
0.001 mM, 80% inhibition
13-oxo-4-(propylsulfanyl)-1,2,7,8,9,10,11,13-octahydro[1]benzothieno[2',3':4,5]pyrimido[1,2-a]azepine-3-carbaldehyde
-
0.001 mM, 74% inhibition
16-oxo-estrone
-
40 mM, pH 8.5, t1/2: 0.8-1 h, at pH 7.2 inhibition is competitive against estradiol and non-competitive against NAD+
16alpha-bromopropyl-estradiol
-
IC50: 0.00046 mM, reduction of estrone, the inhibitor is totally inactive against type 2 17beta-HSD and type type 1 17beta-HSD
17-(1-hydroxy-prop-2-ynyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
-
suicide inhibitor
2'-AMP
-
competitive with respect to NAD(H) or NADP(H) and noncompetitive with respect to the steroid
2'-methoxy-N-(3-methoxyphenyl)-N-methyl-[1,1'-biphenyl]-4-sulfonamide
-
; 23% inhibition at 0.001 mM
2'-methoxy-N-methyl-N-phenyl-[1,1'-biphenyl]-4-sulfonamide
-
; 10% inhibition at 0.001 mM
2,2'-diimino-7,7'-dimethyl-5,5'-bis(1-methylethyl)-2H,2'H-8,8'-binaphtho[1,8-bc]furan-3,3',4,4'-tetrol
-
-
2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
-
44% inhibition at 0.006 mM
2-(2,6-dibromo-4-methylphenoxy)-N'-[(E)-(2,4-dihydroxy-6-methylphenyl)methylidene]acetohydrazide
-
64% inhibition at 0.02 mM
2-(2,6-dibromo-4-methylphenoxy)-N'-[(E)-(2,4-dimethoxyphenyl)methylidene]acetohydrazide
-
38% inhibition at 0.02 mM
2-(2-bromo-4,6-dimethylphenoxy)-N'-[(E)-(2,4-dihydroxyphenyl)methylidene]acetohydrazide
-
91% inhibition at 0.02 mM
2-(2-bromo-4-methylphenoxy)-N'-[(1E)-1-(2,4-dihydroxyphenyl)ethylidene]acetohydrazide
-
-
2-chloro-4-[5-(2,6-difluoro-3-hydroxybenzoyl)thiophen-2-yl]phenyl sulfamate
-
dual inhibitor, acts both on steroid sulfatase and hydroxy steroid dehydrogenase 17beta-HSD1, reverses estrogen-induced T-47D cell proliferation
2-ethyl-17-oxo-16-[2-oxo-2-[(pyridin-3-ylmethyl)amino]ethyl]estra-1(10),2,4-trien-3-yl sulfamate
-
-
2-ethyl-3-sulfamoyloxy-17-oxo-estra-1,3,5(10)-trien-16-methylcarboxylic acid-S-alpha-methylbenzyl amide
-
50% inhibition at 0.001 mM
2-ethyl-3-sulfamoyloxy-17-oxo-estra-1,3,5(10)-trien-16alpha/beta-methylcarboxylic acid-(5-methylpyrimidinyl-2-ylmethyl)amide
-
37% inhibition at 0.001 mM
2-ethyl-3-sulfamoyloxy-17-oxo-estra-1,3,5(10)-trien-16alpha/beta-methylcarboxylic acid-(pyridine-3-ylmethyl)amide
-
64% inhibition at 0.01 mM
2-hydroxy-6-(3-hydroxyphenyl)-N-(5-methyl-1,3,4-thiadiazol-2-yl)-1-naphthamide
-
73% inhibition at 0.001 mM
2-hydroxy-6-(3-hydroxyphenyl)-N-methyl-1-naphthamide
-
76% inhibition at 0.001 mM
2-hydroxy-6-(3-hydroxyphenyl)-N-phenyl-1-naphthamide
-
80% inhibition at 0.001 mM
2-[(16beta)-2-ethyl-3-hydroxy-17-oxoestra-1(10),2,4-trien-16-yl]-N-(pyridin-3-ylmethyl)acetamide
-
-
2-[2-ethyl-3-hydroxy-17-oxoestra-1(10),2,4-trien-16-yl]-N-(pyridin-2-ylmethyl)acetamide
-
-
2-[2-ethyl-3-hydroxy-17-oxoestra-1(10),2,4-trien-16-yl]-N-(pyridin-3-ylmethyl)acetamide
-
-
2-[3-hydroxy-17-oxoestra-1(10),2,4-trien-16-yl]-N-(2-pyridin-2-ylethyl)acetamide
-
0.01 mM, 58% inhibition
2-[3-hydroxy-17-oxoestra-1(10),2,4-trien-16-yl]-N-(pyridin-2-ylmethyl)acetamide
-
0.01 mM, 82% inhibition
2-[3-hydroxy-17-oxoestra-1(10),2,4-trien-16-yl]-N-(pyridin-3-ylmethyl)acetamide
-
-
2-[5-(3-ethyl-4-hydroxyphenyl)-1-oxo-indan-2-yl]-N-pyridin-3-ylmethyl-acetamide
-
37°C, 0.001 mM, 39% inhibition, substrate: estrone, 7beta-HSD type 1; 39% inhibition at 0.001 mM
3'-(1-benzothien-2-yl)biphenyl-3-ol
-
0.001 mM, 10 min, 39% inhibition; 0.001 mM, 10 min, 49% inhibition
3'-(2-thienyl)biphenyl-3-ol
-
0.001 mM, 10 min, 40% inhibition; 0.001 mM, 10 min, 48% inhibition
3'-(5-chloro-2-thienyl)biphenyl-3-ol
-
0.001 mM, 10 min, 31% inhibition; 0.001 mM, 10 min, 71% inhibition
3'-(5-methyl-2-thienyl)biphenyl-3-ol
-
0.001 mM, 10 min, 32% inhibition; 0.001 mM, 10 min, 36% inhibition
3'-hydroxy-N-(3-hydroxybenzyl)-N-methyl-[1,10-biphenyl]-4-sulfonamide
-
; 57% inhibition at 0.001 mM
3'-hydroxy-N-(3-hydroxyphenyl)-N-methyl-[1,10-biphenyl]-3-sulfonamide
-
42% inhibition at 0.001 mM; 68% inhibition at 0.001 mM
3'-hydroxy-N-(3-hydroxyphenyl)-N-methyl-[1,10-biphenyl]-4-sulfonamide
-
14% inhibition at 0.001 mM; 50% inhibition at 0.001 mM
3'-hydroxy-N-(3-methoxyphenyl)-N-methyl-[1,10-biphenyl]-4-sulfonamide
-
15% inhibition at 0.001 mM; 38% inhibition at 0.001 mM
3'-methoxy-N-(2-methoxyphenyl)-N-methyl-[1,1'-biphenyl]-4-sulfonamide
-
10% inhibition at 0.001 mM; 17% inhibition at 0.001 mM
3'-methoxy-N-(3-methoxybenzyl)-N-methyl-[1,10-biphenyl]-4-sulfonamide
-
; 45% inhibition at 0.001 mM
3'-methoxy-N-(3-methoxyphenyl)-N-methyl-[1,1'-biphenyl]-4-sulfonamide
-
10% inhibition at 0.001 mM; 27% inhibition at 0.001 mM
3'-methoxy-N-(3-methoxyphenyl)-N-methyl-[1,10-biphenyl]-3-sulfonamide
-
; 26% inhibition at 0.001 mM
3'-methoxy-N-(3-methoxyphenyl)-N-methylbiphenyl-4-carboxamide
-
; 35% inhibition at 0.001 mM
3'-methoxy-N-(4-methoxyphenyl)-N-methyl-[1,1'-biphenyl]-4-sulfonamide
-
; 22% inhibition at 0.001 mM
3,3',4,4'-tetrahydroxy-7,7'-dimethyl-5,5'-bis(1-methylethyl)-2H,2'H-8,8'-binaphtho[1,8-bc]furan-2,2'-dione
-
-
3,5,7,4'-tetrahydroxyflavone
-
IC50 between 0.001 and 0.005 mM, reduction of estra-4-en-3,17-dione
3,7-dihydroxyflavone
-
IC50 below 0.001 mM, oxidation of 17beta-hydroxyestra-4-en-3-one
3-(17beta-hydroxy-3-methoxy-estra-1,3,5(10)-trien-16beta-ylmethyl)-benzamide
-
0.01 mM, 90% inhibition, substrate: estrone
3-(17beta-hydroxy-estra-1,3,5(10)-trien-16beta-ylmethyl)-benzamide
-
0.01 mM, 79% inhibition, substrate: estrone
3-(2-furylmethyl)-8-hydroxy-2-(2-phenylethyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
-
33% inhibition at 100 nM, 78% inhibition at 0.001 mM
3-(3,17beta-dihydroxy-2-methoxy-estra-1,3,5(10)-trien-16beta-ylmethyl)-benzamide
-
0.01 mM, 81% inhibition, substrate: estrone
3-(3,17beta-dihydroxy-estra-1,3,5(10)-trien-16beta-ylmethyl)-benzamide
-
0.001 mM, 94% inhibition, substrate: estrone
3-(3-hydroxy-17-oxo-estra-1,3,5(10)-trien-16beta-ylmethyl)-benzamide
-
0.001 mM, 88% inhibition, substrate: estrone
3-(3-methoxy-17-oxo-estra-1,3,5(10)-trien-16beta-ylmethyl)-benzamide
-
0.01 mM, 76% inhibition, substrate: estrone
3-(6-hydroxy-2-naphthyl)benzoic acid
-
0.001 mM, 76% inhibition, substrate: estrone
3-(hydroxymethyl)-4-(phenylsulfanyl)-2,7,8,9,10,11-hexahydro[1]benzothieno[2',3':4,5]pyrimido[1,2-a]azepin-13(1H)-one
-
0.001 mM, 52% inhibition
3-([(16beta,17beta)-3,17-dihydroxyestra-1(10),2,4-trien-16-yl]methyl)benzamide
-
-
-
3-([(16beta,17beta)-3-(2-bromoethyl)-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl)benzamide
-
a potent and steroidal nonestrogenic inhibitor of 17beta-HSD1, inhibits the transformation of estrone into estradiol by 17beta-HSD1 in T-47D cells. The comppound does not inhibit enzymes 17beta-HSD2, 17beta-HSD7, 17beta-HSD12, and CYP3A4, and does not stimulate the proliferation of estrogen-sensitive MCF-7 cells. Kinetic and molecular modeling (docking) experiments show that compound is a competitive and irreversible inhibitor of 17beta-HSD1
-
3-acetyl-2-oxo-2H-chromen-7-yl trifluoromethanesulfonate
-
IC50 value of 360 nM against recombinant enzyme in bacterial homogenate
3-acetyl-7-(4-hydroxyphenyl)-2H-chromen-2-one
-
IC50 value of 270 nM against recombinant enzyme in bacterial homogenate, and high selectivity for isoform 17beta-HSD1 over 17beta-HSD2 and against the alpha and beta estrogen receptors
3-benzyl-2-(2-bromo-3,4,5-trimethoxyphenyl)-8-hydroxy[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
3-benzyl-8-hydroxy-2-(2-methylprop-1-en-1-yl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
-
82% inhibition at 100 nM, 97% inhibition at 0.001 mM
3-benzyl-8-hydroxy-2-(2-thienyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
-
83% inhibition at 100 nM, 89% inhibition at 0.001 mM
3-benzyl-8-hydroxy-2-(3-methoxyphenyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
-
89% inhibition at 100 nM, 95% inhibition at 0.001 mM
3-butyl-8-hydroxy-2-(3,4,5-trimethoxybenzyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
-
0.001 mM,k 95% inhibition
3-butyl-8-hydroxy-2-(3,4,5-trimethoxyphenyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
-
86% inhibition at 100 nM, 95% inhibition at 0.001 mM
3-hydroxy-1,3,5(10)-triene-[17,16-c]-(5'-carboxylic acid)-pyrazole
-
0.01 mM: 32% inhibition
3-hydroxy-1,3,5(10)-triene-[17,16-c]-(5'-hydroxymethyl)-pyrazole
-
0.01 mM: 94% inhibition, IC50: 0.00095 mM
3-hydroxy-1,3,5(10)-triene-[17,16-c]-[5'-(carboxylic acid ethyl ester)]-pyrazole
-
0.01 mM: 94% inhibition, IC50: 0.00185 mM
3-hydroxy-13alpha-D-secooxime
-
displays an outstanding cofactor dependence, i.e. more efficient inhibition in the presence of NADH than NADPH
3-hydroxy-13beta-D-secoalcohol
-
displays an outstanding cofactor dependence, i.e. more efficient inhibition in the presence of NADH than NADPH
-
3-hydroxy-2-methoxy-17-oxoestra-1(10),2,4-triene-16-carbonitrile
-
0.01 mM, 35% inhibition
3-hydroxy-7-(3-hydroxyphenyl)-N-methyl-2-naphthamide
-
18% inhibition at 0.001 mM
3-hydroxy-7-(3-hydroxyphenyl)-N-phenyl-2-naphthamide
-
62% inhibition at 0.001 mM
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-(1'-isobutyl)-pyrazole
-
0.01 mM: 77% inhibition
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-(1'-methoxyethyl)-pyrazole
-
0.01 mM: 95% inhibition, IC50: 0.00053 mM
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-(1'-methyl acetate)-pyrazole
-
0.01 mM: 95% inhibition, IC50: 0.00092 mM
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-(1'-methyl)-pyrazole
-
0.01 mM: 94% inhibition, IC50: 0.00275 mM
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-(1'-propionitrile)-pyrazole
-
0.01 mM: 95% inhibition, IC50: 0.00073 mM
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-(2'-isobutyl)-pyrazole
-
0.01 mM: 70% inhibition
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-(2'-methoxy-ethyl)-pyrazole
-
0.01 mM: 83% inhibition
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-(2'-methyl acetate)-pyrazole
-
0.01 mM: 79% inhibition
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-(2'-methyl)-pyrazole
-
0.01 mM: 43% inhibition
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-(5'-ethylme-thylcarbamoyl)-pyrazole
-
0.01 mM: 88% inhibition
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-(5'-isopropylcarbamoyl)-pyrazole
-
0.01 mM: 57% inhibition
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-(5'-methyl)-pyrazole
-
0.01 mM: 75% inhibition
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-(5'-methyl-carbamoyl)-pyrazole
-
0.01 mM: 62% inhibition
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-[5'-(1''-methylpiperazin-4''-ylmethyl)carbamoyl]-pyrazole
-
0.01 mM: 50% inhibition
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-[5'-(1'-methylpyrrol-2''-ylmethyl)carbamoyl]-pyrazole
-
0.01 mM: 89% inhibition, IC50: 0.0023 mM
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-[5'-(5''-methylpyrazin-2''-ylmethyl)carbamoyl]-pyrazole
-
0.01 mM: 80% inhibition
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-[5'-(pyridin-2''-ylmethyl)carbamoyl]-pyrazole
-
0.01 mM: 93% inhibition, IC50: 0.00088 mM
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-[5'-(pyridin-3''-ylethyl)carbamoyl]-pyrazole
-
0.01 mM: 99% inhibition, IC50: 0.0003 mM
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-[5'-(pyridin-3''-ylmethyl)carbamoyl]-pyrazole
-
0.01 mM: 92% inhibition, IC50: 0.00078 mM
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-[5'-(tetrahydrofuran-2''-ylmethyl)carbamoyl]-pyrazole
-
0.01 mM: 87% inhibition
3-hydroxy-N-(3'-hydroxy-[1,1'-biphenyl]-3-yl)-N-methylbenzenesulfonamide
-
17% inhibition at 0.001 mM; 88% inhibition at 0.001 mM
3-hydroxy-N-(3'-hydroxy-[1,1'-biphenyl]-4-yl)-N-methylbenzenesulfonamide
-
22% inhibition at 0.001 mM; 66% inhibition at 0.001 mM
3-hydroxy-N-(6-hydroxy-1,3-benzothiazol-2-yl)benzamide
-
modeling of binding to crystal structure shows five hydrogen bond interactions and a cation-pi-interaction
3-hydroxyestra-1,3,5(10),7-tetraen-17-one
-
IC50: 0.0019 mM, oxidation of estradiol
3-hydroxyflavone
-
IC50 below 0.001 mM, oxidation of 17beta-hydroxyestra-4-en-3-one; IC50 between 0.001 and 0.005 mM, reduction of estra-4-en-3,17-dione
3-methoxy-N-(3'-methoxy-[1,1'-biphenyl]-3-yl)-N-methylbenzenesulfonamide
-
14% inhibition at 0.001 mM; 68% inhibition at 0.001 mM
3-methoxy-N-(3'-methoxy-[1,10-biphenyl]-4-yl)-Nmethylbenzenesulfonamide
-
18% inhibition at 0.001 mM; 25% inhibition at 0.001 mM
3-phenoxybenzyl (2E)-3-(1,3-benzodioxol-5-yl)prop-2-enoate
-
14% inhibition at 0.006 mM
3-[(15beta)-3-hydroxy-17-oxoestra-1(10),2,4-trien-15-yl]-N-(4-methyl-1,3-thiazol-2-yl)propanamide
-
-
3-[(15beta)-3-methoxy-17-oxoestra-1(10),2,4-trien-15-yl]-N-(5-methyl-1,3-thiazol-2-yl)propanamide
-
-
3-[(4bS,6aS,6bR,10S,10aS,11aS,11bR)-9-hexyl-2,10a-dihydroxy-6a-methyl-8-oxo-4b,5,6,6a,6b,8,9,10,10a,11,11a,11b,12,13-tetradecahydronaphtho[20,10:4,5]indeno[2,1-][1,3]oxazin-10-yl]benzamide
-
-
3-[(4bS,6aS,6bR,10S,10aS,11aS,11bR)-9-octyl-2,10a-dihydroxy-6a-methyl-8-oxo-4b,5,6,6a,6b,8,9,10,10a,11,11a,11b,12,13-tetradecahydronaphtho[20,10:4,5]indeno[2,1-][1,3]oxazin-10-yl]benzamide
-
-
3-[(4bS,6aS,6bR,10S,11aR,11bR)-9-butyl-2-hydroxy-6a-methyl-8-oxo-4b,5,6,6a,6b,8,9,10,11a,11b,12,13-dodecahydronaphtho[20,10:4,5]indeno[2,1-e][1,3]oxazin-10-l]benzamide
-
-
3-[(4bS,6aS,6bR,10S,11aR,11bR)-9-ethyl-2-hydroxy-6a-methyl-8-oxo-4b,5,6,6a,6b,8,9,10,11a,11b,12,13-dodecahydronaphtho[20,10:4,5]indeno[2,1-e][1,3]oxazin-10-l]benzamide
-
-
3-[(4bS,6aS,6bR,10S,11aR,11bR)-9-hexyl-2-hydroxy-6a-methyl-8-oxo-4b,5,6,6a,6b,8,9,10,11a,11b,12,13-dodecahydronaphtho[20,10:4,5]indeno[2,1-e][1,3]oxazin-10-l]benzamide
-
-
3-[(4bS,6aS,6bR,10S,11aR,11bR)-9-octyl-2-hydroxy-6a-methyl-8-oxo-4b,5,6,6a,6b,8,9,10,11a,11b,12,13-dodecahydronaphtho[20,10:4,5]indeno[2,1-e][1,3]oxazin-10-l]benzamide
-
-
3-[(5-bromofuran-2-yl)methyl]-8-hydroxy-2-(3,4,5-trimethoxybenzyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
-
0.001 mM, 95% inhibition
3-[(5-bromofuran-2-yl)methyl]-8-hydroxy-2-(3,4,5-trimethoxyphenyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
-
94% inhibition at 100 nM, 99% inhibition at 0.001 mM
3-[(6aS)-2-hydroxy-6a-methyl-4b,6,6a,10,10a,10b,11,12-octahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazol-8(5H)-yl]propanenitrile
-
-
3-[(6aS,6bR,10S,10aS)-9-butyl-2,10a-dihydroxy-6a-methyl-8-oxo-4b,5,6,6a,6b,8,9,10,10a,11,11a,11b,12,13-tetradecahydronaphtho[2',1':4,5]indeno[2,1-e][1,3]oxazin-10-yl]benzamide
-
-
3-[(6aS,6bR,10S,10aS)-9-ethyl-2,10a-dihydroxy-6a-methyl-8-oxo-4b,5,6,6a,6b,8,9,10,10a,11,11a,11b,12,13-tetradecahydronaphtho[2',1':4,5]indeno[2,1-e][1,3]oxazin-10-yl]benzamide
-
-
3-[1-(4-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]-phenol
-
17beta-HSD1; substrate: estradiol-17beta, 17beta-HSD2
3-[2-(2-thienyl)pyridin-4-yl]phenol
-
0.001 mM, 10 min, 33% inhibition; 0.001 mM, 10 min, 62% inhibition
3-[2-(5-chloro-2-thienyl)pyridin-4-yl]phenol
-
0.001 mM, 10 min, 39% inhibition; 0.001 mM, 10 min, 63% inhibition
3-[2-hydroxy-6-(3-hydroxyphenyl)-1-naphthyl]-N-methylpropanamide
-
80% inhibition at 0.001 mM
3-[3-(4-hydroxyphenyl)isoxazol-5-yl]-phenol
-
17beta-HSD1; substrate: estradiol-17beta, 17beta-HSD2
3-[4-(4-hydroxyphenyl)-1,3-oxazol-2-yl]phenol
-
substrate: estradiol-17beta, 17beta-HSD2
3-[4-(4-hydroxyphenyl)-1H-1,2,3-triazol-1-yl]-phenol
-
17beta-HSD1; substrate: estradiol-17beta, 17beta-HSD2
3-[4-(5-chloro-2-thienyl)pyridin-2-yl]phenol
-
0.001 mM, 10 min, 25% inhibition; 0.001 mM, 10 min, 61% inhibition
3-[5-(4-hydroxyphenyl)-1,3-oxazol-2-yl]-phenol
-
substrate: estradiol-17beta, 17beta-HSD2, very good selectivity, high cell permeability and medium CaCo-2 permeability; very good selectivity, high cell permeability and medium CaCo-2 permeability, 17beta-HSD1
3-[5-(5-chloro-2-thienyl)pyridin-3-yl]phenol
-
0.001 mM, 10 min, 40% inhibition; 0.001 mM, 10 min, 46% inhibition
3-[6-(5-chloro-2-thienyl)pyridin-2-yl]phenol
-
0.001 mM, 10 min, 21% inhibition; 0.001 mM, 10 min, 40% inhibition
4'-(2-thienyl)biphenyl-3-ol
-
0.001 mM, 10 min, 22% inhibition; 0.001 mM, 10 min, 36% inhibition
4'-(3-thienyl)biphenyl-3-ol
-
0.001 mM, 10 min, 36% inhibition; 0.001 mM, 10 min, 41% inhibition
4'-(6-methoxypyridin-3-yl)biphenyl-3-ol
-
0.001 mM, 10 min, 35% inhibition; 0.001 mM, 10 min, 58% inhibition
4'-methoxy-N-(3-methoxyphenyl)-N-methyl-[1,1'-biphenyl]-4-sulfonamide
-
; 13% inhibition at 0.001 mM
4-(17beta-hydroxy-3-methoxy-estra-1,3,5(10)-trien-16beta-ylmethyl)-benzamide
-
0.01 mM, 38% inhibition, substrate: estrone
4-(3'-ethyl-4'-hydroxy-3-methyl-biphenyl)-4-oxo-N-pyridin-3-ylethyl-butyramide
-
15% inhibition at 0.001 mM
4-(3'-ethyl-4'-hydroxy-3-methyl-biphenyl)-4-oxo-N-pyridin-3-ylmethyl-butyramide
-
21% inhibition at 0.001 mM; 37°C, 0.001 mM, 21% inhibition, substrate: estrone,7beta-HSD type 1
4-(3'-ethyl-4'-hydroxy-biphenyl)-2,2-dimethyl-4-oxo-N-pyridin-3-ylethyl-butyramide
-
15% inhibition at 0.001 mM; 37°C, 0.001 mM, 15% inhibition, substrate: estrone, 7beta-HSD type 1
4-(3'-ethyl-4'-hydroxy-biphenyl)-2,2-dimethyl-4-oxo-N-pyridin-3-ylmethyl-butyramide
-
38% inhibition at 0.001 mM
4-(3'-ethyl-4'-hydroxy-biphenyl)-4-oxo-N-(2-hydroxyethyl)-butyramide
-
23% inhibition at 0.001 mM; 37°C, 0.001 mM, 23% inhibition, substrate: estrone, 7beta-HSD type 1
4-(3'-ethyl-4'-hydroxy-biphenyl)-4-oxo-N-pyridin-3-ylethyl-butyramide
-
17% inhibition at 0.001 mM; 37°C, 0.001 mM, 17% inhibition, substrate: estrone, 7beta-HSD type 1
4-(3'-ethyl-4'-hydroxy-biphenyl)-4-oxo-N-pyridin-3-ylmethyl-butyramide
-
24% inhibition at 0.001 mM; 37°C, 0.001 mM, 24% inhibition, substrate: estrone, 7beta-HSD type 1; 37°C, 0.01 mM, 12% inhibition, substrate: estradiol-17beta, 7beta-HSD type 2
4-(3'-ethyl-4'-methoxy-biphenyl)-2,2-dimethyl-4-oxo-N-pyridin-3-ylmethyl-butyramide
-
17% inhibition at 0.001 mM; 37°C, 0.001 mM, 17% inhibition, substrate: estrone, 7beta-HSD type 1
4-(3,17beta-dihydroxy-estra-1,3,5(10)-trien-16beta-ylmethyl)-benzamide
-
0.01 mM, 74% inhibition, substrate: estrone
4-(3-ethyl-4-hydroxy-3-methyl-biphenyl)-4-oxo-N-pyridin-3-ylethyl-butyramide
-
37°C, 0.001 mM, 15% inhibition, substrate: estrone, 7beta-HSD type 1
4-(3-ethyl-4-hydroxy-biphenyl)-2,2-dimethyl-4-oxo-N-pyridin-3-ylmethyl-butyramide
-
37°C, 0.001 mM, 38% inhibition, substrate: estrone, 7beta-HSD type 1
4-(3-Hydroxy-17-oxo-estra-1,3,5(10)-trien-16beta-ylmethyl)-benzamide
-
0.01 mM, 76% inhibition, substrate: estrone
4-(3-methoxy-17-oxo-estra-1,3,5(10)-trien-16beta-ylmethyl)-benzamide
-
0.01 mM, 56% inhibition, substrate: estrone
4-chloro-N-(3-hydroxy-4-methylphenyl)benzenesulfonamide
-
45% inhibition at 0.02 mM
4-cyanophenyl (2E)-3-(1,3-benzodioxol-5-yl)prop-2-enoate
-
76% inhibition at 0.006 mM
4-fluoro-3-hydroxy-N-(3'-hydroxybiphenyl-3-yl)-N-methylbenzenesulfonamide
-
80% inhibition at 0.001 mM; 96% inhibition at 0.001 mM
4-fluoro-3-methoxy-N-(3'-methoxybiphenyl-3-yl)-N-methylbenzenesulfonamide
-
; 17% inhibition at 0.001 mM
4-methyl-3-(trifluoromethyl)-5-[[4-(trifluoromethyl)benzyl]sulfanyl]-4H-1,2,4-triazole
-
-
4-methyl-5-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]-4H-1,2,4-triazole-3-thiol
-
-
4-methyl-N-[4-[4-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl]benzenesulfonamide
-
-
4-[(15beta)-3-hydroxy-17-oxo-2-propylestra-1(10),2,4-trien-15-yl]-N-[2-(7-methyl-1H-indol-2-yl)ethyl]butanamide
-
0.0001 mM, 69% inhibition
4-[(15beta)-3-hydroxy-17-oxoestra-1(10),2,4-trien-15-yl]-N-[2-(7-methyl-1H-indol-3-yl)ethyl]butanamide
-
-
5'-O-(10-[3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'alpha-yl]-decanoyl)adenosine
-
IC50: 140 nM
5'-O-(11-[3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'alpha-yl]-undecanoyl) adenosine
-
IC50: 310 nM
5'-O-(11-[3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'alpha/beta-yl]-undecanoyl)adenosine
-
IC50: 90 nM
5'-O-(11-[3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'beta-yl]-undecanoyl)adenosine
-
IC50: 120 nM
5'-O-(12-[3',17'beta-(dihydroxy)-1',3',5'(10')-estratrien-16'alpha-yl]-dodecanoyl)adenosine
-
IC50: 1000 nM
5'-O-(6-[3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'alpha/beta-yl]-hexanoyl)adenosine
-
IC50: 6900 nM
5'-O-(7-[3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'alpha-yl]-heptanoyl)adenosine
-
IC50: 430 nM
5'-O-(8-[3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'alpha-yl]-octanoyl)adenosine
-
IC50: 93 nM
5'-O-(9-[3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'alpha-yl]-nonanoyl)adenosine
-
IC50: 52 nM
5'-O-[9-[(16b,17b)-3,17-dihydroxyestra-1(10),2,4-trien-16-yl]nonanoyl]adenosine
-
-
5'-O-[9-[(16beta,17beta)-3,17-dihydroxyestra-1(10),2,4-trien-16-yl]nonanoyl]adenosine
-
EM-1745, bisubstrate inhibitor of 17beta-HSD1
5,7-dihydroxyflavone
-
IC50 below 0.001 mM, oxidation of 17beta-hydroxyestra-4-en-3-one
5-(3-ethyl-4-hydroxyphenyl)-indan-1-one
-
37°C, 0.01 mM, 48% inhibition, substrate: estradiol-17beta, 7beta-HSD type 2; 37°C, 0.01 mM, 86% inhibition, substrate: estrone, 7beta-HSD type 1; 86% inhibition at 0.001 mM
5-(3-fluoro-4-hydroxyphenyl)-indan-1-one
-
37°C, 0.01 mM, 24% inhibition, substrate: estradiol-17beta, 7beta-HSD type 2; 37°C, 0.01 mM, 75% inhibition, substrate: estrone, 7beta-HSD type 1; 75% inhibition at 0.001 mM
5-(3-fluoro-4-methoxyphenyl)-indan-1-one
-
37°C, 0.01 mM, 56% inhibition, substrate: estrone, 7beta-HSD type 1; 56% inhibition at 0.001 mM
5-(4-cyanophenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
-
; 48% inhibition
5-(4-hydroxyphenyl)-indan-1-one
-
37°C, 0.01 mM, 17% inhibition, substrate: estradiol-17beta, 7beta-HSD type 2; 37°C, 0.01 mM, 81% inhibition, substrate: estrone, 7beta-HSD type 1; 81% inhibition at 0.001 mM
5-(6-hydroxy-2-naphthyl)pyridin-3-ol
-
0.001 mM, 58% inhibition, substrate: estrone
5-benzyl-3-(furan-2-ylmethyl)-8-hydroxy-2-(2-phenylethyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
-
5% inhibition at 100 nM, 26% inhibition at 0.001 mM
5-bromo-3-(2-methylpropyl)-2-(3,4,5-trimethoxyphenyl)-6,7-dihydro[1]benzothieno[2,3-d]pyrimidine-4,8(3H,5H)-dione
-
0.001 mM, 54% inhibition
5-butyl-3-(furan-2-ylmethyl)-8-hydroxy-2-(2-phenylethyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
-
9% inhibition at 100 nM, 27% inhibition at 0.001 mM
5-hydroxyflavone
-
IC50 below 0.001 mM, oxidation of 17beta-hydroxyestra-4-en-3-one
5-methoxyflavone
-
IC50 between 0.001 and 0.005 mM, reduction of estra-4-en-3,17-dione
5-[(15beta)-3-methoxy-17-oxoestra-1(10),2,4-trien-15-yl]-N-(2-thiophen-2-ylethyl)pentanamide
-
-
6-(3-ethyl-4-hydroxyphenyl)-3,4-dihydro-2H-naphthalen-1-one
-
37°C, 0.01 mM, 51% inhibition, substrate: estrone, 7beta-HSD type 1; 51% inhibition at 0.001 mM
6-(3-ethyl-4-methoxyphenyl)-3,4-dihydro-2H-naphthalen-1-one
-
37°C, 0.01 mM, 71% inhibition, substrate: estrone, 7beta-HSD type 1; 71% inhibition at 0.001 mM
6-(3-hydroxyphenyl)-1-((4-methylphenyl)sulfonyl)-2-naphthol
-
75% inhibition at 0.001 mM
6-(3-hydroxyphenyl)-1-(morpholin-4-ylcarbonyl)-2-naphthol
-
62% inhibition at 0.001 mM
6-(3-hydroxyphenyl)-1-(piperazin-1-ylcarbonyl)-2-naphthol
-
45% inhibition at 0.001 mM
6-(3-hydroxyphenyl)-1-(piperidin-1-ylcarbonyl)-2-naphthol
-
73% inhibition at 0.001 mM
6-(3-hydroxyphenyl)-3,4-dihydronaphthalen-1(2H)-one
-
0.001 mM, 23% inhibition, substrate: estrone
6-(4-hydroxy-phenyl)-3,4-dihydro-2H-naphthalen-1-one
-
37°C, 0.01 mM, 89% inhibition, substrate: estrone, 7beta-HSD type 1; 89% inhibition at 0.001 mM
6-(hexylsulfanyl)estra-1(10),2,4-triene-3,17beta-diol
-
30% inhibition at 0.001 mM, reduction of estrone with NADH as cofactor
6-butyl-3-(furan-2-ylmethyl)-8-hydroxy-2-(2-phenylethyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
-
52% inhibition at 100 nM, 81% inhibition at 0.001 mM
6-[(1,3-benzothiazol-2-ylsulfanyl)methyl]-4-butoxy-2-(trifluoromethyl)quinoline
-
-
6-[4-(hydroxymethyl)phenyl]-2-naphthol
-
0.001 mM, 13% inhibition, substrate: estrone
8-((13S,16S,17S)-3,17-Dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-16-yl)-octanoic acid 5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester
-
IC50: 93 nM
8-hydroxy-3-(2-methylbutyl)-2-(3,4,5-trimethoxyphenyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
-
91% inhibition at 100 nM, 94% inhibition at 0.001 mM
8-hydroxy-3-(2-methylprop-1-en-1-yl)-2-(3,4,5-trimethoxyphenyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
-
0.001 mM, 97% inhibition
8-hydroxy-3-(2-methylpropyl)-2-(3,4,5-trimethoxyphenyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
-
93% inhibition at 100 nM, 98% inhibition at 0.001 mM
9-((13S,16S,17S)-3,17-Dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-16-yl)-nonanoic acid 5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester
-
IC50: 52 nM
9-(5-O-(9-[(16alpha,17alpha)-3,17-dihydroxyestra-1(10),2,4-trien-16-yl]nonanoyl)-alpha-L-arabinofuranosyl)-9H-purin-6-amine
-
shows key interactions with two different enzyme-binding sites, namely the substrate- and the cofactor-binding sites
Benzoic acid (13S,17R)-7-[10-(butyl-methyl-carbamoyl)-decyl]-17-ethynyl-17-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl ester
-
-
benzyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
-
60% inhibition at 0.006 mM
chrysoeriol
-
i.e. 4',5,7-trihydroxy-3'-methoxyflavone, 82% inhibition at 0.006 mM
cyclobutyl-(4-hydroxyphenyl)-methanone
-
weak inhibitor with 43.9% inhibition at 0.1 mM
cycloheptyl-(4-hydroxyphenyl)-methanone
-
weak inhibitor with 47.2% inhibition at 0.1 mM
cyclohexyl-(4-hydroxyphenyl)-methanone
-
weak inhibitor with 47.2% inhibition at 0.1 mM
cyclopentyl-(4-hydroxyphenyl)-methanone
-
weak inhibitor with 49.5% inhibition at 0.1 mM
diosmetin
-
i.e. 3',5,7-trihydroxy-4'-methoxyflavone, more than 90% inhibition at 0.006 mM
Dithiocarbamate
-
irreversible inhibition of 17beta-HSD1, preincubation with NADPH protects from inhibition
ethyl (2Z)-hydroxy[(16Z)-3-hydroxy-17-oxoestra-1(10),2,4-trien-16-ylidene]ethanoate
-
-
ethyl 4-[([4-[(15alpha)-3-hydroxy-17-oxoestra-1(10),2,4-trien-15-yl]butyl]carbamoyl)amino]benzoate
-
-
ethyl [(6aS)-2-hydroxy-6a-methyl-4b,5,6,6a,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazol-9-yl]acetate
-
-
gossypol
-
and derivatives of gossypol, competitive with respect to NAD+ in reverse reaction
medrogestone
-
although the inhibitor is not selective for the type 1 17beta-HSD, it is weakly active and has a mechanism that appears to be complex, it offers new possibilities in treatment of estrogen-dependent diseases
methyl 3-hydroxy-17-oxoestra-1(10),2,4-triene-16-carboxylate
-
0.01 mM, 69% inhibition
methyl [(6aS)-2-hydroxy-6a-methyl-4b,6,6a,10,10a,10b,11,12-octahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazol-8(5H)-yl]acetate
-
-
N'-[(2,4-difluorophenyl)sulfonyl]-2-pyridin-3-yl-4,5-dihydro-1,3-thiazole-4-carbohydrazide
-
-
N-(1,3-benzodioxol-5-ylmethyl)-5-[(15beta)-3-methoxy-17-oxoestra-1(10),2,4-trien-15-yl]pentanamide
-
-
N-(2,1,3-benzothiadiazol-4-yl)-2-[(4-hydroxypyrimidin-2-yl)sulfanyl]acetamide
-
92% inhibition at 0.02 mM
N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methyl-1,2,3-thiadiazole-5-carboxamide
-
-
N-(2,4-difluorobenzyl)-4-[(15beta)-3-hydroxy-17-oxoestra-1(10),2,4-trien-15-yl]butanamide
-
-
N-(2-hydroxyphenyl)-2-methyl-4-(trifluoromethyl)benzenesulfonamide
-
94% inhibition at 0.02 mM
N-(3-chloro-4-fluorophenyl)-4-fluorobenzenesulfonamide
-
45% inhibition at 0.02 mM
N-(3-chloro-4-hydroxyphenyl)-4-fluorobenzenesulfonamide
-
91% inhibition at 0.02 mM
N-(3-hydroxy-4-methylphenyl)-3-(trifluoromethyl)benzenesulfonamide
-
75% inhibition at 0.02 mM
N-(3-hydroxy-4-methylphenyl)-4-methoxybenzenesulfonamide
-
47% inhibition at 0.02 mM
N-(3-hydroxyphenyl)-2,4,5-trimethylbenzenesulfonamide
-
47% inhibition at 0.02 mM
N-(3-hydroxyphenyl)-3'-methoxy-N-methyl-[1,1'-biphenyl]-4-sulfonamide
-
; 18% inhibition at 0.001 mM
N-(3-hydroxyphenyl)-4-methoxy-2,5-dimethylbenzenesulfonamide
-
85% inhibition at 0.02 mM
N-(3-hydroxyphenyl)-4-methoxy-2-methyl-5,6,7,8-tetrahydronaphthalene-1-sulfonamide
-
-
N-(3-hydroxyphenyl)-N,3'-dimethyl-[1,1'-biphenyl]-4-sulfonamide
-
15% inhibition at 0.001 mM; 22% inhibition at 0.001 mM
N-(3-hydroxyphenyl)-N-methyl-4-(thiophen-2-yl)benzenesulfonamide
-
; 31% inhibition at 0.001 mM
N-(3-methoxyphenyl)-N-methyl-4-(thiophen-2-yl)benzenesulfonamide
-
; 32% inhibition at 0.001 mM
N-(3-methoxyphenyl)-N-methyl-4-(thiophen-3-yl)benzenesulfonamide
-
; 23% inhibition at 0.001 mM
N-(4-hydroxyphenyl)-2,4,6-trimethylbenzenesulfonamide
-
33% inhibition at 0.02 mM
N-(4-hydroxyphenyl)-N-methyl-4-(pyridin-3-yl)benzenesulfonamide
-
14% inhibition at 0.001 mM; 15% inhibition at 0.001 mM
N-(5-chloro-2-hydroxyphenyl)-4-fluoro-3-methylbenzenesulfonamide
-
44% inhibition at 0.02 mM
N-benzyl-4-[(15alpha)-3-hydroxy-17-oxoestra-1(10),2,4-trien-15-yl]butanamide
-
-
N-benzyl-4-[(15beta)-3-methoxy-17-oxoestra-1(10),2,4-trien-15-yl]-N-methylbutanamide
-
-
N-butyl-6-[[(6beta,17beta)-17-hydroxyestra-1(10),2,4-trien-6-yl]sulfanyl]-N-methylhexanamide
N-butyl-6-[[(6beta,17beta)-3,17-dihydroxyestra-1(10),2,4-trien-6-yl]oxy]-N-methylhexanamide
N-butyl-6-[[(6beta,17beta)-3,17-dihydroxyestra-1(10),2,4-trien-6-yl]sulfanyl]-N-methylhexanamide
N-butyl-7-[(6beta,17beta)-3,17-dihydroxyestra-1(10),2,4-trien-6-yl]-N-methylheptanamide
-
-
N-butyl-N-methyl-11-[16beta-(3-carbamoylbenzyl)-3,17-dihydroxy-estra-1,3,5(10)-trien-7alpha-yl]-undecanamide
-
0.01 mM, 61% inhibition, substrate: estrone
N-cyclohexyl-3-[(15beta)-3-hydroxy-17-oxoestra-1(10),2,4-trien-15-yl]propanimidamide
-
-
N-cyclohexyl-3-[(15beta)-3-methoxy-17-oxoestra-1(10),2,4-trien-15-yl]-N-methylpropanamide
-
-
N-cyclohexyl-3-[(15beta)-3-methoxy-17-oxoestra-1(10),2,4-trien-15-yl]propanamide
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N-cyclooctyl-3-[(15beta)-3-methoxy-17-oxoestra-1(10),2,4-trien-15-yl]propanamide
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N-ethylmaleimide
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irreversible inhibition; irreversible inhibition of 17beta-HSD1, preincubation with NADPH protects from inhibition
N-n-butyl-N-methyl-11-(16'a-bromo-3',17'b-dihydroxyestra-1',3',5'(10')-trien-7'a-yl)undecanamide
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N-n-butyl-N-methyl-11-(16'a-chloro-3',17'a-dihydroxyestra-1',3',5'(10')-trien-7'a-yl)undecanamide
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N-n-butyl-N-methyl-11-(16'a-chloro-3',17'b-dihydroxyestra-1',3',5'(10')-trien-7'a-yl)undecanamide
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N-n-butyl-N-methyl-11-(16'a-fluoro-3',17'a-dihydroxyestra-1',3',5'(10')-trien-7'a-yl)undecanamide
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N-n-butyl-N-methyl-11-(16'a-fluoro-3',17'b-dihydroxyestra-1',3',5'(10')-trien-7'a-yl)undecanamide
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N-n-butyl-N-methyl-11-(16'a-iodo-3',17'b-dihydroxyestra-1',3',5'(10')-trien-7'a-yl)undecanamide
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N-n-Butyl-N-methyl-11-(3,17b-dihydroxyestra-1,3,5(10)-trien-7a-yl)undecanamide
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N-[2-(4-hydroxyphenyl)ethyl]-3-[(15beta)-3-methoxy-17-oxoestra-1(10),2,4-trien-15-yl]propanamide
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N-[3-(6-hydroxy-2-naphthyl)phenyl]acetamide
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0.001 mM, 19% inhibition, substrate: estrone
N-[[(15alpha)-3-hydroxy-17-oxoestra-1(10),2,4-trien-15-yl]methyl]-N-methylthiophene-2-sulfonamide
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N-[[(15alpha)-3-hydroxy-17-oxoestra-1(10),2,4-trien-15-yl]methyl]benzenesulfonamide
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N-[[(15alpha)-3-hydroxy-17-oxoestra-1(10),2,4-trien-15-yl]methyl]thiophene-2-sulfonamide
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N-[[5-(2,5-dichlorophenyl)furan-2-yl]methyl]-2H-tetrazol-5-amine
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71% inhibition at 0.02 mM
naphthalen-2-yl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
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56% inhibition at 0.006 mM
nomegestrol acetate
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although the inhibitor is not selective for the type 1 17beta-HSD, it is weakly active and has a mechanism that appears to be complex, it offers new possibilities in treatment of estrogen-dependent diseases
palm oil carotenoids
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0.0001 mM, significant inhibition of the conversion of estradiol to estrone in the MCF-7 cell line
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phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
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35% inhibition at 0.006 mM
S-[(7R,10R,13S,17R)-10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,9,10,11,12,13,14,15,16-hexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-yl] ethanethioate
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0.003 mM, 57% inhibition, substrate: 4-androstene-3,17-dione
tibolone
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although the inhibitor is not selective for the type 1 17beta-HSD, it is weakly active and has a mechanism that appears to be complex, it offers new possibilities in treatment of estrogen-dependent diseases
[6-(3,4-dihydroxyphenyl)pyridin-2-yl]-(4-fluoro-3-hydroxyphenyl)methanone
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a potent nonsteroidal inhibitor, binding structure, overview
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(6aS)-2-hydroxy-6a-methyl-N-(2-pyridin-3-ylethyl)-4b,5,6,6a,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazole-9-carboxamide
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0.01 mM, 99% inhibition, IC50: 0.0003 mM
(6aS)-2-hydroxy-6a-methyl-N-(2-pyridin-3-ylethyl)-4b,5,6,6a,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazole-9-carboxamide
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(6aS)-2-hydroxy-6a-methyl-N-(pyridin-2-ylmethyl)-4b,5,6,6a,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazole-9-carboxamide
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0.01 mM, 93% inhibition, IC50: 0.00088 mM
(6aS)-2-hydroxy-6a-methyl-N-(pyridin-2-ylmethyl)-4b,5,6,6a,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazole-9-carboxamide
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(6aS)-2-hydroxy-6a-methyl-N-(pyridin-3-ylmethyl)-4b,5,6,6a,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazole-9-carboxamide
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0.01 mM, 92% inhibition, IC50: 0.00078 mM
(6aS)-2-hydroxy-6a-methyl-N-(pyridin-3-ylmethyl)-4b,5,6,6a,8,10,10a,10b,11,12-decahydronaphtho[2',1':4,5]indeno[1,2-c]pyrazole-9-carboxamide
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1-(3'-ethyl-4'-hydroxy-biphenyl-4-yl)-ethanone
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37°C, 0.01 mM, 51% inhibition, substrate: estradiol-17beta, 7beta-HSD type 2
1-(3'-ethyl-4'-hydroxy-biphenyl-4-yl)-ethanone
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37°C, 0.01 mM, 73% inhibition, substrate: estrone, 7beta-HSD type 1