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Information on EC 1.1.1.62 - 17beta-estradiol 17-dehydrogenase and Organism(s) Homo sapiens
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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
- progesterone
- estrone
- androgen
- testosterone
- 17beta-hsds
- ovarian
- aromatase
-
steroidogenic
- endometrium
- androstenedione
-
aldo-keto
-
steroidogenesis
- progestin
-
granulosa
- luteal
- akr1c2
-
alpha-hsd
-
sulfatase
- medicine
-
alpha-dihydroprogesterone
-
corpora
- pregnenolone
-
d-bifunctional
-
endometriotic
- hsd17b3
-
3beta-hydroxysteroid
-
luteolysis
- cyp19a1
-
alpha-hydroxyprogesterone
-
vlcfas
- cochliobolus
-
17-ketosteroids
- hsd3b2
-
3alpha-hydroxysteroid
- sult1e1
-
5alpha-reductase
- srd5a1
- 5alpha-dihydrotestosterone
- lunatus
- 3betahsd
- p450arom
-
alpha-diol
-
17-keto
-
c19-steroids
- diagnostics
- drug development
The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea
Synonyms
hsd17b4, hsd17b2, 20 alpha-hydroxysteroid dehydrogenase, 17betahsd, 17-hsd, akr1c4, hsd17b12, 17hsd1, 17beta-hsd type 1, 17betahsd1, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
17-HOR
-
-
-
-
17-HSD
-
-
-
-
17beta,20alpha-hydroxysteroid dehydrogenase
-
-
-
-
17beta-estradiol dehydrogenase
-
-
-
-
17beta-HSD
17beta-HSD1
17beta-HSD10
17beta-HSD2
17beta-hydroxysteroid dehydrogenase
17beta-hydroxysteroid dehydrogenase type 1
17beta-hydroxysteroid dehydrogenase type 10
17beta-hydroxysteroid dehydrogenase type 2
17beta-hydroxysteroid dehydrogenase type 7
17betaHSD1
20 alpha-hydroxysteroid dehydrogenase
-
-
-
-
20-alpha-HSD
-
-
-
-
20alpha-hydroxysteroid dehydrogenase
AKR1C3
dehydrogenase, estradiol 17beta-
-
-
-
-
E2DH
-
-
-
-
EDH
-
-
-
-
estradiol 17beta-dehydrogenase
-
-
-
-
estradiol dehydrogenase
-
-
-
-
estrogen 17-oxidoreductase
-
-
-
-
HSD17B1
Ke6 protein
-
-
-
-
microsomal 17-beta-hydroxysteroid dehydrogenase
-
-
-
-
oestradiol-17beta hydroxysteroid dehydrogenase
-
-
-
-
placental 17-beta-hydroxysteroid dehydrogenase
-
-
-
-
PRAP
-
-
-
-
PRL receptor associated protein
-
-
-
-
testicular 17-beta-hydroxysteroid dehydrogenase
-
-
-
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type 1 17beta-hydroxysteroid dehydrogenase
type 2 3alpha-hydroxysteroid dehydrogenase/type 5 17beta-hydroxysteroid dehydrogenase
-
additional information
17beta-HSD
-
-
-
-
17beta-HSD1
-
-
17beta-HSD1
-
17beta-hydroxysteroid dehydrogenase
-
-
-
-
17beta-hydroxysteroid dehydrogenase type 1
-
-
17beta-hydroxysteroid dehydrogenase type 1
-
20alpha-hydroxysteroid dehydrogenase
-
-
-
-
additional information
-
17beta-HSDs belong to the aldo-keto reductase family or the short-chain dehydrogenase family, overview
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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+
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
-
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
-
17beta-estradiol + NAD(P)+ = estrone + NAD(P)H + H+
active site structure of isozymes 17beta-HSD1 and 17beta-HSD14
-
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
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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)+.
CAS REGISTRY NUMBER
COMMENTARY
9028-61-9
-
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+
-
-
-
-
?
1,4-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+
-
-
-
-
?
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-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-androstane-3alpha,17beta-diol + NAD+
androsterone + NADH + H+
-
-
-
?
5alpha-dihydrotestosterone + NAD+
5alpha-androstan-3,17-dione + NADH + H+
-
3.2% of the activity with estradiol
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstane-3beta,17beta-diol + 5alpha-androstane-3,17-dione + NADP+
-
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
? + NADP+
kinetics demonstrates positive cooperativity
-
-
?
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+
-
-
-
-
?
androstendiol + NAD(P)+
dehydroepiandrosterone + NAD(P)H + H+
-
-
-
?
androsterone + NADH + H+
5alpha-androstane-3alpha,17beta-diol + NAD+
-
-
-
?
dehydroepiandrosterone + NAD(P)H
androst-5-ene-3beta,17beta-diol + NAD(P)+
-
-
-
?
dehydroepiandrosterone + NAD(P)H + H+
androstendiol + NAD(P)+
-
-
-
?
dehydroepiandrosterone + NADPH + H+
5-androstene-3beta,17beta-diol + NADP+
-
-
-
?
dehydroepiandrosterone + NADPH + H+
androstenediol + NADP+
-
-
-
?
dihydrotestosterone + NAD(P)H + H+
androstane-3beta,17beta-diol + NAD(P)+
-
-
-
-
?
DL-6-methoxy-3-deoxy-equilenin + NADH + H+
17beta-hydroxy-DL-6-methoxy-3-deoxyequilenin + NAD+
-
-
-
-
?
estradiol + NADP+
estrone + NADPH
-
the equilibrium state is 92% estradiol to 8% estrone
-
-
?
estrogenic estrone + NAD(P)H + H+
17beta-estradiol + NAD(P)+
the product 17beta-estradiol plays a central role in the etiology of estrogen dependent diseases
-
-
?
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
-
-
?
testosterone + NAD+
4-androstene-3,17-dione + NADH + H+
-
2.4% of the activity with estradiol
-
-
?
20alpha-hydroxy-4-pregnen-3-one + NADP+
4-pregnen-3,20-dione + NADPH
-
low activity
-
-
?
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
-
-
?
dihydrotestosterone + NADPH + H+
5alpha-androstane-3beta,17beta-diol + NADP+
-
-
-
?
dihydrotestosterone + NADPH + H+
5alpha-androstane-3beta,17beta-diol + NADP+
-
-
-
?
dihydrotestosterone + NADPH + H+
5alpha-androstane-3beta,17beta-diol + NADP+
the enzyme show positive cooperativity
-
-
?
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
-
-
-
-
?
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 + 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 + 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
-
-
?
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 + 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 + H+
17beta-estradiol + NAD(P)+
steroid hormone pathway
-
-
?
estrone + NADPH + H+
17beta-estradiol + NADP+
most active enzyme in regards to 17beta-estradiol production
-
-
?
estrone + NADPH + H+
17beta-estradiol + NADP+
the enzyme show positive cooperativity
-
-
?
estrone + NADPH + H+
estradiol + NADP+
kinetics demonstrates positive cooperativity
-
-
?
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
-
-
?
testosterone + NADP+
4-androstene-3,17-dione + NADPH + H+
-
-
-
-
?
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
-
-
?
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
-
-
?
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
-
-
?
5alpha-androstane-3alpha,17beta-diol + NAD+
androsterone + NADH + H+
-
-
-
?
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
-
-
?
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
-
-
?
estrogenic estrone + NAD(P)H + H+
17beta-estradiol + NAD(P)+
the product 17beta-estradiol plays a central role in the etiology of estrogen dependent diseases
-
-
?
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
-
-
?
estrone + NADPH + H+
17beta-estradiol + NAD(P)+
steroid hormone pathway
-
-
?
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
-
-
?
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
-
-
?
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 + 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 + 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 + H+
17beta-estradiol + NADP+
most active enzyme in regards to 17beta-estradiol production
-
-
?
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+
-
final step in synthesis of estradiol
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NAD+
-
cofactor
NADPH
-
-
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
(16alpa,17beta)-16-(3-bromopropyl)estra-1(10),2,4-triene-3,17-diol
EM-251
(16beta)-3-hydroxy-16-methyl-17-oxoestra-1(10),2,4-triene-16-carbonitrile
-
(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
-
(4aR,6aS,7S)-7-[heptyl(methyl)amino]-1,4a,6a-trimethylhexadecahydro-2H-indeno[5,4-f]quinolin-2-one
-
(4aR,6aS,7S)-7-[heptyl(methyl)amino]-4a,6a-dimethylhexadecahydro-2H-indeno[5,4-f]quinolin-2-one
-
(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
-
-
([4-[(3-methoxyphenyl)methyl]piperazin-1-yl]methyl)-17alpha-methylandrostane-3alpha,17beta-diol
0.1 mM, 21.9% inhibition in the reaction with allopregnanolone. 0.3 mM, 22.6% inhibition in the reaction with 17beta-estradiol
([4-[(3-methoxyphenyl)methyl]piperazin-1-yl]methyl)-17alpha-pregn-20-yne-3alpha,17-diol
0.1 mM, 20.0% inhibition in the reaction with allopregnanolone. 0.3 mM, 44.5% inhibition in the reaction with 17beta-estradiol
1-(4'-hydroxy-2'-methyl-biphenyl-4-yl)-ethanone
89% inhibition at 0.001 mM
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-(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
17,17-difluoro-3beta-([4-[(3-methoxyphenyl)methyl]piperazin-1-yl]methyl)androstan-3alpha-ol
0.1 mM, 38.6% inhibition in the reaction with allopregnanolone. 0.3 mM, 13.3% inhibition in the reaction with 17beta-estradiol
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-(3-hydroxyphenyl)quinolin-6-ol
0.001 mM, 63% inhibition, substrate: estrone
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-hydroxy-N,6-bis(3-hydroxyphenyl)-1-naphthamide
70% 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-hydroxyphenyl)-N-methylbiphenyl-3-carboxamide
35% inhibition
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-methoxybenzyl)-N-methylbiphenyl-3-carboxamide
11% inhibition
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-(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-hydroxyphenyl)quinolin-7-ol
0.001 mM, 57% 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)-1-naphthonitrile
99% inhibition at 0.001 mM
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-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
3-[[(16beta,17beta)-3-(2-bromoethyl)-17-hydroxyestra-1,3,5(10)-trien-16-yl]methyl] benzamide
irreversible inhibitor
3alpha-hydroxy-3beta-([4-[(2-methoxy-4-methylphenyl)methyl]piperazin-1-yl]methyl)-androstan-17-one
-
-
3alpha-hydroxy-3beta-([4-[(3-methoxy-4-methylphenyl)methyl]piperazin-1-yl]methyl)-androstan-17-one
-
-
3alpha-hydroxy-3beta-([4-[(3-methoxy-4-methylphenyl)methyl]piperazin-1-yl]methyl)androstan-17-one
0.1 mM, 12.5% inhibition in the reaction with allopregnanolone. 0.3 mM, 31.0% inhibition in the reaction with 17beta-estradiol
3alpha-hydroxy-3beta-([4-[(3-methoxyphenyl)methyl]piperazin-1-yl]methyl)-16,16-dimethylandrostan-17-one
0.1 mM, 11.1% inhibition in the reaction with allopregnanolone. 0.3 mM, 24.6% inhibition in the reaction with 17beta-estradiol
3alpha-hydroxy-3beta-([4-[(3-methoxyphenyl)methyl]piperazin-1-yl]methyl)-androstan-17-one
-
-
3alpha-hydroxy-3beta-([4-[(3-methoxyphenyl)methyl]piperazin-1-yl]methyl)androstan-17-one
0.1 mM, 14.7% inhibition in the reaction with allopregnanolone. 0.3 mM, 30.0% inhibition in the reaction with 17beta-estradiol
3alpha-hydroxy-3beta-([4-[(quinolin-3-yl)methyl]piperazin-1-yl]methyl)-androstan-17-one
-
-
3alpha-hydroxy-3beta-([4-[(quinolin-3-yl)methyl]piperazin-1-yl]methyl)androstan-17-one
0.1 mM, 15.2% inhibition in the reaction with allopregnanolone. 0.3 mM, 36.1% inhibition in the reaction with 17beta-estradiol
3alpha-hydroxy-3beta-[(4-[[3-methoxy-4-(trifluoromethyl)phenyl]methyl]piperazin-1-yl)methyl]-androstan-17-one
-
-
3beta-([4-[(3-methoxyphenyl)methyl]piperazin-1-yl]methyl)androstane-3alpha,17alpha-diol
0.1 mM, 41.7% inhibition in the reaction with allopregnanolone. 0.3 mM, 31.7% inhibition in the reaction with 17beta-estradiol
3beta-([4-[(3-methoxyphenyl)methyl]piperazin-1-yl]methyl)androstane-3alpha,17beta-diol
0.1 mM, no inhibition in the reaction with allopregnanolone. 0.3 mM, 13.7% inhibition in the reaction with 17beta-estradiol
3beta-[(4-[[3-methoxy-4-(trifluoromethyl)phenyl]methyl]piperazin-1-yl)methyl]-17alpha-pregn-20-yne-3alpha,17-diol
-
metabolic stability and selectivity of inhibition for 17beta-HSD10 over 17beta-HSD3
-
3beta-[(4-[[3-methoxy-4-(trifluoromethyl)phenyl]methyl]piperazin-1-yl)methyl]-androstane-3alpha,17alpha-diol
-
metabolic stability and selectivity of inhibition for 17beta-HSD10 over 17beta-HSD3
3beta-[[4-(4-benzoylbenzoyl)piperazin-1-yl]methyl]-3alpha-hydroxyandrostan-17-one
0.1 mM, 8.0% inhibition in the reaction with allopregnanolone. 0.3 mM, 58.8% inhibition in the reaction with 17beta-estradiol
3beta-[[4-([1,1'-biphenyl]-4-carbonyl)piperazin-1-yl]methyl]-3?-hydroxyandrostan-17-one
0.1 mM, 19.3% inhibition in the reaction with allopregnanolone. 0.3 mM, 29.4% inhibition in the reaction with 17beta-estradiol
3beta-[[4-([1,1'-biphenyl]-4-carbonyl)piperazin-1-yl]methyl]-3alpha-hydroxyandrostan-17-one
-
-
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-(4-[[3alpha-hydroxy-17-oxoandrostan-3beta-yl]methyl]piperazine-1-carbonyl)benzonitrile
-
-
4-(dimethylsulfamoyl)-N-(4-[[3alpha-hydroxy-17-oxoandrostan-beta?-yl]methyl]piperazin-1-yl)benzene-1-carbothioamide
0.1 mM, 13.3% inhibition in the reaction with allopregnanolone. 0.3 mM, 0.3% inhibition in the reaction with 17beta-estradiol
4-(octanoylamino)phenyl (2E)-3-phenylprop-2-enoate
15% inhibition at 0.006 mM
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-propanoylphenyl 3-(acetylamino)benzenesulfonate
67% inhibition at 0.02 mM
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
-
4-[[3alpha-hydroxy-17-oxoandrostan-3beta-yl]methyl]-N-[[3-(trifluoromethyl)phenyl]methyl]piperazine-1-carbothioamide
-
-
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-(2-fluoro-3-methoxyphenyl)-N-(3-hydroxybenzyl)-N-methylthiophene-2-carboxamide
-
5-(2-fluoro-3-methoxyphenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
-
5-(2-fluoro-3-methoxyphenyl)-N-methyl-N-(3-methylphenyl)thiophene-2-carboxamide
-
5-(2-hydroxyphenyl)-N-(3-hydroxyphenyl)-N-methylthiophene-2-carboxamide
-
5-(2-methoxyphenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
-
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-[(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-(phenylsulfonyl)-2-naphthol
33% 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)-1-naphthol
0.001 mM, 23% inhibition, substrate: estrone
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-(4-hydroxyphenyl)-1-naphthol
0.001 mM, 55% inhibition, substrate: estrone
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
7-(3-hydroxyphenyl)-2-naphthol
0.001 mM, 62% inhibition, substrate: estrone
7-hydroxy-3-(3-hydroxyphenyl)-1-naphthonitrile
53% inhibition at 0.001 mM
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
cholest-4-ene-3,6-dione
cholest-4-ene-3,6-dione arrests the enzymatic conversion of estrone to 17-beta estradiol, by inhibiting AKR1C3 in intact MCF-7 cells. It can be used as a molecular scaffold for further development of l small-molecules with better specificity towards AKR1C3; the inhibitor occupies the binding region of AKR1C3 with almost similar orientation as indomethacin, thereby acting as an antagonistic agent for AKR1C3. It induces inhibition of AKR1C3 and cell death in MCF-7 cells. IT can be used as a molecular scaffold for development of novel small-molecules with better specificity towards AKR1C3
chrysoeriol
i.e. 4',5,7-trihydroxy-3'-methoxyflavone, 82% inhibition at 0.006 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
-
myricetin
i.e. 3,3',4',5',5,7-hexahydroxyflavone, 52% inhibition at 0.006 mM
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-hydroxybenzyl)-5-(3-hydroxyphenyl)-N-methylthiophene-2-carboxamide
-
N-(3-hydroxybenzyl)-5-(4-hydroxyphenyl)-N-methylthiophene-2-carboxamide
-
N-(3-hydroxybenzyl)-5-(4-methoxyphenyl)-N-methylthiophene-2-carboxamide
-
N-(3-hydroxybenzyl)-N-methyl-5-(3-methylphenyl)thiophene-2-carboxamide
-
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-methoxybenzyl)-5-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
-
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-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)-4-methoxybenzenesulfonamide
-
N-(4-hydroxyphenyl)-2,4,6-trimethylbenzenesulfonamide
33% inhibition at 0.02 mM
N-(4-hydroxyphenyl)-2,5-dimethylbenzenesulfonamide
39% 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-(4-[[3alpha-hydroxy-17-oxoandrostan-3beta-yl]methyl]piperazin-1-yl)[3-(trifluoromethyl)phenyl]ethanethioamide
0.1 mM, 34.2% inhibition in the reaction with allopregnanolone. 0.3 mM, 8.5% inhibition in the reaction with 17beta-estradiol
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-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
-
N-cyclooctyl-3-[(15beta)-3-methoxy-17-oxoestra-1(10),2,4-trien-15-yl]propanamide
-
N-decyl-N-[(4aR,6aS,7S)-1,4a,6a-trimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinolin-7-yl]formamide
-
N-decyl-N-[(4aR,6aS,7S)-4a,6a-dimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinolin-7-yl]formamide
-
N-ethyl-4-[[3alpha-hydroxy-17-oxoandrostan-3beta-yl]methyl]-N-methylpiperazine-1-sulfonamide
N-ethylmaleimide
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
-
-
N-n-butyl-N-methyl-11-(16'a-chloro-3',17'a-dihydroxyestra-1',3',5'(10')-trien-7'a-yl)undecanamide
-
-
N-n-butyl-N-methyl-11-(16'a-chloro-3',17'b-dihydroxyestra-1',3',5'(10')-trien-7'a-yl)undecanamide
-
-
N-n-butyl-N-methyl-11-(16'a-fluoro-3',17'a-dihydroxyestra-1',3',5'(10')-trien-7'a-yl)undecanamide
-
-
N-n-butyl-N-methyl-11-(16'a-fluoro-3',17'b-dihydroxyestra-1',3',5'(10')-trien-7'a-yl)undecanamide
-
-
N-n-butyl-N-methyl-11-(16'a-iodo-3',17'b-dihydroxyestra-1',3',5'(10')-trien-7'a-yl)undecanamide
-
-
N-n-Butyl-N-methyl-11-(3,17b-dihydroxyestra-1,3,5(10)-trien-7a-yl)undecanamide
-
-
N-nonyl-N-[(4aR,6aS,7S)-1,4a,6a-trimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinolin-7-yl]formamide
-
N-[2-(4-hydroxyphenyl)ethyl]-3-[(15beta)-3-methoxy-17-oxoestra-1(10),2,4-trien-15-yl]propanamide
-
N-[3-(6-hydroxy-2-naphthyl)phenyl]acetamide
0.001 mM, 19% inhibition, substrate: estrone
N-[4-(dimethylsulfamoyl)phenyl]-4-[[3alpha-hydroxy-17-oxoandrostan-3beta-yl]methyl]piperazine-1-carbothioamide
-
-
N-[[(15alpha)-3-hydroxy-17-oxoestra-1(10),2,4-trien-15-yl]methyl]-N-methylthiophene-2-sulfonamide
-
N-[[(15alpha)-3-hydroxy-17-oxoestra-1(10),2,4-trien-15-yl]methyl]benzenesulfonamide
-
N-[[(15alpha)-3-hydroxy-17-oxoestra-1(10),2,4-trien-15-yl]methyl]thiophene-2-sulfonamide
-
N-[[5-(2,5-dichlorophenyl)furan-2-yl]methyl]-2H-tetrazol-5-amine
71% inhibition at 0.02 mM
naphthalen-2-yl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
56% inhibition at 0.006 mM
nomegestrol acetate
-
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
-
0.0001 mM, significant inhibition of the conversion of estradiol to estrone in the MCF-7 cell line
-
phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
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
-
0.003 mM, 57% inhibition, substrate: 4-androstene-3,17-dione
scutellarein
i.e. 4',5,6,7-tetrahydroxyflavone, 88% inhibition at 0.006 mM
tibolone
-
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
a potent nonsteroidal inhibitor, binding structure, overview
(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
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
-
(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
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
-
(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
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
-
1-(3'-ethyl-4'-hydroxy-biphenyl-4-yl)-ethanone
37°C, 0.01 mM, 51% inhibition, substrate: estradiol-17beta, 7beta-HSD type 2
1-(3'-ethyl-4'-hydroxy-biphenyl-4-yl)-ethanone
37°C, 0.01 mM, 73% inhibition, substrate: estrone, 7beta-HSD type 1
1-(3'-ethyl-4'-hydroxy-biphenyl-4-yl)-ethanone
73% inhibition at 0.001 mM
1-(3-ethyl-4'-hydroxy-biphenyl-4-yl)-ethanone
37°C, 0.01 mM, 71% inhibition, substrate: estrone, 7beta-HSD type 1
3'-hydroxy-N-(3-hydroxyphenyl)-N-methylbiphenyl-4-carboxamide
13% inhibition at 0.001 mM
3-benzyl-2-(2-bromo-3,4,5-trimethoxyphenyl)-8-hydroxy[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
87% inhibition at 100 nM, 95% inhibition at 0.001 mM. IC50: 5 nM
3-benzyl-2-(2-bromo-3,4,5-trimethoxyphenyl)-8-hydroxy[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
0.001 mM, 95% inhibition
3-benzyl-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. IC50: 5 nM
3-benzyl-8-hydroxy-2-(3,4,5-trimethoxyphenyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
0.001 mM, 99% inhibition
3beta-[[4-(3,5-dimethylbenzoyl)piperazin-1-yl]methyl]-3alpha-hydroxyandrostan-17-one
0.1 mM, 1.5% inhibition in the reaction with allopregnanolone
3beta-[[4-(3,5-dimethylbenzoyl)piperazin-1-yl]methyl]-3alpha-hydroxyandrostan-17-one
-
-
3beta-[[4-(3-acetylbenzoyl)piperazin-1-yl]methyl]-3alpha-hydroxyandrostan-17-one
0.1 mM, 5.0% inhibition in the reaction with allopregnanolone
3beta-[[4-(3-acetylbenzoyl)piperazin-1-yl]methyl]-3alpha-hydroxyandrostan-17-one
-
-
6-(3-hydroxyphenyl)-2-naphthol
0.0001 mM, 91% inhibition, substrate: estrone
EM-1745
strong competitive inhibitor, inhibition reversible, 50% inhibition at 52 nM
N-butyl-6-[[(6beta,17beta)-17-hydroxyestra-1(10),2,4-trien-6-yl]sulfanyl]-N-methylhexanamide
-
38% inhibition at 0.001 mM, reduction of estrone with NADH as cofactor
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
-
73% inhibition at 0.001 mM, IC50: 0.0008 mM, reduction of estrone with NADH as cofactor
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
-
92% inhibition at 0.001 mM, IC50: 0.00016 mM, reduction of estrone with NADH as cofactor
N-butyl-6-[[(6beta,17beta)-3,17-dihydroxyestra-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]sulfanyl]-N-methylhexanamide
EM-678
N-ethyl-4-[[3alpha-hydroxy-17-oxoandrostan-3beta-yl]methyl]-N-methylpiperazine-1-sulfonamide
0.1 mM, no inhibition in the reaction with allopregnanolone. 0.3 mM, 10.2% inhibition in the reaction with 17beta-estradiol
N-ethyl-4-[[3alpha-hydroxy-17-oxoandrostan-3beta-yl]methyl]-N-methylpiperazine-1-sulfonamide
-
-
additional information
-
activity with estradiol-17beta is not inhibited by high concentrations of C19-steroids or C21-steroids
-
additional information
-
steroids which inhibit conversion of estrone to estradiol in normal breast tissue fail to do so when added to growing monolayers in the breast cancer cell lines T47D and MCF-7
-
additional information
-
modulation of local synthesis of estradiol is one potential mechanism through which genistein, enterolactone and enterodiol may protect against breast cancer
-
additional information
-
not inhibited by 1-(4'-methoxy-biphenyl-4-yl)-ethanone, 1-(4-benzo[1,3]dioxol-5-yl-phenyl)-ethanone, 1-(3'-ethyl-4'-methoxy-biphenyl-4-yl)-ethanone, 1-(4'-methoxy-2'-methyl-biphenyl-4-yl)-ethanone, 1-(4'-methoxy-2-methyl-biphenyl-4-yl)-ethanone, 1-(4'-hydroxy-2-methyl-biphenyl-4-yl)-ethanone, 1-(7-methoxy-9H-fluoren-2-yl)-ethanone, 5-(4-methoxyphenyl)-indan-1-one, 5-(3-ethyl-4-methoxyphenyl)-indan-1-one, 2,3-dihydro-5-phenylinden-1-one, 6-(4-methoxy-phenyl)-3,4-dihydro-2H-naphthalen-1-one, 4-(3'-ethyl-4'-hydroxy-biphenyl)-4-oxo-N-pyridin-2-ylmethyl-butyramide, 2-[5-(3-ethyl-4-hydroxyphenyl)-1-oxo-indan-2-yl]-N-pyridin-2-ylmethyl-acetamide, and 2-[5-(3-ethyl-4-hydroxyphenyl)-1-oxo-indan-2-yl]-N-(5-methyl-pyrazin-2-ylmethyl)-acetamide
-
additional information
not inhibited by 1-(4'-methoxy-biphenyl-4-yl)-ethanone, 1-(4-benzo[1,3]dioxol-5-yl-phenyl)-ethanone, 1-(3'-ethyl-4'-methoxy-biphenyl-4-yl)-ethanone, 1-(4'-methoxy-2'-methyl-biphenyl-4-yl)-ethanone, 1-(4'-methoxy-2-methyl-biphenyl-4-yl)-ethanone, 1-(4'-hydroxy-2-methyl-biphenyl-4-yl)-ethanone, 1-(7-methoxy-9H-fluoren-2-yl)-ethanone, 5-(4-methoxyphenyl)-indan-1-one, 5-(3-ethyl-4-methoxyphenyl)-indan-1-one, 2,3-dihydro-5-phenylinden-1-one, 6-(4-methoxy-phenyl)-3,4-dihydro-2H-naphthalen-1-one, 4-(3'-ethyl-4'-hydroxy-biphenyl)-4-oxo-N-pyridin-2-ylmethyl-butyramide, 2-[5-(3-ethyl-4-hydroxyphenyl)-1-oxo-indan-2-yl]-N-pyridin-2-ylmethyl-acetamide, and 2-[5-(3-ethyl-4-hydroxyphenyl)-1-oxo-indan-2-yl]-N-(5-methyl-pyrazin-2-ylmethyl)-acetamide
-
additional information
not inhibited by 2-hydroxy-6-(3-hydroxyphenyl)-N-pyridin-2-yl-1-naphthamide and 2-hydroxy-6-(3-hydroxyphenyl)-N-(pyrimidin-2-yl)-1-naphthamide
-
additional information
-
not inhibited by 3,3'-(1-methyl-1H-1,2,4-triazole-3,5-diyl)diphenol, 3-[5-(4-hydroxyphenyl)-1-methyl-1H-1,2,4-triazol-3-yl]phenol, 3-[3-(4-hydroxyphenyl)-1-methyl-1H-1,2,4-triazol-5-yl]phenol, 3,3'-(1-phenyl-1H-1,2,4-triazole-3,5-diyl)diphenol, 3-[5-(4-hydroxyphenyl)-1-phenyl-1H-1,2,4-triazol-3-yl]phenol, and 3-[3-(4-hydroxyphenyl)-1-phenyl-1H-1,2,4-triazol-5-yl]phenol
-
additional information
synthesis, physicochemical properties, and biological evaluation of novel N-methylsulfonamide and retro-N-methylsulfonamide derivatives as 17beta-HSD2 inhibitors showing high potency with a good selectivity toward 17beta-HSD1 (the isoenzyme responsible of the reverse reaction), and a likely good in vitro ADME profile, overview; synthesis, physicochemical properties, and biological evaluation of novel N-methylsulfonamide and retro-N-methylsulfonamide derivatives as 17beta-HSD2 (the isoenzyme responsible of the reverse reaction) inhibitors showing high potency with a good selectivity toward 17beta-HSD1, and a likely good in vitro ADME profile, overview. No inhibition by 9b, 9c, 9e, 9f, 9g, 9h, 9k, 9o, and 10a
-
additional information
synthesis, physicochemical properties, and biological evaluation of novel N-methylsulfonamide and retro-N-methylsulfonamide derivatives as 17beta-HSD2 inhibitors showing high potency with a good selectivity toward 17beta-HSD1 (the isoenzyme responsible of the reverse reaction), and a likely good in vitro ADME profile, overview; synthesis, physicochemical properties, and biological evaluation of novel N-methylsulfonamide and retro-N-methylsulfonamide derivatives as 17beta-HSD2 (the isoenzyme responsible of the reverse reaction) inhibitors showing high potency with a good selectivity toward 17beta-HSD1, and a likely good in vitro ADME profile, overview. No inhibition by 9b, 9c, 9e, 9f, 9g, 9h, 9k, 9o, and 10a
-
additional information
fused 16beta,17beta-oxazinone-estradiol derivatives act as a family of non-estrogenic 17beta-hydroxysteroid dehydrogenase type 1 inhibitors, activities in T-47D breast cancer cells, molecular docking, structure-activity relationships, overview
-
additional information
the enzyme shows sensitivity towards sulfhydryl modifying chemicals. 17beta-HSD1 is irreversibly inhibited by the sulfhydrylmodifying agents N-ethylmaleimide and dithiocarbamates. Preincubation with increasing concentrations of NADPH protects 17beta-HSD1 from inhibition by these chemicals
-
additional information
inhibitory effects of 13-epimeric estrones, D-secooxime and D-secoalcohol estrone compounds on placental enzyme 17beta-HSD1
-
additional information
-
design of a series of estradiol-derivatives from potent inhibitor 16beta-(m-carbamoylbenzyl)-E2 to eliminate estrogenic activity, evaluation as 17beta-HSD1 inhibitors, and their proliferative (estrogenic) activity on estrogen-sensitive cells, structure-activity relationship study, overview
-
additional information
ligand-based pharmacophore models for 17beta-HSD2 inhibitors are constructed and employed for virtual screening, structure-activity relationships, overview. No inhibition by 18, 25, 26, 27, 28, 33, 34, 36, 37, 38, 41, 42, 43, 44, 45, and 47
-
additional information
design of inhibitors displaying h17beta-HSD2 inhibitory activity and selectivity toward h17beta-HSD1. No inhibition by 5-(4-cyanophenyl)-N-(3-hydroxybenzyl)-N-methylthiophene-2-carboxamide
-
additional information
17beta-HSD1 and 17beta-HSD2 inhibitor structures and their biological activities are reviewed; 17beta-HSD1 and 17beta-HSD2 inhibitor structures and their biological activities are reviewed. Dual 17beta-HSD1/STS inhibitors and inhibitors are covered
-
additional information
17beta-HSD1 and 17beta-HSD2 inhibitor structures and their biological activities are reviewed; 17beta-HSD1 and 17beta-HSD2 inhibitor structures and their biological activities are reviewed. Dual 17beta-HSD1/STS inhibitors and inhibitors are covered
-
additional information
the status of inhibitors against 17beta-hydroxysteroid dehydrogenases 1 is reviewed
-
additional information
the status of inhibitors against 17beta-hydroxysteroid dehydrogenases 1 is reviewed
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
palm oil carotenoids
-
0.001 mM, significant stimulation of the conversion of estradiol to estrone in the MCF-7 cell line
-
retinoic acid
-
0.001 mM, significant stimulation of the conversion of estradiol to estrone in the MCF-7 cell line and MDA-MB-231 cell line, 0.0001 mM has no effect
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0192
5alpha-androstane 3alpha,17beta-diol
pH 7.4, 37°C recombinant His-tagged enzyme
0.015
allopregnanolone
pH and temperature not specified in the publication
0.0019
DELTA4-3,17-androstendione
pH 7.4, 37°C recombinant His-tagged enzyme
0.00062
17beta-estradiol
17beta-HSD14 variant S205, pH and temperature not specified in the publication
0.00079
17beta-estradiol
17beta-HSD14 variant T205, pH and temperature not specified in the publication
0.043
17beta-estradiol
pH and temperature not specified in the publication
0.0066
5-androstene-3beta,17beta-diol
17beta-HSD14 variant S205, pH and temperature not specified in the publication
0.0078
5-androstene-3beta,17beta-diol
17beta-HSD14 variant T205, pH and temperature not specified in the publication
additional information
additional information
-
Km-values for mutant enzymes in cell homogenate
-
additional information
additional information
-
effects of ethanol, glycerol, propanediol and other organic solvents on the Km-values
-
additional information
additional information
Michaelis-Menten kinetics
-
additional information
additional information
kinetics of wild-type and mutant enzymes, overview
-
additional information
additional information
Michaelis-Menten kinetics, binding of dinucleotide cofactors to AKR1B15.1, overview
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
3
5alpha-androstane 3alpha,17beta-diol
pH 7.4, 37°C recombinant His-tagged enzyme
1.1
DELTA4-3,17-androstendione
pH 7.4, 37°C recombinant His-tagged enzyme
0.0004
17beta-estradiol
17beta-HSD14 variant S205, pH and temperature not specified in the publication
0.00055
17beta-estradiol
17beta-HSD14 variant T205, pH and temperature not specified in the publication
0.011
17beta-estradiol
pH and temperature not specified in the publication
0.00028
5-androstene-3beta,17beta-diol
17beta-HSD14 variant S205, pH and temperature not specified in the publication
0.00032
5-androstene-3beta,17beta-diol
17beta-HSD14 variant T205, pH and temperature not specified in the publication
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2.67
5alpha-androstane 3alpha,17beta-diol
pH 7.4, 37°C recombinant His-tagged enzyme
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0041
(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
-
0.4245
(S)-2-Methoxy-6a-methyl-5,6,6a,10,10a,10b,11,12-octahydro-4bH-7-oxa-8-aza-pentaleno[2,1-a]phenanthrene
-
-
0.0694
(S)-6a-Methyl-5,6,6a,10,10a,10b,11,12-octahydro-4bH-7-oxa-8-aza-pentaleno[2,1-a]phenanthren-2-ol
-
-
0.00061
1-[2-[4-(6-Methoxy-2-phenyl-3,4-dihydro-naphthalen-1-yl)-phenoxy]-ethyl]-pyrrolidine
-
-
0.0000009
3-([(16beta,17beta)-3,17-dihydroxyestra-1(10),2,4-trien-16-yl]methyl)benzamide
-
pH and temperature not specified in the publication
0.000007
[6-(3,4-dihydroxyphenyl)pyridin-2-yl]-(4-fluoro-3-hydroxyphenyl)methanone
pH and temperature not specified in the publication
0.000004
3-bromo-5-phenylsalicylic acid
-
pH not specified in the publication, 25°C
0.000087
3-bromo-5-phenylsalicylic acid
-
pH not specified in the publication, 25°C
0.0042
3-bromo-5-phenylsalicylic acid
-
pH not specified in the publication, 25°C
0.0182
3-bromo-5-phenylsalicylic acid
-
pH not specified in the publication, 25°C
0.00014
3-phenyl-5-bromosalicylic acid
-
pH not specified in the publication, 25°C
0.00197
3-phenyl-5-bromosalicylic acid
-
pH not specified in the publication, 25°C
0.021
3-phenyl-5-bromosalicylic acid
-
pH not specified in the publication, 25°C
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0012
(13alpha)-3-hydroxyestra-1(10),2,4-trien-17-one
Homo sapiens
pH and temperature not specified in the publication
0.000049
(13S,17R)-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
Homo sapiens
-
-
0.000019
(13S,17R)-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
Homo sapiens
-
-
0.000016
(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
Homo sapiens
-
-
0.000028
(13S,17R)-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
Homo sapiens
-
-
0.000107
(13S,17R)-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
Homo sapiens
-
-
0.00002
(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
Homo sapiens
-
-
0.000042
(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
Homo sapiens
-
-
0.000101
(16alpha)-2-chloro-16-fluoro-3-hydroxyestra-1(10),2,4-trien-17-one
Homo sapiens
-
0.00032
(16beta)-16-(ethoxymethyl)-3-hydroxyestra-1(10),2,4-trien-17-one
Homo sapiens
-
0.000035
(16beta)-2-chloro-16-fluoro-3-hydroxyestra-1(10),2,4-trien-17-one
Homo sapiens
-
0.01
(16beta)-3-hydroxy-16-methyl-17-oxoestra-1(10),2,4-triene-16-carbonitrile
Homo sapiens
-
0.00011
(16Z)-3-hydroxy-16-(hydroxymethylidene)estra-1(10),2,4-trien-17-one
Homo sapiens
-
0.00051
(17beta)-3,17-dihydroxy-N-(pyridin-3-ylmethyl)estra-1(10),2,4-triene-16-carboxamide
Homo sapiens
-
0.000087
(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
Homo sapiens
-
0.000126
(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
Homo sapiens
-
0.00203
(3alpha,7alpha,17beta)-17-ethynyl-7-methylestr-5(10)-ene-3,17-diol
Homo sapiens
-
0.00483
(3beta,7alpha,17beta)-17-ethynyl-7-methylestr-5(10)-ene-3,17-diol
Homo sapiens
-
0.00041 - 0.0006
(4aR,6aS,7S)-7-[heptyl(methyl)amino]-1,4a,6a-trimethylhexadecahydro-2H-indeno[5,4-f]quinolin-2-one
0.00096
(4aR,6aS,7S)-7-[heptyl(methyl)amino]-4a,6a-dimethylhexadecahydro-2H-indeno[5,4-f]quinolin-2-one
Homo sapiens
pH and temperature not specified in the publication
0.000015
(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
Homo sapiens
-
0.000024
(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
Homo sapiens
-
0.000052
(4aS,4bR,10bS,12aS)-8-hydroxy-9-iodo-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydrochrysen-1(2H)-one
Homo sapiens
-
0.000085
(4aS,4bR,10bS,12aS)-8-hydroxy-9-methoxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydrochrysen-1(2H)-one
Homo sapiens
-
0.000052
(4aS,4bR,10bS,12aS)-9-bromo-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydrochrysen-1(2H)-one
Homo sapiens
-
0.000077
(4aS,4bR,10bS,12aS)-9-chloro-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydrochrysen-1(2H)-one
Homo sapiens
-
0.00001
(4R,5R)-4-(2-fluorophenyl)-5-[hydroxy(5-phenylthiophen-2-yl)methyl]-1-methylpyrrolidin-2-one
Homo sapiens
pH 7.4, 37°C
0.00005
(4R,5R)-5-[hydroxy[5-(pyridin-3-yl)thiophen-2-yl]methyl]-1-methyl-4-phenylpyrrolidin-2-one
Homo sapiens
pH 7.4, 37°C
0.00042
(4S,5S)-5-[biphenyl-3-yl(hydroxy)methyl]-4-(2-fluorophenyl)-1-methylpyrrolidin-2-one
Homo sapiens
pH 7.4, 37°C
0.00102
(4S,5S)-5-[biphenyl-4-yl(hydroxy)methyl]-4-(2-fluorophenyl)-1-methylpyrrolidin-2-one
Homo sapiens
pH 7.4, 37°C
0.00005
(4S,5S)-5-[hydroxy[5-(pyridin-3-yl)thiophen-2-yl]methyl]-1-methyl-4-phenylpyrrolidin-2-one
Homo sapiens
pH 7.4, 37°C
0.000044
(6-hydroxy-1,3-benzothiazol-2-yl)(3-hydroxyphenyl)methanone
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.0003
(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
Homo sapiens
0.01 mM, 99% inhibition, IC50: 0.0003 mM
0.00088
(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
Homo sapiens
0.01 mM, 93% inhibition, IC50: 0.00088 mM
0.00078
(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
Homo sapiens
0.01 mM, 92% inhibition, IC50: 0.00078 mM
0.0023
(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
Homo sapiens
0.01 mM, 90% inhibition, IC50: 0.0023 mM
0.0007
(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
Homo sapiens
-
0.00053
(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
Homo sapiens
-
0.00095
(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
Homo sapiens
-
0.000066
(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
Homo sapiens
-
-
0.000173
1,1':4',1''-terphenyl-3,3''-diol
Homo sapiens
-
at 37°C in phosphate buffer (50 mM) with 20% (v/v) glycerol and 1 mM EDTA
0.00004
1-bromo-6-(3-hydroxyphenyl)-2-naphthol
Homo sapiens
in 20 mM KH2PO4, pH 7.4, at 25°C
0.00014
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
Homo sapiens
-
IC50: 140 nM
0.00046
16alpha-bromopropyl-estradiol
Homo sapiens
-
IC50: 0.00046 mM, reduction of estrone, the inhibitor is totally inactive against type 2 17beta-HSD and type type 1 17beta-HSD
0.0043
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
Homo sapiens
-
0.023
2-(2-bromo-4,6-dimethylphenoxy)-N'-[(E)-(2,4-dihydroxyphenyl)methylidene]acetohydrazide
Homo sapiens
pH 7.4, 37°C
0.0000222
2-chloro-4-[5-(2,6-difluoro-3-hydroxybenzoyl)thiophen-2-yl]phenyl sulfamate
Homo sapiens
whole cell assay, pH not specified in the publication, temperature not specified in the publication
0.0051
2-ethyl-17-oxo-16-[2-oxo-2-[(pyridin-3-ylmethyl)amino]ethyl]estra-1(10),2,4-trien-3-yl sulfamate
Homo sapiens
-
0.00000362 - 0.000165
2-[2-ethyl-3-hydroxy-17-oxoestra-1(10),2,4-trien-16-yl]-N-(pyridin-2-ylmethyl)acetamide
0.000027
2-[2-ethyl-3-hydroxy-17-oxoestra-1(10),2,4-trien-16-yl]-N-(pyridin-3-ylmethyl)acetamide
Homo sapiens
-
0.000037
2-[3-hydroxy-17-oxoestra-1(10),2,4-trien-16-yl]-N-(pyridin-3-ylmethyl)acetamide
Homo sapiens
-
0.0047
2-[5-(3-ethyl-4-hydroxyphenyl)-1-oxo-indan-2-yl]-N-pyridin-3-ylmethyl-acetamide
Homo sapiens
-
0.00064
3'-hydroxy-N-(3-hydroxybenzyl)-N-methylbiphenyl-3-carboxamide
Homo sapiens
pH 7.4, 37°C
0.000594
3'-hydroxy-N-(3-hydroxybenzyl)-N-methylbiphenyl-4-carboxamide
Homo sapiens
pH 7.4, 37°C
0.00054
3'-hydroxy-N-(3-hydroxyphenyl)-N-methyl-[1,10-biphenyl]-3-sulfonamide
Homo sapiens
pH 7.4, 37°C
0.000061
3'-hydroxy-N-(3-hydroxyphenyl)-N-methylbiphenyl-4-carboxamide
Homo sapiens
pH 7.4, 37°C
0.000494
3'-methoxy-N-(3-methoxybenzyl)-N-methylbiphenyl-4-carboxamide
Homo sapiens
pH 7.4, 37°C
0.00052
3'-methoxy-N-(3-methoxyphenyl)-N-methylbiphenyl-3-carboxamide
Homo sapiens
pH 7.4, 37°C
0.000517
3'-methoxy-N-(3-methoxyphenyl)-N-methylbiphenyl-4-carboxamide
Homo sapiens
pH 7.4, 37°C
0.0022
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
Homo sapiens
-
0.041
3,3'-(1-phenyl-1H-1,2,4-triazole-3,5-diyl)diphenol
Homo sapiens
-
37°C, pH not specified in the publication
0.000101
3,3'-pyridine-2,5-diyldiphenol
Homo sapiens
-
at 37°C in phosphate buffer (50 mM) with 20% (v/v) glycerol and 1 mM EDTA
0.000044
3-(3,17beta-dihydroxy-estra-1,3,5(10)-trien-16beta-ylmethyl)-benzamide
Homo sapiens
-
0.000171
3-(3-hydroxy-17-oxo-estra-1,3,5(10)-trien-16beta-ylmethyl)-benzamide
Homo sapiens
-
0.000042
3-([(16beta,17beta)-3,17-dihydroxyestra-1(10),2,4-trien-16-yl]methyl)benzamide
Homo sapiens
-
pH and temperature not specified in the publication
0.000083
3-([(16beta,17beta)-3-(2-bromoethyl)-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl)benzamide
Homo sapiens
-
pH and temperature not specified in the publication
0.000005
3-benzyl-2-(2-bromo-3,4,5-trimethoxyphenyl)-8-hydroxy[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
Homo sapiens
87% inhibition at 100 nM, 95% inhibition at 0.001 mM. IC50: 5 nM
0.000005
3-benzyl-8-hydroxy-2-(3,4,5-trimethoxyphenyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
0.00046
3-bromo-5-phenylsalicylic acid
Homo sapiens
-
pH not specified in the publication, 25°C
0.0063
3-bromo-N-(3-hydroxy-4-methylphenyl)benzenesulfonamide
Homo sapiens
pH 7.4, 37°C
0.00095
3-hydroxy-1,3,5(10)-triene-[17,16-c]-(5'-hydroxymethyl)-pyrazole
Homo sapiens
-
0.01 mM: 94% inhibition, IC50: 0.00095 mM
0.00185
3-hydroxy-1,3,5(10)-triene-[17,16-c]-[5'-(carboxylic acid ethyl ester)]-pyrazole
Homo sapiens
-
0.01 mM: 94% inhibition, IC50: 0.00185 mM
0.00007
3-hydroxy-13alpha-D-secooxime
Homo sapiens
pH and temperature not specified in the publication
0.00053
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-(1'-methoxyethyl)-pyrazole
Homo sapiens
-
0.01 mM: 95% inhibition, IC50: 0.00053 mM
0.00092
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-(1'-methyl acetate)-pyrazole
Homo sapiens
-
0.01 mM: 95% inhibition, IC50: 0.00092 mM
0.00275
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-(1'-methyl)-pyrazole
Homo sapiens
-
0.01 mM: 94% inhibition, IC50: 0.00275 mM
0.00073
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-(1'-propionitrile)-pyrazole
Homo sapiens
-
0.01 mM: 95% inhibition, IC50: 0.00073 mM
0.0023
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-[5'-(1'-methylpyrrol-2''-ylmethyl)carbamoyl]-pyrazole
Homo sapiens
-
0.01 mM: 89% inhibition, IC50: 0.0023 mM
0.00088
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-[5'-(pyridin-2''-ylmethyl)carbamoyl]-pyrazole
Homo sapiens
-
0.01 mM: 93% inhibition, IC50: 0.00088 mM
0.0003
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-[5'-(pyridin-3''-ylethyl)carbamoyl]-pyrazole
Homo sapiens
-
0.01 mM: 99% inhibition, IC50: 0.0003 mM
0.00078
3-hydroxy-estra-1,3,5(10)-triene-[17,16-c]-[5'-(pyridin-3''-ylmethyl)carbamoyl]-pyrazole
Homo sapiens
-
0.01 mM: 92% inhibition, IC50: 0.00078 mM
0.000159
3-hydroxy-N-(3'-hydroxy-[1,1'-biphenyl]-3-yl)-N-methylbenzenesulfonamide
Homo sapiens
pH 7.4, 37°C
0.000511
3-hydroxy-N-(3'-hydroxy-[1,1'-biphenyl]-4-yl)-N-methylbenzenesulfonamide
Homo sapiens
pH 7.4, 37°C
0.000243
3-hydroxy-N-(6-hydroxy-1,3-benzothiazol-2-yl)benzamide
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.0019
3-hydroxyestra-1,3,5(10),7-tetraen-17-one
Homo sapiens
-
IC50: 0.0019 mM, oxidation of estradiol
0.00073
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
Homo sapiens
-
0.021
3-[3-(4-hydroxyphenyl)-1-methyl-1H-1,2,4-triazol-5-yl]phenol
Homo sapiens
-
37°C, pH not specified in the publication
0.000077
3-[4-(4-hydroxyphenyl)thiophen-2-yl]phenol
Homo sapiens
-
at 37°C in phosphate buffer (50 mM) with 20% (v/v) glycerol and 1 mM EDTA
0.02
3-[5-(4-hydroxyphenyl)-1-methyl-1H-1,2,4-triazol-3-yl]phenol
Homo sapiens
-
37°C, pH not specified in the publication
0.044
3-[5-(4-hydroxyphenyl)-1-phenyl-1H-1,2,4-triazol-3-yl]phenol
Homo sapiens
-
37°C, pH not specified in the publication
0.000069
3-[5-(4-hydroxyphenyl)thiophen-2-yl]phenol
Homo sapiens
-
at 37°C in phosphate buffer (50 mM) with 20% (v/v) glycerol and 1 mM EDTA
0.000151
3-[5-(4-hydroxyphenyl)thiophen-3-yl]phenol
Homo sapiens
-
at 37°C in phosphate buffer (50 mM) with 20% (v/v) glycerol and 1 mM EDTA
0.0031
3alpha-hydroxy-3beta-([4-[(2-methoxy-4-methylphenyl)methyl]piperazin-1-yl]methyl)-androstan-17-one
Homo sapiens
-
pH and temperature not specified in the publication, transformation of E2 to E1 by HEK-293[17beta-HSD10] cells
0.00042
3alpha-hydroxy-3beta-([4-[(3-methoxy-4-methylphenyl)methyl]piperazin-1-yl]methyl)-androstan-17-one
Homo sapiens
-
pH and temperature not specified in the publication, transformation of E2 to E1 by HEK-293[17beta-HSD10] cells
0.0026
3alpha-hydroxy-3beta-([4-[(3-methoxyphenyl)methyl]piperazin-1-yl]methyl)-androstan-17-one
Homo sapiens
-
pH and temperature not specified in the publication, transformation of E2 to E1 by HEK-293[17beta-HSD10] cells
0.00097
3alpha-hydroxy-3beta-([4-[(quinolin-3-yl)methyl]piperazin-1-yl]methyl)-androstan-17-one
Homo sapiens
-
pH and temperature not specified in the publication, transformation of E2 to E1 by HEK-293[17beta-HSD10] cells
0.00014
3alpha-hydroxy-3beta-[(4-[[3-methoxy-4-(trifluoromethyl)phenyl]methyl]piperazin-1-yl)methyl]-androstan-17-one
Homo sapiens
-
pH and temperature not specified in the publication, transformation of E2 to E1 by HEK-293[17beta-HSD10] cells
0.00126
3beta-[(4-[[3-methoxy-4-(trifluoromethyl)phenyl]methyl]piperazin-1-yl)methyl]-17alpha-pregn-20-yne-3alpha,17-diol
Homo sapiens
-
pH and temperature not specified in the publication, transformation of E2 to E1 by HEK-293[17beta-HSD10] cells
-
0.00095
3beta-[(4-[[3-methoxy-4-(trifluoromethyl)phenyl]methyl]piperazin-1-yl)methyl]-androstane-3alpha,17alpha-diol
Homo sapiens
-
pH and temperature not specified in the publication, transformation of E2 to E1 by HEK-293[17beta-HSD10] cells
0.00205
3beta-[[4-(3,5-dimethylbenzoyl)piperazin-1-yl]methyl]-3alpha-hydroxyandrostan-17-one
Homo sapiens
-
pH and temperature not specified in the publication, transformation of E2 to E1 by HEK-293[17beta-HSD10] cells
0.0023
3beta-[[4-(3-acetylbenzoyl)piperazin-1-yl]methyl]-3alpha-hydroxyandrostan-17-one
Homo sapiens
-
pH and temperature not specified in the publication, transformation of E2 to E1 by HEK-293[17beta-HSD10] cells
0.0026
3beta-[[4-([1,1'-biphenyl]-4-carbonyl)piperazin-1-yl]methyl]-3alpha-hydroxyandrostan-17-one
Homo sapiens
-
pH and temperature not specified in the publication, transformation of E2 to E1 by HEK-293[17beta-HSD10] cells
0.0012
4'-methoxy-N-(3-methoxyphenyl)-N-methylbiphenyl-3-carboxamide
Homo sapiens
pH 7.4, 37°C
0.0018
4-(3'-ethyl-4'-hydroxy-biphenyl)-2,2-dimethyl-4-oxo-N-pyridin-3-ylmethyl-butyramide
Homo sapiens
-
0.0037
4-(3'-ethyl-4'-hydroxy-biphenyl)-4-oxo-N-pyridin-3-ylmethyl-butyramide
Homo sapiens
-
0.0018
4-(3-ethyl-4-hydroxy-biphenyl)-2,2-dimethyl-4-oxo-N-pyridin-3-ylmethyl-butyramide
Homo sapiens
-
0.0017
4-(4-[[3alpha-hydroxy-17-oxoandrostan-3beta-yl]methyl]piperazine-1-carbonyl)benzonitrile
Homo sapiens
-
pH and temperature not specified in the publication, transformation of E2 to E1 by HEK-293[17beta-HSD10] cells
0.001
4-chloro-N-(3-hydroxyphenyl)-2,5-dimethylbenzenesulfonamide
Homo sapiens
pH 7.4, 37°C
0.000023
4-fluoro-3-hydroxy-N-(3'-hydroxybiphenyl-3-yl)-N-methylbenzenesulfonamide
Homo sapiens
pH 7.4, 37°C
0.000046
4-[5-(3-hydroxyphenyl)thiophen-2-yl]-2-methylphenol
Homo sapiens
-
at 37°C in phosphate buffer (50 mM) with 20% (v/v) glycerol and 1 mM EDTA
0.0014
4-[[3alpha-hydroxy-17-oxoandrostan-3beta-yl]methyl]-N-[[3-(trifluoromethyl)phenyl]methyl]piperazine-1-carbothioamide
Homo sapiens
-
pH and temperature not specified in the publication, transformation of E2 to E1 by HEK-293[17beta-HSD10] cells
0.00014
5'-O-(10-[3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'alpha-yl]-decanoyl)adenosine
Homo sapiens
-
IC50: 140 nM
0.00031
5'-O-(11-[3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'alpha-yl]-undecanoyl) adenosine
Homo sapiens
-
IC50: 310 nM
0.00009
5'-O-(11-[3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'alpha/beta-yl]-undecanoyl)adenosine
Homo sapiens
-
IC50: 90 nM
0.00012
5'-O-(11-[3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'beta-yl]-undecanoyl)adenosine
Homo sapiens
-
IC50: 120 nM
0.001
5'-O-(12-[3',17'beta-(dihydroxy)-1',3',5'(10')-estratrien-16'alpha-yl]-dodecanoyl)adenosine
Homo sapiens
-
IC50: 1000 nM
0.0069
5'-O-(6-[3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'alpha/beta-yl]-hexanoyl)adenosine
Homo sapiens
-
IC50: 6900 nM
0.00043
5'-O-(7-[3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'alpha-yl]-heptanoyl)adenosine
Homo sapiens
-
IC50: 430 nM
0.000093
5'-O-(8-[3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'alpha-yl]-octanoyl)adenosine
Homo sapiens
-
IC50: 93 nM
0.000052
5'-O-(9-[3',17'beta-dihydroxy-1',3',5'(10')-estratrien-16'alpha-yl]-nonanoyl)adenosine
Homo sapiens
-
IC50: 52 nM
0.000052
5'-O-[9-[(16b,17b)-3,17-dihydroxyestra-1(10),2,4-trien-16-yl]nonanoyl]adenosine
Homo sapiens
-
0.000061
5-(2-fluoro-3-methoxyphenyl)-N-(3-hydroxybenzyl)-N-methylthiophene-2-carboxamide
Homo sapiens
pH 7.4, 37°C
0.000062
5-(2-fluoro-3-methoxyphenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
Homo sapiens
pH 7.4, 37°C
0.000062
5-(2-fluoro-3-methoxyphenyl)-N-methyl-N-(3-methylphenyl)thiophene-2-carboxamide
Homo sapiens
pH 7.4, 37°C
0.00041
5-(2-hydroxyphenyl)-N-(3-hydroxyphenyl)-N-methylthiophene-2-carboxamide
Homo sapiens
pH 7.4, 37°C
0.00049
5-(2-methoxyphenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
Homo sapiens
pH 7.4, 37°C
0.00033
5-(3-fluorophenyl)-N-(3-hydroxybenzyl)-N-methylthiophene-2-carboxamide
Homo sapiens
pH 7.4, 37°C
0.00017
5-(3-fluorophenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
Homo sapiens
pH 7.4, 37°C
0.00051
5-(4-cyanophenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
Homo sapiens
pH 7.4, 37°C
0.00002
6-(3-hydroxyphenyl)-1-phenyl-2-naphthol
Homo sapiens
in 20 mM KH2PO4, pH 7.4, at 25°C
0.000093
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
Homo sapiens
-
IC50: 93 nM
0.000052
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
Homo sapiens
-
IC50: 52 nM
0.00185
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
Homo sapiens
-
0.000072
methyl (13S,17R)-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
Homo sapiens
-
-
0.00092
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
Homo sapiens
-
0.0011
N,4'-dimethyl-N-(3-methylphenyl)biphenyl-4-carboxamide
Homo sapiens
pH 7.4, 37°C
0.000068
N,5-bis(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
Homo sapiens
pH 7.4, 37°C
0.0011
N-(2,1,3-benzothiadiazol-4-yl)-2-[(4-hydroxypyrimidin-2-yl)sulfanyl]acetamide
Homo sapiens
pH 7.4, 37°C
0.24 - 0.52
N-(2-hydroxyphenyl)-2-methyl-4-(trifluoromethyl)benzenesulfonamide
Homo sapiens
pH 7.4, 37°C
0.003 - 0.01
N-(3-chloro-4-hydroxyphenyl)-4-fluorobenzenesulfonamide
Homo sapiens
pH 7.4, 37°C
0.0071
N-(3-hydroxy-4-methylphenyl)-3-(trifluoromethyl)benzenesulfonamide
Homo sapiens
pH 7.4, 37°C
0.00039
N-(3-hydroxybenzyl)-5-(3-hydroxyphenyl)-N-methylthiophene-2-carboxamide
Homo sapiens
pH 7.4, 37°C
0.00033
N-(3-hydroxybenzyl)-5-(4-hydroxyphenyl)-N-methylthiophene-2-carboxamide
Homo sapiens
pH 7.4, 37°C
0.000161
N-(3-hydroxybenzyl)-5-(4-methoxyphenyl)-N-methylthiophene-2-carboxamide
Homo sapiens
pH 7.4, 37°C
0.0033
N-(3-hydroxyphenyl)-2,4,5-trimethylbenzenesulfonamide
Homo sapiens
pH 7.4, 37°C
0.0069
N-(3-hydroxyphenyl)-4-methoxy-2,5-dimethylbenzenesulfonamide
Homo sapiens
pH 7.4, 37°C
0.015
N-(3-hydroxyphenyl)-4-methoxy-2-methyl-5,6,7,8-tetrahydronaphthalene-1-sulfonamide
Homo sapiens
pH 7.4, 37°C
0.00037
N-(3-methoxybenzyl)-5-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
Homo sapiens
pH 7.4, 37°C
0.000058
N-(3-methoxyphenyl)-N-methyl-5-(3-methylphenyl)thiophene-2-carboxamide
Homo sapiens
pH 7.4, 37°C
0.0096
N-(4-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)-4-methoxybenzenesulfonamide
Homo sapiens
pH 7.4, 37°C
0.0008
N-butyl-6-[[(6beta,17beta)-3,17-dihydroxyestra-1(10),2,4-trien-6-yl]oxy]-N-methylhexanamide
Homo sapiens
-
73% inhibition at 0.001 mM, IC50: 0.0008 mM, reduction of estrone with NADH as cofactor
0.00016
N-butyl-6-[[(6beta,17beta)-3,17-dihydroxyestra-1(10),2,4-trien-6-yl]sulfanyl]-N-methylhexanamide
0.00291 - 0.00396
N-decyl-N-[(4aR,6aS,7S)-1,4a,6a-trimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinolin-7-yl]formamide
0.00112 - 0.00578
N-decyl-N-[(4aR,6aS,7S)-4a,6a-dimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinolin-7-yl]formamide
0.0016
N-ethyl-4-[[3alpha-hydroxy-17-oxoandrostan-3beta-yl]methyl]-N-methylpiperazine-1-sulfonamide
Homo sapiens
-
pH and temperature not specified in the publication, transformation of E2 to E1 by HEK-293[17beta-HSD10] cells
0.000052
N-methyl-N,5-bis(3-methylphenyl)thiophene-2-carboxamide
Homo sapiens
pH 7.4, 37°C
0.0007 - 0.00332
N-nonyl-N-[(4aR,6aS,7S)-1,4a,6a-trimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinolin-7-yl]formamide
0.00107
N-[4-(dimethylsulfamoyl)phenyl]-4-[[3alpha-hydroxy-17-oxoandrostan-3beta-yl]methyl]piperazine-1-carbothioamide
Homo sapiens
-
pH and temperature not specified in the publication, transformation of E2 to E1 by HEK-293[17beta-HSD10] cells
0.00285
[[4-(4-benzoylbenzoyl)piperazin-1-yl]methyl]-3alpha-hydroxyandrostan-17-one
Homo sapiens
-
pH and temperature not specified in the publication, transformation of E2 to E1 by HEK-293[17beta-HSD10] cells
0.00041
(4aR,6aS,7S)-7-[heptyl(methyl)amino]-1,4a,6a-trimethylhexadecahydro-2H-indeno[5,4-f]quinolin-2-one
Homo sapiens
pH and temperature not specified in the publication
0.0006
(4aR,6aS,7S)-7-[heptyl(methyl)amino]-1,4a,6a-trimethylhexadecahydro-2H-indeno[5,4-f]quinolin-2-one
Homo sapiens
pH and temperature not specified in the publication, substrate: progesterone
0.00291
17beta-[(N-decyl)formamido]-4-methyl-4-aza-5alpha-androstan-3-one
Homo sapiens
pH 7.4, 37°C, reduction of estrone
-
0.00396
17beta-[(N-decyl)formamido]-4-methyl-4-aza-5alpha-androstan-3-one
Homo sapiens
pH 7.4, 37°C, reduction of dihydrotestosterone
-
0.00424
17beta-[(N-decyl)formamido]-4-methyl-4-aza-5alpha-androstan-3-one
Homo sapiens
pH 7.4, 37°C, reduction of progesterone
-
0.00578
17beta-[(N-heptyl)methylamino]-4-aza-5alpha-androstan-3-one
Homo sapiens
pH 7.4, 37°C, reduction of dihydrotestosterone
-
0.00601
17beta-[(N-heptyl)methylamino]-4-aza-5alpha-androstan-3-one
Homo sapiens
pH 7.4, 37°C, reduction of progesterone
-
0.00041
17beta-[(N-heptyl)methylamino]-4-methyl-4-aza-5alpha-androstan-3-one
Homo sapiens
pH 7.4, 37°C, reduction of estrone
-
0.0006
17beta-[(N-heptyl)methylamino]-4-methyl-4-aza-5alpha-androstan-3-one
Homo sapiens
pH 7.4, 37°C, reduction of progesterone
-
0.00119
17beta-[(N-heptyl)methylamino]-4-methyl-4-aza-5alpha-androstan-3-one
Homo sapiens
pH 7.4, 37°C, reduction of dihydrotestosterone
-
0.0007
17beta-[(N-nonyl)formamido]-4-methyl-4-aza-5alpha-androstan-3-one
Homo sapiens
pH 7.4, 37°C, reduction of estrone
-
0.00316
17beta-[(N-nonyl)formamido]-4-methyl-4-aza-5alpha-androstan-3-one
Homo sapiens
pH 7.4, 37°C, reduction of progesterone
-
0.00332
17beta-[(N-nonyl)formamido]-4-methyl-4-aza-5alpha-androstan-3-one
Homo sapiens
pH 7.4, 37°C, reduction of dihydrotestosterone
-
0.00000362
2-[2-ethyl-3-hydroxy-17-oxoestra-1(10),2,4-trien-16-yl]-N-(pyridin-2-ylmethyl)acetamide
Homo sapiens
-
0.000165
2-[2-ethyl-3-hydroxy-17-oxoestra-1(10),2,4-trien-16-yl]-N-(pyridin-2-ylmethyl)acetamide
Homo sapiens
-
0.00137
3'-(1-benzothien-2-yl)biphenyl-3-ol
Homo sapiens
37°C, pH not specified in the publication
0.00194
3'-(1-benzothien-2-yl)biphenyl-3-ol
Homo sapiens
37°C, pH not specified in the publication
0.00056
3'-(5-chloro-2-thienyl)biphenyl-3-ol
Homo sapiens
37°C, pH not specified in the publication
0.00237
3'-(5-chloro-2-thienyl)biphenyl-3-ol
Homo sapiens
37°C, pH not specified in the publication
0.000934
3'-hydroxy-N-(3-hydroxybenzyl)-N-methyl-[1,10-biphenyl]-4-sulfonamide
Homo sapiens
pH 7.4, 37°C
0.004299
3'-hydroxy-N-(3-hydroxybenzyl)-N-methyl-[1,10-biphenyl]-4-sulfonamide
Homo sapiens
pH 7.4, 37°C
0.001179
3'-hydroxy-N-(3-hydroxyphenyl)-N-methyl-[1,10-biphenyl]-4-sulfonamide
Homo sapiens
pH 7.4, 37°C
0.002031
3'-hydroxy-N-(3-hydroxyphenyl)-N-methyl-[1,10-biphenyl]-4-sulfonamide
Homo sapiens
pH 7.4, 37°C
0.017
3,3'-(1H-1,2,3-triazole-1,4-diyl)diphenol
Homo sapiens
-
37°C, pH not specified in the publication
0.000005
3-benzyl-8-hydroxy-2-(3,4,5-trimethoxyphenyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
Homo sapiens
-
0.000005
3-benzyl-8-hydroxy-2-(3,4,5-trimethoxyphenyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
Homo sapiens
94% inhibition at 100 nM, 99% inhibition at 0.001 mM. IC50: 5 nM
0.00132
3-[1-(4-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]-phenol
Homo sapiens
substrate: estrone, 17beta-HSD1
0.00812
3-[1-(4-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]-phenol
Homo sapiens
substrate: estradiol-17beta, 17beta-HSD2
0.00132
3-[1-(4-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]phenol
Homo sapiens
-
37°C, pH not specified in the publication
40.88
3-[1-(4-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]phenol
Homo sapiens
-
37°C, pH not specified in the publication
0.00047
3-[2-(5-chloro-2-thienyl)pyridin-4-yl]phenol
Homo sapiens
37°C, pH not specified in the publication
0.00238
3-[2-(5-chloro-2-thienyl)pyridin-4-yl]phenol
Homo sapiens
37°C, pH not specified in the publication
0.00027
3-[3-(4-hydroxyphenyl)isoxazol-5-yl]-phenol
Homo sapiens
substrate: estradiol-17beta, 17beta-HSD2
0.00161
3-[3-(4-hydroxyphenyl)isoxazol-5-yl]-phenol
Homo sapiens
substrate: estrone, 17beta-HSD1
0.00025
3-[4-(4-hydroxyphenyl)-1,3-oxazol-2-yl]-phenol
Homo sapiens
substrate: estradiol-17beta, 17beta-HSD2
0.00185
3-[4-(4-hydroxyphenyl)-1,3-oxazol-2-yl]-phenol
Homo sapiens
substrate: estrone, 17beta-HSD1
0.00084
3-[4-(4-hydroxyphenyl)-1H-1,2,3-triazol-1-yl]-phenol
Homo sapiens
substrate: estrone, 17beta-HSD1
0.00728
3-[4-(4-hydroxyphenyl)-1H-1,2,3-triazol-1-yl]-phenol
Homo sapiens
substrate: estradiol-17beta, 17beta-HSD2
0.00084
3-[4-(4-hydroxyphenyl)-1H-1,2,3-triazol-1-yl]phenol
Homo sapiens
-
37°C, pH not specified in the publication
46.94
3-[4-(4-hydroxyphenyl)-1H-1,2,3-triazol-1-yl]phenol
Homo sapiens
-
37°C, pH not specified in the publication
0.00085
3-[4-(5-chloro-2-thienyl)pyridin-2-yl]phenol
Homo sapiens
37°C, pH not specified in the publication
0.00364
3-[4-(5-chloro-2-thienyl)pyridin-2-yl]phenol
Homo sapiens
37°C, pH not specified in the publication
0.00031
3-[5-(4-hydroxyphenyl)-1,3-oxazol-2-yl]-phenol
Homo sapiens
substrate: estrone, 17beta-HSD1
0.0175
3-[5-(4-hydroxyphenyl)-1,3-oxazol-2-yl]-phenol
Homo sapiens
substrate: estrone, 17beta-HSD2
0.00139
3-[6-(5-chloro-2-thienyl)pyridin-2-yl]phenol
Homo sapiens
37°C, pH not specified in the publication
0.00711
3-[6-(5-chloro-2-thienyl)pyridin-2-yl]phenol
Homo sapiens
37°C, pH not specified in the publication
0.00102
4'-(5-chloro-2-thienyl)biphenyl-3-ol
Homo sapiens
37°C, pH not specified in the publication
0.01
4'-(5-chloro-2-thienyl)biphenyl-3-ol
Homo sapiens
value higher than 0.01, 37°C, pH not specified in the publication
0.00069
4'-(6-methoxypyridin-3-yl)biphenyl-3-ol
Homo sapiens
37°C, pH not specified in the publication
0.00297
4'-(6-methoxypyridin-3-yl)biphenyl-3-ol
Homo sapiens
37°C, pH not specified in the publication
0.00048
4'-hydroxy-N-(3-hydroxybenzyl)-N-methylbiphenyl-3-carboxamide
Homo sapiens
pH 7.4, 37°C
0.000482
4'-hydroxy-N-(3-hydroxybenzyl)-N-methylbiphenyl-3-carboxamide
Homo sapiens
pH 7.4, 37°C
0.00016
N-(3-hydroxybenzyl)-N-methyl-5-(3-methylphenyl)thiophene-2-carboxamide
Homo sapiens
pH 7.4, 37°C
0.000164
N-(3-hydroxybenzyl)-N-methyl-5-(3-methylphenyl)thiophene-2-carboxamide
Homo sapiens
pH 7.4, 37°C
0.00016
N-butyl-6-[[(6beta,17beta)-3,17-dihydroxyestra-1(10),2,4-trien-6-yl]sulfanyl]-N-methylhexanamide
Homo sapiens
-
0.00016
N-butyl-6-[[(6beta,17beta)-3,17-dihydroxyestra-1(10),2,4-trien-6-yl]sulfanyl]-N-methylhexanamide
Homo sapiens
-
92% inhibition at 0.001 mM, IC50: 0.00016 mM, reduction of estrone with NADH as cofactor
0.00291
N-decyl-N-[(4aR,6aS,7S)-1,4a,6a-trimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinolin-7-yl]formamide
Homo sapiens
pH and temperature not specified in the publication, substrate: progesterone
0.00396
N-decyl-N-[(4aR,6aS,7S)-1,4a,6a-trimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinolin-7-yl]formamide
Homo sapiens
pH and temperature not specified in the publication, substrate: progesterone
0.00112
N-decyl-N-[(4aR,6aS,7S)-4a,6a-dimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinolin-7-yl]formamide
Homo sapiens
pH and temperature not specified in the publication
0.00578
N-decyl-N-[(4aR,6aS,7S)-4a,6a-dimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinolin-7-yl]formamide
Homo sapiens
pH and temperature not specified in the publication, substrate: progesterone
0.0007
N-nonyl-N-[(4aR,6aS,7S)-1,4a,6a-trimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinolin-7-yl]formamide
Homo sapiens
pH and temperature not specified in the publication
0.00332
N-nonyl-N-[(4aR,6aS,7S)-1,4a,6a-trimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinolin-7-yl]formamide
Homo sapiens
pH and temperature not specified in the publication, substrate: progesterone
additional information
(2,4-dihydroxyphenyl)-phenylmethanone
Homo sapiens
-
value higher than 0.02, pH 7.4, 37°C
additional information
(2,4-dihydroxyphenyl)-phenylmethanone
Homo sapiens
-
value higher than 0.065, pH 7.4, 37°C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.4
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
24 - 54
-
24°C: about 60% of maximal activity, 54°C: about 50% of maximal activity, enzyme from crude washed mitochondria
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
HSD17B2 is normally expressed in the epithelial cells of the colon lumen, and to a lesser extent in the crypt epithelium small intestine endometrium
-
cultured cells, enzyme expression is stimulated with all-trans and 9-cis retinoic acid
-
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
-
of fallopian tube. Increased expression of 17HSD1 in epithelial cells of fallopian tube may lead to a local estradiol supply sufficient for maintenance of tubal pregnancy
-
association of 17HSD1 with extravillous cells indicates that the enzyme perhaps plays a role in trophoblast invasion
-
epithelial cells. Increased expression of 17HSD1 in epithelial cells of fallopian tube may lead to a local estradiol supply sufficient for maintenance of tubal pregnancy
HSD17B2 expression is significantly higher in invasive lobular carcinoma (ILC) than in invasive ductal carcinoma
HSD17B2 expression is significantly higher in invasive lobular carcinoma (ILC) than in invasive ductal carcinoma
NSCLC, immunihostichemic enzyme analysis: higher 17betaHSD1 immunoreactivity tends to be positively associated with aromatase and tumor stage. A higher 17betaHSD1 immunoreactivity is also significantly associated with lower intratumoral estrone concentration and a higher intratumoral estradiol/estrone concentration ratio. On the other hand a higher 17betaHSD2 immunoreactivity is significantly associated with higher intratumoral estrone concentration
-
normal and tubal pregancies possess identical expression of 17HSD1 in syncytiotrophoblast cells and therefore, similar estradiol production in the placenta
additional information
the inhibition of the enzyme (17beta-HSD7) constitutes the basis of breast cancer cell proliferation
-
17beta-HSD type 12 in 83% of the breast cancer specimen. The expression of 17beta-HSD type 12 is significantly higher in breast carcinoma specimen than in normal tissues
-
17beta-HSD type 7 activity is detected in 47% of the breast cancer specimen
-
breast cells, activity is far greater in epithelial cells than in fibroblasts
-
cultured cells, enzyme expression is stimulated with all-trans and 9-cis retinoic acid
-
modulation of local synthesis of estradiol is one potential mechanism through which genistein, enterolactone and enterodiol may protect against breast cancer
-
MCF-7.8H cell derived from MCF-7 via transfection, high enzyme activity
-
enzyme type 2 from ovarian tumors: OVCAR-3, CAOV-3 and epidermoid tumor of the vulva, A431
type 12 17beta-hydroxysteroid dehydrogenase is most highly expressed in ovary and mammary gland
-
17beta-HSD8 in cumulus cells, not in granulosa and luteal cells, vice versa for isozymes 17beta-HSD1 and 17beta-HSD7
the enzyme is primarily expressed in the placenta and ovarian granulose cells
-
-
285977, 285981, 287172, 287173, 287174, 287176, 287181, 287182, 287183, 287184, 287186, 287187, 287188, 287190, 287191, 655219, 656371, 658489, 669797, 670265, 688956, 700183
-
normal and tubal pregancies possess identical expression of 17HSD1 in syncytiotrophoblast cells and therefore, similar estradiol production in the placenta
-
organotin compounds are potent stimulators of 17beta-estradiol biosynthesis to enhance 17beta-HSD I activity in placenta
the enzyme is primarily expressed in the placenta and ovarian granulose cells
expressed in estrogen receptor beta-positive epithelial cells of the human prostate
-
17beta-hydroxysteroid dehydrogenase has a pivotal role in regulating the synthesis of estradiol within breast tumours
additional information
in prostate cancers of Gleason grade higher than 3, both estrogen receptor beta and isoform 17betaHSD6 are undetectable
additional information
17beta-HSD1 is highly expressed in breast and ovary tissues and represents a prognostic marker for the tumor progression and survival of patients with breast cancer and other estrogen-dependent tumors
additional information
isozyme tissue-specific expression analysis, overview
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
drug target
evolution
17beta-HSD1 belongs to the short-chain dehydrogenase/reductase (SDR) family and contains the conserved Rossmann-fold for nucleotide binding, the catalytic triad with residues Ser142, Tyr155, and Lys159 and a dimerization region. Residue Cys10 is highly conserved among species, including rodents and zebrafish, suggesting a role for this residue in the stability and/or function of the protein. The cysteine residue at this position is conserved in all members of the SDR9C family, except for 17beta-HSD2, which has a cysteine residue downstream by two positions
malfunction
metabolism
physiological function
additional information
drug target
inhibition of 17beta-hydroxysteroid dehydrogenases 1 is proposed to be a prime candidate for inhibition in patients who develop aromatase inhibitor resistance or in combination with aromatase inhibitors as a first line treatment
drug target
inhibition of 17beta-hydroxysteroid dehydrogenases 1 may be a prime candidate for inhibition in patients with breast cancer who develop aromatase inhibitor resistance or in combination with aromatase inhibitors as a first line treatment
drug target
-
possible role in Alzheimer's disease, inhibition appears to be a therapeutic strategy
drug target
the ratio of HSD17B1 to HSD17B2 is a good indicator of tamoxifen treatment benefit, as post-menopausal patients with tumors expressing a high HSD17B1/HSD17B2 protein ratio have less benefit from tamoxifen treatment
drug target
inhibition of 17beta-HSD7 constitutes the basis of breast cancer cell proliferation
malfunction
enzyme inhibition can lead to desired increase of estradiol and testosterone levels in the bone tissue and may be used for the treatment of osteoporosis
malfunction
estrone treatment in 17betaHSD1 positive NSCLC cells, A-549 and LK-87, results in estradiol production and enhances cell proliferation, which is abrogated effectively by 17betaHSD1 siRNA knockdown
malfunction
substitution of Cys10 with Ser in the enzyme results in a decreased protein half-life, without significantly altering kinetic properties
malfunction
knockdown of 17beta-HSD1 gene, HSD17B1, modulates the transcript profile of the hormone-dependent breast cancer cell line T47D, T47D, with 105 genes regulated 1.5 fold or higher in estradiol-independent manner
malfunction
knockdown of 17beta-HSD1 gene, HSD17B1, modulates the transcript profile of the hormone-dependent breast cancer cell line T47D, with 105 genes regulated 1.5fold or higher in estradiol-independent manner. Genes that are primarily involved in the cell cycle progression, such as the cyclin A2 gene, CCNA2, are generally down-regulated whereas genes involved in apoptosis and cell death, including the pro-apoptotic gene XAF1, IFIH1 and FGF12, are upregulated by 17beta-HSD1 knockdown
metabolism
AKR1B15.1 is a mitochondrial carbonyl reductase. Two alternatively spliced protein isoforms encoded by the human AKRgene AKR1B15 exist, the AKR1B15.1 isoform catalyzes reduction of steroids and 3-keto-acyl-CoA conjugates
metabolism
besides as a biomarker in cancer, AKR1C3 is important in the reduction of steroids and prostaglandins, and function as part of a chemical barrier to defend the body from intrusion of toxic chemicals
metabolism
by acting as a 17-ketosteroid reductase, AKR1C3 produces potent androgens in peripheral tissues which activate the androgen receptor or act as substrates for aromatase. AKR1C3 is implicated in the production of androgens in castration-resistant prostate cancer and polycystic ovarian syndrome and is implicated in the production of aromatase substrates in breast cancer
metabolism
HSD17B2 is controlled by estradiol, dihydrotestosterone, and miRNAs, as well as modulated by several breast cancer related genes
metabolism
-
the enzyme can oxidize estradiol into estrone, thus reducing concentration of this neuroprotective steroid
physiological function
-
enzyme involved in maintaining high estradiol levels in breast tumors of postmenopausal women. In certain breast cancer patients, intratumoral estradiol is produced by the 17beta-HSD1-mediated reduction of estrone produced by aromatase. A high level of 17-beta-HSD1 correlates with an increased risk of developing a late relapse of breast cancer in ER-positive breast cancer patients
physiological function
17beta-hydroxysteroid dehydrogenase type 6 converts the androgen 5alpha-dihydrotestosterone to the estrogen 5alpha-androstane-3beta,17beta-diol, and this leads to activation of the estrogen receptor beta reporter. This conversion of dihydrotestosterone occurs at concentrations that are in the physiological range of this hormone in the prostate
physiological function
17beta-hydroxysteroid dehydrogenase 2 catalyzes the inactivation of estradiol into estrone
physiological function
endogenous production of 17beta-estradiol in hematological malignant cells might also contribute to immunohormonal imbalance in patients with these disorders. Human T and B lymphocytes are positive for ERa, ERb and GPR30 receptors. Using putative membrane receptors, estrogens are able to modulate cytokine profiles in T cells and the control of B-cell maturation and selection. In particular, estrogens are able to inhibit T cell proliferation, interleukin-2 (IL-2) biosynthesis, and increase B-cell proliferation and antibody production. 17beta-Estradiol is able to upregulate cyclic AMP response element modulator alpha leading to reduced IL-2 gene expression in human T lymphocytes. HSD17B1 may play a crucial role in the development of estrogen-dependent diseases
physiological function
estrone treatment in 17betaHSD1 positive NSCLC cells, A-549 and LK-87, results in estradiol production and enhances cell proliferation, which is abrogated effectively by 17betaHSD1 siRNA knockdown
physiological function
the drop in 17beta-estradiol (E2) and testosterone levels, occurring with ageing, is the main factor driving the onset and progression of osteoporosis
physiological function
-
the enzyme is thought to play a pivotal role in the progression of estrogen-sensitive breast cancer by transforming estrone into estradiol
physiological function
17beta-HSD1 may be involved in oncogenesis by favoring antiapoptosis pathway in breast cancer cells
physiological function
by its oxidative activity, the enzyme can decrease the concentration of two important neurosteroids, allopregnanolone (ALLOP) and 17beta-estradiol, respectively preventing their neurogenesis and neuroprotective effects
physiological function
the enzyme 17beta-HSD1 may be involved in oncogenesis by favoring antiapoptosis pathway in breast cancer cells and correborates with its previously shown role in increasing breast cancer cell proliferation. The gene regulation occurring in steroid-deprived conditions shows that 17beta-HSD1 can modulate endogenous gene expression in steroid-independent manners
physiological function
the enzyme increases breast cancer cell proliferation via a dual effect on 17-beta-estradiol and 5alpha-dihydrotestosterone levels and impacts gene expression and protein profile of breast cancer cells cultured in 17-beta-estradiol-contained medium
physiological function
the enzyme is involved in estrogen-dependent diseases
physiological function
the enzyme is involved in the biosynthesis of estradiol
physiological function
the enzyme is involved in the metabolism of steroid hormones and in the biosynthesis of cholesterol
physiological function
the expression of 17beta-hydroxysteroid dehydrogenase 1 and 2 alone and in combination predicts outcome of patients with breast cancer
additional information
Lys149 is a critical residue for the discrimination between C-18 and C-19 steroid substrate. Analysis of the role of Cys10 for 17beta-HSD1 function, overview
additional information
role of a cysteine residue, Cys10 in the Rossmann-fold NADPH binding region, for 17beta-HSD1 function, important interactions of Cys10 with residues involved in the stabilization of amino acids of the NADPH binding pocket, three-dimensional enzyme structure modeling, overview
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). DHR11_HUMAN
260
1
28308
Swiss-Prot
Mitochondrion (Reliability: 3)
H17B6_HUMAN
317
0
35966
Swiss-Prot
Secretory Pathway (Reliability: 2)
HCD2_HUMAN
261
0
26923
Swiss-Prot
other Location (Reliability: 5)
AK1C1_HUMAN
323
0
36788
Swiss-Prot
other Location (Reliability: 2)
AK1C2_HUMAN
323
0
36735
Swiss-Prot
other Location (Reliability: 2)
AK1C3_HUMAN
323
0
36853
Swiss-Prot
other Location (Reliability: 2)
AK1C4_HUMAN
323
0
37067
Swiss-Prot
other Location (Reliability: 2)
DHB7_HUMAN
341
0
38206
Swiss-Prot
other Location (Reliability: 5)
DHB8_HUMAN
261
0
26974
Swiss-Prot
Mitochondrion (Reliability: 1)
DHB14_HUMAN
270
0
28317
Swiss-Prot
other Location (Reliability: 5)
DHB1_HUMAN
328
0
34950
Swiss-Prot
Mitochondrion (Reliability: 3)
DHB2_HUMAN
387
2
42785
Swiss-Prot
Secretory Pathway (Reliability: 1)
DHB3_HUMAN
310
3
34516
Swiss-Prot
Secretory Pathway (Reliability: 1)
DHB11_HUMAN
300
0
32936
Swiss-Prot
Secretory Pathway (Reliability: 1)
DHB12_HUMAN
312
3
34324
Swiss-Prot
Secretory Pathway (Reliability: 3)
A0A0A0MQS7_HUMAN
329
0
35037
TrEMBL
Mitochondrion (Reliability: 3)
PDB
SCOP
CATH
UNIPROT
ORGANISM
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
additional information
additional information
-
sequence of a tryptic peptide containing an essential cysteine
additional information
-
sequence of a histidine-bearing peptide in the catalytic region
additional information
enzyme three-dimensional structural modeling, overview
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
phosphoprotein
-
enzyme is phosphorylated by protein kinase A exclusively at Ser134 in vitro, but this phosphorylation has no effect on the catalytic properties of the type 1 enzyme, and most likely it does not occur in vivo
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
active site analysis of 17beta-hydroxysteroid dehydrogenase type 1 enzyme complexes (estradiol/NADP+, equilin/NADP+, dehydroepiandrosterone) using the SPROUT program
crystal structure of 17beta-HSD1 complexed with testosterone or estradiol are shown. Both testosterone and estradiol bind in the narrow hydrophobic tunnel of 17beta-HSD1 with a high degree of complementarity. Testosterone is bound in an alternative orientation to 17beta-HSD1 compared with estradiol. Residue L149 plays an important role in the discrimination between C19 androgen and C18 estrogen
-
crystallization and crystal structure of the complex of the enzyme with the dual-site inhibitor, EM-139
-
hanging-drop vapour diffusion method at 27°C, binary and ternary crystal structures of the enzyme complexed with estrone and NADP+, crystals in this study belonged to the space group P212121 and contain a dimer per asymmetric unit
hanging-drop vapour diffusion method at 27°C, crystallization of the enzyme in complex with estrone and NADP+. His221 is the key residue responsible for the reorganization and stabilization of the reversely bound estrone, leading to the formation of a dead end complex, which exists widely in NADP(H)-preferred enzymes for the regulation of their enzymatic activity
in complex with ligands estradiol, equiline, 5-alpha-dihydrotestosterone, O5'-[9-(3,17beta-dihydroxy-1,3,5(10)-estratrien-16beta-yl)nonanoyl]adenosine and 3-[[(16beta,17beta)-3,17-dihydroxyestra-1,3,5(10)trien-16-yl]methyl]benzamide. Construction of pharmacophore model
ternary complex of the 17beta-hydroxysteroid dehydrogenase type 1 with 3-hydroxyestra-1,3,5,7-tetraen-17-one and NADP+
the purified enzyme variants T205 and S205 in apoform, as holoenzyme, or in complex with estrone or inhibitor [6-(3,4-dihydroxyphenyl)pyridin-2-yl]-(4-fluoro-3-hydroxyphenyl)methanone, ternary complex enzyme-cofactor-inhibitor, X-ray diffraction structure determination and analysis at 1.52-2.02 A resolution
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C10S
H221A
-
catalytic efficiency is reduced 20fold for oxidative reaction and 11fold for the reductive reaction
K159A
-
almost inactive enzyme, catalytic efficiencies of the substituted enzyme are more than 200fold lower for both reduction and oxidation compared with the values measured for the wild type enzyme
S142A
-
almost inactive enzyme, catalytic efficiencies of the substituted enzyme are more than 200fold lower for both reduction and oxidation compared with the values measured for the wild type enzyme
additional information
C10S
site-directed mutagenesis, substitution of Cys10 with Ser results in a decreased protein half-life, without significantly altering kinetic properties. Mutant Cys10Ser shows approximately 50% lower activity compared to the wild-type. Mutating Cys10 to Ser does not lead to significant changes in contacts between Ser10 and Ile7, Gly9 and Ala34. But all three contacts between Ser10 and Gly15 are shorter than between Cys10 and Gly15, and Gly15 is more distant from a phosphate oxygen on NADP+
C10S
site-directed mutagenesis, the Cys10Ser mutant 17beta-HSD1 is partially protected from inhibition by NEM and dithiocarbamates. Mutating Cys10 to Ser does not lead to significant changes in contacts between Ser10 and Ile7, Gly9 and Ala34, but all three contacts between Ser10 and Gly15 are shorter than between Cys10 and Gly15, and Gly15 is more distant from a phosphate oxygen on NADP+
additional information
-
deleting the last 36 amino acids does not have a dramatic effect on the catalytic properties
additional information
72 h treatment with 17betaHSD1 siRNA 2 significantly reduces the endogenous 17betaHSD1 expression in both A-549 and LK-87 cells
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
enzyme is cold sensitive, cold inactivation is reduced by NAD+, NADP+, estradiol or glycerol
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
copurification of 17beta-estradiol dehydrogenase and 20alpha-hydroxysteroid dehydrogenase
-
recombinant His-tagged isozymes AKR1B15.1 and AKR1B15.2 isozymes from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
chromosomal localizations of isozymes, DNA and amino acid sequence determination and analysis of isozymes 17beta-HSD1, 17beta-HSD3, 17beta-HSD4, overview
-
expressed in Sf9 insect cells
expression in Escherichia coli as an enzymatically active His-tag fusion protein
-
gene AKR1B15 located on chromosome 7, cloning of two isoforms: AKR1B15.1 and AKR1B15.2, DNA and amino acid sequence determination and analysis, recombinant expression of N-terminally His-tagged isozymes in Escherichia coli strain BL21(DE3), recombinant expression of C- or N-terminally c-Myc-tagged isozymes in HEK-293 cells
gene HSD17B1, sequence comparisons, recombinant expression in HEK-293 cells
recombinant expression of 17beta-HSD14 wild-type variants S205 and T205 in Escherichia coli strain BL21 pLysS
the complete 17beta-HSD1 (HSD17B131) and 17beta-HSD12 (HSD17B12) cDNA sequences are cloned into the pCEP4 expression vector for expression in 293-EBNA cells
transgenic mouse lines universally overexpressing human HSD17B1 are generated and characterized at fetal and adult ages
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
application of medroxyprogestrone acetate, dydrogesterone and dienogest significantly decreases isoforms HSD17B1 and CYP19A1 expression and significantly increases isoform HSD17B2 expression. Dydrogesterone and dienogest also significantly suppress estrogen receptors ESR1 and ESR2 transcription, whereas medroxyprogestrone acetate and dydrogesterone significantly reduce mRNA levels of G protein-coupled estrogen receptor 1. Results thus suggest that in peritoneal endometriosis the beneficial effects of these progestins can be explained by lower HSD17B1 and higher HSD17B2 mRNA and protein levels, which lead to reduced local estradiol biosynthesis
aromatase inhibitor treatment results in 17betaHSD1 upregulation in both A-549 and LK-87 cells
dihydrotestosterone treatment increases HSD17B2 expression, with limited effect on HSD17B1 expression
downregulation of CX3CL1, EPHB6, and TP63 increases HSD17B1 and HSD17B2 expression
elevated levels of 17beta-estradiol occur in male patients with chronic lymphocytic leukemia
expression is relatively low in most tissues and high in prostate and mammary glands in regulating androgen and estrogen levels. In many cancers, overexpression of AKR1C3 is observed
expression of HSD17B2 is increased in ERalpha-negative breast cancer
higher expression of 17beta-HSD1 mRNA is demonstrated in almost 50% of breast cancer tissues. Expression and activity of 17beta-HSD1 are significantly higher in breast cancer than in normal breast tissue
-
HSD17B1 expression is increased in breast cancer compared with unchanged tissue
HSD17B2 expression is reduced in breast cancer compared with benign tumors
HSD17B2 expression is significantly higher in invasive lobular carcinoma (ILC) than in invasive ductal carcinoma
in non-small cell lung cancer (NSCLC) the expression of HSD17B1 is increased as compared with healthy tissue
significant increment of 17beta HSD1 immunoreactivity is found in breast cancer patients treated with aromatase inhibitor exemestane
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
diagnostics
drug development
medicine
diagnostics
17beta-HSD1 is highly expressed in breast and ovary tissues and represents a prognostic marker for the tumor progression and survival of patients with breast cancer and other estrogen-dependent tumors
diagnostics
a high HSD17B1 to HSD17B2 ratio, as well as high HSD17B1 on its own is associated with worse prognosis and increased risk of recurrence in patients with ERalpha-positive tumors. An increased copy number of the HSD17B1 gene is correlated with decreased breast cancer survival
diagnostics
the expression of 17beta-hydroxysteroid dehydrogenases 1 and 2 alone and in combination predicts outcome of patients with breast cancer
diagnostics
the mouse monoclonal antibody for AKR1C3, 10B10, is highly specific and sensitive for detecting AKR1C3 expression including patient samples. The proper detection of AKR1C3 expression is critical for therapeutics targeting AKR1C3, 10B10 will be a valuable tool in clinic for AKR1C3 precision therapy. 10B10 is specific to AKR1C3 protein and has a very low cross-activity against other AKR1 proteins
drug development
-
several 17beta-HSD isozymes are targets for drug development with importance in cancer, metabolic diseases, neurodegeneration and possibly immunity
drug development
the enzyme is considered a promising drug target against estrogen-dependent cancers
drug development
the enzyme constitutes an interesting therapeutic target for estrogen-dependent diseases
medicine
binding of equilin at the active site of the enzyme is the basis for inhibition of reduction of estrone to estradiol. One possible outcome of estrogen replacement therapy in vivo can be the reduction of estradiol levels in breast tissues and hence the reduced risk of estrogen-dependent breast cancer
medicine
-
as estradiol stimulates the growth and development of hormone-dependent breast cancer, inhibition of the final step of its synthesis is an attractive target for the treatment of this disease
medicine
-
estrogenic response for estrone is enhanced by the local action of HSD17B1 in vivo. Thus the enzyme is a potential target for pharmacological inhibition of estrogen activation. Targeted inhibition of HSD17B1 is a promising therapeutic approach to modulate estrogen response in the target tissue with less severe side effects as compared with antiestrogens
medicine
-
type 1 17beta-hydroxysteroid dehydrogenase is an interesting biological target for designing drugs for the treatment of estrogen-sensitive diseases such as breast cancer
medicine
17beta-HSD1 inhibitors such as STX1040 may provide a treatment for hormone-dependent breast cancer
medicine
17beta-HSD1 is an attractive target for the treatment of mammary tumours
medicine
17beta-HSD1 is overexpressed in many breast tumors. Thus, it is an attractive target for the treatment of these diseases
medicine
disease iondications for HSD17B1 inhibitors in disorders in the female reproductive organs associated with enhanced androgen action, such as ovarian serous cystadenomas
medicine
inhibitors of the enzyme have potential as treatments for hormone dependent breast cancer
medicine
17beta-hydroxysteroid dehydrogenase type 2 is mainly involved in the conversion of estradiol into estrone. Their ratio is decreased from 9/1 to 7/3 after over-expression of 17beta-hydroxysteroid dehydrogenase type 2 in MCF-7 cells already over-expressing 17beta-hydroxysteroid dehydrogenase type 1. The ratio is further decreased by the addition of the oxidative cofactor, NAD, to the cell culture to facilitate the estradiol to estrone conversion catalyzed by 17beta-hydroxysteroid dehydrogenase type 2
medicine
application of medroxyprogestrone acetate, dydrogesterone and dienogest significantly decreases isoforms HSD17B1 and CYP19A1 expression and significantly increases isoform HSD17B2 expression. Dydrogesterone and dienogest also significantly suppress estrogen receptors ESR1 and ESR2 transcription, whereas medroxyprogestrone acetate and dydrogesterone significantly reduce mRNA levels of G protein-coupled estrogen receptor 1. Results thus suggest that in peritoneal endometriosis the beneficial effects of these progestins can be explained by lower HSD17B1 and higher HSD17B2 mRNA and protein levels, which lead to reduced local estradiol biosynthesis
medicine
isoform 17betaHSD6 is expressed in estrogen receptor beta-positive epithelial cells of the human prostate. In prostate cancers of Gleason grade higher than 3, both estrogen receptor beta and isoform 17betaHSD6 are undetectable
medicine
Patients with oestrogen positive tumours with high isoform 17betaHSD14 expression have fewer local recurrences when treated with tamoxifen compared to patients with lower tumoural 17betaHSD14 expression, for whom tamoxifen does not reduce the number of local recurrences. No prognostic importance of 17betaHSD14 is seen for systemically untreated patients
medicine
twenty four hours after addition of different concentrations of estrone and estradiol, the ratio stabilizes to around 9/1 in breast cancer cell lines with high expression of 17beta-hydroxysteroid dehydrogenase type 1, such as T47D, BT 20, and JEG 3 cells, whereas it approaches 1/5 in cells with low expression of 17beta-hydroxysteroid dehydrogenase type 1, such as MCF-7 cells. The estradiol/estrone concentration ratio is modified to 9/1 in MCF-7 and HEK-293 cells over-expressing 17beta-hydroxysteroid dehydrogenase type 1. In T47D and BT 20 cells , this ratio is decreased from 9/1 to nearly 1/5 after 17beta-hydroxysteroid dehydrogenase type 1 knockdown by specific siRNAs
medicine
17betaHSD1 is an important prognostic factor in non-small cell lung carcinoma, NSCLC, patients and targeting 17betaHSD1 activity may further improve the clinical response in estrogen responsive NSCLC patients
medicine
enzyme inhibition can lead to desired increase of estradiol and testosterone levels in the bone tissue and may be used for the treatment of osteoporosis
medicine
enzyme inhibition is considered as a treatment option for osteoporosis to ameliorate estrogen deficiency
medicine
inhibition of 17beta-hydroxysteroid dehydrogenase type 2 (17beta-HSD2) can help maintaining the appropriate bone mass density in osteoporosis by increasing the level of estradiol and testosterone in bone
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Strickler, R.C.; Tobias, B.; Covey, D.F.
Human placental 17beta-estradiol dehydrogenase and 20alpha-hydroxysteroid dehydrogenase. Two activities at a single enzyme active site
J. Biol. Chem.
256
316-321
1981
Homo sapiens
Blomquist, C.H.; Lindemann, N.J.; Hakanson, E.Y.
17beta-Hydroxysteroid and 20alpha-hydroxysteroid dehydrogenase activities of human placental microsomes: kinetic evidence for two enzymes differing in substrate specificity
Arch. Biochem. Biophys.
239
206-215
1985
Homo sapiens
Murdock, G.L.; Warren, J.C.; Sweet, F.
Human placental estradiol 17beta-dehydrogenase: evidence for inverted substrate orientation (wrong-way binding) at the active site
Biochemistry
27
4452-4458
1988
Homo sapiens
Mendoza-Hernandez, G.; Lopez-Solache, I.; Diaz-Zagoya, J.C.
Periodate-oxidized NADP+ is a powerful inhibitor of human placental estradiol-17beta dehydrogenase
Biochem. Biophys. Res. Commun.
146
645-651
1987
Homo sapiens
Mendoza-Hernandez, G.; Rendon, J.L.; Diaz-Zagoya, J.C.
A single step procedure for purification of estradiol 17beta-dehydrogenase from human placenta
Biochem. Biophys. Res. Commun.
126
477-481
1985
Homo sapiens
Mendoza-Hernandez, G.; Calcagno, M.; Sanchez-Nuncio, H.R.; Diaz-Zagoya, J.C.
Dehydroepiandrosterone is a substrate for estradiol 17beta-dehydrogenase from human placenta
Biochem. Biophys. Res. Commun.
119
83-87
1984
Homo sapiens
Pollow, K.; Luebbert, H.; Pollow, B.
On the mitochondrial 17beta-hydroxysteroid dehydrogenase from human endometrium and endometrial carcinoma: characterization and intramitochondrial distribution
J. Steroid Biochem.
7
45-50
1976
Homo sapiens
Nicolas, J.C.
Purification of an enzyme containing a NADP-protected cysteine on organomercuri-agarose 17beta-estradiol dehydrogenase
Methods Enzymol.
34
552-554
1974
Homo sapiens
Nicolas, J.C.
The soluble 17beta-estradiol dehydrogenase of human placenta
Methods Enzymol.
34
555-557
1974
Homo sapiens
Nicolas, J.C.; Harris, J.I.
Human placental 17-oestradiol dehydrogenase. Sequence of a tryptic peptide containing an essential cysteine
FEBS Lett.
29
173-176
1973
Homo sapiens
Nicolas, J.C.; Pons, M.; Descomps, B.; de Paulet, A.C
Affinity chromatography: large-scale purification of the soluble oestradiol-17-dehydrogenase of human placenta
FEBS Lett.
23
175-179
1972
Homo sapiens
Burns, D.J.W.; Engel, L.L.; Bethune, J.L.
Amino acid composition and subunit structure. Human placental 17-estradiol dehydrogenase
Biochemistry
11
2699-2703
1972
Homo sapiens
Langer, L.J.; Alexander, J.A.; Engel, L.L.
Human placental estradiol-17beta dehydrogenase
J. Biol. Chem.
234
2609-2614
1959
Homo sapiens
Luebbert, H.
Effects of ethanol and other organic solvents on the kinetic behaviour of purified human placental oestradiol-17beta-dehydrogenase
Acta Endocrinol.
99
448-453
1982
Homo sapiens
Engel, L.L.; Inano, H.
Some kinetic properties of human placental 17beta-estradiol dehydrogenase: patterns of inhibition by adenine nucleotides
Adv. Enzyme Regul.
17
363-371
1979
Homo sapiens
Pollow, K.; Luebbert, H.; Jeske, R.; Pollow, B.
Studies on 17beta-hydroxysteroid dehydrogenase in human endometrium and endometrial carcinoma
Acta Endocrinol.
79
146-156
1975
Homo sapiens
Murdock, G.L.; Chin, C.C.; Warren, J.C.
Human placental estradiol 17beta-dehydrogenase: sequence of a histidine-bearing peptide in the catalytic region
Biochemistry
25
641-646
1986
Homo sapiens
Chin, C.C.; Dence, J.B.; Warren, J.C.
Crystallization of human placental estradiol 17beta-dehydrogenase. A new method for crystallizing labile enzymes
J. Biol. Chem.
251
3700-3705
1976
Homo sapiens
Zhu, D.W.; Campbell, R.; Labrie, F.; Lin, S.X.
Crystallization and preliminary crystal structure of the complex of 17beta-hydroxysteroid dehydrogenase with a dual-site inhibitor
J. Steroid Biochem. Mol. Biol.
70
229-235
1999
Homo sapiens
Puranen, T.; Poutanen, M.; Ghosh, D.; Vihko, P.; Vihko, R.
Characterization of structural and functional properties of human 17beta-hydroxysteroid dehydrogenase type 1 using recombinant enzymes and site-directed mutagenesis
Mol. Endocrinol.
11
77-86
1997
Homo sapiens
Blomquist, C.H.; Leung, B.S.; Zhang, R.; Zhu, Y.; Chang, P.M.
Properties and regulation of 17beta-hydroxysteroid oxidoreductase of OVCAR-3, CAOV-3, and A431 cells: effects of epidermal growth factor, estradiol, and progesterone
J. Cell. Biochem.
59
409-417
1995
Homo sapiens
Ng, J.H.; Nesaretnam, K.; Reimann, K.; Lai, L.C.
Effect of retinoic acid and palm oil carotenoids on oestrone sulphatase and oestradiol-17beta hydroxysteroid dehydrogenase activities in MCF-7 and MDA-MB-231 breast cancer cell lines
Int. J. Cancer
88
135-138
2000
Homo sapiens
Malet, C.; Vacca, A.; Kuttenn, F.; Mauvais-Jarvis, P.
17beta-Estradiol dehydrogenase (E2DH) activity in T47D cells
J. Steroid Biochem. Mol. Biol.
39
769-775
1991
Homo sapiens
Newton, C.J.; Butta, A.; Nicholls, J.; Dowsett, M.
Oestradiol synthesis from oestrone in malignant breast epithelial cells: studies on a high affinity, 80 kDa form of oestradiol dehydrogenase
J. Steroid Biochem. Mol. Biol.
42
891-900
1992
Homo sapiens
Sawicki, M.W.; Erman, M.; Puranen, T.; Vihko, P.; Ghosh, D.
Structure of the ternary complex of human 17beta-hydroxysteroid dehydrogenase type 1 with 3-hydroxyestra-1,3,5,7-tetraen-17-one (equilin) and NADP+
Proc. Natl. Acad. Sci. USA
96
840-845
1999
Homo sapiens (P14061), Homo sapiens
Ghosh, D.; Pletnev, V.Z.; Zhu, D.W.; Wawrzak, Z.; Duax, W.L.; Pangborn, W.; Labrie, F.; Lin, S.X.
Structure of human estrogenic 17beta-hydroxysteroid dehydrogenase at 2.20 A resolution
Structure
3
503-513
1995
Homo sapiens
Reed, M.J.; Rea, D.; Duncan, L.J.; Parker, M.G.
Regulation of estradiol 17beta-hydroxysteroid dehydrogenase expression and activity by retinoic acid in T47D breast cancer cells
Endocrinology
135
4-9
1994
Homo sapiens
Puranen, T.J.; Poutanen, M.H.; Peltoketo, H.E.; Vihko, P.T.; Vihko, R.K.
Site-directed mutagenesis of the putative active site of human 17beta-hydroxysteroid dehydrogenase type 1
Biochem. J.
304
289-293
1994
Homo sapiens
Brown, W.M.; Metzger, L.E.; Barlow, J.P.; Hunsaker, L.A.; Deck, L.M.; Royer, R.E.; Vander Jagt, D.L.
17-beta-Hydroxysteroid dehydrogenase type 1: computational design of active site inhibitors targeted to the Rossmann fold
Chem. Biol. Interact.
143-144
481-491
2003
Homo sapiens
Qiu, W.; Campbell, R.L.; Gangloff, A.; Dupuis, P.; Boivin, R.P.; Tremblay, M.R.; Poirier, D.; Lin, S.X.
A concerted, rational design of type 1 17beta-hydroxysteroid dehydrogenase inhibitors: estradiol-adenosine hybrids with high affinity
FASEB J.
16
1829-1831
2002
Homo sapiens (P14061), Homo sapiens
Zhu, S.J.; Li, Y.; Li, H.; Wang, Y.L.; Xiao, Z.J.; Vihko, P.; Piao, Y.S.
Retinoic acids promote the action of aromatase and 17beta-hydroxysteroid dehydrogenase type 1 on the biosynthesis of 17beta-estradiol in placental cells
J. Endocrinol.
172
31-43
2002
Homo sapiens
Fiorelli, G.; Picariello, L.; Martineti, V.; Tognarini, I.; Tonelli, F.; Brandi, M.L.
Estrogen metabolism in human colorectal cancer cells
J. Steroid Biochem. Mol. Biol.
81
281-289
2002
Homo sapiens
Blomquist, C.H.; Bonenfant, M.; McGinley, D.M.; Posalaky, Z.; Lakatua, D.J.; Tuli-Puri, S.; Bealka, D.G.; Tremblay, Y.
Androgenic and estrogenic 17beta-hydroxysteroid dehydrogenase/17-ketosteroid reductase in human ovarian epithelial tumors: evidence for the type 1, 2 and 5 isoforms
J. Steroid Biochem. Mol. Biol.
81
343-351
2002
Homo sapiens
Steckelbroeck, S.; Watzka, M.; Reissinger, A.; Wegener-Toper, P.; Bidlingmaier, F.; Bliesener, N.; Hans, V.H.; Clusmann, H.; Ludwig, M.; Siekmann, L.; Klingmuller, D.
Characterisation of estrogenic 17beta-hydroxysteroid dehydrogenase (17beta-HSD) activity in the human brain
J. Steroid Biochem. Mol. Biol.
86
79-92
2003
Homo sapiens
Khan, N.; Sharma, K.K.; Andersson, S.; Auchus, R.J.
Human 17beta-hydroxysteroid dehydrogenases types 1, 2, and 3 catalyze bi-directional equilibrium reactions, rather than unidirectional metabolism, in HEK-293 cells
Arch. Biochem. Biophys.
429
50-59
2004
Homo sapiens
Poirier, D.
Inhibitors of 17beta-hydroxysteroid dehydrogenases
Curr. Med. Chem.
10
453-477
2003
Homo sapiens
Li, Y.; Qin, L.; Xiao, Z.J.; Wang, Y.L.; Herva, R.; Leng, J.H.; Lang, J.H.; Isomaa, V.; Piao, Y.S.
Expression of P450 aromatase and 17beta-hydroxysteroid dehydrogenase type 1 at fetal-maternal interface during tubal pregnancy
J. Steroid Biochem. Mol. Biol.
87
241-246
2003
Homo sapiens
Nakanishi, T.; Hiromori, Y.; Yokoyama, H.; Koyanagi, M.; Itoh, N.; Nishikawa, J.; Tanaka, K.
Organotin compounds enhance 17beta-hydroxysteroid dehydrogenase type I activity in human choriocarcinoma JAr cells: potential promotion of 17beta-estradiol biosynthesis in human placenta
Biochem. Pharmacol.
71
1349-1357
2006
Homo sapiens
Vicker, N.; Lawrence, H.R.; Allan, G.M.; Bubert, C.; Smith, A.; Tutill, H.J.; Purohit, A.; Day, J.M.; Mahon, M.F.; Reed, M.J.; Potter, B.V.
Focused libraries of 16-substituted estrone derivatives and modified e-ring steroids: inhibitors of 17beta-hydroxysteroid dehydrogenase type 1
ChemMedChem
1
464-481
2006
Homo sapiens
Husen, B.; Huhtinen, K.; Saloniemi, T.; Messinger, J.; Thole, H.H.; Poutanen, M.
Human hydroxysteroid (17-beta) dehydrogenase 1 expression enhances estrogen sensitivity of MCF-7 breast cancer cell xenografts
Endocrinology
147
5333-5339
2006
Homo sapiens
Tremblay, M.R.; Boivin, R.P.; Luu-The, V.; Poirier, D.
Inhibitors of type 1 17beta-hydroxysteroid dehydrogenase with reduced estrogenic activity: modifications of the positions 3 and 6 of estradiol
J. Enzyme Inhib. Med. Chem.
20
153-163
2005
Homo sapiens
Fischer, D.S.; Allan, G.M.; Bubert, C.; Vicker, N.; Smith, A.; Tutill, H.J.; Purohit, A.; Wood, L.; Packham, G.; Mahon, M.F.; Reed, M.J.; Potter, B.V.
E-ring modified steroids as novel potent inhibitors of 17beta-hydroxysteroid dehydrogenase type 1
J. Med. Chem.
48
5749-5770
2005
Homo sapiens
Poirier, D.; Boivin, R.P.; Tremblay, M.R.; Berube, M.; Qiu, W.; Lin, S.X.
Estradiol-adenosine hybrid compounds designed to inhibit type 1 17beta-hydroxysteroid dehydrogenase
J. Med. Chem.
48
8134-8147
2005
Homo sapiens
Song, D.; Liu, G.; Luu-The, V.; Zhao, D.; Wang, L.; Zhang, H.; Xueling, G.; Li, S.; Desy, L.; Labrie, F.; Pelletier, G.
Expression of aromatase and 17beta-hydroxysteroid dehydrogenase types 1, 7 and 12 in breast cancer. An immunocytochemical study
J. Steroid Biochem. Mol. Biol.
101
136-144
2006
Homo sapiens
Liu, H.; Robert, A.; Luu-The, V.
Cloning and characterization of human form 2 type 7 17beta-hydroxysteroid dehydrogenase, a primarily 3beta-keto reductase and estrogen activating and androgen inactivating enzyme
J. Steroid Biochem. Mol. Biol.
94
173-179
2005
Homo sapiens (Q5MGS6)
Brooks, J.D.; Thompson, L.U.
Mammalian lignans and genistein decrease the activities of aromatase and 17beta-hydroxysteroid dehydrogenase in MCF-7 cells
J. Steroid Biochem. Mol. Biol.
94
461-467
2005
Homo sapiens
Otsuka, M.; Kato, N.; Ichimura, T.; Abe, S.; Tanaka, Y.; Taniguchi, H.; Hoshida, Y.; Moriyama, M.; Wang, Y.; Shao, R.X.; Narayan, D.; Muroyama, R.; Kanai, F.; Kawabe, T.; Isobe, T.; Omata, M.
Vitamin K2 binds 17beta-hydroxysteroid dehydrogenase 4 and modulates estrogen metabolism
Life Sci.
76
2473-2482
2005
Homo sapiens
Messinger, J.; Hirvelae, L.; Husen, B.; Kangas, L.; Koskimies, P.; Pentikaeinen, O.; Saarenketo, P.; Thole, H.
New inhibitors of 17beta-hydroxysteroid dehydrogenase type 1
Mol. Cell. Endocrinol.
248
192-198
2006
Homo sapiens (P14061), Homo sapiens
Purohit, A.; Tutill, H.J.; Day, J.M.; Chander, S.K.; Lawrence, H.R.; Allan, G.M.; Fischer, D.S.; Vicker, N.; Newman, S.P.; Potter, B.V.; Reed, M.J.
The regulation and inhibition of 17beta-hydroxysteroid dehydrogenase in breast cancer
Mol. Cell. Endocrinol.
248
199-203
2006
Homo sapiens
Allan, G.M.; Bubert, C.; Vicker, N.; Smith, A.; Tutill, H.J.; Purohit, A.; Reed, M.J.; Potter, B.V.
Novel, potent inhibitors of 17beta-hydroxysteroid dehydrogenase type 1
Mol. Cell. Endocrinol.
248
204-207
2006
Homo sapiens (P14061)
Alho-Richmond, S.; Lilienkampf, A.; Waehaelae, K.
Active site analysis of 17beta-hydroxysteroid dehydrogenase type 1 enzyme complexes with SPROUT
Mol. Cell. Endocrinol.
248
208-213
2006
Homo sapiens (P14061)
Poirier, D.; Chang, H.J.; Azzi, A.; Boivin, R.P.; Lin, S.X.
Estrone and estradiol C-16 derivatives as inhibitors of type 1 17beta-hydroxysteroid dehydrogenase
Mol. Cell. Endocrinol.
248
236-238
2006
Homo sapiens (P14061)
Day, J.M.; Tutill, H.J.; Newman, S.P.; Purohit, A.; Lawrence, H.R.; Vicker, N.; Potter, B.V.; Reed, M.J.
17beta-Hydroxysteroid dehydrogenase type 1 and type 2: association between mRNA expression and activity in cell lines
Mol. Cell. Endocrinol.
248
246-249
2006
Homo sapiens
Lin, S.X.; Shi, R.; Qiu, W.; Azzi, A.; Zhu, D.W.; Dabbagh, H.A.; Zhou, M.
Structural basis of the multispecificity demonstrated by 17beta-hydroxysteroid dehydrogenase types 1 and 5
Mol. Cell. Endocrinol.
248
38-46
2006
Homo sapiens
Luu-The, V.; Tremblay, P.; Labrie, F.
Characterization of type 12 17beta-hydroxysteroid dehydrogenase, an isoform of type 3 17beta-hydroxysteroid dehydrogenase responsible for estradiol formation in women
Mol. Endocrinol.
20
437-443
2006
Homo sapiens (Q53GQ0), Homo sapiens
Nagayoshi, Y.; Ohba, T.; Yamamoto, H.; Miyahara, Y.; Tashiro, H.; Katabuchi, H.; Okamura, H.
Characterization of 17beta-hydroxysteroid dehydrogenase type 4 in human ovarian surface epithelial cells
Mol. Hum. Reprod.
11
615-621
2005
Homo sapiens
Brozic, P.; Golob, B.; Gomboc, N.; Rizner, T.L.; Gobec, S.
Cinnamic acids as new inhibitors of 17beta-hydroxysteroid dehydrogenase type 5 (AKR1C3)
Mol. Cell. Endocrinol.
248
233-235
2006
Homo sapiens
Moeller, G.; Adamski, J.
Multifunctionality of human 17beta-hydroxysteroid dehydrogenases
Mol. Cell. Endocrinol.
248
47-55
2006
Homo sapiens
Lukacik, P.; Kavanagh, K.L.; Oppermann, U.
Structure and function of human 17beta-hydroxysteroid dehydrogenases
Mol. Cell. Endocrinol.
248
61-71
2006
Homo sapiens
Laplante, Y.; Cadot, C.; Fournier, M.A.; Poirier, D.
Estradiol and estrone C-16 derivatives as inhibitors of type 1 17beta-hydroxysteroid dehydrogenase: blocking of ER+ breast cancer cell proliferation induced by estrone
Bioorg. Med. Chem.
16
1849-1860
2008
Homo sapiens (P14061), Homo sapiens
Allan, G.M.; Vicker, N.; Lawrence, H.R.; Tutill, H.J.; Day, J.M.; Huchet, M.; Ferrandis, E.; Reed, M.J.; Purohit, A.; Potter, B.V.
Novel inhibitors of 17beta-hydroxysteroid dehydrogenase type 1: templates for design
Bioorg. Med. Chem.
16
4438-4456
2008
Homo sapiens, Homo sapiens (P14061)
Bey, E.; Marchais-Oberwinkler, S.; Kruchten, P.; Frotscher, M.; Werth, R.; Oster, A.; Alguel, O.; Neugebauer, A.; Hartmann, R.W.
Design, synthesis and biological evaluation of bis(hydroxyphenyl) azoles as potent and selective non-steroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 1 (17beta-HSD1) for the treatment of estrogen-dependent diseases
Bioorg. Med. Chem.
16
6423-6435
2008
Homo sapiens, Homo sapiens (P14061)
Brozic, P.; Lanisnik Risner, T.; Gobec, S.
Inhibitors of 17beta-hydroxysteroid dehydrogenase type 1
Curr. Med. Chem.
15
137-150
2008
Homo sapiens (P14061)
Bydal, P.; Luu-The, V.; Labrie, F.; Poirier, D.
Steroidal lactones as inhibitors of 17beta-hydroxysteroid dehydrogenase type 5: Chemical synthesis, enzyme inhibitory activity, and assessment of estrogenic and androgenic activities
Eur. J. Med. Chem.
44
632-644
2008
Homo sapiens
Day, J.M.; Foster, P.A.; Tutill, H.J.; Parsons, M.F.; Newman, S.P.; Chander, S.K.; Allan, G.M.; Lawrence, H.R.; Vicker, N.; Potter, B.V.; Reed, M.J.; Purohit, A.
17beta-Hydroxysteroid dehydrogenase type 1, and not type 12, is a target for endocrine therapy of hormone-dependent breast cancer
Int. J. Cancer
122
1931-1940
2008
Homo sapiens (P14061), Homo sapiens
Frotscher, M.; Ziegler, E.; Marchais-Oberwinkler, S.; Kruchten, P.; Neugebauer, A.; Fetzer, L.; Scherer, C.; Mueller-Vieira, U.; Messinger, J.; Thole, H.; Hartmann, R.W.
Design, synthesis, and biological evaluation of (hydroxyphenyl)naphthalene and -quinoline derivatives: potent and selective nonsteroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 1 (17beta-HSD1) for the treatment of estrogen-dependent disease
J. Med. Chem.
51
2158-2169
2008
Homo sapiens (P14061)
Luu-The, V.; Ferraris, C.; Duche, D.; Belanger, P.; Leclaire, J.; Labrie, F.
Steroid metabolism and profile of steroidogenic gene expression in Episkin: high similarity with human epidermis
J. Steroid Biochem. Mol. Biol.
107
30-36
2007
Homo sapiens
Ohno, S.; Nishikawa, K.; Honda, Y.; Nakajin, S.
Expression in E. coli and tissue distribution of the human homologue of the mouse Ke 6 gene, 17beta-hydroxysteroid dehydrogenase type 8
Mol. Cell. Biochem.
309
209-215
2008
Homo sapiens
Saloniemi, T.; Lamminen, T.; Huhtinen, K.; Welsh, M.; Saunders, P.; Kujari, H.; Poutanen, M.
Activation of androgens by hydroxysteroid (17beta) dehydrogenase 1 in vivo as a cause of prenatal masculinization and ovarian benign serous cystadenomas
Mol. Endocrinol.
21
2627-2636
2007
Homo sapiens (P14016)
Fournier, D.; Poirier, D.; Mazumdar, M.; Lin, S.X.
Design and synthesis of bisubstrate inhibitors of type 1 17beta-hydroxysteroid dehydrogenase: overview and perspectives
Eur. J. Med. Chem.
43
2298-2306
2008
Homo sapiens (P14061)
Marchais-Oberwinkler, S.; Kruchten, P.; Frotscher, M.; Ziegler, E.; Neugebauer, A.; Bhoga, U.; Bey, E.; Mueller-Vieira, U.; Messinger, J.; Thole, H.; Hartmann, R.W.
Substituted 6-phenyl-2-naphthols. Potent and selective nonsteroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 1 (17beta-HSD1): design, synthesis, biological evaluation, and pharmacokinetics
J. Med. Chem.
51
4685-4698
2008
Homo sapiens (P14061)
El-Kabbani, O.; Scammells, P.J.; Gosling, J.; Dhagat, U.; Endo, S.; Matsunaga, T.; Soda, M.; Hara, A.
Structure-guided design, synthesis, and evaluation of salicylic acid-based inhibitors targeting a selectivity pocket in the active site of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1)
J. Med. Chem.
52
3259-3264
2009
Homo sapiens
Bellemare, V.; Laberge, P.; Noel, S.; Tchernof, A.; Luu-The, V.
Differential estrogenic 17beta-hydroxysteroid dehydrogenase activity and type 12 17beta-hydroxysteroid dehydrogenase expression levels in preadipocytes and differentiated adipocytes
J. Steroid Biochem. Mol. Biol.
114
129-134
2009
Homo sapiens
Kruchten, P.; Werth, R.; Bey, E.; Oster, A.; Marchais-Oberwinkler, S.; Frotscher, M.; Hartmann, R.W.
Selective inhibition of 17beta-hydroxysteroid dehydrogenase type 1 (17betaHSD1) reduces estrogen responsive cell growth of T47-D breast cancer cells
J. Steroid Biochem. Mol. Biol.
114
200-206
2009
Homo sapiens
Al-Soud, Y.A.; Bey, E.; Oster, A.; Marchais-Oberwinkler, S.; Werth, R.; Kruchten, P.; Frotscher, M.; Hartmann, R.W.
The role of the heterocycle in bis(hydroxyphenyl)triazoles for inhibition of 17beta-hydroxysteroid dehydrogenase (17beta-HSD) type 1 and type 2
Mol. Cell. Endocrinol.
301
212-215
2009
Homo sapiens
Messinger, J.; Husen, B.; Koskimies, P.; Hirvelae, L.; Kallio, L.; Saarenketo, P.; Thole, H.
Estrone C15 derivatives--a new class of 17beta-hydroxysteroid dehydrogenase type 1 inhibitors
Mol. Cell. Endocrinol.
301
216-224
2009
Homo sapiens (P14061), Homo sapiens
Karkola, S.; Alho-Richmond, S.; Wahala, K.
Pharmacophore modelling of 17beta-HSD1 enzyme based on active inhibitors and enzyme structure
Mol. Cell. Endocrinol.
301
225-228
2009
Homo sapiens (P14061)
Brozic, P.; Kocbek, P.; Sova, M.; Kristl, J.; Martens, S.; Adamski, J.; Gobec, S.; Lanisnik Rizner, T.
Flavonoids and cinnamic acid derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 1
Mol. Cell. Endocrinol.
301
229-234
2009
Homo sapiens (P14061)
Nashev, L.G.; Schuster, D.; Laggner, C.; Sodha, S.; Langer, T.; Wolber, G.; Odermatt, A.
The UV-filter benzophenone-1 inhibits 17beta-hydroxysteroid dehydrogenase type 3: Virtual screening as a strategy to identify potential endocrine disrupting chemicals
Biochem. Pharmacol.
79
1189-1199
2010
Homo sapiens
Oster, A.; Klein, T.; Werth, R.; Kruchten, P.; Bey, E.; Negri, M.; Marchais-Oberwinkler, S.; Frotscher, M.; Hartmann, R.W.
Novel estrone mimetics with high 17beta-HSD1 inhibitory activity
Bioorg. Med. Chem.
18
3494-3505
2010
Homo sapiens (P14061)
Chanplakorn, N.; Chanplakorn, P.; Suzuki, T.; Ono, K.; Chan, M.; Miki, Y.; Saji, S.; Ueno, T.; Toi, M.; Sasano, H.
Increased estrogen sulfatase (STS) and 17hydroxysteroid dehydrogenase type l(17-HSD1) following neoadjuvant aromatase inhibitor therapy in breast cancer patients
Breast Cancer Res. Treat.
120
639-648
2010
Homo sapiens
Hong, Y.; Chen, S.
Aromatase, estrone sulfatase, and 17beta-hydroxysteroid dehydrogenase: Structure-function studies and inhibitor development
Mol. Cell. Endocrinol.
340
120-126
2011
Homo sapiens
Negri, M.; Recanatini, M.; Hartmann, R.W.
Insights in 17beta-HSD1 enzyme kinetics and ligand binding by dynamic motion investigation
PLoS ONE
5
e12026
2010
Homo sapiens (P14061)
Starcevic, S.; Brozic, P.; Turk, S.; Cesar, J.; Lanisnik Rizner, T.; Gobec, S.
Synthesis and biological evaluation of (6- and 7-Phenyl) coumarin derivatives as selective nonsteroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 1
J. Med. Chem.
54
248-261
2011
Homo sapiens (P14061)
Beranic, N.; Rizner, T.L.
Effects of progestins on local estradiol biosynthesis and action in the Z-12 endometriotic epithelial cell line
J. Steroid Biochem. Mol. Biol.
132
303-310
2012
Homo sapiens (P14061), Homo sapiens (P37059), Homo sapiens
Spadaro, A.; Negri, M.; Marchais-Oberwinkler, S.; Bey, E.; Frotscher, M.
Hydroxybenzothiazoles as new nonsteroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 1 (17beta-HSD1)
PLoS ONE
7
e29252
2012
Homo sapiens (P14061)
Zhang, C.; Chen, J.; Yin, D.; Lin, S.
The contribution of 17beta-hydroxysteroid dehydrogenase type 1 to the estradiol-estrone ratio in estrogen-sensitive breast cancer cells
PLoS ONE
7
e29835
2012
Homo sapiens (P14061), Homo sapiens (P37059)
Sivik, T.; Gunnarsson, C.; Fornander, T.; Nordenskjoeld, B.; Skoog, L.; Stal, O.; Jansson, A.
17beta-Hydroxysteroid dehydrogenase type 14 is a predictive marker for tamoxifen response in oestrogen receptor positive breast cancer
PLoS ONE
7
e40568
2012
Homo sapiens (Q9BPX1)
Muthusamy, S.; Andersson, S.; Kim, H.J.; Butler, R.; Waage, L.; Bergerheim, U.; Gustafsson, J.A.
Estrogen receptor beta and 17beta-hydroxysteroid dehydrogenase type 6, a growth regulatory pathway that is lost in prostate cancer
Proc. Natl. Acad. Sci. USA
108
20090-20094
2011
Homo sapiens (O14756)
Strugala, A.J.; Jagodzinski, P.P.
Conversion of estrone to 17 beta-estradiol in Jurkat acute T cell leukemia Hut-78 T- and Raji B lymphoma cell lines in vitro
Biomed. Pharmacother.
67
299-303
2013
Homo sapiens (P14061)
Perspicace, E.; Giorgio, A.; Carotti, A.; Marchais-Oberwinkler, S.; Hartmann, R.W.
Novel N-methylsulfonamide and retro-N-methylsulfonamide derivatives as 17beta-hydroxysteroid dehydrogenase type 2 (17beta-HSD2) inhibitors with good ADME-related physicochemical parameters
Eur. J. Med. Chem.
69
201-215
2013
Homo sapiens (P14061), Homo sapiens (P37059)
Maltais, R.; Trottier, A.; Delhomme, A.; Barbeau, X.; Laguee, P.; Poirier, D.
Identification of fused 16beta,17beta-oxazinone-estradiol derivatives as a new family of non-estrogenic 17beta-hydroxysteroid dehydrogenase type 1 inhibitors
Eur. J. Med. Chem.
93
470-480
2015
Homo sapiens (P14061)
Nashev, L.; Atanasov, A.; Baker, M.; Odermatt, A.
Cysteine-10 on 17beta-hydroxysteroid dehydrogenase 1 has stabilizing interactions in the cofactor binding region and renders sensitivity to sulfhydryl modifying chemicals
Int. J. Cell Biol.
2013
769536
2013
Homo sapiens (P14061)
Weber, S.; Salabei, J.K.; Moeller, G.; Kremmer, E.; Bhatnagar, A.; Adamski, J.; Barski, O.A.
Aldo-keto Reductase 1B15 (AKR1B15): a mitochondrial human aldo-keto reductase with activity toward steroids and 3-keto-acyl-CoA conjugates
J. Biol. Chem.
290
6531-6545
2015
Homo sapiens (C9JRZ8)
Herman, B.E.; Szabo, J.; Bacsa, I.; Woelfling, J.; Schneider, G.; Balint, M.; Hetenyi, C.; Mernyak, E.; Szecsi, M.
Comparative investigation of the in vitro inhibitory potencies of 13-epimeric estrones and D-secoestrones towards 17beta-hydroxysteroid dehydrogenase type 1
J. Enzyme Inhib. Med. Chem.
36 (Suppl.3)
61-69
2016
Homo sapiens (P14061)
Maltais, R.; Ayan, D.; Trottier, A.; Barbeau, X.; Laguee, P.; Bouchard, J.E.; Poirier, D.
Discovery of a non-estrogenic irreversible inhibitor of 17beta-hydroxysteroid dehydrogenase type 1 from 3-substituted-16beta-(m-carbamoylbenzyl)-estradiol derivatives
J. Med. Chem.
57
204-222
2014
Homo sapiens
Vuorinen, A.; Engeli, R.; Meyer, A.; Bachmann, F.; Griesser, U.J.; Schuster, D.; Odermatt, A.
Ligand-based pharmacophore modeling and virtual screening for the discovery of novel 17beta-hydroxysteroid dehydrogenase 2 inhibitors
J. Med. Chem.
57
5995-6007
2014
Homo sapiens (P37059)
Bertoletti, N.; Braun, F.; Lepage, M.; Moeller, G.; Adamski, J.; Heine, A.; Klebe, G.; Marchais-Oberwinkler, S.
New insights into human 17beta-hydroxysteroid dehydrogenase type 14: first crystal structures in complex with a steroidal ligand and with a potent nonsteroidal inhibitor
J. Med. Chem.
59
6961-6967
2016
Homo sapiens (Q9BPX1)
Verma, M.; Miki, Y.; Abe, K.; Suzuki, T.; Niikawa, H.; Suzuki, S.; Kondo, T.; Sasano, H.
Intratumoral localization and activity of 17beta-hydroxysteroid dehydrogenase type 1 in non-small cell lung cancer: A potent prognostic factor
J. Transl. Med.
11
167-177
2013
Homo sapiens (P14061)
Gargano, E.M.; Allegretta, G.; Perspicace, E.; Carotti, A.; Van Koppen, C.; Frotscher, M.; Marchais-Oberwinkler, S.; Hartmann, R.W.
17beta-Hydroxysteroid dehydrogenase type 2 inhibition: discovery of selective and metabolically stable compounds inhibiting both the human enzyme and its murine ortholog
PLoS ONE
10
e0134754
2015
Homo sapiens (P37059), Mus musculus (P51658)
Salah, M.; Abdelsamie, A.S.; Frotscher, M.
First dual inhibitors of steroid sulfatase (STS) and 17beta-hydroxysteroid dehydrogenase type 1 (17beta-HSD1) designed multiple ligands as novel potential therapeutics for estrogen-dependent diseases
J. Med. Chem.
60
4086-4092
2017
Homo sapiens (P14061)
Trottier, A.; Maltais, R.; Ayan, D.; Barbeau, X.; Roy, J.; Perreault, M.; Poulin, R.; Laguee, P.; Poirier, D.
Insight into the mode of action and selectivity of PBRM, a covalent steroidal inhibitor of 17beta-hydroxysteroid dehydrogenase type 1
Biochem. Pharmacol.
144
149-161
2017
Homo sapiens (P14061)
Ferrante, T.; Adinolfi, S.; DArrigo, G.; Poirier, D.; Daga, M.; Lolli, M.L.; Balliano, G.; Spyrakis, F.; Oliaro-Bosso, S.
Multiple catalytic activities of human 17beta-hydroxysteroid dehydrogenase type 7 respond differently to inhibitors
Biochimie
170
106-117
2020
Homo sapiens (P56937)
Boutin, S.; Roy, J.; Maltais, R.; Alata, W.; Calon, F.; Poirier, D.
Identification of steroidal derivatives inhibiting the transformations of allopregnanolone and estradiol by 17beta-hydroxysteroid dehydrogenase type 10
Bioorg. Med. Chem. Lett.
28
3554-3559
2018
Homo sapiens (Q99714)
Boutin, S.; Maltais, R.; Roy, J.; Poirier, D.
Synthesis of 17beta-hydroxysteroid dehydrogenase type 10 steroidal inhibitors selectivity, metabolic stability and enhanced potency
Eur. J. Med. Chem.
209
112909
2021
Homo sapiens
Li, T.; Stephen, P.; Zhu, D.W.; Shi, R.; Lin, S.X.
Crystal structures of human 17beta-hydroxysteroid dehydrogenase type 1 complexed with estrone and NADP+ reveal the mechanism of substrate inhibition
FEBS J.
286
2155-2166
2019
Homo sapiens (P14061)
Theriault, J.F.; Lin, S.X.
The dual sex hormone specificity for human reductive 17beta-hydroxysteroid dehydrogenase type 7 Synergistic function in estrogen and androgen control
J. Steroid Biochem. Mol. Biol.
186
61-65
2019
Homo sapiens (P56937)
Aka, J.; Calvo, E.; Lin, S.
Estradiol-independent modulation of breast cancer transcript profile by 17beta-hydroxysteroid dehydrogenase type 1
Mol. Cell. Endocrinol.
439
175-186
2017
Homo sapiens (P14061)
Salah, M.; Abdelsamie, A.S.; Frotscher, M.
Inhibitors of 17?-hydroxysteroid dehydrogenase type 1, 2 and 14 Structures, biological activities and future challenges
Mol. Cell. Endocrinol.
489
66-81
2019
Homo sapiens (P14061), Homo sapiens (P37059)
Penning, T.M.
AKR1C3 (type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase) Roles in malignancy and endocrine disorders
Mol. Cell. Endocrinol.
489
82-91
2019
Homo sapiens (P42330)
Hilborn, E.; Stal, O.; Jansson, A.
Estrogen and androgen-converting enzymes 17beta-hydroxysteroid dehydrogenase and their involvement in cancer with a special focus on 17beta-hydroxysteroid dehydrogenase type 1, 2, and breast cancer
Oncotarget
8
30552-30562
2017
Homo sapiens (P14061), Homo sapiens (P37059)
Hilborn, E.; Stal, O.; Alexeyenko, A.; Jansson, A.
The regulation of hydroxysteroid 17beta-dehydrogenase type 1 and 2 gene expression in breast cancer cell lines by estradiol, dihydrotestosterone, microRNAs, and genes related to breast cancer
Oncotarget
8
62183-62194
2017
Homo sapiens (P37059)
Liu, J.; He, P.; Lin, L.; Zhao, Y.; Deng, W.; Ding, H.; Li, Q.; Wang, Z.
Characterization of a highly specific monoclonal antibody against human aldo-keto reductase AKR1C3
Steroids
143
73-79
2019
Homo sapiens (P42330), Homo sapiens
Sali, V.K.; Mani, S.; Meenaloshani, G.; Velmurugan Ilavarasi, A.; Vasanthi, H.R.
Type 5 17-hydroxysteroid dehydrogenase/prostaglandin F synthase (AKR1C3) inhibition and potential anti-proliferative activity of cholest-4-ene-3,6-dione in MCF-7 breast cancer cells
Steroids
159
108638
2020
Homo sapiens (P42330)
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