Information on EC 1.1.1.62 - 17beta-estradiol 17-dehydrogenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.1.1.62
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RECOMMENDED NAME
GeneOntology No.
17beta-estradiol 17-dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
17beta-estradiol + NAD(P)+ = estrone + NAD(P)H + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
estradiol biosynthesis I (via estrone)
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Steroid hormone biosynthesis
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
17beta-estradiol:NAD(P)+ 17-oxidoreductase
The enzyme oxidizes or reduces the hydroxy/keto group on C17 of estrogens and androgens in mammals and regulates the biological potency of these steroids. The mammalian enzyme is bifunctional and also catalyses EC 1.1.1.270, 3beta-hydroxysteroid 3-dehydrogenase [3]. The enzyme also acts on (S)-20-hydroxypregn-4-en-3-one and related compounds, oxidizing the (S)-20-group, but unlike EC 1.1.1.149, 20alpha-hydroxysteroid dehydrogenase, it is Si-specific with respect to NAD(P)+.
CAS REGISTRY NUMBER
COMMENTARY hide
9028-61-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(S)-indan-1-ol + NADP+
indan-1-one + NADPH
show the reaction diagram
-
-
-
?
1,2-dimethyl-6-dehydroestrone + NADH
1,2-dimethyl-6-dehydroestradiol + NAD+
show the reaction diagram
-
-
-
-
?
1,2-dimethylestradiol + NAD+
1,2-dimethylestrone + NADH
show the reaction diagram
-
-
-
-
r
1,2-dimethylestrone + NADH
1,2-dimethylestradiol + NAD+
show the reaction diagram
-
-
-
-
r
1,3-dimethyl-6-dehydroestrone + NADH
1,3-dimethyl-6-dehydroestradiol + NAD+
show the reaction diagram
-
-
-
-
?
1,4-diacetoxy-1,3,5(10)-estratrien-17-one + NADH
17beta-hydroxy-1,4-diacetoxy-1,3,5(10)-estratriene + NAD+
show the reaction diagram
-
-
-
-
?
1,4-dihydroxy-1,3,5(10)-estratrien-17-one + NADH
1,4,17-trihydroxy-1,3,5(10)-estratrien + NAD+
show the reaction diagram
-
-
-
-
?
1-methyl-6-dehydroestradiol + NAD+
1-methyl-6-dehydroestrone + NADH
show the reaction diagram
-
-
-
-
r
1-methyl-6-dehydroestrone + NADH
1-methyl-6-dehydroestradiol + NAD+
show the reaction diagram
-
-
-
-
r
1-methylestradiol + NAD+
1-methylestrone + NADH
show the reaction diagram
-
-
-
-
?
11-ketoequilenin acetate + NADH
17beta-hydroxy-11-ketoequilenin acetate + NAD+
show the reaction diagram
-
-
-
-
?
11alpha-hydroxyestradiol + NAD+
11alpha-hydroxyestrone + NADH
show the reaction diagram
-
-
-
-
?
11beta-hydroxyestradiol + NAD+
11beta-hydroxyestrone + NADH
show the reaction diagram
-
-
-
-
?
16-ketoestrone + NADH
16-ketoestradiol + NAD+
show the reaction diagram
-
-
-
-
?
17beta-estradiol + NADP+
estrone + NADPH
show the reaction diagram
17beta-hydroxyestra-4-en-3-one + NADP+
estra-4-en-3,17-dione + NADPH + H+
show the reaction diagram
-
-
-
-
r
18-nor-D-homoestrone 3-methyl ether + NADH
18-nor-D-homoestradiol 3-methyl ether + NAD+
show the reaction diagram
-
-
-
-
?
19-nortestosterone + NAD+
4-estren-3,17-dione + NADH
show the reaction diagram
-
2% of the activity with estradiol-17beta
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-
?
2,4-dinitroestradiol + NAD+
2,4-dinitroestrone + NADH
show the reaction diagram
-
-
-
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r
2,4-dinitroestrone + NADH
2,4-dinitroestradiol + NAD+
show the reaction diagram
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-
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r
2,4-dinitroestrone 3-oxyacetic acid ether + NADH
2,4-dinitroestradiol 3-oxyacetic acid ether + NAD+
show the reaction diagram
-
-
-
-
?
2,5(10)-estradiene-1,4,17-trione + NADH
17beta-hydroxy-2,5(10)-estradiene-1,4-dione + NAD+
show the reaction diagram
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-
-
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?
2-aminoestradiol + NAD+
2-aminoestrone + NADH
show the reaction diagram
-
-
-
-
?
2-methoxyestrone + NADH
2-methoxyestradiol + NAD+
show the reaction diagram
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-
-
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?
2-methylestradiol + NAD+
2-methylestrone + NADH
show the reaction diagram
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-
-
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?
2-nitroestradiol + NAD+
2-nitroestrone + NADH
show the reaction diagram
-
-
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r
2-nitroestrone + NADH
2-nitroestradiol + NAD+
show the reaction diagram
-
-
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r
2-nitroestrone 3-oxyacetic acid ester + NADH + H+
2-nitroestradiol-17beta-3-oxyacetic acid ester + NAD+
show the reaction diagram
-
-
-
-
?
20alpha-hydroxy-4-pregnen-3-one + NADP+
4-pregnen-3,20-dione + NADPH
show the reaction diagram
3-hydroxy-2,5(10)-estradiene-1,4,17-trione + NADH
3,17beta-dihydroxy-2,5(10)-estradiene-1,4-dione + NAD+
show the reaction diagram
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-
-
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?
3-methyl-O-estradiol + NAD(P)+
3-methyl-O-estrone + NAD(P)H
show the reaction diagram
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-
-
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?
3-O-methyl-17beta-estradiol + NAD+
3-O-methylestrone + NADH
show the reaction diagram
3beta-hydroxyandrost-5-en-17-one + NADPH
3beta,17beta-dihydroxyandrost-5-ene + NADP+
show the reaction diagram
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i.e. dehydroepiandrosterone
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?
4-aminoestrone + NADH
4-aminoestradiol + NAD+
show the reaction diagram
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-
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?
4-aminoestrone 3,4-diacetate + NADH
4-aminoestradiol 3,4-diacetate + NAD+
show the reaction diagram
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-
-
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?
4-androstene-3,17-dione + NADPH + H+
testosterone + NADP+
show the reaction diagram
4-androstenedione + NAD(P)H + H+
testosterone + NAD(P)+
show the reaction diagram
-
-
-
?
4-estrene-3,17-dione + NADH + H+
4-estrene-17beta-ol-3-one + NAD+
show the reaction diagram
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-
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r
4-estrene-3,17-dione + NADPH
4-estrene-17beta-ol-3-one + NADP+
show the reaction diagram
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-
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r
4-estrene-3,17-dione + NADPH + H+
4-estrene-17beta-ol-3-one + NADP+
show the reaction diagram
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-
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r
4-methyl-1,3,5(10)-estratriene-1,17beta-diol + NAD+
1-hydroxy-4-methyl-1,3,5(10)-estratriene-17-one + NADH
show the reaction diagram
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-
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?
4-nitrestrone + NADH
4-nitroestradiol + NAD+
show the reaction diagram
-
-
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r
4-nitroestradiol + NAD+
4-nitroestrone + NADH
show the reaction diagram
-
-
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r
5,7,9-estratrien-3beta-ol-17-one + NADH
5,7,9-estratriene-3beta,17beta-diol + NAD+
show the reaction diagram
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?
5,7,9-estratriene-3beta,17beta-diol + NAD+
5,7,9-estratriene-3beta-ol-17-one + NADH
show the reaction diagram
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-
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?
5-androstene-3beta,17beta-diol + NAD+
5-androstene-3-beta-ol-17-one + NADH
show the reaction diagram
-
5.9% of the activity with estradiol
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?
5-androstene-3beta-ol-17-one + NADPH
5-androstene-3beta,17beta-diol + NADP+
show the reaction diagram
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-
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?
5alpha-adrostane-3alpha,17beta-diol + NAD+
androsterone + NADH
show the reaction diagram
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-
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?
5alpha-androstane-3,17-dione + NADH + H+
5alpha-androstane-17beta-ol-3-one + NAD+
show the reaction diagram
-
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r
5alpha-dihydrotestosterone + NAD+
5alpha-androstan-3,17-dione + NADH
show the reaction diagram
-
3.2% of the activity with estradiol
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?
5alpha-dihydrotestosterone + NADH
5alpha-androstanedione + NAD+
show the reaction diagram
-
-
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?
5alpha-dihydrotestosterone + NADP+
5alpha-androstan-3,17-dione + NADPH
show the reaction diagram
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3,17-dione + NADP+
show the reaction diagram
-
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstane-3beta,17beta-diol + 5alpha-androstane-3,17-dione + NADP+
show the reaction diagram
-
-
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?
5beta-pregnan-20alpha-ol-3-one + NADPH
5beta-pregnane-3,20-dione + NADP+
show the reaction diagram
-
-
-
?
6-dehydroestrone 3-benzoate + NADH
6-dehydro-17beta-estradiol 3-benzoate + NAD+
show the reaction diagram
-
-
-
-
?
6-ketoestrone + NADH
6-ketoestradiol-17beta + NAD+
show the reaction diagram
-
-
-
-
?
6alpha,7alpha-dihydroxyestrone + NADH
6alpha,7alpha-dihydroxyestradiol + NAD+
show the reaction diagram
-
-
-
-
?
6alpha-hydroxyestradiol + NAD+
6alpha-hydroxyestrone + NADH
show the reaction diagram
-
-
-
-
?
7-ketoestrone + NADH
7-ketoestradiol-17beta + NAD+
show the reaction diagram
-
-
-
-
?
7alpha-hydroxyestradiol + NAD+
7alpha-hydroxyestrone + NADH
show the reaction diagram
-
-
-
-
?
7alpha-hydroxyestrone + NADH
7alpha-hydroxyestradiol + NAD+
show the reaction diagram
-
-
-
-
r
7beta-hydroxyestrone + NADH
7beta-hydroxyestradiol + NAD+
show the reaction diagram
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
show the reaction diagram
-
-
-
-
?
androst-4-ene-3,17-dione + NADH + H+
testosterone + NAD+
show the reaction diagram
-
-
-
r
androst-4-ene-3,17-dione + NADPH
androst-4-ene-17beta-ol-3-one + NADP+
show the reaction diagram
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-
-
-
-
androstenedione + NAD(P)H + H+
testosterone + NADP+
show the reaction diagram
-
-
-
?
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
androsterone + NAD(P)H
5alpha-androstane-3alpha,17beta-diol + NAD(P)+ + H+
show the reaction diagram
-
-
-
?
benzene dihydrodiol + NADP+
catechol + NADPH
show the reaction diagram
-
-
-
?
dehydroepiandrosterone + NAD(P)H
5-androstene-3beta,17beta-diol + NAD(P)+
show the reaction diagram
-
-
-
?
dehydroepiandrosterone + NAD(P)H
androst-5-ene-3beta,17beta-diol + NAD(P)+
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone + NADP+
?
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone + NADPH + H+
5-androstene-3beta,17beta-diol + NADP+
show the reaction diagram
-
-
-
-
?
dihydrotestosterone + NAD(P)H + H+
androstane-3beta,17beta-diol + NAD(P)+
show the reaction diagram
-
-
-
-
?
dihydrotestosterone + NADPH + H+
5alpha-androstane-3beta,17beta-diol + NADP+
show the reaction diagram
-
-
-
-
?
DL-3-deoxyequilenin + NADH
17beta-hydroxy-DL-3-deoxyequilin + NAD+
show the reaction diagram
-
-
-
-
?
DL-6-methoxy-3-deoxy-equilenin + NAD+
17beta-hydroxy-DL-6-methoxy-3-deoxyequilenin + NAD+
show the reaction diagram
-
-
-
-
?
epitestosterone + NADP+
4-androsten-3,17-dione + NADPH + H+
show the reaction diagram
-
poor substrate
-
-
?
equilenin + NADH
17beta-hydroxyequilenin + NAD+
show the reaction diagram
-
-
-
-
?
equilin + NADH
17beta-hydroxyequilin + NAD+
show the reaction diagram
-
-
-
-
?
estradiol + NAD(P)+
estrone + NAD(P)H
show the reaction diagram
-
-
-
-
?
estradiol + NAD+
estrone + NADH + H+
show the reaction diagram
estradiol + NADP+
estrone + NADPH
show the reaction diagram
-
the equilibrium state is 92% estradiol to 8% estrone
-
-
?
estradiol + NADP+
estrone + NADPH + H+
show the reaction diagram
-
-
-
-
?
estradiol-17alpha + NADP+
estrone + NADPH
show the reaction diagram
-
at about 3% of the activity with estradiol-17beta
-
-
?
estradiol-17beta + NAD(P)+
estrone + NAD(P)H
show the reaction diagram
estradiol-17beta + NAD(P)+
estrone + NAD(P)H + H+
show the reaction diagram
estradiol-17beta + NAD+
estrone + NADH
show the reaction diagram
estradiol-17beta + NAD+
estrone + NADH + H+
show the reaction diagram
estradiol-17beta + NADP+
estrone + NADPH
show the reaction diagram
estradiol-17beta + NADP+
estrone + NADPH + H+
show the reaction diagram
estrone + NAD(P)H
estradiol + NAD(P)+
show the reaction diagram
estrone + NAD(P)H
estradiol-17beta + NAD(P)+
show the reaction diagram
estrone + NAD(P)H + H+
estradiol + NAD(P)+
show the reaction diagram
estrone + NAD(P)H + H+
estradiol-17beta + NAD(P)+
show the reaction diagram
estrone + NADH
estradiol-17beta + NAD+
show the reaction diagram
estrone + NADH + H+
estradiol + NAD+
show the reaction diagram
estrone + NADH + H+
estradiol-17beta + NAD+
show the reaction diagram
estrone + NADPH
17beta-estradiol + NADP+
show the reaction diagram
estrone + NADPH
estradiol + NADP+ + H+
show the reaction diagram
-
-
-
-
?
estrone + NADPH + H+
estradiol + NADP+
show the reaction diagram
-
-
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP
show the reaction diagram
-
-
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
show the reaction diagram
estrone 3-methyl ether + NADH
3-O-methyl-17beta-estradiol + NAD+
show the reaction diagram
-
-
-
-
?
estrone 3-oxyacetic acid ether + NADH
17beta-estradiol 3-O-oxyacetic acid ether + NAD+
show the reaction diagram
-
-
-
-
?
estronesulfate + NADPH
17beta-estradiolsulfate + NADP+
show the reaction diagram
-
-
-
-
r
pregn-4-en-20alpha-ol-3-one + NADP+
progesterone + NADPH
show the reaction diagram
-
-
-
?
progesterone + NADPH
? + NADP+
show the reaction diagram
-
low activity
-
-
?
S-tetralol + NADP+
?
show the reaction diagram
-
-
-
-
?
testosterone + NAD(P)+
4-androstene-3,17-dione + NAD(P)H
show the reaction diagram
-
17beta-HSD2 and 5, key role in regulating steroid receptor occupancy in normal and tumor tissues
-
-
?
testosterone + NAD+
4-androstene-3,17-dione + NADH
show the reaction diagram
testosterone + NADP+
4-androstene-3,17-dione + NADPH + H+
show the reaction diagram
zymosterone + NAD(P)H
zymosterol + NAD(P)+
show the reaction diagram
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
17beta-estradiol + NADP+
estrone + NADPH
show the reaction diagram
-
-
-
-
?
4-androstene-3,17-dione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
17beta-HSD3 and 5, formation of active androgens in testis and prostate
-
-
?
4-estrene-3,17-dione + NADPH
4-estrene-17beta-ol-3-one + NADP+
show the reaction diagram
-
-
-
-
r
5alpha-dihydrotestosterone + NADP+
5alpha-androstan-3,17-dione + NADPH
show the reaction diagram
Q5MGS6
the enzyme could play a critical role in estrogen-sensitive cells, since it inactivates 5alpha-dihydrotestosterone that generally shows antagonistic effect in the cells
-
-
?
androstenedione + NAD(P)H + H+
testosterone + NADP+
show the reaction diagram
P14016
-
-
-
?
estradiol-17beta + NAD(P)+
estrone + NAD(P)H
show the reaction diagram
-
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+
show the reaction diagram
-
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
show the reaction diagram
-
-
-
-
-
estradiol-17beta + NAD+
estrone + NADH + H+
show the reaction diagram
-
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
show the reaction diagram
-
17beta-HSD2, important role in peripheral inactivation of androgens and estrogens, 17beta-HSD4, low substrate affinity
-
-
?
estrone + NAD(P)H
estradiol + NAD(P)+
show the reaction diagram
-
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)+
show the reaction diagram
estrone + NAD(P)H + H+
estradiol + NAD(P)+
show the reaction diagram
estrone + NAD(P)H + H+
estradiol-17beta + NAD(P)+
show the reaction diagram
-
type 1 17beta-hydroxysteroid dehydrogenase plays a critical role in the biosynthesis of estradiol
-
-
?
estrone + NADH
estradiol-17beta + NAD+
show the reaction diagram
estrone + NADPH
17beta-estradiol + NADP+
show the reaction diagram
estrone + NADPH + H+
estradiol-17beta + NADP+
show the reaction diagram
estronesulfate + NADPH
17beta-estradiolsulfate + NADP+
show the reaction diagram
-
-
-
-
r
testosterone + NAD(P)+
4-androstene-3,17-dione + NAD(P)H
show the reaction diagram
-
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+
show the reaction diagram
-
17beta-HSD2, important role in peripheral inactivation of androgens and estrogens
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NAD(P)+
NAD(P)H
-
-
additional information
-
cofactor binding mechanism and specificity involving residues Tyr49, Thr202, Ala50, and Asn51, overview
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
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
(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
(15beta)-3-hydroxy-15-(3-hydroxypropyl)estra-1(10),2,4-trien-17-one
-
-
(15beta)-3-hydroxy-15-(5-hydroxypentyl)estra-1(10),2,4-trien-17-one
-
-
(16alpa,17beta)-16-(3-bromopropyl)estra-1(10),2,4-triene-3,17-diol
-
EM-251
(16alpha)-2-chloro-16-fluoro-3-hydroxyestra-1(10),2,4-trien-17-one
-
-
(16alpha)-3-hydroxy-17-oxoestra-1(10),2,4-triene-16-carbonitrile
-
-
(16beta)-16-(ethoxymethyl)-3-hydroxyestra-1(10),2,4-trien-17-one
-
-
(16beta)-2-chloro-16-fluoro-3-hydroxyestra-1(10),2,4-trien-17-one
-
-
(16beta)-3-hydroxy-16-methyl-17-oxoestra-1(10),2,4-triene-16-carbonitrile
-
-
(16beta)-3-hydroxy-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
-
-
(16Z)-3-hydroxy-16-(hydroxymethylidene)estra-1(10),2,4-trien-17-one
-
-
(17beta)-3,17-dihydroxy-N-(pyridin-3-ylmethyl)estra-1(10),2,4-triene-16-carboxamide
-
-
(17E)-3-hydroxyestra-1(10),2,4-trien-17-one oxime
-
-
(17Z)-3-hydroxyestra-1(10),2,4-triene-16,17-dione dioxime
-
-
(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
(2,4-dihydroxyphenyl)-phenylmethanone
-
-
(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
-
-
(3alpha,7alpha,17beta)-17-ethynyl-7-methylestr-5(10)-ene-3,17-diol
-
-
(3beta,7alpha,17beta)-17-ethynyl-7-methylestr-5(10)-ene-3,17-diol
-
-
(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
-
-
(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
(6beta,17beta)-6-(hexylsulfanyl)estra-1(10),2,4-triene-3,17-diol
-
-
(6Z,17E)-3-hydroxyestra-1(10),2,4-triene-6,17-dione dioxime
-
-
(7alpha,17beta)-17-ethynyl-17-hydroxy-7-methylestr-4-en-3-one
-
-
(S)-2-Methoxy-6a-methyl-5,6,6a,10,10a,10b,11,12-octahydro-4bH-7-oxa-8-aza-pentaleno[2,1-a]phenanthrene
-
-
(S)-6a-Methyl-5,6,6a,10,10a,10b,11,12-octahydro-4bH-7-oxa-8-aza-pentaleno[2,1-a]phenanthren-2-ol
-
-
1'(2')H-estra-1,3,5(10)-trieno[17,16-c]pyrazol-3-ol
-
IC50: 0.0041 mM
1,1':4',1''-terphenyl-3,3''-diol
-
-
1,2-Cyclohexanedione
-
40 mM, pH 8.5, t1/2: 4.4 h
1,3,5(10),16-estratetraen-3-ol
-
-
1,3,5(10)-estratrien-3,16beta,17beta-triol
-
-
1,3,5(10)-estratrien-3,16beta-diol
-
-
1,3,5(10)-estratrien-3,17alpha-diol
-
-
1,3,5(10)-estratrien-3-ol
-
-
1,4-dibromo-2,3-butanedione
-
40 mM, pH 8.5, t1/2: 0.02 h
1,9-decanediol
-
-
1-(3'-ethyl-4'-hydroxy-biphenyl-4-yl)-ethanone
1-(3-ethyl-4'-hydroxy-biphenyl-4-yl)-ethanone
1-(4'-hydroxy-2'-methyl-biphenyl-4-yl)-ethanone
-
89% inhibition at 0.001 mM
1-(4'-hydroxy-2'_methyl-biphenyl-4-yl)-ethanone
-
37C, 0.01 mM, 89% inhibition, substrate: estrone, 7beta-HSD type 1
1-(4'-hydroxy-biphenyl-4-yl)-ethanone
-
37C, 01 mM, 97% inhibition, substrate: estrone, 7beta-HSD type 1; 97% inhibition at 0.001 mM
1-(4-fluorophenyl)-3-[4-(1,2,3-thiadiazol-4-yl)benzyl]urea
-
-
1-(4-hydroxy-phenyl)-butan-1-one
-
weak inhibitor with 35.1% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-decan-1-one
-
weak inhibitor with 28.2% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-dodecan-1-one
-
weak inhibitor with 42.5% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-ethanone
-
weak inhibitor with 20.8% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-heptan-1-one
-
weak inhibitor with 47.6% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-hexan-1-one
-
weak inhibitor with 45.7% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-octan-1-one
-
weak inhibitor with 36.9% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-pentan-1-one
-
weak inhibitor with 39.8% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-propan-1-one
-
weak inhibitor with 17.5% inhibition at 0.1 mM
1-(4-hydroxy-phenyl)-undecan-1-one
-
weak inhibitor with 30.6% inhibition at 0.1 mM
1-(4-hydroxyphenyl)-nonan-1-one
-
weak inhibitor with 36.3% inhibition at 0.1 mM
1-(6-hydroxy-9H-fluoren-2-yl)-ethanone
-
37C, 0.01 mM, 86% inhibition, substrate: estrone, 7beta-HSD type 1; 86% inhibition at 0.001 mM
1-bromo-6-(3-hydroxyphenyl)-2-naphthol
-
88% 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-phenyl-1,2-propanedione
-
40 mM, pH 8.5, t1/2: 0.19 h
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-cyano-17-oxoestra-1(10),2,4-trien-3-yl sulfamate
-
-
16-cyano-2-methoxy-17-oxoestra-1(10),2,4-trien-3-yl sulfamate
-
-
16-difluoro-estradiol
-
oxidation of estradiol
16-methylen-estra-1,3,5(10)-triene-3,17beta-diol
-
suicide inhibitor
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-Bromoacetoxyprogesterone
-
-
16alpha-bromobutyl-estradiol
-
-
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
16beta-bromobutyl-estradiol
-
-
16beta-m-pyridylmethylamidomethyl-2-methoxyoestrone
-
IC50: 0.00029 mM
17(R,S)-14,15-secoestra-1,3,5(10)-trien-15-yne-3,17-diol
-
suicide inhibitor
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
17-deoxy-estradiol
-
oxidation of estradiol
2',4',4-trihydroxy-4'-chalcone
-
IC50: 0.0338 mM
2',4'-dihydroxy-chalcone
-
IC50: 0.0346 mM
2',5'-ADP
-
-
2'-AMP
-
competitive with respect to NAD(H) or NADP(H) and noncompetitive with respect to the steroid
2,2',4,4'-tetrahydroxybenzophenone
-
-
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
-
-
2,3-Butanedione
-
40 mM, pH 8.5, t1/2: 2 h
2,3-Pentanedione
-
40 mM, pH 8.5, t1/2: 5.3 h
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-(3-hydroxyphenyl)quinolin-6-ol
-
0.001 mM, 63% inhibition, substrate: estrone
2-chloro-3-hydroxyestra-1(10),2,4-trien-17-one
-
-
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-methoxyoestrone
-
IC50: 0.0024 mM
2-methylcinnamic acid
-
IC50: 0.0064 mM
2-nitrophenyl (2E)-3-phenylprop-2-enoate
-
45% inhibition at 0.006 mM
2-phenylethyl (2E)-3-phenylprop-2-enoate
-
-
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
-
37C, 0.001 mM, 39% inhibition, substrate: estrone, 7beta-HSD type 1; 39% inhibition at 0.001 mM
3',4',5,7-tetrahydroxy-flavone
-
IC50: 0.0006 mM
3',4',7-trihydroxy-isoflavone
-
IC50: 0.0052 mM
3',5'-ADP
-
-
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
3,3',4',7-tetrahydroxy-flavone
-
-
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
-
-
3,3'-(1-methyl-1H-1,2,4-triazole-3,5-diyl)diphenol
-
-
3,3'-(1-phenyl-1H-1,2,4-triazole-3,5-diyl)diphenol
-
-
3,3'-(1H-1,2,3-triazole-1,4-diyl)diphenol
-
; 17% inhibition at 0.001 mM
3,3'-pyridine-2,5-diyldiphenol
-
-
3,4,5-trimethoxycinnamic acid
3,5,7,4'-tetrahydroxyflavone
-
IC50 between 0.001 and 0.005 mM, reduction of estra-4-en-3,17-dione
3,5,7-trihydroxy-4'-methoxy-flavone
-
IC50: 15 mM
3,5,7-trihydroxy-flavone
-
-
3,5-dibromosalicylic acid
-
-
3,7-dihydroxyflavone
-
IC50 below 0.001 mM, oxidation of 17beta-hydroxyestra-4-en-3-one
3-(17beta-hydroxy-3-methoxy-estra-1,3,5(10)-trien-16beta-ylmethyl)-benzamide
-
0.01 mM, 90% inhibition, substrate: estrone
3-(17beta-hydroxy-estra-1,3,5(10)-trien-16beta-ylmethyl)-benzamide
-
0.01 mM, 79% inhibition, substrate: estrone
3-(2-furylmethyl)-8-hydroxy-2-(2-phenylethyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
-
33% inhibition at 100 nM, 78% inhibition at 0.001 mM
3-(2-naphthyl)phenol
-
0.001 mM, 61% inhibition, substrate: estrone
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-(quinolin-3-yl)phenol
-
0.001 mM, 18% inhibition, substrate: estrone
3-(trifluoromethyl)-cinnamic acid
-
-
3-([(16beta,17beta)-3,17-dihydroxyestra-1(10),2,4-trien-16-yl]methyl)benzamide
-
-
-
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-(3,4,5-trimethoxyphenyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
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-benzylidene camphor
-
-
3-bromo-5-phenylsalicylic acid
-
-
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-coumaric acid
-
34% inhibition at 0.05 mM
3-cyclohexylpropanoic acid
-
weak inhibition, IC50: 0.1 mM, above
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-17-oxoestra-1(10),2,4-triene-16-carboxylic acid
-
-
3-hydroxy-17-oxoestra-1(10),2,4-triene-2-carbonitrile
-
-
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-(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(10),2,4-triene-16,17-dione 16-oxime
-
-
3-hydroxyestra-1,3,5(10),7-tetraen-17-one
-
IC50: 0.0019 mM, oxidation of estradiol
3-hydroxyflavone
-
IC50 below 0.001 mM, oxidation of 17beta-hydroxyestra-4-en-3-one; IC50 between 0.001 and 0.005 mM, reduction of estra-4-en-3,17-dione
3-methoxy-1'(2')H-estra-1,3,5(10)-trieno[17,16-c]pyrazole
-
-
3-phenoxybenzyl (2E)-3-(1,3-benzodioxol-5-yl)prop-2-enoate
-
14% inhibition at 0.006 mM
3-phenoxybenzyl (2E)-3-phenylprop-2-enoate
-
13% inhibition at 0.006 mM
3-phenyl-5-bromosalicylic acid
-
-
3-trifluoromethylcinnamic acid
-
IC50: 0.043 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-[(4-chlorophenyl)sulfanyl]-6-(2,4-dimethyl-1H-pyrrol-1-yl)pyridazine
-
-
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-[1-(4-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]-phenol
-
17beta-HSD1; substrate: estradiol-17beta, 17beta-HSD2
3-[1-(4-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]phenol
-
-
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)-1-methyl-1H-1,2,4-triazol-5-yl]phenol
-
-
3-[3-(4-hydroxyphenyl)-1-phenyl-1H-1,2,4-triazol-5-yl]phenol
-
-
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
-
17beta-HSD1
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-(4-hydroxyphenyl)-1H-1,2,3-triazol-1-yl]phenol
-
-
3-[4-(4-hydroxyphenyl)thiophen-2-yl]phenol
-
-
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-(4-hydroxyphenyl)-1-methyl-1H-1,2,4-triazol-3-yl]phenol
-
-
3-[5-(4-hydroxyphenyl)-1-phenyl-1H-1,2,4-triazol-3-yl]phenol
-
-
3-[5-(4-hydroxyphenyl)thiophen-2-yl]phenol
-
-
3-[5-(4-hydroxyphenyl)thiophen-3-yl]phenol
-
-
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
3beta-hydroxy-5,16-androstadiene
-
-
3beta-hydroxy-5-androsten-16-one
-
-
4',5,7-trihydroxy-flavanone
-
-
4',5,7-trihydroxy-flavone
-
IC50: 0.0003 mM
4',5,7-trihydroxy-isoflavone
-
IC50: 0.001 mM
4',7-dihydroxy-isoflavone
-
IC50: 0.01 mM
4'-(2-thienyl)biphenyl-3-ol
-
0.001 mM, 10 min, 22% inhibition; 0.001 mM, 10 min, 36% inhibition
4'-(3-furyl)biphenyl-3-ol
-
0.001 mM, 10 min, 17% inhibition
4'-(3-thienyl)biphenyl-3-ol
-
0.001 mM, 10 min, 36% inhibition; 0.001 mM, 10 min, 41% inhibition
4'-(5-chloro-2-thienyl)biphenyl-3-ol
-
; 0.001 mM, 10 min, 48% inhibition
4'-(6-methoxypyridin-3-yl)biphenyl-3-ol
-
0.001 mM, 10 min, 35% inhibition; 0.001 mM, 10 min, 58% inhibition
4'-cyanophenyl 3,4-methylenedioxycinnamate
-
-
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; 37C, 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; 37C, 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; 37C, 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; 37C, 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; 37C, 0.001 mM, 24% inhibition, substrate: estrone, 7beta-HSD type 1; 37C, 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; 37C, 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
-
37C, 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
-
37C, 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-(octanoylamino)phenyl (2E)-3-phenylprop-2-enoate
-
15% inhibition at 0.006 mM
4-cyanophenyl (2E)-3-(1,3-benzodioxol-5-yl)prop-2-enoate
-
76% inhibition at 0.006 mM
4-hydroxychalcone
-
IC50: 0.016 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-methylbenzylidene camphor
-
-
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-[5-(3-hydroxyphenyl)thiophen-2-yl]-2-methylphenol
-
-
5'-ADP
-
-
5'-ADP-ribose
-
-
5'-AMP
-
-
5'-ATP
-
-
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
5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one
-
-
5,7-dihydroxy-4'-methoxy-flavone
-
-
5,7-dihydroxyflavone
-
IC50 below 0.001 mM, oxidation of 17beta-hydroxyestra-4-en-3-one
5-(3-ethyl-4-hydroxyphenyl)-indan-1-one
-
37C, 0.01 mM, 48% inhibition, substrate: estradiol-17beta, 7beta-HSD type 2; 37C, 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
-
37C, 0.01 mM, 24% inhibition, substrate: estradiol-17beta, 7beta-HSD type 2; 37C, 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
-
37C, 0.01 mM, 56% inhibition, substrate: estrone, 7beta-HSD type 1; 56% inhibition at 0.001 mM
5-(4-hydroxyphenyl)-indan-1-one
-
37C, 0.01 mM, 17% inhibition, substrate: estradiol-17beta, 7beta-HSD type 2; 37C, 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-androsten-3beta-ol
-
-
5-androstene-3beta,16beta-diol
-
-
5-benzyl-3-(furan-2-ylmethyl)-8-hydroxy-2-(2-phenylethyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
-
5% inhibition at 100 nM, 26% inhibition at 0.001 mM
5-bromo-3-(2-methylpropyl)-2-(3,4,5-trimethoxyphenyl)-6,7-dihydro[1]benzothieno[2,3-d]pyrimidine-4,8(3H,5H)-dione
-
0.001 mM, 54% inhibition
5-butyl-3-(furan-2-ylmethyl)-8-hydroxy-2-(2-phenylethyl)[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
-
9% inhibition at 100 nM, 27% inhibition at 0.001 mM
5-hydroxyflavone
-
IC50 below 0.001 mM, oxidation of 17beta-hydroxyestra-4-en-3-one
5-methoxyflavone
-
IC50 between 0.001 and 0.005 mM, reduction of estra-4-en-3,17-dione
5-[(15beta)-3-methoxy-17-oxoestra-1(10),2,4-trien-15-yl]-N-(2-thiophen-2-ylethyl)pentanamide
-
-
6-(3-ethyl-4-hydroxyphenyl)-3,4-dihydro-2H-naphthalen-1-one
-
37C, 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
-
37C, 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)-1-phenyl-2-naphthol
-
89% inhibition at 0.001 mM
6-(3-hydroxyphenyl)-2-naphthol
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
-
37C, 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-hydroxyflavone
-
53.3% inhibition at 0.006 mM
6-pyridin-3-yl-2-naphthol
-
0.001 mM, 32% inhibition, substrate: estrone
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
6-[4-(trifluoromethyl)phenoxy]pyridin-3-amine
-
-
7,4'-Dihydroxyflavone
-
more than 90% inhibition at 0.006 mM
7-(3-hydroxyphenyl)-2-naphthol
-
0.001 mM, 62% inhibition, substrate: estrone
7-hydroxy-2-phenyl-4H-chromen-4-one
-
-
7-hydroxy-3-(3-hydroxyphenyl)-1-naphthonitrile
-
53% inhibition at 0.001 mM
7-hydroxy-flavanone
-
IC50: 0.028 mM
7-hydroxy-flavone
-
IC50: 0.0009 mM
7-hydroxyflavone
-
weak inhibitor with 14.2% inhibition at 0.1 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
-
androstenedione
-
-
androsterone
-
-
arachidonic acid
-
0.018 mM, complete inhibition, oxidation of estradiol
baicalein
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
benzyl (2E)-3-phenylprop-2-enoate
-
35% inhibition at 0.006 mM
benzyl alcohol
-
-
caffeic acid
-
18% inhibition at 0.05 mM
chrysin
-
0.02 mM, about 65% inhibition
chrysoeriol
-
i.e. 4',5,7-trihydroxy-3'-methoxyflavone, 82% inhibition at 0.006 mM
Cinnamic acid
coumarin-3-carboxylic acid
coumestrol
cyclobutyl-(4-hydroxyphenyl)-methanone
-
weak inhibitor with 43.9% inhibition at 0.1 mM
cycloheptyl-(4-hydroxyphenyl)-methanone
-
weak inhibitor with 47.2% inhibition at 0.1 mM
Cyclohexanol
-
-
cyclohexyl (2E)-3-phenylprop-2-enoate
-
25% inhibition at 0.006 mM
cyclohexyl-(4-hydroxyphenyl)-methanone
-
weak inhibitor with 47.2% inhibition at 0.1 mM
Cyclopentanol
-
-
cyclopentyl-(4-hydroxyphenyl)-methanone
-
weak inhibitor with 49.5% inhibition at 0.1 mM
daidzein
-
0.02 mM, about 75% inhibition
diethylstilbestrol
diosmetin
-
i.e. 3',5,7-trihydroxy-4'-methoxyflavone, more than 90% inhibition at 0.006 mM
EM-139
EM-1745
enterodiol
-
-
enterolactone
-
0.05 mM, 84% inhibition
equilin
estrone
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
-
-
eupatorin
-
37% inhibition at 0.006 mM
fisetin
-
72% inhibition at 0.006 mM
genistein
genkwanin
-
3',5-dihydroxy-7-methoxyflavone, 81% inhibition at 0.006 mM
Glyoxal
-
40 mM, pH 8.5, t1/2: 29 h
gossypol
-
and derivatives of gossypol, competitive with respect to NAD+ in reverse reaction
iodoacetamide
-
1 mM, 78% inhibition
linoleic acid
-
0.018 mM, 58% inhibition, oxidation of estradiol
linolenic acid
-
0.018 mM, 34% inhibition, oxidation of estradiol
luteolin
-
0.02 mM, about 40% inhibition
m-coumaric acid
-
-
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-(2,3-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-benzyl-2-oxo-2H-chromene-3-carboxamide
-
-
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-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-[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-[[(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
-
-
NADP+
-
strong inhibitor of NAD+-linked activity
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
oleic acid
-
0.018 mM, complete inhibition, oxidation of estradiol
p-aminocinnamic acid
-
-
p-carboxycinnamic acid
-
-
p-nitro-cinnamic acid
-
-
palm oil carotenoids
-
0.0001 mM, significant inhibition of the conversion of estradiol to estrone in the MCF-7 cell line
-
Phenol
-
noncompetitive
phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
-
35% inhibition at 0.006 mM
Phenylglyoxal
-
40 mM, pH 8.5, t1/2: 0.33 h
progesterone
-
-
S-(4-fluorophenyl) 2-methyl-4-(trifluoromethyl)benzenecarbothioate
-
-
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
STX1040
-
-
testosterone
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
vitamin D3
-
inhibits reductive activity in HCT8 and LoVo cells
[4-[4-(2-methoxyphenyl)piperidin-1-yl]-3-nitrophenyl]methanol
-
-
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
activin A
-
stimulates an increase in transcription and enzymatic activity in LbetaT2 cells
-
palm oil carotenoids
-
0.001 mM, significant stimulation of the conversion of estradiol to estrone in the MCF-7 cell line
-
R5020
-
stimulates conversion of estradiol to estrone in T47D cells in culture
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
vitamin D3
-
activates oxidative activity in HCT8 and LoVo cells
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.508
(S)-indan-1-ol
-
recombinant enzyme
0.0085
1-methyl-6-dehydroestradiol
-
-
0.015
1-methylestradiol
-
-
0.012
11-ketoequilenin acetate
-
-
0.207
20alpha-dihydroprogesterone
-
-
0.0022
3-methyl-O-estradiol
-
-
0.032
4-methyl-1,3,5(10)-estratriene-1,17beta-diol
-
-
0.0067 - 0.118
5alpha-dihydrotestosterone
0.0011 - 0.0033
5beta-pregnan-20alpha-ol-3-one
0.047
7-ketoestrone
-
-
0.124
androstenedione
-
-
0.056
benzene dihydrodiol
-
recombinant enzyme
0.0172 - 0.0598
dehydroepiandrosterone
0.0043 - 0.033
dihydrotestosterone
0.02
equilenin
-
-
0.013
equilin
-
-
0.0036 - 0.118
estradiol
0.03
estradiol 3-methyl ether
-
-
0.0008 - 0.025
estradiol-17beta
0.00003 - 0.9
estrone
0.357 - 0.5
NAD+
0.86
NADH
25C, pH 8.0, mutant enzyme Y49D, cosubstrate: 4-estrene-3,17-dione
0.00006 - 9
NADP+
0.00035 - 0.16
NADPH
0.0097 - 0.263
testosterone
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE