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Information on EC 1.1.1.62 - 17beta-estradiol 17-dehydrogenase and Organism(s) Mus musculus and UniProt Accession O88736

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IUBMB 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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Mus musculus
UNIPROT: O88736
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The taxonomic range for the selected organisms is: Mus musculus
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea
Synonyms
hsd17b4, hsd17b2, 20 alpha-hydroxysteroid dehydrogenase, 17betahsd, 17-hsd, akr1c4, hsd17b12, 17beta-hsd type 1, 17hsd1, 17beta-hsdcl, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
type 7 17beta-hydroxysteroid dehydrogenase
-
17-HOR
-
-
-
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17-HSD
-
-
-
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17beta,20alpha-hydroxysteroid dehydrogenase
-
-
-
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17beta-estradiol dehydrogenase
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-
-
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17beta-HSD
-
-
-
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17beta-HSD1
-
-
17beta-HSD12
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17beta-HSD2
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17beta-hydroxysteroid dehydrogenase
-
-
-
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17beta-hydroxysteroid dehydrogenase type 2
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17beta-hydroxysteroid dehydrogenase type I
-
-
20 alpha-hydroxysteroid dehydrogenase
-
-
-
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20-alpha-HSD
-
-
-
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20alpha-hydroxysteroid dehydrogenase
-
-
-
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dehydrogenase, estradiol 17beta-
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-
-
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E2DH
-
-
-
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EDH
-
-
-
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estradiol 17beta-dehydrogenase
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-
-
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estradiol dehydrogenase
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-
-
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estrogen 17-oxidoreductase
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-
-
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Ke6 protein
-
-
-
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microsomal 17-beta-hydroxysteroid dehydrogenase
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-
-
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oestradiol-17beta hydroxysteroid dehydrogenase
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-
-
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placental 17-beta-hydroxysteroid dehydrogenase
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-
-
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PRAP
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-
-
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PRL receptor associated protein
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-
-
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testicular 17-beta-hydroxysteroid dehydrogenase
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-
-
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type 8 17beta-HSD
-
-
type 8 17beta-hydroxysteroid dehydrogenase
-
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
17beta-estradiol + NAD(P)+ = estrone + NAD(P)H + H+
show the reaction diagram
ordered bi bi mechanism
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
-
-
-
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oxidation
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-
-
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reduction
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-
-
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PATHWAY SOURCE
PATHWAYS
-
-
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
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
estrone + NAD(P)H + H+
estradiol-17beta + NAD(P)+
show the reaction diagram
-
-
-
?
(S)-indan-1-ol + NADP+
indan-1-one + NADPH
show the reaction diagram
-
-
-
?
17beta-estradiol + NAD+
estrone + NADH + H+
show the reaction diagram
-
-
-
?
4-androstenedione + NAD(P)H + H+
testosterone + NAD(P)+
show the reaction diagram
-
-
-
?
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3,17-dione + NADP+
show the reaction diagram
-
-
-
?
5beta-pregnan-20alpha-ol-3-one + NADPH
5beta-pregnane-3,20-dione + 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
-
-
-
?
estradiol-17beta + NAD(P)+
estrone + NAD(P)H + H+
show the reaction diagram
-
-
-
-
?
estradiol-17beta + NAD+
estrone + NADH
show the reaction diagram
-
-
-
-
?
estradiol-17beta + NADP+
estrone + NADPH
show the reaction diagram
-
-
-
-
?, r
estrone + NADPH
17beta-estradiol + NADP+
show the reaction diagram
estrone + NADPH + H+
estradiol-17beta + NADP+
show the reaction diagram
pregn-4-en-20alpha-ol-3-one + NADP+
progesterone + NADPH
show the reaction diagram
-
-
-
?
testosterone + NAD+
androstenedione + NADH + H+
show the reaction diagram
-
-
-
?
testosterone + NADP+
4-androstene-3,17-dione + NADPH + H+
show the reaction diagram
-
-
-
?
additional information
?
-
-
A-stereospecificity in hydrogen transfer
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
17beta-estradiol + NAD+
estrone + NADH + H+
show the reaction diagram
-
-
-
?
estrone + NADPH
17beta-estradiol + NADP+
show the reaction diagram
-
type 8 17beta-HSD can downregulate 17beta-estradiol levels in a large variety of tissues
-
-
?
estrone + NADPH + H+
estradiol-17beta + NADP+
show the reaction diagram
-
final step in the synthesis of active estrogens
-
-
?
testosterone + NAD+
androstenedione + NADH + H+
show the reaction diagram
-
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NAD(P)+
-
-
NADP+
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cofactor
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3'-methoxy-N-(3-methoxyphenyl)-N-methylbiphenyl-3-carboxamide
1 micromol, 25% inhibition
4'-methoxy-N-(3-methoxyphenyl)-N-methylbiphenyl-3-carboxamide
1 micromol, 11% inhibition
5-(2-fluoro-3-methoxyphenyl)-N-(3-hydroxybenzyl)-N-methylthiophene-2-carboxamide
1 micromol, 65% inhibition
5-(2-fluoro-3-methoxyphenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
1 micromol, 26% inhibition
5-(2-fluoro-3-methoxyphenyl)-N-methyl-N-(3-methylphenyl)thiophene-2-carboxamide
1 micromol, 45% inhibition
5-(2-hydroxyphenyl)-N-(3-hydroxyphenyl)-N-methylthiophene-2-carboxamide
1 micromol, 18% inhibition
5-(2-methoxyphenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
1 micromol, 19% inhibition
5-(3-fluorophenyl)-N-(3-hydroxybenzyl)-N-methylthiophene-2-carboxamide
1 micromol, 37% inhibition
5-(3-fluorophenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
1 micromol, 40% inhibition
N,4'-dimethyl-N-(3-methylphenyl)biphenyl-4-carboxamide
1 micromol, 50% inhibition
N,5-bis(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
1 micromol, 29% inhibition
N-(3-hydroxybenzyl)-5-(3-hydroxyphenyl)-N-methylthiophene-2-carboxamide
1 micromol, 26% inhibition
N-(3-hydroxybenzyl)-5-(4-hydroxyphenyl)-N-methylthiophene-2-carboxamide
1 micromol, 35% inhibition
N-(3-hydroxybenzyl)-N-methyl-5-(3-methylphenyl)thiophene-2-carboxamide
1 micromol, 45% inhibition
N-(3-methoxybenzyl)-5-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
1 micromol, 16% inhibition
N-(3-methoxyphenyl)-N-methyl-5-(3-methylphenyl)thiophene-2-carboxamide
1 micromol, 30% inhibition
N-methyl-N,5-bis(3-methylphenyl)thiophene-2-carboxamide
1 micromol, 42% inhibition
additional information
design of inhibitors displaying h17beta-HSD2 inhibitory activity and selectivity toward h17beta-HSD1. No inhibition by N,5-bis(3-hydroxyphenyl)-N-methylthiophene-2-carboxamide, 5-(4-cyanophenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide, 5-(4-cyanophenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide, 5-(4-cyanophenyl)-N-(3-hydroxybenzyl)-N-methylthiophene-2-carboxamide, 3'-hydroxy-N-(3-hydroxyphenyl)-N-methylbiphenyl-3-carboxamide, and 3'-methoxy-N-(3-methoxybenzyl)-N-methylbiphenyl-3-carboxamide
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
activin A
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stimulates an increase in transcription and enzymatic activity in LbetaT2 cells
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.508
(S)-indan-1-ol
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recombinant enzyme
0.0067
5alpha-dihydrotestosterone
-
recombinant enzyme
0.0011 - 0.0033
5beta-pregnan-20alpha-ol-3-one
0.056
benzene dihydrodiol
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recombinant enzyme
0.011
estradiol-17beta
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recombinant enzyme
0.0097
testosterone
-
recombinant enzyme
additional information
additional information
-
-
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4.2
(S)-indan-1-ol
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recombinant enzyme
1.13
5alpha-dihydrotestosterone
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recombinant enzyme
0.433
benzene diohydrodiol
-
recombinant enzyme
0.95
estradiol-17beta
-
recombinant enzyme
1.73
testosterone
-
recombinant enzyme
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2.48
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.4
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
assay at
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
expression of type 7 17beta-hydroxysteroid dehydrogenase in zona fasciculata and reticularis in the cortex
Manually annotated by BRENDA team
type 7 17beta-hydroxysteroid dehydrogenase is expressed in epithelial cells of both acini and small ducts
Manually annotated by BRENDA team
type 7 17beta-hydroxysteroid dehydrogenase is restricted to epithelial cells of the mucosa
Manually annotated by BRENDA team
type 7 17beta-hydroxysteroid dehydrogenase is found in all the hepatocytes
Manually annotated by BRENDA team
type 7 17beta-hydroxysteroid dehydrogenase is expressed in stromal cells surrounding the duct
Manually annotated by BRENDA team
type 7 17beta-hydroxysteroid dehydrogenase is restricted to corpus luteum cells
Manually annotated by BRENDA team
type 7 17beta-hydroxysteroid dehydrogenase
Manually annotated by BRENDA team
retroperitonea, high mRNA expression
Manually annotated by BRENDA team
low mRNA expression
Manually annotated by BRENDA team
high mRNA expression
Manually annotated by BRENDA team
low mRNA expression
Manually annotated by BRENDA team
low mRNA expression
Manually annotated by BRENDA team
-
bronchial epithelial cells and walls of pulmonary arteries
Manually annotated by BRENDA team
high mRNA expression
Manually annotated by BRENDA team
-
only in epithelial cells
Manually annotated by BRENDA team
-
epithelial cells of the acini and stromal cells
Manually annotated by BRENDA team
-
detectable in sebaceous glands, absent in epidermis, stroma, hair follicles and sweat glands
Manually annotated by BRENDA team
low mRNA expression
Manually annotated by BRENDA team
low mRNA expression
Manually annotated by BRENDA team
low mRNA expression
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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
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
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
DHB7_MOUSE
334
1
37317
Swiss-Prot
Secretory Pathway (Reliability: 5)
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
-
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Hara, A.; Nakayama, T.; Nakagawa, M.; Inoue, Y.; Tanabe, H.; Sawada, H.
Kinetic and stereochemical studies on reaction mechanism of mouse liver 17beta-hydroxysteroid dehydrogenases
J. Biochem.
102
1585-1592
1987
Mus musculus
Manually annotated by BRENDA team
Deyashiki, Y.; Ohshima, K.; Nakanishi, M.; Sato, K.; Matsuura, K.; Hara, A.
Molecular cloning and characterization of mouse estradiol 17beta-dehydrogenase (A-specific), a member of the aldoketoreductase family
J. Biol. Chem.
270
10461-10467
1995
Mus musculus
Manually annotated by BRENDA team
Pelletier, G.; Luu-The, V.; Li, S.; Ren, L.; Labrie, F.
Localization of 17beta-hydroxysteroid dehydrogenase type 1 mRNA in mouse tissues
J. Mol. Endocrinol.
33
459-465
2004
Mus musculus
Manually annotated by BRENDA team
Pelletier, G.; Luu-The, V.; Li, S.; Labrie, F.
Localization of type 7 17beta-hydroxysteroid dehydrogenase in mouse tissues. In situ hybridization studies
J. Steroid Biochem. Mol. Biol.
93
49-57
2005
Mus musculus (O88736), Mus musculus
Manually annotated by BRENDA team
Pelletier, G.; Van, L.; Li, S.; Labrie, F.
Localization of type 8 17beta-hydroxysteroid dehydrogenase mRNA in mouse tissues as studied by in situ hybridization
J. Histochem. Cytochem.
53
1257-1271
2005
Mus musculus
Manually annotated by BRENDA team
Blanchard, P.G.; Luu-The, V.
Differential androgen and estrogen substrates specificity in the mouse and primates type 12 17beta-hydroxysteroid dehydrogenase
J. Endocrinol.
194
449-455
2007
Mus musculus (Q0VGQ1), Mus musculus
Manually annotated by BRENDA team
Bak, B.; Carpio, L.; Kipp, J.L.; Lamba, P.; Wang, Y.; Ge, R.S.; Hardy, M.P.; Mayo, K.E.; Bernard, D.J.
Activins regulate 17beta-hydroxysteroid dehydrogenase type I transcription in murine gonadotrope cells
J. Endocrinol.
201
89-104
2009
Mus musculus
Manually annotated by BRENDA team
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)
Manually annotated by BRENDA team