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Information on EC 1.1.1.145 - 3beta-hydroxy-DELTA5-steroid dehydrogenase and Organism(s) Bos taurus

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IUBMB Comments
This activity is found in several bifunctional enzymes that catalyse the oxidative conversion of Delta5-3-hydroxy steroids to a Delta4-3-oxo configuration. This conversion is carried out in two separate, sequential reactions; in the first reaction, which requires NAD+, the enzyme catalyses the dehydrogenation of the 3beta-hydroxy steroid to a 3-oxo intermediate. In the second reaction the reduced coenzyme, which remains attached to the enzyme, activates the isomerization of the Delta5 form to a Delta4 form (cf. EC 5.3.3.1, steroid Delta-isomerase). Substrates include dehydroepiandrosterone (which is converted into androst-5-ene-3,17-dione), pregnenolone (converted to progesterone) and cholest-5-en-3-one, an intermediate of cholesterol degradation.
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The taxonomic range for the selected organisms is: Bos taurus
The enzyme appears in selected viruses and cellular organisms
Synonyms
hsd3b2, hsd3b, dhrs4, 3-beta-hydroxysteroid dehydrogenase, hsd3b6, 3betahsd2, 3beta hydroxysteroid dehydrogenase, 3beta-hydroxysteroid dehydrogenase type ii, 3beta-hydroxysteroid dehydrogenase type 2, 3beta-hsd type ii, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3-beta-hydroxy-5-ene steroid dehydrogenase
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3-beta-hydroxy-delta(5)-steroid dehydrogenase
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3beta-HSDH
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3beta-hydroxy steroid dehydrogenase/5-ene-4-ene isomerase
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3beta-hydroxy steroid dehydrogenase/isomerase
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3beta-hydroxy-5-ene steroid dehydrogenase
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3beta-hydroxy-5-ene-steroid dehydrogenase
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3beta-hydroxy-5-ene-steroid oxidoreductase
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3beta-hydroxy-DELTA5-C27-steroid dehydrogenase/isomerase
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3beta-hydroxy-DELTA5-C27-steroid oxidoreductase
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5-ene-3-beta-hydroxysteroid dehydrogenase
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5alpha-dihydrotestosterone 3beta-hydroxysteroid dehydrogenase
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dehydrogenase, 3beta-hydroxy-DELTA5-steroid
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DELTA5-3beta-hydroxysteroid dehydrogenase
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progesterone reductase
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steroid-DELTA5-3beta-ol dehydrogenase
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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SYSTEMATIC NAME
IUBMB Comments
3beta-hydroxy-DELTA5-steroid:NAD+ 3-oxidoreductase
This activity is found in several bifunctional enzymes that catalyse the oxidative conversion of Delta5-3-hydroxy steroids to a Delta4-3-oxo configuration. This conversion is carried out in two separate, sequential reactions; in the first reaction, which requires NAD+, the enzyme catalyses the dehydrogenation of the 3beta-hydroxy steroid to a 3-oxo intermediate. In the second reaction the reduced coenzyme, which remains attached to the enzyme, activates the isomerization of the Delta5 form to a Delta4 form (cf. EC 5.3.3.1, steroid Delta-isomerase). Substrates include dehydroepiandrosterone (which is converted into androst-5-ene-3,17-dione), pregnenolone (converted to progesterone) and cholest-5-en-3-one, an intermediate of cholesterol degradation.
CAS REGISTRY NUMBER
COMMENTARY hide
9044-85-3
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+
17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H
show the reaction diagram
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-
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-
?
3beta-hydroxyandrostan-17-one + NAD+
androstan-3,17-dione + NADH
show the reaction diagram
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-
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-
?
4-androsten-3beta,17beta-diol + NAD+
4-androsten-17beta-ol-3-one + NADH
show the reaction diagram
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-
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-
?
5alpha-pregnan-3beta-ol-20-one + NAD+
5alpha-pregnan-3,20-dione + NADH
show the reaction diagram
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?
allopregnanolone + NAD+
?
show the reaction diagram
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r
androstenediol + NAD+
testosterone + NADH + H+
show the reaction diagram
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-
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r
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH + H+
show the reaction diagram
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-
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-
?
pregnenolone + NAD(P)+
pregn-5-en-3,20-dione + NAD(P)H + H+
show the reaction diagram
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?
additional information
?
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no reaction with OH in 3alpha, 17beta, 11beta, 21 position
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?
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
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH + H+
show the reaction diagram
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?
pregnenolone + NAD(P)+
pregn-5-en-3,20-dione + NAD(P)H + H+
show the reaction diagram
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?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
additional information
-
no reaction with 3-acetylpyridine-adenine dinucleotide, nicotinamide-hypoxanthine dinucleotide, 3-acetylpyridine-hypoxanthine dinucleotide
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
17alpha-hydroxypregnenolone
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competitive inhibition
17beta-estradiol
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3-Chloroacetylpyridine adenine dinucleotide
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apigenin
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Biochanin A
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daidzein
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diethyldicarbonate
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formononetin
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genistein
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N-(Anilino-naphthyl-4)-maleimide
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N-Iodoacetyl-N'-(5-sulfo-1-naphthyl)ethylene diamine
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p-chloromercuribenzoate
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pregnenolone
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competitive inhibition
prunetin
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puerarin
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trilostane
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i.e. 4alpha,5-epoxy-3,17beta-dihydroxy-5alpha-androst-2-en-2-carbonitrile
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
iodoacetamide
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p-chloromercuribenzoate
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0053
3beta,17alpha-dihydroxy-5-pregen-20-one
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0.001
allopregnanolone
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0.001
androstenediol
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0.001 - 0.0045
dehydroepiandrosterone
0.0062 - 0.0066
NAD+
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4.9
NADP+
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0.002 - 0.0032
pregnenolone
additional information
additional information
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0233
allopregnanolone
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0.0333
androstenediol
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0.0333
dehydroepiandrosterone
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0.04
pregnenolone
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0043
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mitochondria
0.0158
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microsomes
0.677
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.2
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7.8 - 8.5
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.8 - 9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
3BHS_BOVIN
373
0
42220
Swiss-Prot
other Location (Reliability: 3)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
41000
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x * 41000, SDS-PAGE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 41000, SDS-PAGE
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80°C, 0.1 M potassium phosphate buffer, pH 7.4, 10 mg protein/ml, at least 3 months
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Hiwatashi, A.; Hamamoto, I.; Ichikawa, Y.
Purification and kinetic properties of 3beta-hydroxysteroid dehydrogenase from bovine adrenocortical microsomes
J. Biochem.
98
1519-1526
1985
Bos taurus
Manually annotated by BRENDA team
Vincent, M.; Gallay, J.; de Paillerets, C.; Alfsen, A.; Biellmann, J.F.
Role of thiol group(s) in the enzymatic activity of the membrane-bound delta5-3beta-hydroxysteroid dehydrogenase from bovine adrenal cortex microsomes
Biochim. Biophys. Acta
525
1-8
1978
Bos taurus
Manually annotated by BRENDA team
Cheatum, S.G.; Warren, J.C.
Purification and properties of 3-beta-hydroxysteroid dehydrogenase and delta-5-3-ketosteroid isomerase from bovine corpora lutea
Biochim. Biophys. Acta
122
1-13
1966
Bos taurus
Manually annotated by BRENDA team
Wong, C.K.; Keung, W.M.
Bovine adrenal 3beta-hydroxysteroid dehydrogenase (E.C. 1.1.1.145)/5-ene-4-ene isomerase (E.C. 5.3.3.1): characterization and its inhibition by isoflavones
J. Steroid Biochem. Mol. Biol.
71
191-202
1999
Bos taurus, Cricetinae
Manually annotated by BRENDA team
Cherradi, N.; Defaye, G.; Chambaz, E.M.
Characterization of the 3beta-hydroxysteroid dehydrogenase activity associated with bovine adrenocortical mitochondria
Endocrinology
134
1358-1364
1994
Bos taurus
Manually annotated by BRENDA team
Perry, J.E.; Ishii-Ohba, H.; Stalvey, J.R.
Subcellular distribution of 3beta-hydroxysteroid dehydrogenase-isomerase in bovine and murine adrenocortical tissue: species differences in the localization of activity and immunoreactivity
Steroids
56
329-336
1991
Bos taurus, Mus musculus, Rattus norvegicus
Manually annotated by BRENDA team