Ligand 17beta-hydroxy-5alpha-androstan-3-one

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Basic Ligand Information

Molecular Structure
Picture of 17beta-hydroxy-5alpha-androstan-3-one (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C19H30O2
17beta-hydroxy-5alpha-androstan-3-one
NVKAWKQGWWIWPM-ABEVXSGRSA-N
Synonyms:
(5alpha)-androstan-17-beta-ol-3-one, (5alpha,17beta)-17-hydroxyandrostan-3-one, 5alpha-androstan-3-one-17beta-ol, 5alpha-androstan-17-beta-ol-3-one, 5alpha-androstan-17beta-ol-3-one, 5alpha-androstane-17beta-ol-3-one, 5alpha-dihydrotestosterone, 17beta-hydoxy-5alpha-androstan-3-one, 17beta-hydroxy-5alpha-androstane-3-one, 17beta-hydroxy-dihydrotestosterone, 17beta-hydroxyandrostan-3-one, 17beta-hydroxyetiocholan-3-one, androstan-17beta-ol-3-one, dihydrotestosterone, stanolone

Show all pahtways known for Show all pathways known for 17beta-hydroxy-5alpha-androstan-3-one

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (27 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
17beta-hydroxy-5alpha-androstan-3-one + NADPH = 5alpha-androstan-3beta,17beta-diol + NADP+
show the reaction diagram
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5alpha-dihydrotestosterone + NAD+ = androstandione + NADH
show the reaction diagram
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dihydrotestosterone + NADPH + H+ = 5alpha-androstane-3beta,17beta-diol + NADP+
show the reaction diagram
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5alpha-dihydrotestosterone + NADPH = 5alpha-androstan-3alpha,17beta-diol + NADP+
show the reaction diagram
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5alpha-dihydrotestosterone + acceptor = ?
show the reaction diagram
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UDP-D-glucuronate + dihydrotestosterone = UDP + dihydrotestosterone 17-O-beta-D-glucuronoside
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5alpha-dihydrotestosterone = ?
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3alpha-androstanediol + NAD+ = 5alpha-dihydrotestosterone + NADH + H+
show the reaction diagram
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5alpha-androstane-3,17-diol + NAD+ = 5alpha-dihydrotestosterone + NADH
show the reaction diagram
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testosterone + reduced acceptor = 5alpha-dihydrotestosterone + acceptor
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Substrate in Enzyme-catalyzed Reactions (108 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5alpha-dihydrotestosterone + NADPH = 5alpha-androstane-3alpha,17alpha-diol + NADP+
show the reaction diagram
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dihydrotestosterone + NADH = androstanediol + NAD+
show the reaction diagram
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5alpha-dihydrotestosterone + NADPH = ?
show the reaction diagram
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5alpha-dihydrotestosterone + NADPH = ? + NADP+
show the reaction diagram
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5alpha-dihydrotestosterone + NADH = (3beta,5alpha,17beta)-androstane-3,17-diol + NAD+
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5alpha-androstane-17beta-ol-3-one + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = 9alpha,17beta-dihydroxy-5alpha-androstane-3-one + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O
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5alpha-dihydrotestosterone + NADPH + O2 = ?
show the reaction diagram
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5alpha-dihydrotestosterone + NADPH = 5alpha-androstan-3alpha,17beta-diol + NADP+
show the reaction diagram
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5alpha-dihydrotestosterone + acceptor = ?
show the reaction diagram
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5alpha-dihydrotestosterone = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (35 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3alpha-androstanediol + NAD+ = 5alpha-dihydrotestosterone + NADH
show the reaction diagram
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5alpha-androstane-3,17-diol + NAD+ = 5alpha-dihydrotestosterone + NADH
show the reaction diagram
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androstanedione + NADPH = dihydrotestosterone + NADP+
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
significantly increases 5alpha-R1 mRNA and 5alpha-R2 mRNA expression in male rats
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stimulating and stabilizing, promotes formation of ternary complexes, restores specific activity after hypophysectomy
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hormonal treatment of BT-474 cells with dihydrotestosterone (an androgen) for 48 h triggers an increase of prostate-specific antigen concentration in the supernatant of these cells
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induces a time-dependent increase in neprilysin expression. Dihydrotestosterone also significantly decreases levels of amyloid beta in androgen receptor-expressing cells transfected with amyloid precursor protein, but does not affect levels of either full-length or non-amyloidogenic, soluble amyloid precursor protein. The dihydrotestosterone-induced decrease of amyloid beta is blocked by pharmacological inhibition of neprilysin. The dihydrotestosterone-mediated increase in neprilysin expression and decrease in amyloid beta levels are not observed in rat pheochromocytoma cell 12 lacking androgen receptor and blocked in androgen receptor-expressing cells by the antagonists, cyproterone acetate and flutamide
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10 nM, in the presence of 10 or 50 ng/ml insulin-like growth factor, 1.8fold upregulation of the 100-kDa proform and 3 to 4 fold stimulation of the active 60-kDa form
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regulation in a bell-shaped, dose-dependent manner, maximal, 5fold increase in activity at 0.000001 mM
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upregulation, 1.5fold increase in activity at 0.000001 mM, 1.7fold at 0.00001 mM
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Inhibitor in Enzyme-catalyzed Reactions (14 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
i.e. 5alpha-dihydrotestosterone, allosteric, competitive against substrate cyclohexanone, noncompetitive against NAD+ nd ethanol
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i.e. 5alpha-dehydrotestosterone
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inhibition of 20alpha-reductase activity
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inhibits oxidation of testosterone
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significantly decreases 5alpha-R1 mRNA and 5alpha-R2 mRNA expression in female rats
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0.01 mM, 57% inhibition
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inhibits esterification of endogenous cholesterol
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inhibits the hepatic enzyme in sham-operated and castrated male rats, prevents activation by 6-methylene-4-pregnene-3,20-dione
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3D Structure of Enzyme-Ligand-Complex (PDB) (5 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (43 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.095
-
pH 7.4, 25C

KM Value (88 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.074
-
-
0.002
-
similar values of other 17beta-hydroxysteroids
0.0043
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pH 7.0, 37C, spectrophotometric analysis, formation of 3beta-androstanediol or 3alpha-androstanediol
0.077
-
-
0.0196
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isoform UGT1A4, pH 7.4, 37C

Ki Value (4 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.038
-
pH 8.1, 37C

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.00051
-
in 0.1 M potassium phosphate, pH 7.4, at 25C

References & Links

Links to other databases for 17beta-hydroxy-5alpha-androstan-3-one

ChEBI
PubChem
ChEBI
PubChem