Ligand dehydroepiandrosterone

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Basic Ligand Information

Molecular Structure
Picture of dehydroepiandrosterone (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C19H28O2
dehydroepiandrosterone
FMGSKLZLMKYGDP-USOAJAOKSA-N
Synonyms:
(3beta)-3-hydroxyandrost-5-en-17-one, 3beta-hydroxy-5-androsten-17-one, 3beta-hydroxy-5-androstene-17-one, 3beta-hydroxy-androst-5-en-17-one, 3beta-hydroxy-androst-5-ene-17-one, 3beta-hydroxyandrost-5-en-17-one, 3beta-hydroxyandrost-5-ene-17-one, 5-androsten-3beta-ol-17-one, 5-androstene-3-beta-ol-17-one, 5-androstene-3beta-ol-17-one, androst-5-en-3beta-ol-17-one, androst-5-ene-3beta-ol,17-one, androst-5-ene-3beta-ol-17-one, androstenolone, dehydro-epi-androsterone, dehydroandrosterone, dehydroepiandrostenedione, dehydroisoandrosterone, DELTA5-androsten-3beta-ol-17-one, prasterone, trans-dehydroandrosterone

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (24 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
dehydroepiandrosterone + NADPH + H+ + O2 = 7alpha-hydroxy-dehydroepiandrosterone + NADP+ + H2O
show the reaction diagram
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3'-phosphoadenylyl sulfate + dehydroepiandrosterone = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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3'-phosphoadenylyl sulfate + dehydroepiandrosterone = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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3'-phosphoadenylyl 5'-phosphosulfate + dehydroepiandrosterone = adenosine 3',5'-bisphosphate + dehydroepiandrosterone 3-sulfate
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

Substrate in Enzyme-catalyzed Reactions (81 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
dehydroepiandrosterone + NADPH = 5-androstene-3alpha,17alpha-diol + NADP+
show the reaction diagram
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dehydroepiandrosterone + NADPH + H+ = ?
show the reaction diagram
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dehydroepiandrosterone + NAD+ = ? + NADH + H+
show the reaction diagram
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5-androstene-3beta-ol-17-one + NADPH + H+ = ? + NADP+
show the reaction diagram
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dehydroepiandrosterone + NADH + H+ = 5-androstene-3,17-dione + NAD+
show the reaction diagram
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dehydroepiandrosterone + NADP+ = ?
show the reaction diagram
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dehydroepiandrostenedione + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = ? + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O
show the reaction diagram
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dehydroepiandrosterone + reduced adrenodoxin + O2 = 7beta-hydroxy-dehydroepiandrosterone + oxidized adrenodoxin + H2O
show the reaction diagram
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androst-5-en-3beta-ol-17-one + UDP-glucose = UDP + androst-5-en-3beta-ol-17-one 3-O-beta-D-glucoside
show the reaction diagram
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3'-phosphoadenylylsulfate + dehydroepiandrosterone = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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3'-phosphoadenylyl 5'-phosphosulfate + dehydroepiandrosterone = adenosine 3',5'-bisphosphate + dehydroepiandrosterone 3-sulfate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (23 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
androst-5-ene-3beta,17beta-diol + NAD+ = androst-5-ene-3beta-ol-17-one + NADH
show the reaction diagram
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5-androstene-3,17-dione + NAD+ = dehydroepiandrosterone + NADH + H+
show the reaction diagram
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androst-5-ene-3beta,17beta-diol + NADP+ = dehydroepiandrosterone + NADPH
show the reaction diagram
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5-androstene-3beta,17beta-diol + NAD+ = 5-androstene-3-beta-ol-17-one + NADH
show the reaction diagram
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dehydroepiandrosterone oleate + H2O = dehydroepiandrosterone + oleate
show the reaction diagram
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dehydroepiandrosterone 3-sulfate + H2O = dehydroepiandrosterone + sulfate
show the reaction diagram
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dehydroisoandrosterone sulfate + H2O = dehydroisoandrosterone + sulfate
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
stimulation of ATPase-activity arising from co-expression of isoforms ABCG5 and ABCG8
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Inhibitor in Enzyme-catalyzed Reactions (26 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.01 mM reduced conversion of pregnenolone to 50%
-
treatment of rats induces a shift from isoform 11beta-HSD1 to 11beta-HSD2 expression, increasing conversion from active to inactive glucocorticoids. Dehydroepiandrosterone likely modulates the transcription of 11beta-HSD2 in a phosphatidylinositol-3 kinase/Akt-dependent manner by increasing CCAAT/enhancer-binding protein beta mRNA and protein expression
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i.e. dehydroepiandrosterone
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treatment of rats induces a shift from isoform 11beta-HSD1 to 11beta-HSD2 expression, increasing conversion from active to inactive glucocorticoids. Dehydroepiandrosterone likely modulates the transcription of 11beta-HSD2 in a phosphatidylinositol-3 kinase/Akt-dependent manner by increasing CCAAT/enhancer-binding protein beta mRNA and protein expression
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inhibits hydroxylation of 5alpha-androstane-3beta,17beta-diol
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good in vitro inhibitory activity, but compound does not bind to the androgen receptors
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at 0.1 mM, inhibition of MAO-A by 44.2%; at 0.1 mM, inhibition of MAO-B by 61.2%
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about 30% residual activity at 0.1 mM (isoform PanK3)
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3D Structure of Enzyme-Ligand-Complex (PDB) (3 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (67 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.155
-
at pH 7.4 and 37°C
0.01
-
pH 7.4, 25°C, recombinant enzyme
0.033
-
-
0.0072
-
for the cytosolic enzyme
0.1
-
pH 7.5, 37°C
2
-
pH 7.5, 37°C

KM Value (147 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.006
-
at pH 7.4 and 37°C
0.326
-
wild-type, pH 7.5, 37°C, S50 value, Hill coefficient 1.55
0.00072
-
pH 6.5, 37°C, 5 mM MgCl2

Ki Value (18 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.024
-
-
0.17
-
pH 8.1, 37°C

IC50 Value (7 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0011
-
in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0056
-
pH 7.6, temperature not specified in the publication
0.000025
-
pH 6.5, 37°C

References & Links

Links to other databases for dehydroepiandrosterone

ChEBI
PubChem
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PubChem