Ligand 5alpha-androstane-3,17-dione

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Basic Ligand Information

Molecular Structure
Picture of 5alpha-androstane-3,17-dione (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C19H28O2
5alpha-androstane-3,17-dione
RAJWOBJTTGJROA-WZNAKSSCSA-N
Synonyms:
(5alpha)-androstane-3,17-dione, 5alpha-androstanedione

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5alpha-androstane-3,17-dione + NAD(P)H + H+ = androsterone + NAD(P)+
show the reaction diagram

In Vivo Product in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
17alpha-hydroxy-5alpha-dihydroprogesterone + [reduced NADPH-hemoprotein reductase] + O2 = 5alpha-androstanedione + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (18 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5alpha-androstane-3,17-dione + NAD(P)H = 5alpha-androstane-3alpha-ol-17-one + NAD(P)+
show the reaction diagram
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5alpha-androstane-3,17-dione + NADH + H+ = ? + NAD+
show the reaction diagram
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5alpha-androstane-3,17-dione + NADPH + H+ = ? + NADP+
show the reaction diagram
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5alpha-androstane-3,17-dione + NADPH = epi-androsterone + NADP+
show the reaction diagram
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5alpha-androstane-3,17-dione + NAD(P)H + H+ = androsterone + NAD(P)+
show the reaction diagram
5alpha-androstane-3,17-dione + NADPH = ?
show the reaction diagram
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5alpha-androstane-3,17-dione + NADH + H+ = 5alpha-androstane-17beta-ol-3-one + NAD+
show the reaction diagram
5alpha-androstane-3,17-dione + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = 9alpha-hydroxy-5alpha-androstane-3,17-dione + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O
show the reaction diagram
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5alpha-androstane-3,17-dione + 2,6-dichlorophenol-indophenol = 5beta-androst-1-en-3,17-dione + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
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5alpha-androstane-3,17-dione + N,N,N',N'-tetramethyl-1,4-phenylendiamine = androst-4-ene-3,17-dione + reduced N,N,N',N'-tetramethyl-1,4-phenylendiamine
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (21 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5alpha-androstane-17beta-ol-3-one + NADP+ = 5alpha-androstane-3,17-dione + NADPH
show the reaction diagram
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17alpha-hydroxy-5alpha-dihydroprogesterone + [reduced NADPH-hemoprotein reductase] + O2 = 5alpha-androstanedione + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitive inhibition with respect to geraniol
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30% inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (4 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (4 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.097
-
pH 7.4, 25°C
0.42
-
pH 7.0, 25, reduction reaction
0.03
-
isoform AKR1C4, at pH 7.4 and 25°C
0.42
-
pH 7.0, 25, reduction reaction

KM Value (14 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.15
-
form CR2
0.00144
-
isoform AKR1C4, at pH 7.4 and 25°C
0.0161
-
reaction with N,N,N‘,N‘-tetramethyl-1,4-phenylenediamine

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.00039
-
in 0.1 M potassium phosphate, pH 7.4, at 25°C

References & Links

Links to other databases for 5alpha-androstane-3,17-dione

ChEBI
PubChem
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PubChem