Ligand androsterone

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Basic Ligand Information

Molecular Structure
Picture of androsterone (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C19H30O2
androsterone
QGXBDMJGAMFCBF-HLUDHZFRSA-N
Synonyms:
(3alpha,5alpha)-3-hydroxyandrostan-17-one, 3alpha-hydroxy-5alpha-androstan-17-one, 5alpha-androstane-3alpha-ol-17-one, trans-androsterone, transandrosterone

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (14 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
UDP-D-glucuronate + androsterone = UDP + androsterone 3-O-beta-D-glucuronoside
show the reaction diagram
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3'-phosphoadenylylsulfate + androsterone = adenosine 3',5'-bisphosphate + 5alpha-androstane-17-one 3-sulfate
show the reaction diagram
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3'-phosphoadenylyl sulfate + androsterone = adenosine 3',5'-bisphosphate + androsterone 3-sulfate
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
dehydroepiandrosterone + NADH + H+ = androsterone + NAD+
show the reaction diagram
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androstenedione + NADPH + H+ = androsterone + NADP+
show the reaction diagram
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androstandiol + NAD+ = androsterone + NADH
show the reaction diagram
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5alpha-androstane-3,17-dione + NAD(P)H + H+ = androsterone + NAD(P)+
show the reaction diagram
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5alpha-androstane-3alpha,17beta-diol + NAD+ = androsterone + NADH + H+
show the reaction diagram
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17-hydroxy-5alpha-pregnan-3alpha-ol-20-one + [reduced NADPH-hemoprotein reductase] + O2 = androsterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (43 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
androsterone + NAD+ = ? + NADH
show the reaction diagram
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androsterone + NADPH = 5alpha-androstane-3alpha,17alpha-diol + NADP+
show the reaction diagram
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3alpha-hydroxy-5alpha-androstan-17-one + NAD(P)+ = 5alpha-androstan-3,17-dione + NAD(P)H
show the reaction diagram
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5alpha-androstane-3alpha-ol-17-one + NADPH + H+ = ? + NADP+
show the reaction diagram
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androsterone + NAD+ = androstanedione + NADH
show the reaction diagram
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androsterone + NAD+ = ? + NADH
show the reaction diagram
androsterone + NADPH = androstane-3beta,17beta-diol + NADP+
show the reaction diagram
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trans-androsterone + O2 = ?
show the reaction diagram
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androsterone + NADPH = ?
show the reaction diagram
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androsterone + acceptor = 3-alpha-hydroxy-1-androstene-17-one + reduced acceptor
show the reaction diagram
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UDP + transandrosterone = UDP + trans-androsterone 3beta-D-glucoside
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (23 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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dehydroepiandrosterone + NADH + H+ = androsterone + NAD+
show the reaction diagram
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5alpha-androstane-3,17-dione + NAD(P)H + H+ = androsterone + NAD(P)+
show the reaction diagram
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androsterone 3-sulfate + H2O = androsterone + sulfate
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (14 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
CR2 inhibited, CR1 not
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competitive vs. epitestosterone
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inhibits esterification of endogenous cholesterol
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stronger substrate inhibition than dehydroepiandrosterone adenosine
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3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (41 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.000367
-
-
0.011
-
enzyme from brain
456
-
pH 6.0, 30°C, reaction with NAD+
1.7
-
pH 7.4, 37°C recombinant His-tagged enzyme
0.13
-
pH 7.5, 37°C

KM Value (74 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0002
-
pH 7.3, 37°C
0.045
-
enzyme from brain
0.024
-
pH 6.0, 30°C, reaction with NAD+, mutant enzyme I6T/V47M/T69K
0.0028
-
pH 7.4, 37°C recombinant His-tagged enzyme
0.0066
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i.e. 4-androstene-3,11,17-trione

Ki Value (12 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.006
-
DD3
0.0038
-
pH 7.5, 37°C

IC50 Value (2 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.000182
-
pH and temperature not specified in the publication
0.0271
-
pH 7.5, 37°C, recombinant isozyme UGT1A9

References & Links

Links to other databases for androsterone

ChEBI
PubChem
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PubChem