Ligand epiandrosterone

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Basic Ligand Information

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

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
epiandrosterone + NAD+ = 5alpha-androstan-3,17-dione + NADH + H+
show the reaction diagram
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epiandrosterone + O2 = ?
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (14 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3beta-hydroxy-5alpha-androstane-17-one + NAD+ = 5alpha-androstane-3,17-dione + NADH
show the reaction diagram
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5alpha-androstane-3beta-ol-17-one + NADPH + H+ = ? + NADP+
show the reaction diagram
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epiandrosterone + NAD(P)+ = (5alpha)-androstane-3,17-dione + NAD(P)H + H+
show the reaction diagram
epiandrosterone + NAD+ = ? + NADH
show the reaction diagram
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epiandrosterone + NADPH = androstane-3beta,17beta-diol + NADP+
show the reaction diagram
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epiandrosterone + O2 = ?
show the reaction diagram
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UDP-glucose + epiandrosterone = UDP + epiandrosterone 3-beta-glucoside
show the reaction diagram
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3'-phosphoadenylylsulfate + 3beta-hydroxy-5alpha-androstan-17-one = adenosine 3',5'-bisphosphate + 5alpha-androstan-17-one 3-sulfate
show the reaction diagram
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3'-phosphoadenylylsulfate + epiandrosterone = adenosine 3',5'-bisphosphate + 5alpha-androstan-17-one 3-sulfate
show the reaction diagram

Product in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5alpha-androstan-3beta,17alpha-diol + NADP+ = 3beta-hydroxy-5alpha-androstan-17-one + NADPH
show the reaction diagram
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5alpha-androstane-3beta,17beta-diol + NAD+ = 5alpha-androstane-3beta-ol-17-one + NADH
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-3beta,17beta-diol + NADP+ = 3beta-hydroxy-5alpha-androstan-17-one + NADPH
show the reaction diagram
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epiandrosterone 3-sulfate + H2O = epiandrosterone + sulfate
show the reaction diagram
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epiandrosterone 3-sulfate + H2O = epiandrosterone + sulfate
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.1 mM, 77% inhibition
-
exhibits an IC50 of 0.12 mM against androstendione 6beta-hydroxylase activity and an IC50 of 0.14 against androstendione 16beta-hydroxylase activity
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3D Structure of Enzyme-Ligand-Complex (PDB) (16 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (1 result)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
7
-
H2O2 production assayed, 100 mM phosphate buffer

KM Value (1 result)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0207
-
pH 8.9, temperature not specified in the publication, NAD(P)+

Ki Value (7 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE

IC50 Value (3 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.003
-
wild type enzyme, at pH 7.5 and 25°C

References & Links

Links to other databases for epiandrosterone

ChEBI
PubChem
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PubChem