Ligand Epitestosterone

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Basic Ligand Information

Molecular Structure
Picture of Epitestosterone (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C19H28O2
Epitestosterone
MUMGGOZAMZWBJJ-KZYORJDKSA-N
Synonyms:
(17alpha)-17-hydroxyandrost-4-en-3-one, 4-androsten-17alpha-ol-3-one, 17-epitestosterone, 17alpha-Hydroxy-4-androsten-3-one, 17alpha-hydroxyandrosten-3-one

Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (13 results)

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EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
17alpha-hydroxy-4-androsten-3-one + NADP+ = 4-androsten-3,17-dione + NADPH
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show the reaction diagram
epitestosterone + NADP+ = 4-androsten-3,17-dione + NADPH + H+
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show the reaction diagram
epitestosterone + NAD(P)+ = ?
show the reaction diagram
epitestosterone + NADPH + H+ = ?
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show the reaction diagram
3'-phosphoadenylylsulfate + epitestosterone = adenosine 3',5'-bisphosphate + epitestosterone sulfate
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Product in Enzyme-catalyzed Reactions (3 results)

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EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
androstenedione + NADPH + H+ = epitestosterone + NADP+
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show the reaction diagram
epitestosterone 17-sulfate + H2O = epitestosterone + sulfate
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show the reaction diagram
epitestosterone 17-sulfate + H2O = epitestosterone + sulfate
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Inhibitor in Enzyme-catalyzed Reactions (4 results)

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COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
substrate inhibition for all isoforms at concentration above 0.003 mM, not observed with other substrates
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i.e. epitestosterone
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competitive inhibitor of 17alpha-hydroxylation of pregnenolone and of the subsequent C17,20-side chain cleavage reaction
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3D Structure of Enzyme-Ligand-Complex (PDB) (3 results)

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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (6 results)

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COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
mutant G225P/G226P
0.25
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mutant Q222N, pH 7.0, 25°C
0.23
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mutant Y224F, pH 7.0, 25°C
0.57
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wild-type
0.3
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wild-type, pH 7.0, 25°C
0.3
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pH 6.0, 37°C
0.1
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KM Value (17 results)

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COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
for six isoforms
0.0002
0.0052
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0.07
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kidney isozyme II
0.00061
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wild-type, pH 7.0, 25°C
0.0006
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wild-type
0.0006
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mutant Y224F, pH 7.0, 25°C
0.014
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mutant Q222N, pH 7.0, 25°C
0.02
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mutant G225P/G226P
0.018
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liver isozyme IB, androsterone, kidney, isozyme IB
0.0021
0.0024
liver isozyme IB
0.00053
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kidney isozyme IB
0.00291
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cofactor NADP+
0.0001
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in living cells
0.00078
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in homogenates
0.00057
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pH 6.0, 37°C
0.0029
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isoform UGT2B7, pH 7.4, 37°C
0.0017
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isoform UGT2A1, pH 7.4, 37°C
0.0116
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Ki Value (2 results)

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COMMENTARY
EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
LITERATURE
17alpha-hydroxylase activity
0.0096
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C17,20-lyase activity
0.00124
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IC50 Value (1 result)

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COMMENTARY
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
LITERATURE
in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0033
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References & Links

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Links to other databases for Epitestosterone

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ChEBI
PubChem
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PubChem