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BRENDA support

Ligand androst-4-ene-3,17-dione

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Basic Ligand Information

Molecular Structure
Picture of androst-4-ene-3,17-dione (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C19H26O2
androst-4-ene-3,17-dione
AEMFNILZOJDQLW-QAGGRKNESA-N
Synonyms:
(8R,9S,10R,13S,14S)-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione, 4-androsten-3,17-dione, 4-androstene-3,17-dione, 4-androstene-3, 17-dione, 4-androstenedione, 17-oxo-testosterone, androst-4-en-3,17-dione, androst-4-enedione, androstendione, androstene-3,17-dione, androstenedione, D4-androstene-3,17-dione, DELTA4-3,17-androstendione, DELTA4-androstene-3,17-dione
Pathway Source
Pathways
BRENDA
androgen and estrogen metabolism
KEGG
Endocrine resistance, Microbial metabolism in diverse environments, Ovarian steroidogenesis, Pathways in cancer, Prolactin signaling pathway more
MetaCyc
11-oxyandrogens biosynthesis, androgen biosynthesis, androstenedione degradation I (aerobic), androstenedione degradation II (anaerobic), cholesterol degradation to androstenedione I (cholesterol oxidase) more


Show all pahtways known for Show all BRENDA pathways known for androst-4-ene-3,17-dione

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (27 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
androstenedione + NADPH + H+ = testosterone + NADP+
show the reaction diagram
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androstenedione + NADPH + H+ = androsterone + NADP+
show the reaction diagram
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androstenedione + NAD(P)H = ?
show the reaction diagram
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androst-4-ene-3,17-dione + O2 = ? + H2O2
show the reaction diagram
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androst-4-ene-3,17-dione + AH2 + O2 = 3-oxo-13,17-secoandrost-4-ene-17,13alpha-lactone + A + H2O
show the reaction diagram
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3'-phosphoadenylyl sulfate + 4-androstene-3,17-dione = adenosine 3',5'-bisphosphate + 3-O-sulfo-3,5-androstadien-3-ol-17-one
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (28 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
testosterone + NAD(P)H + H+ = DELTA4-androstene-3,17-dione + NAD(P)+
show the reaction diagram
17alpha-hydroxyprogesterone + [reduced NADPH-hemoprotein reductase] + O2 = androstenedione + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (100 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
androstenedione + NADPH + H+ = 3beta-hydroxy-5-androsten-17-one + NADP+
show the reaction diagram
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androstenedione + NADPH + H+ = testosterone + NADP+
show the reaction diagram
-
androstenedione + NADPH + H+ = epitestosterone + NADP+
show the reaction diagram
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4-androstene-3,17-dione + NADPH + H+ = ?
show the reaction diagram
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androst-4-ene-3,17-dione + NADPH = ? + NADP+
show the reaction diagram
4-androstene-3,17-dione + NADH + H+ = 4-androsten-3alpha-ol-17-one + NAD+
show the reaction diagram
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4-androstenedione + NADPH + H+ = testosterone + NADP+
show the reaction diagram
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4-androstene-3,17-dione + NADPH + H+ = ? + NADP+
show the reaction diagram
-
androstenedione + NAD(P)H = ?
show the reaction diagram
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4-androstenedione + NADPH = ?
show the reaction diagram
4-androstene-3,17-dione + NADH + H+ = 4-androsten-3alpha-ol-17-one + NAD+
show the reaction diagram
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4-androstene-3,17-dione + NADPH + H+ = ?
show the reaction diagram
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androst-4-ene-3,17-dione + O2 = ? + H2O2
show the reaction diagram
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androstenedione + NADPH + O2 = 3-oxo-13,17-secoandrost-4-eno-17,13-alpha-lactone + NADP+ + H2O
show the reaction diagram
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4-androstene-3,17-dione + NADPH + H+ + O2 = 7alpha-hydroxy-4-androstene-3,17-dione + NADP+ + H2O
show the reaction diagram
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androstenedione + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = ? + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O
show the reaction diagram
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androstenedione + NADPH + O2 = ?
show the reaction diagram
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androstenedione + NADPH + H+ = 5alpha-androstan-3,17-dione + NADP+
show the reaction diagram
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3'-phosphoadenylyl sulfate + 4-androstene-3,17-dione = adenosine 3',5'-bisphosphate + 3-O-sulfo-3,5-androstadien-3-ol-17-one
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (79 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
testosterone + NAD(P)+ = androst-4-ene-3,17-dione + NADH + H+
show the reaction diagram
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dehydroepiandrosterone + NAD+ = androstenedione + NADH + H+
show the reaction diagram
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testosterone + NAD(P)H + H+ = DELTA4-androstene-3,17-dione + NAD(P)+
show the reaction diagram
17alpha-Hydroxyprogesterone + NADPH + O2 = androstenedione + acetate + NADP+ + H2O
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

Activator in Enzyme-catalyzed Reactions (2 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
in male foreskin fibroblasts
-
stimulation of ATPase-activity arising from co-expression of isoforms ABCG5 and ABCG8
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Inhibitor in Enzyme-catalyzed Reactions (25 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitive against substrate cyclohexanone
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most inhibitory at pH 8.0
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versus substrate, the products, 4-androstene-3,17-dione and NADH, inhibit the activity uncompetitively and competitively, respectively, with respect to NAD+ in the presence of a saturated concentration of 0.004 mM of the substrate
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strong substrate inhibition; strong substrate inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (319 results)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (39 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.043
-
at pH 7.4 and 37°C
0.0027
-
pH 7.0, 37°C
0.0038
-
pH 7.4, 37°C
1.1
-
pH 7.4, 37°C recombinant His-tagged enzyme
0.02
-
pH 7.4, temperature not specified in the publication

KM Value (79 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0703
-
-
0.031
-
-
0.001
-
at pH 7.4 and 37°C
0.0066
-
pH 7.0, 37°C
0.00212
-
pH 7.4, 37°C
0.04
-
-
0.004
-
pH 7.4, 37°C
0.031
-
pH and temperature not specified in the publication
0.013
-
identical for both enzyme activities
0.625
-
22°C
0.04
-
-

Ki Value (3 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0047
-
pH 7.3, 37°C, versus cyclohexanone

IC50 Value (3 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0005
-
in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.000337
0.000341
pH 7.4, 37°C
0.5
-
value above 0.5 mM

References & Links

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Links to other databases for androst-4-ene-3,17-dione

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ChEBI
PubChem
ChEBI
PubChem