Ligand testosterone

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Basic Ligand Information

Molecular Structure
Picture of testosterone (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C19H28O2
testosterone
MUMGGOZAMZWBJJ-DYKIIFRCSA-N
Synonyms:
4-androsten-17beta-ol-3-one, 4-androstene-17beta-ol-3-one, 4-pregnen-17-ol-3-one, 17beta-hydroxy-4-androsten-3-one, 17beta-hydroxyandrost-4-en-3-one, androst-4-ene-17beta-ol-3-one, DELTA4-androstan-17beta-ol-3-one


Show all pahtways known for Show all BRENDA pathways known for testosterone

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (24 results)

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
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testosterone + 3 O2 + 3 reduced flavoproteins = 17beta-estradiol + formate + 4 H2O + 3 oxidized flavoproteins
show the reaction diagram
testosterone + reduced ferredoxin [iron-sulfur] cluster + O2 + H+ = 1alpha-hydroxytestosterone + H2O + oxidized ferredoxin [iron-sulfur] cluster
show the reaction diagram
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testosterone + AH2 + O2 = 11alpha-hydroxytestosterone + A + H2O
show the reaction diagram
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testosterone + reduced acceptor = 5alpha-dihydrotestosterone + acceptor
show the reaction diagram
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testosterone + UDP-glucuronate = ?
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
DELTA5-androstenediol + NAD+ = testosterone + NADH + H+
show the reaction diagram
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androstenedione + NADPH + H+ = testosterone + NADP+
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (108 results)

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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17beta-hydroxy-4-androsten-3-one + NADP+ = 4-androsten-3,17-dione + NADPH
show the reaction diagram
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testosterone + NADP+ = ?
show the reaction diagram
testosterone + NADPH = ?
show the reaction diagram
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testosterone + NAD(P)H + H+ = DELTA4-androstene-3,17-dione + NAD(P)+
show the reaction diagram
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testosterone + H2O2 = 17beta-hydroxy-4,5-epoxy-5beta-androstan-3-one + 16alpha,17beta-dihydroxyandrost-4-en-3-one + H2O
show the reaction diagram
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testosterone + 3 O2 + 3 reduced flavoproteins = 17beta-estradiol + formate + 4 H2O + 3 oxidized flavoproteins
show the reaction diagram
testosterone + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = ? + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O
show the reaction diagram
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testosterone + AH2 + O2 = 11alpha-hydroxytestosterone + A + H2O
show the reaction diagram
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testosterone + NADPH + H+ = 4-androsten-3alpha,17beta-diol + NADP+
show the reaction diagram
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testosterone + NADPH = ? + NADP+
show the reaction diagram
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testosterone + NADH = 17beta-hydroxy-5beta-androstan-3-one + NAD+
show the reaction diagram
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NADH + testosterone = ?
show the reaction diagram
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UDP-alpha-D-glucose + testosterone = UDP + testosterone 17-beta-D-glucoside
show the reaction diagram
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UDP-glucose + testosterone = UDP + testosterone-17-yl beta-D-glucopyranoside
show the reaction diagram
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3'-phosphoadenylylsulfate + testosterone = adenosine 3',5'-bisphosphate + testosterone sulfate
show the reaction diagram
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3'-phosphoadenylylsulfate + testosterone = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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3'-phosphoadenylylsulfate + testosterone = adenosine 3',5'-bisphosphate + testosterone 3-sulfate
show the reaction diagram
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3'-phosphoadenosine 5'-phosphosulfate + testosterone = adenosine 3',5'-diphosphate + testosterone sulfate
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3'-phosphoadenylyl 5'-phosphosulfate + testosterone = adenosine 3',5'-bisphosphate + ?
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Product in Enzyme-catalyzed Reactions (35 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
androstenedione + NADPH + H+ = testosterone + NADP+
show the reaction diagram
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epitestosterone + NADP+ = testosterone + NADPH + H+
show the reaction diagram
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deoxycorticosterone + NADPH + O2 = testosterone + NADP+ + ?
show the reaction diagram
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17beta-hydroxy-5beta-androstan-3-one + menaphthone = testosterone + reduced acceptor
show the reaction diagram
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testosterone oleate + H2O = testosterone + oleate
show the reaction diagram
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testosterone 17-sulfate + H2O = testosterone + sulfate
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (14 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
at low dose, increase in mRNA expression. At doses above 0.2 mg/kg/day, downregulation of 3beta-hydroxysteroid dehydrogenase mRNA
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0.023 mM, 2.6fold increase in androstenedione reduction
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significantly increases activity in castrated males and normal female mice
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stimulates isozyme type I in liver
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5alpha-reductase activity in males is increased by testosterone regardless of breeding season, thus, testosterone appears to regulate its own metabolism in male, but not female, anoles
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treatment of meibomian gland stimulates a significant increase in the mRNA levels of mevalonate kinase, phosphomevalonate kinase, mevalonate diphosphate decarboxylase, isopentenyl diphosphate isomerase, geranylgeranyl diphosphate synthase, squalene epoxidase, lanosterol synthase, lanosterol demethylase, and DELTA7-sterol reductase
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treatment of meibomian gland stimulates a significant increase in the mRNA levels of mevalonate kinase, phosphomevalonate kinase, mevalonate diphosphate decarboxylase, isopentenyl diphosphate isomerase, geranylgeranyl diphosphate synthase, squalene epoxidase, lanosterol synthase, lanosterol demethylase, and DELTA7-sterol reductase
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left ventricle HSL activity against triglycerides is significantly elevated in intact rats supplemented with testosterone, testosterone replacement fully reverses this effect
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activates the neutral alpha-glucosidase in epididymal corpus
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Inhibitor in Enzyme-catalyzed Reactions (45 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibition of isoenzyme BB-ADH, no inhibition of isoenzyme AA-ADH and TT-ADH
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0.003 mM, 50% inhibition of oxido-reductase reaction; 0.02 mM, 50% inhibition of dehydrogenase reaction
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1 mM, 48% inhibition
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i.e. testosterone
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0.01 mM, 70% inhibition, reaction with 0.002 mM estradiol
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1 mM, 62.8% inhibition of androstendione reduction
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lactonization of androstenedione
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substrate inhibition
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potent inhibition of CYP11B2, recombinant enzyme
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IC50: 0.03-0.072 mM
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ornithine aminotransferase is naturally downregulated in the presence of testosterone
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competitive inhibitor, inhibits cortisol sulfotransferase activity
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cortisol as substrate, strong
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19% inhibition at 0.035 mM
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inhibits the neutral alpha-glucosidase in epididymal cauda and caput
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29% decrease in activity in female mice, more important chnage in female compared to male mice, overview
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3D Structure of Enzyme-Ligand-Complex (PDB) (66 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (27 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.057
-
at pH 7.4 and 37C
0.6
-
pH 6.5, 25C
0.0757
-
-
0.26
-
at pH 7.0 and 22C
351.9
-
pH 7.8, 30C
0.467
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pH 7.5, 37C

KM Value (118 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0583
-
-
0.013
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at pH 7.4 and 37C
0.04
-
pH 6.5, 25C
0.0057
-
-
0.009
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cosubstrate NAD+
0.00021
-
pH 7.2, 37C
0.04
-
pH and temperature not specified in the publication
0.278
-
wild-type, pH 7.5, 37C, S50 value, Hill coefficient 1.64
1.11
-
22C
0.0051
-
-
0.025
0.089
depending on phosphate concentration
0.8379
-
pH 7.8, 30C
0.17
-
pH 8.0, 30C
0.0002
-
pH 7.7, 37C, 3-alphaHST isoform

Ki Value (7 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.13
-
pH 7.0, 22C

IC50 Value (6 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0016
-
in 0.1 M potassium phosphate, pH 7.4, at 25C
0.03
0.072
IC50: 0.03-0.072 mM
0.5
-
value above 0.5 mM
0.0535
-
-

References & Links

Links to other databases for testosterone

ChEBI
PubChem
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PubChem