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BRENDA support

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
Pathway Source
Pathways
BRENDA
androgen and estrogen metabolism
KEGG
Endocrine resistance, GnRH secretion, Microbial metabolism in diverse environments, Ovarian steroidogenesis, Pathways in cancer more
MetaCyc
11-oxyandrogens biosynthesis, androgen biosynthesis, estradiol biosynthesis II, testosterone and androsterone degradation to androstendione (aerobic), testosterone degradation (anaerobic)


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

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (26 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
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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 = UDP + testosterone beta-D-glucuronoside
show the reaction diagram
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3'-phosphoadenylyl sulfate + testosterone = adenosine 3',5'-bisphosphate + testosterone sulfate
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (12 results)

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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 (107 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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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 + H+ = ?
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 + H+ = ? + 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 + ?
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
show the reaction diagram
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3'-phosphoadenylyl 5'-phosphosulfate + testosterone = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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3'-phosphoadenylyl sulfate + testosterone = adenosine 3',5'-bisphosphate + testosterone sulfate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (34 results)

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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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4-androstenedione + NADPH + H+ = testosterone + NADP+
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)

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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 (46 results)

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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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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)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (32 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.057
-
at pH 7.4 and 37°C
0.6
-
pH 6.5, 25°C
0.032
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pH 7.4, 37°C
0.0757
-
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0.26
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at pH 7.0 and 22°C
351.9
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pH 7.8, 30°C
0.467
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pH 7.5, 37°C

KM Value (125 results)

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

Ki Value (7 results)

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

IC50 Value (7 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.00137
-
pH and temperature not specified in the publication
0.0016
-
in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.03
0.072
IC50: 0.03-0.072 mM
0.5
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value above 0.5 mM
0.0535
-
-

References & Links

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Links to other databases for testosterone

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ChEBI
PubChem
ChEBI
PubChem