Ligand cortisone

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Basic Ligand Information

Molecular Structure
Picture of cortisone (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C21H28O5
cortisone
MFYSYFVPBJMHGN-ZPOLXVRWSA-N
Synonyms:
4-pregnene-17alpha,21-diol-3,11,20-trione, 17alpha,21-dihydroxy-4-pregnen-3,11,20-trione, 17alpha,21-dihydroxy-pregn-4-ene-3,11,20-trione, 17alpha,21-dihydroxypregn-4-ene-3,11,20-trione

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
cortisone + NADPH = cortisol + NADP+
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In Vivo Product in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE

Substrate in Enzyme-catalyzed Reactions (24 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
cortisone + NADH = ? + NAD+
-
show the reaction diagram
cortisone + NADP+ = ? + NADPH
-
show the reaction diagram
Cortisone + NADPH + O2 = ?
-
show the reaction diagram
cortisone + reduced adrenodoxin + O2 = 15beta-hydroxycortisone + oxidized adrenodoxin + H2O
-
show the reaction diagram
17alpha,21-dihydroxypregn-4-ene-3,11,20-trione + NADPH = 17alpha,21-dihydroxy-5alpha-pregnan-3,11,20-trione + NADP+
-
show the reaction diagram
cortisone + acceptor = 1,4-pregnene-17alpha,21-diol-3,11,20-trione + reduced acceptor
-
show the reaction diagram
3'-phosphoadenylyl sulfate + cortisone = adenosine 3',5'-bisphosphate + ?
-
show the reaction diagram
3'-phosphoadenylylsulfate + cortisone = adenosine 3',5'-bisphosphate + cortisone sulfate
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Product in Enzyme-catalyzed Reactions (12 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
17alpha-hydroxy-pregn-4-ene-3,11,20,21-tetraone + NADPH = 17alpha,21-dihydroxy-pregn-4-ene-3,11,20-trione + NADP+
-
show the reaction diagram
cortisol + reduced adrenal ferredoxin + O2 = cortisone + oxidized adrenal ferredoxin + H2O
-
-
show the reaction diagram
cortisone 21-sulfate + H2O = cortisone + sulfate
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Activator in Enzyme-catalyzed Reactions (3 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (6 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
i.e. cortisone
-
competitive
-
cortisol as substrate, weak, 0.012 mM
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (10 results)

COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
37°C, pH 7.4, recombinant 11beta-HSD1 expressed in Escherichia coli
NADH
0.333
-
-
0.0375
-
mutant P133R, pH not specified in the publication, temperature not specified in the publication
0.01
-
pH 6.0, 37°C
0.195
-
pH 6.0, 37°C, mutant P133R
0.01
-
pH 6.0, 37°C, wild-type enzyme
0.165
-
wild-type, pH not specified in the publication, temperature not specified in the publication
0.17
-
pH 7.5, 37°C cosubstrate ethanol
0.15
-

KM Value (37 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
pH 7.4, 28°C
0.0044
-
at pH 7.5 and 37°C
0.193
-
37°C, pH 7.4, V149R mutant 11beta-HSD1, V149E mutant 11beta-HSD1, and N-terminal 15 amino acid truncated V149R and V149E mutant 11beta-HSD1
0.1
-
37°C, pH 7.4, reduction of cortisone in intact HEK-293 cells transfected with 11beta-HSD1
0.0008
-
37°C, pH 7.4, reduction of cortisone by lysates of HEK-293 cells transfected with 11beta-HSD1
0.00034
-
37°C, pH 7.4, recombinant 11beta-HSD1 measured in intact COS cells transfected with 11beta-HSD1
37°C, pH 7.4, recombinant 11beta-HSD1 measured in extracts of COS cells transfected with 11beta-HSD1
37°C, pH 7.4, recombinant 11beta-HSD1 expressed in Pichia pastoris
0.002
-
37°C, pH 7.4, recombinant 11beta-HSD1 expressed in Escherichia coli
37°C, pH 7.4, recombinant 11beta-HSD1
0.0006
-
37°C, pH 7.4, Hill coefficient of 1.6
0.014
-
kidney enzyme, pH 7.4, 37°C
0.0008
-
liver enzyme, pH 7.4, 37°C
0.01
-
NADH, pH 6.3
0.022
-
pH 7.3, 28°C
0.142
-
-
0.318
-
immobilized enzyme
0.085
0.098
free enzyme
0.042
0.048
-
0.024
-
pH 7.4, 37°C, recombinant isozyme 11beta-HSD1
-
0.14
-
wild-type, pH not specified in the publication, temperature not specified in the publication
0.0151
-
pH 6.0, 37°C, wild-type enzyme
0.0151
-
pH 6.0, 37°C, mutant P133R
0.0013
-
pH 6.0, 37°C
0.0151
-
-
0.0015
-
mutant P133R, pH not specified in the publication, temperature not specified in the publication
0.0013
-
i.e. 4-pregnene-17alpha,21diol-3,11,20-trione
0.0256
-

Ki Value (1 result)

COMMENTARY
EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
LITERATURE
androsterone oxidation
0.285
-

IC50 Value (1 result)

COMMENTARY
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
LITERATURE
in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0022
-

References & Links

Links to other databases for cortisone

ChEBI
PubChem
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PubChem