Ligand 11-deoxycorticosterone

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.

Basic Ligand Information

Molecular Structure
Picture of 11-deoxycorticosterone (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C21H30O3
11-deoxycorticosterone
ZESRJSPZRDMNHY-YFWFAHHUSA-N
Synonyms:
4-pregenene-21-ol-3,20-dione, 4-pregnene-21-ol-3,20-dione, 11-deoxydorticosterone, 11-desoxycorticosterone, 21-hydroxy-pregn-4-en-3,20-dione, 21-hydroxy-pregn-4-ene-3,20-dione, 21-hydroxy-progesterone, 21-hydroxypregn-4-ene-3,20-dione, 21-hydroxyprogesterone, 21beta-hydroxy progesterone, bradykinin-potentiating factor SQ 20881, cortexone, deoxycorticosterone

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
11-deoxycorticosterone + AH2 + O2 = ? + A + H2O
-
show the reaction diagram
deoxycorticosterone + reduced acceptor = 21-hydroxy-5alpha-pregnan-3,20-dione + acceptor
-
show the reaction diagram
21-hydroxyprogesterone + UDP-glucuronate = UDP + 21-hydroxyprogesterone-21-O-alpha-D-glucuronate
-

In Vivo Product in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
corticosterone + reduced adrenal ferredoxin + O2 = 11-deoxycorticosterone + adrenal ferredoxin + H2O

Substrate in Enzyme-catalyzed Reactions (35 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
11-deoxycorticosterone + NAD(P)H = 4-pregnen-20alpha,21-diol-3-one + NAD(P)+
-
show the reaction diagram
deoxycorticosterone + NADPH = 20,21-dihydroxypregn-4-ene-3-one + NADP+
-
show the reaction diagram
deoxycorticosterone + NADPH + O2 = ?
-
show the reaction diagram
11-deoxycorticosterone + AH2 + O2 = ? + A + H2O
-
show the reaction diagram
deoxycorticosterone + NADPH + O2 = testosterone + NADP+ + ?
-
show the reaction diagram
deoxycorticosterone + reduced acceptor = 21-hydroxy-5alpha-pregnan-3,20-dione + acceptor
-
show the reaction diagram
21-hydroxyprogesterone + UDP-glucuronate = UDP + 21-hydroxyprogesterone-21-O-alpha-D-glucuronate
-
show the reaction diagram
UDP-alpha-D-glucose + 21-hydroxyprogesterone = UDP + 3,20-dioxopregn-4-en-21-yl beta-D-glucopyranoside
-
show the reaction diagram
3'-phosphoadenylylsulfate + 11-deoxycorticosterone = adenosine 3',5'-bisphosphate + 11-deoxycorticosterone sulfate
-
show the reaction diagram
3'-phosphoadenylylsulfate + deoxycorticosterone = adenosine 3',5'-bisphosphate + ?
-
show the reaction diagram
3'-phosphoadenylylsulfate + 11-deoxycorticosterone = adenosine 3',5'-bisphosphate + 11-deoxycorticosterone sulfate
-
show the reaction diagram
11-Deoxycorticosterone = 20-Hydroxy-3-oxopregn-4-en-21-al
-
show the reaction diagram
ATP + H2O + deoxycorticosterone/in = ADP + phosphate + deoxycorticosterone/out
-

Product in Enzyme-catalyzed Reactions (14 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
pregn-4-ene-3,20,21-trione + NADH = 21-hydroxy-pregn-4-ene-3,20-dione + NAD+
-
show the reaction diagram
pregn-4-ene-3,20,21-trione + NADPH = 21-hydroxy-pregn-4-ene-3,20-dione + NADP+
-
-
show the reaction diagram
corticosterone + reduced adrenal ferredoxin + O2 = 11-deoxycorticosterone + adrenal ferredoxin + H2O
-
show the reaction diagram
21-hydroxy-5beta-pregnan-3,20-dione + acceptor = 21-hydroxy-pregn-4-en-3,20-dione + reduced acceptor
-
-
show the reaction diagram
ATP + H2O + deoxycorticosterone/in = ADP + phosphate + deoxycorticosterone/out
-

Activator in Enzyme-catalyzed Reactions (1 result)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
activates
-

Inhibitor in Enzyme-catalyzed Reactions (18 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
IC50: 0.031 mM
-
i.e. 11-deoxycorticosterone
-
0.010 mM, 73% inhibition
-
IC50: 0.001 mM
-
competitive substrate inhibition
this inhibition may play a role in cataract formation in patients maintained on systemic corticosteroids and in tablet-dependent diabetics
-
inhibits esterification of endogenous cholesterol
-
competitive inhibitor, inhibits cortisol sulfotransferase activity
-
cortisol as substrate, strong
-

3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (7 results)

COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
+/-2.112, calculatetd from Kcat/Km
0.66
-
11beta-hydroxylation
1.83
-
18-hydroxylation
0.3
-
dipalmitoyl phosphatidylcholine vesicles
0.583
-
dipalmitoyl phosphatidylcholine vesicles + diphosphatidyl glycerol
0.133
-
pH 7.4, recombinant enzyme
0.85
-
pH 7.5, 37°C
0.183
-

KM Value (33 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
pH 7.4, 37°C
0.0033
-
without phospholipids
0.00087
-
with phospholipids
0.0011
-
presence of methyltrienolone
0.0008
-
pH 7.4, recombinant enzyme
0.18
-
identical for both enzymes activities
0.02
-
identical for both enzyme activities
0.006
-
dipalmitoyl/diphytanoyl-phosphatidylcholine vesicles
0.01
-
dipalmitoyl-phosphatidylcholine vesicles
0.005
-
absence of methyltrienolone
0.002
-
37°C
0.0073
-
+/-0.00008
0.0015
-
+/-0.00026
0.00197
-
dipalmitoyl phosphatidylcholine/diphosphatidyl glycerol vesicles
0.033
-
pH 7.4, 30°C, mutant K27R/I71T/I215T
0.0024
-
pH 7.4, 30°C, wild-type enzyme
0.0015
-
pH 7.4, 30°C, mutant S394I
0.0047
-
pH 7.4, 30°C, mutant Q398S
0.0056
-
pH 7.4, 30°C, mutant I86T
0.0012
-
pH 7.4, 30°C, mutant G397P
0.0046
-
pH 7.4, 30°C, mutant E90V/D185G
0.0019
-
pH 7.4, 30°C, mutant A395L
0.0042
-
22°C
0.06
-
pH 7.0, 30°C
pH 8.0, 30°C
0.07
-
pH 7.5, 37°C
0.52
-
-
0.0038
-

Ki Value (1 result)

COMMENTARY
EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
LITERATURE
22°C
0.11
-

IC50 Value (3 results)

COMMENTARY
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
LITERATURE
IC50: 0.031 mM
0.031
-
in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0025
-
IC50: 0.001 mM
0.001
-

References & Links

Links to other databases for 11-deoxycorticosterone

ChEBI
PubChem
-
PubChem