Ligand deoxycholate

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 deoxycholate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C24H40O4
deoxycholate
KXGVEGMKQFWNSR-LLQZFEROSA-N
Synonyms:
3alpha,12alpha-dihydroxy-5-beta-cholanate, 3alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid, 3alpha,12alpha-dihydroxy-5beta-cholanate, 3alpha,12alpha-dihydroxy-5beta-cholanoate, 3alpha,12alphadihydroxy-5beta-cholanate, 5beta-cholanic acid-3alpha,12alpha-diol, deoxycholic acid, deoxycholic acid[side 1], deoxycholic acid[side 2]

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
deoxycholic acid + NADP+ = ? + NADPH + H+
show the reaction diagram
-
UDP-D-glucuronate + deoxycholic acid = UDP + hyodeoxycholic acid 6-O-glucuronoside
show the reaction diagram
-
3'-phosphoadenylylsulfate + deoxycholic acid = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-

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

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
12alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid + NADH + H+ = 3alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid + NAD+
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (20 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
deoxycholic acid + NADH = ?
show the reaction diagram
-
deoxycholic acid + NAD+ = 12alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid + NADH + H+
show the reaction diagram
-
deoxycholic acid + NADP+ = ?
show the reaction diagram
-
3'-phosphoadenylyl 5'-phosphosulfate + deoxycholate = adenosine 3',5'-bisphosphate + deoxycholate 3-sulfate
show the reaction diagram
-
ATP + deoxycholate + CoA = AMP + diphosphate + deoxycholoyl-CoA
show the reaction diagram
-
ATP + H2O + deoxycholic acid[side 1] = ADP + phosphate + deoxycholic acid[side 2]
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
12alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid + NADH + H+ = 3alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid + NAD+
show the reaction diagram
-
-
taurodeoxycholic acid + H2O = taurine + deoxycholic acid
show the reaction diagram
-
-
ATP + H2O + deoxycholic acid[side 1] = ADP + phosphate + deoxycholic acid[side 2]
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (58 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activity is slightly enhanced, but is enhanced by 50% together with Triton X-100
-
0.01% (v/v) promotes small enhancement in activity
-
activating the enzyme membrane-bound in the microsomal fraction
-
stimulates enzyme from intestinal mucosa
-
2% w/v, activation by pretreatment
-
0.025%, stimulates slightly
-
activates solubilized enzyme
-
5 to 7fold less effective compared to Triton CF-54
-
8% stimulation compared to Triton CF-54
-
stimulates solubilized activity
-
required, most effective detergent
-
9fold stimulation at 0.25%, inhibition at 0.5%
-
microsomal enzyme and enzyme released from microsomes are maximally activated at 5 mM. In the absence of deoxycholate, the released enzyme is inactive, while the microsomal enzyme has significant activity
-
activation at 0.05%
-
stimulation at 0.01%, inactivation at 0.2%
-
76% activation at 0.1% w/v
-
activation
-
Triton X-100 or deoxycholate required
-
presence of deoxycholate stabilizes the enzyme dimer and increases the catalytic activity with EC50 value of 0.186 mM. Binding is rapid and reversible
10 mM, 137% of initial activity activity
-
0.1%, activates
-
activation, 0.5-1 mg/ml, neutral enzyme form, not acidic enzyme form, inhibits above 1 mg/ml
-
the effective concentration range for enzyme activation is extremely narrow, around 0.1%. The enzyme activity may depend not only on the final concentration of sodium deoxycholate but also on its ratio to protein
-

Inhibitor in Enzyme-catalyzed Reactions (111 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
loss of activity within 40 h, if detergent is not removed by chromatography
-
i.e. chenodeoxycholic acid
-
0.1% (w/v), 30% inhibition
-
competitive inhibitor
-
1% w/v: 36% inhibition, deoxycholate, 1%, readily releases membrane-bound activity, but is slightly inhibitory
-
about 68% residual activity at 6% (v/v)
-
1% (v/v) promotes inhibition of activity
-
0.1%, 51% inhibition
-
inactivation
-
strong, almost complete inactivation at 0.04%
-
inhibition of liver enzyme
-
0.25%, 90% inhibition
-
total inactivation
-
9fold stimulation at 0.25%, inactivation at 0.5%
-
complete inhibition at 0.5%
-
0.01%, 70% inhibition
-
0.05%, almost complete inhibition
-
inactivation, 0.2%
-
inactivation at 0.2%, activation at 0.01%
-
partial inhibition
-
50% inhibition at 1%
-
17% inhibition at 5 mM
-
substrate: phosphatidylcholine
-
75-80% loss of activity at 2% concentration
-
24% inhibition at 10 mM; 25% inhibition at 10 mM
-
84% inhibition at 0.05 vol%
-
2 mM, 50% decrease in activity
-
even 0.025%
-
0.45%, 26% residual activity
-
89% inhibition at 1%, w/v
-
slight inhibition
-
competitive inhibition
at 1%; at 1%
-
complete inhibition of the hydrolytic and synthetic activity
-
0.1%, 92% residual activity
-
neutral enzyme form, above 1 mg/ml, activation at 0.5-1 mg/ml
-
at 20-30°C
-

3D Structure of Enzyme-Ligand-Complex (PDB) (26 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (4 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.133
-
DD1

KM Value (12 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0136
-
-
0.0045
-
DD1
0.053
-
-

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.46
-
pH 6.5, 40°C, recombinant wild-type enzyme

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.00021
-
in 0.1 M potassium phosphate, pH 7.4, at 25°C

References & Links

Links to other databases for deoxycholate

ChEBI
PubChem
-
PubChem