Ligand cholic acid

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Basic Ligand Information

Molecular Structure
Picture of cholic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C24H40O5
cholic acid
BHQCQFFYRZLCQQ-OELDTZBJSA-N
Synonyms:
(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxycholan-24-oic acid, 3alpha,7alpha,12alpha-trihydroxy-5 beta-cholanate, 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanate, 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoate, 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoic acid, 5beta-cholanic acid-3alpha,7alpha,12alpha-triol, bile acid, cholate, cholic acid[side 1], cholic acid[side 2], choloate, ursocholic acid


Show all pahtways known for Show all BRENDA pathways known for cholic acid

Roles as Enzyme Ligand

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

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cholate + NAD+ = 3alpha,12alpha-dihydroxy-7-oxo-5beta-cholanate + NADH + H+
show the reaction diagram
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cholic acid + NADP+ = ? + NADPH + H+
show the reaction diagram
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3'-phosphoadenylylsulfate + cholic acid = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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cholic acid + H2O = ? + glycine
show the reaction diagram
ATP + H2O + cholate/in = ADP + phosphate + cholate/out
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
12-ketochenodeoxycholic acid + NADH = cholic acid + NAD+
show the reaction diagram
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choloyl-CoA + H2O = cholate + CoA
show the reaction diagram
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ATP + H2O + cholate/in = ADP + phosphate + cholate/out
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (37 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cholic acid + NAD+ = 7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic acid + NADH
show the reaction diagram
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cholic acid + 2 reduced ferredoxin [iron-sulfur] cluster + H+ + O2 = ?
show the reaction diagram
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cholic acid + NADP+ = ?
show the reaction diagram
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cholic acid + H2O = ? + glycine
show the reaction diagram

Product in Enzyme-catalyzed Reactions (26 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
dehydrocholic acid + NAD(P)H = cholic acid + NAD(P)+
show the reaction diagram
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choloyl-CoA + H2O = CoA + choloate
show the reaction diagram
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choloyl-CoA + H2O = cholate + CoA
show the reaction diagram
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taurocholic acid + H2O = taurine + cholic acid
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (28 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
stimulates without a significant change in Km in the presence of low Triton X-100 concentrations, changes the sigmoidal kinetic into normal Michaelis-Menten kinetic with reduced Km in the presence of high Triton X-100 concentrations
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activation
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activates only CPTi
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increase of activity in cholate-fed animals
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activation
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activity is dependent on the presence of primary bile salts such as cholate, taurocholate and taurochenodeoxycholate
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slight stimulation at 0.1 and 0.01% w/v. Strong inhibition at 1% w/v
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Inhibitor in Enzyme-catalyzed Reactions (88 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibition of the ADH from Lactobacillus brevis by bile acids, acetone prevents partially
-
i.e. cholic acid
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0.1 mM, 10% inhibition
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0.1% (w/v), 30% inhibition
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complete inhibition
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IC50: 3.529 mM
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feedback inhibition preventing the accumulation of cytotoxic hydrophobic bile acids
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10 mM, 89% inhibition
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weak inhibition
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high concentration
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only CPTo
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1%, 90% inhibition
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41.78% inhibition at 1 mM
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inactivation at solubilization concentration, full recovery of activity after reconstituting the membrane by adding excess lipid and removing detergent by gel filtration, dialysis or absorption to Bio-Beads, if membrane is solubilized with octylglucoside or cholate at weight ratios of detergent:membrane protein of at least 10, the activity is irreversibly lost unless stabilizers are added with detergent, diacylglycerol and glycerol are effective stabilizers
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bile salt regulation of lipid metabolism via both activation and inhibition of PLA2, interaction and binding structure analysis, overview
slight stimulation at 0.1 and 0.01% w/v. Strong inhibition at 1% w/v
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inhibits PLC-beta1 activity
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inhibitory to both the separate protease domain and to protease-reverse transcriptase. Cholic acid binds in the proposed protease domain dimerization interface and appears to impair formation of the correct dimer
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from dried bile of Ursus arctos or Selenarctos thibetanus
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3D Structure of Enzyme-Ligand-Complex (PDB) (120 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (17 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE

KM Value (37 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.16
-
DD1

Ki Value (2 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE

IC50 Value (4 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0022
-
in 0.1 M potassium phosphate, pH 7.4, at 25°C
3.529
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IC50: 3.529 mM

References & Links

Links to other databases for cholic acid

ChEBI
PubChem
ChEBI
PubChem