Ligand cholic acid

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Basic Ligand Information

Molecular Structure

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

BRENDA

bile acid biosynthesis, neutral pathway

KEGG

Bile secretion, Primary bile acid biosynthesis, Secondary bile acid biosynthesis

MetaCyc

bile acid 7alpha-dehydroxylation, bile acid 7beta-dehydroxylation, bile acids 12-O-epimerization, bile acids 3-O-epimerization, bile acids 7-O epimerization

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Show all BRENDA pathways known for cholic acid

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (10 results)

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1.1.1.159

cholate + NAD+ = 3alpha,12alpha-dihydroxy-7-oxo-5beta-cholanate + NADH + H+

740787, 741371, 740971

cholic acid + H2O = ? + glycine

712204

2rlc, 3D-view

6.2.1.7

ATP + cholate + CoA = AMP + diphosphate + choloyl-CoA

834, 830, 840, 651997

7.6.2.2

ATP + H2O + cholate/in = ADP + phosphate + cholate/out

701356

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

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1.1.1.176

12-ketochenodeoxycholic acid + NADH = cholic acid + NAD+

347748

3.1.2.27

choloyl-CoA + H2O = cholate + CoA

3.5.1.24

6 entries

7.6.2.2

ATP + H2O + cholate/in = ADP + phosphate + cholate/out

Substrate in Enzyme-catalyzed Reactions (47 results)

cholic acid + NAD(P)+ = 3-oxo-cholic acid + NAD(P)H + H+

cholic acid + NAD+ = 7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic acid + NADH

287082

1.14.15.30

cholic acid + 2 reduced ferredoxin [iron-sulfur] cluster + H+ + O2 = ?

745648

1.3.1.20

cholic acid + NADP+ = ?

349255, 349256, 349252

cholic acid + H2O = ? + glycine

Product in Enzyme-catalyzed Reactions (34 results)

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1.1.1.112

dehydrocholic acid + NAD(P)H = cholic acid + NAD(P)+

3-oxo-cholic acid + NAD(P)H + H+ = cholic acid + NAD(P)+

1.1.1.270

3-oxocholic acid + NAD(P)H + H+ = cholic acid + NAD(P)+

1.1.1.357

dehydrocholic acid + NADH + H+ = cholic acid + NAD+

3.1.2.2

2 entries

3.1.2.20

choloyl-CoA + H2O = CoA + choloate

3.1.2.27

choloyl-CoA + H2O = cholate + CoA

3.5.1.24

17 entries

3.5.1.74

taurocholic acid + H2O = taurine + cholic acid

7.6.2.2

2 entries

Activator in Enzyme-catalyzed Reactions (29 results)

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1.1.3.6

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

activation

activates only CPTi

increase of activity in cholate-fed animals

activation

activity is dependent on the presence of primary bile salts such as cholate, taurocholate and taurochenodeoxycholate

94406

3.1.2.21

slight stimulation at 0.1 and 0.01% w/v. Strong inhibition at 1% w/v

23906

3.1.3.106

activity is completely dependent on the presence of detergents such as Triton X-100, CHAPS, cholate and octyl-beta-glucoside

Inhibitor in Enzyme-catalyzed Reactions (53 results)

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1.1.1.2

inhibition of the ADH from Lactobacillus brevis by bile acids, acetone prevents partially

i.e. cholic acid

0.1 mM, 10% inhibition

667890

1.1.1.307

0.1% (w/v), 30% inhibition

complete inhibition

IC50: 3.529 mM

feedback inhibition preventing the accumulation of cytotoxic hydrophobic bile acids

712117

1.14.18.2

10 mM, 89% inhibition

weak inhibition

high concentration

only CPTo

1%, 90% inhibition

41.78% inhibition at 1 mM

684256

2.7.8.2

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

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

23906

3.1.4.11

inhibits PLC-beta1 activity

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

717211