Ligand taurocholic acid

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Basic Ligand Information

Molecular Structure
Picture of taurocholic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C26H45NO7S
taurocholic acid
WBWWGRHZICKQGZ-HZAMXZRMSA-N
Synonyms:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl taurine, cholyltaurine, taurocholate

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Roles as Enzyme Ligand

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

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ATP + H2O + taurocholate/in = ADP + phosphate + taurocholate/out
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
choloyl-CoA + taurine = CoA + taurocholate
show the reaction diagram
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ATP + H2O + taurocholate/in = ADP + phosphate + taurocholate/out
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (14 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
taurocholic acid + NAD+ = 2[[3alpha,12alpha-dihydroxy-7,24-dioxo-5beta-cholan-24-yl]amino]ethane sulfonic acid + NADH
show the reaction diagram
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taurocholic acid + NAD(P)+ = 3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanoyl taurine + NAD(P)H
show the reaction diagram
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taurocholic acid + NAD+ = 3-oxotaurocholic acid + NADH + H+
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taurocholate + O2 = ? + H2O2
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taurocholic acid + NADP+ = ?
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3'-phosphoadenylyl-sulfate + taurocholate = adenosine 3',5'-bisphosphate + taurocholate monosulfate + taurocholate disulfate + taurocholate trisulfate
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taurocholic acid + H2O = taurine + cholic acid
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ATP + H2O + taurocholate/in = ADP + phosphate + taurocholate/out
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (2 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
choloyl-CoA + taurine = CoA + taurocholate
show the reaction diagram
-
ATP + H2O + taurocholate/in = ADP + phosphate + taurocholate/out
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (28 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
about 36% as effective as G-3634-A
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stimulates solubilized activity
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stimulates
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activates; non-essential activator
bile salt regulation of lipid metabolism via both activation and inhibition of PLA2, interaction and binding structure analysis, overview
114% activity at 1% (w/v); 136.3% activity at 1% (w/v); 168.3% activity at 1% (w/v)
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stimulates
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required for hydrolysis of lipid substrates
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concentrations of 0.05 M and 0.1 M cause 140% and 160% of activity
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increases the efflux of phospholipids and cholesterol from cells, the taurocholate monomer plays an important role in ABCB4-mediated lipid secretion
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Inhibitor in Enzyme-catalyzed Reactions (23 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
IC50 is above 0.1 mM
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in presence of Triton X-100
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high concentrations, above 0.3% w/v
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IC50 is 0.09 mM
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at low concentrations of 0.00001-0.1 mM it increases caspase-3 activity, but at larger doses of 0.5-10 mM it reverses stimulation to inhibition. It inhibits the caspase-3 pathway and prevents ethanol-induced caspase-3 activation leading to inhibition of apoptosis, overview
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competitive inhibition of glycocholic acid hydrolysis
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Metals and Ions (1 result)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
1.6fold stimulation at 200 mM
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3D Structure of Enzyme-Ligand-Complex (PDB) (3 results)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (10 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
3.13
-
-
74
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pH 8.5, 37°C, with cofactor NAD+
0.07
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DD1

KM Value (17 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.043
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pH 8.5, 37°C, with cofactor NAD+
0.5
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pH 6.75, 35°C
0.21
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DD1

Ki Value (1 result)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
2.5
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pH 8.0, 50°C

IC50 Value (2 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.1
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IC50 is above 0.1 mM
0.09
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IC50 is 0.09 mM

References & Links

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Links to other databases for taurocholic acid

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ChEBI
PubChem
ChEBI
PubChem