Ligand lithocholic acid

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Basic Ligand Information

Molecular Structure
Picture of lithocholic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C24H40O3
lithocholic acid
SMEROWZSTRWXGI-HVATVPOCSA-N
Synonyms:
3alpha-hydroxy-5beta-cholanate, 5beta-cholanic acid-3alpha-ol, lithocholate, lithocholic acid[side 1], lithocholic acid[side 2]

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
lithocholic acid + NADPH + H+ = ursodeoxycholic acid + NADP+
show the reaction diagram
-
lithocholic acid + NADP+ = ? + NADPH + H+
show the reaction diagram
-
3alpha-hydroxy-5beta-cholanate + NAD+ = 3-oxo-5beta-cholanate + NADH
show the reaction diagram
-
lithocholate + [reduced NADPH-hemoprotein reductase] + O2 = 6beta-hydroxylithocholate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
3'-phosphoadenylyl sulfate + lithocholic acid = adenosine 3',5'-bisphosphate + lithocholate 3-sulfate
show the reaction diagram
-
3'-phosphoadenylyl 5'-phosphosulfate + lithocholate = adenosine 3',5'-bisphosphate + lithocholate 3-sulfate
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

Substrate in Enzyme-catalyzed Reactions (29 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
lithocholic acid + NAD(P)+ = 3-oxo-5beta-cholan-24-oic acid + NAD(P)H
show the reaction diagram
-
lithocholic acid + NADPH + H+ = ursodeoxycholic acid + NADP+
show the reaction diagram
-
lithocholic acid + NADPH + H+ = ursodeoxycholic acid + NADP+
show the reaction diagram
-
lithocholic acid + NADP+ = ? + NADPH + H+
show the reaction diagram
-
lithocholic acid + NADP+ = ? + NADPH + H+
show the reaction diagram
-
3alpha-hydroxy-5beta-cholanate + NAD+ = 3-oxo-5beta-cholanate + NADH
show the reaction diagram
-
lithocholate + [reduced NADPH-hemoprotein reductase] + O2 = 6beta-hydroxylithocholate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
lithocholic acid + NADP+ = ?
show the reaction diagram
-
3'-phosphoadenylyl sulfate + lithocholic acid = adenosine 3',5'-bisphosphate + lithocholate 3-sulfate
show the reaction diagram
-
3'-phosphoadenylyl 5'-phosphosulfate + lithocholate = adenosine 3',5'-bisphosphate + lithocholate 3-sulfate
show the reaction diagram
-
ATP + lithocholate + CoA = AMP + diphosphate + lithocholoyl-CoA
show the reaction diagram
-
ATP + H2O + lithocholic acid[side 1] = ADP + phosphate + lithocholic acid[side 2]
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ATP + H2O + lithocholic acid[side 1] = ADP + phosphate + lithocholic acid[side 2]
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
24% activation at 0.1% w/v
-
5 mM, 226% of initial activity
-

Inhibitor in Enzyme-catalyzed Reactions (23 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
50% inhibition at 0.022 mM
-
50% inhibition at 0.1 mM
-
substrate inhibition
substrate inhibition
-
substrate inhibition
-
natural inhibitor against PTP1B
-
IC50: 0.015 mM, the lithocholic interaction interface has a pocket comprised of three amino acids, Lys720, Leu760 and Thr791
-

3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (15 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.217
-
-
72
-
pH 8.5, 37°C, with cofactor NAD+

KM Value (24 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.068
-
pH 8.5, 37°C, with cofactor NAD+
0.0016
-
-
0.04
-
-

Ki Value (6 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.00039
-
pH 7.4, 25°C, recombinant enzyme
0.00004
-
DD2

IC50 Value (10 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0033
-
pH 6.0
0.00012
-
in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0044
-
pH 7.4, 25°C, recombinant enzyme
0.0698
-
isoform UGT1A3, at pH 7.6 and 37°C
1
-
protease-reverse transcriptase, pH 6.4, 20°C, presence of 3 M NaCl
0.015
-
IC50: 0.015 mM, the lithocholic interaction interface has a pocket comprised of three amino acids, Lys720, Leu760 and Thr791

References & Links

Links to other databases for lithocholic acid

ChEBI
PubChem
ChEBI
PubChem