Ligand lipoic acid

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Basic Ligand Information

Molecular Structure
Picture of lipoic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C8H14O2S2
lipoic acid
AGBQKNBQESQNJD-SSDOTTSWSA-N
Synonyms:
(R)-5-(1,2-dithiolan-3-yl) pentanoic acid, (R)-5-(1,2-dithiolan-3-yl)pentanoic acid, (R)-lipoate, (R)-lipoic acid, alpha-lipoate, alpha-lipoic acid, D-lipoic acid, lipoate, lipoic acid oxidized, lipoic acid[side 2], oxidized lipoate, oxidized lipoic acid, R-lipoic acid


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

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
lipoic acid + NADPH + O2 = ?
show the reaction diagram
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lipoic acid + CoA + NAD+ = ?
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (26 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
lipoic acid + O2 = ?
show the reaction diagram
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lipoic acid + NADPH + O2 = ?
show the reaction diagram
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lipoic acid + CoA + NAD+ = ?
show the reaction diagram
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lipoic acid + NADH + H+ = dihydrolipoic acid + NAD+
show the reaction diagram
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glycine + lipoate = ?
show the reaction diagram
lipoic acid + NADH = dihydrolipoic acid + NAD+
show the reaction diagram
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alpha-lipoate + protein disulfide = ?
show the reaction diagram
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lipoic acid oxidized + GSH = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ribonucleoside triphosphate + dihydrolipoate = 2'-deoxyribonucleoside triphosphate + lipoate + H2O
show the reaction diagram
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lipoyl 4-aminobenzoate + H2O = 4-aminobenzoate + lipoic acid
show the reaction diagram
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ATP + H2O + lipoic acid-[sulfonate-binding protein][side 1] = ADP + phosphate + lipoic acid[side 2] + [sulfonate-binding protein][side 1]
show the reaction diagram
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Enzyme Cofactor/Cosubstrate (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Activator in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
enhances activity
-
both glycine decarboxylation and the glycine-CO2 exchange catalyzed by P-protein are stimulated 100fold or more by the addition of lipoic acid
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increase in activity might be due to formation of dihydrolipoic acid in the assay system
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lipoic acid and pilocarpine together increase enzyme activity in the hippocampus of healthy and epileptic rats, lipoic acid alone does not alter hippocampal ChAT activity. Lipoic acid protects rats against pilocarpine-induced seizures and eliminates lethality, overview
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slight (20%) stimulation of activity at 10 mM
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causes an increase in cardiac enzyme activity at doses of 35 and 70 mg/kg of 1.3 and 2.4fold in the animals
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Inhibitor in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
30% inhibition at 5 mM on phosphorylation at site 1 of E1, 20% inhibition at 5 mM on phosphorylation at site 2 of E1, 25% inhibition at 5 mM on phosphorylation at site 3 of E1
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i.e. alpha-lipoic acid, inhibits both activities of the enzyme at concentrations lower than 0.010 mM. The carboxylate group of alpha lipoic acid situates at 3 A from important residues R563 and K565 in the catalytic pocket of the protein, suggesting that alpha lipoic acid participates in electrostatic interactions with these residues
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80% inhibition
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competitive
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significant inhibition
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weak
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3D Structure of Enzyme-Ligand-Complex (PDB) (44 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (5 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
70
-
-
1.8
-
isoform TrxR1, in 50 mM Tris-HCl, 1 mM EDTA, pH 8.0, at 37°C

KM Value (12 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.01
-
splice variant 15-LOb1
0.83
-
pH 6.3, 25°C
0.0027
-
isoform TrxR1, in 50 mM Tris-HCl, 1 mM EDTA, pH 8.0, at 37°C

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.000026
-
-

IC50 Value (3 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.00005
-
-
0.14
-
-
0.00023
-
pH 7.4, 37°C

References & Links

Links to other databases for lipoic acid

ChEBI
PubChem
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PubChem