Ligand dihydrolipoic acid

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.

Basic Ligand Information

Molecular Structure
Picture of dihydrolipoic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C8H16O2S2
dihydrolipoic acid
IZFHEQBZOYJLPK-UHFFFAOYSA-N
Synonyms:
dihydro-DL-lipoic acid, dihydrolipoate, DL-6,8-dimercaptooctanoate, DL-dihydrolipoate, Reduced lipoic acid
Pathway Source
Pathways

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
dihydrolipoic acid + NADPH + O2 = ?
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (17 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
dihydrolipoic acid + NADPH + O2 = ?
show the reaction diagram
-
ribonucleoside triphosphate + dihydrolipoate = 2'-deoxyribonucleoside triphosphate + lipoate + H2O
show the reaction diagram
-
dihydrolipoic acid + H2O + NAD+ = ? + NADH + 2 H+
show the reaction diagram
-
dihydrolipoic acid + NAD+ = alpha-lipoic acid + NADH + H+
show the reaction diagram
-
succinyl-CoA + dihydrolipoic acid = CoA + succinyldihydrolipoate
show the reaction diagram
-
thiosulfate + dihydrolipoate = ?
show the reaction diagram
-
3-mercaptopyruvate + dihydrolipoic acid = ?
show the reaction diagram
-
S-methyl-1-thio-D-xylulose 5-phosphate + dihydrolipoate = 1-deoxy-D-xylulose 5-phosphate + S-(methylsulfanyl)dihydrolipoate
show the reaction diagram
-
ATP + dihydro-DL-lipoic acid = diphosphate + dihydro-DL-lipoyl-AMP
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
lipoic acid + NADH + H+ = dihydrolipoic acid + NAD+
show the reaction diagram
-
-
lipoic acid + NADH = dihydrolipoic acid + NAD+
show the reaction diagram
-

Enzyme Cofactor/Cosubstrate (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Activator in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
stimulation of chloroplastic form, 147% of enzyme activity
-
slight stimulation
-
it is proposed that dihydrolipoic acid serves an essential role in the regulation of the activity of the the enzyme and that the ratio of reduced to oxidized lipoic acid in the cell may play an important role in the regulation of the activity of the enzyme
-
increases activity at low concentrations
-

Inhibitor in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitive inhibition of 2-hydroxybutyrate oxidation
-
inhibition of prostaglandin G1 synthesis
-
35% residual activity at 3 mM
-
incubation with 3 mM for 30 min at 25°C, in 0.1 ml 0.1 M Tris buffer, pH 7.8, causes 65% loss of activity
-

3D Structure of Enzyme-Ligand-Complex (PDB) (11 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (2 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
1.7
-
in 200 mM of HEPES, pH 7.4, at 37°C
4.3
-
pH not specified in the publication, temperature not specified in the publication

KM Value (4 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
4.7
-
-
0.2
-
-
4.4
-
in 200 mM of HEPES, pH 7.4, at 37°C
0.46
-
pH not specified in the publication, temperature not specified in the publication

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.13
-
-

References & Links

Links to other databases for dihydrolipoic acid

ChEBI
PubChem
ChEBI
PubChem