Ligand methylglyoxal

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 methylglyoxal (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C3H4O2
methylglyoxal
AIJULSRZWUXGPQ-UHFFFAOYSA-N
Synonyms:
1,2-propanedione, 2-oxo-propanal, 2-oxo-propionaldehyde, 2-oxopropanal, Acetoaldehyde, methyl glyoxal, perdeuteriomethylglyoxal, Pyruvaldehyde, Pyruvic aldehyde


Show all pahtways known for Show all BRENDA pathways known for methylglyoxal

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (24 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
methylglyoxal + NADH + H+ = acetol + NAD+
show the reaction diagram
-
pyruvic aldehyde + NAD(P)H + H+ = ?
show the reaction diagram
-
methylglyoxal + NAD+ + H2O = pyruvate + NADH + H+
show the reaction diagram
-

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

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
aminoacetone + H2O + O2 = methylglyoxal + NH3 + H2O2
show the reaction diagram
-
-
(R)-lactate = 2-oxopropanal + H2O
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (98 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
methylglyoxal + NADPH = ?
show the reaction diagram
-
methylglyoxal + NADPH = ?
show the reaction diagram
-
methylglyoxal + NADH = L-lactaldehyde
show the reaction diagram
-
methyl glyoxal + NAD(P)H = ? + NAD(P)+
show the reaction diagram
-
methylglyoxal + NADP+ = ? + NADPH + H+
show the reaction diagram
-
methylglyoxal + NADPH = ? + NADP+
show the reaction diagram
-
methylglyoxal + glutathione + NAD+ = S-pyruvylglutathione + NADH
show the reaction diagram
-
methyl glyoxal + NADH + H+ = ? + NAD+
show the reaction diagram
-
methylglyoxal + NADPH + H+ = ?
show the reaction diagram
-
methylglyoxal + NADPH + H+ = ?
show the reaction diagram
-
methylglyoxal + NADPH = ?
show the reaction diagram
-
methylglyoxal + NADH = lactaldehyde + NAD+
show the reaction diagram
-
methylglyoxal + NADPH = 1-hydroxyacetone + NADP+
show the reaction diagram
-
methylglyoxal + NAD+ + H2O = pyruvate + NADH
show the reaction diagram
-
methylglyoxal + NAD+ + H2O = pyruvate + NADH + H+
show the reaction diagram
-
methylglyoxal + NADP+ + H2O = ?
show the reaction diagram
-
pyruvaldehyde + NAD+ + H2O = pyruvate + NADH
show the reaction diagram
-
methylglyoxal + phosphate + O2 + H2O = ? + H2O2
show the reaction diagram
-
methylglyoxal + ferricyanide = 2-oxopropanoic acid + ferrocyanide + H+
show the reaction diagram
-
methylglyoxal + NADPH = ?
show the reaction diagram
-
L-ornithine + methylglyoxal + NADPH + H+ = ? + NADP+ + H2O
show the reaction diagram
-
pyruvic aldehyde + (S)-alpha-methylbenzylamine = ? + acetophenone
show the reaction diagram
-
D-ribulose 5-phosphate + methylglyoxal = ?
show the reaction diagram
-
pyruvate + methylglyoxal = ?
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (21 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
propane-1,2-diol + NAD+ = methylglyoxal + NADH
show the reaction diagram
-
-
(S)-lactaldehyde + NADP+ = methylglyoxal + NADPH + H+
show the reaction diagram
-
-
S-pyruvylglutathione + NADH = methylglyoxal + glutathione + NAD+
show the reaction diagram
-
hydroxyacetone + NAD+ = 2-oxopropanal + NADH
show the reaction diagram
-
-
1,2-propanediol + O2 = 1,2-propanedione + H2O2
show the reaction diagram
-
-
acetol + O2 = pyruvaldehyde + H2O2
show the reaction diagram
-
aminoacetone + H2O + O2 = methylglyoxal + NH3 + H2O2
show the reaction diagram
-
-
(RS)-3-chloropropane-1,2-diol + NAD+ = (R)-3-chloropropane-1,2-diol + 2-oxo-propionaldehyde + CH3COOH + Cl- + HCOOH + NADH
show the reaction diagram
-
-
dihydroxyacetone phosphate = methylglyoxal + phosphate
show the reaction diagram
-
-
(R)-lactate = 2-oxopropanal + H2O
show the reaction diagram
-
-
glycerone phosphate = methylglyoxal + phosphate
show the reaction diagram
-
malonic dialdehyde = methylglyoxal
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
up to 4.5fold induction of mRNA, activity and protein level, abolished in presence of cycloheximide or actinomycin D
-
induces the PI3K/PKC/Raf-1-independent MEK/ERK signaling pathway by activation of MEKK1, accumulates in case of diabetes
-
addition at pH 5.0 results in a significant 98% increase in the glycolytic rate
-

Inhibitor in Enzyme-catalyzed Reactions (26 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
1.0 mM, 42% inhibition, 2 mM, 63% inhibition, methylglyoxal binds at an allosteric site of the enzyme
-
in absence of NADPH
-
strain CETC 978, 277 mM, complete inactivation after 50 min, in the presence of 30 mM benzoylformic acid complete inactivation after 20 min
-
Arg184 and Arg185, located in the glutathione binding site of the enzyme are irreversibly modified by treatment with methylglyoxal
-
substrate inhibition
-
substrate inhibition
-
with 1 mM methylglyoxal, GDH activity significantly decreases at 30 min of incubation, and markedly drops by 37% within 5 h compared to control
-
decreases specific activity in a concentration-dependent manner
-
photochemical inactivation: effect only in UV-light, Ki: 1.8-2.0 mM
-
competitive inhibition
-
26% inhibition at 4 mM
-
linear noncompetitive inhibitor
-

Metals and Ions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
10 mM, enhanced tolerance to toxic stress in transgenic Vigna mungo
-

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (50 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.12
-
at pH 7.4 and 37°C
18.17
-
pH and temperature not specified in the publication
198
-
at pH 4.5 and 25°C

KM Value (124 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
35
-
-
2.651
-
-
4.4
-
-
1.1
-
-
75
-
pH 7.0, 25°C
0.4
-
at pH 7.0 and 30°C
75
-
-
9
-
; in 100 mM Tris-HCl buffer (pH 8.8), at 37°C
0.4
-
-
5.1
-
-

Ki Value (3 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.8
2
photochemical inactivation: effect only in UV-light

References & Links

Links to other databases for methylglyoxal

ChEBI
PubChem
ChEBI
PubChem