Compound

methylglyoxal

An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.

Definition from MeSH (D011765), National Library of Medicine, read 2026-09-23. NLM revises MeSH; this copy may not reflect its current record.

CHEBI:17158ChEBI

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Structure

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A generated conformer of methylglyoxal — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound
Formula: C3H4O2
Mass: 72.063 g/mol
Charge: 0
InChIKey: AIJULSRZWUXGPQ-UHFFFAOYSA-N
SMILES: [H]C(=O)C(C)=O
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. Not evidence.

What it touches on the way

Mechanistic reach

9 entities

9 entities reached.

0 reported hops9 assembled from the scaffold

What the reference databases state

Statements

38 statements

38 statements · 2 reference databases · Subject: methylglyoxal · Sources: Human-GEM, Rhea

Order

(R)-lactaldehyde is converted to methylglyoxalCompoundRhea RHEA:24528Inferred only
methylglyoxal is converted to (R)-lactaldehydeCompoundHuman-GEM MAR03856Inferred only
methylglyoxal is converted to (R)-lactaldehydeCompoundHuman-GEM MAR08501Inferred only
methylglyoxal is converted to (R)-lactaldehydeCompoundRhea RHEA:24528Inferred only
methylglyoxal is converted to (R)-lactateCompoundRhea RHEA:27754Inferred only
(R)-lactate is converted to methylglyoxalCompoundRhea RHEA:27754Inferred only
CHEBI:16108 is converted to methylglyoxalCompoundHuman-GEM MAR08516Inferred only
CHEBI:29052 is converted to methylglyoxalCompoundHuman-GEM MAR08517Inferred only
methylglyoxal is converted to dihydroxyacetone phosphateCompoundRhea RHEA:17937Inferred only
dihydroxyacetone phosphate is converted to methylglyoxalCompoundRhea RHEA:17937Inferred only
methylglyoxal is converted to hydroxyacetoneCompoundRhea RHEA:27986Inferred only
methylglyoxal is converted to hydroxyacetoneCompoundHuman-GEM MAR08497Inferred only

Show the remaining 26

methylglyoxal is converted to hydroxyacetoneCompoundRhea RHEA:35615Inferred only
hydroxyacetone is converted to methylglyoxalCompoundHuman-GEM MAR08499Inferred only
hydroxyacetone is converted to methylglyoxalCompoundRhea RHEA:35615Inferred only
methylglyoxal is converted to N(2)-(1-hydroxy-2-oxopropyl)-GDPCompoundRhea RHEA:57232Inferred only
N(2)-(1-hydroxy-2-oxopropyl)-GDP is converted to methylglyoxalCompoundRhea RHEA:57232Inferred only
N(2)-(1-hydroxy-2-oxopropyl)-GMP is converted to methylglyoxalCompoundRhea RHEA:57236Inferred only
methylglyoxal is converted to N(2)-(1-hydroxy-2-oxopropyl)-GMPCompoundRhea RHEA:57236Inferred only
N(2)-(1-hydroxy-2-oxopropyl)-GTP is converted to methylglyoxalCompoundRhea RHEA:57220Inferred only
methylglyoxal is converted to N(2)-(1-hydroxy-2-oxopropyl)-GTPCompoundRhea RHEA:57220Inferred only
pyruvate is converted to methylglyoxalCompoundRhea RHEA:52004Inferred only
pyruvate is converted to methylglyoxalCompoundRhea RHEA:49636Inferred only
methylglyoxal is converted to pyruvateCompoundRhea RHEA:49636Inferred only
methylglyoxal is converted to pyruvateCompoundHuman-GEM MAR04360Inferred only
methylglyoxal is converted to pyruvateCompoundRhea RHEA:52004Inferred only
methylglyoxal is a substrate of AKR1A1ProteinRhea RHEA:27986Inferred only
methylglyoxal is a substrate of AKR1A1ProteinHuman-GEM MAR08497Inferred only
methylglyoxal is a substrate of AKR1B1ProteinHuman-GEM MAR08497Inferred only
methylglyoxal is a substrate of AKR1B1ProteinHuman-GEM MAR03854Inferred only
methylglyoxal is a substrate of AKR1B10ProteinHuman-GEM MAR03854Inferred only
methylglyoxal is a substrate of AKR7A2ProteinHuman-GEM MAR08497Inferred only
methylglyoxal is a substrate of GLO1ProteinHuman-GEM MAR03853Inferred only
methylglyoxal is a substrate of GLO1ProteinRhea RHEA:19069Inferred only
methylglyoxal is a substrate of GLOD4ProteinHuman-GEM MAR03853Inferred only
methylglyoxal is a substrate of GRHPRProteinHuman-GEM MAR08501Inferred only
methylglyoxal is a substrate of KCNAB2ProteinRhea RHEA:27986Inferred only
methylglyoxal is a substrate of TPI1ProteinRhea RHEA:17937Inferred only

Reactions

37 reactions

MAM01332c+water+dioxygenproton+hydrogen peroxide+methylglyoxal+ammonium
Catalysed by AOC3
Reaction pageLeft to rightBalancedEC 1.4.3.21cytosol
Human-GEM MAR03852CC BY 4.0Reference data
CHEBI:16856+methylglyoxal(R)-S-lactoylglutathione
Catalysed by GLO1 or GLOD4
Reaction pageLeft to rightBalancedEC 4.4.1.5cytosol
Human-GEM MAR03853CC BY 4.0Reference data
proton+methylglyoxal+NADH(2-)MAM02329c+NAD(+)
Catalysed by AKR1B1 or AKR1B10
Reaction pageLeft to rightBalancedEC 1.1.1.21cytosol
Human-GEM MAR03854CC BY 4.0Reference data
proton+methylglyoxal+NADH(2-)(R)-lactaldehyde+NAD(+)
Reaction pageLeft to rightBalancedEC 1.1.1.79, 1.1.1.81cytosol
Human-GEM MAR03856CC BY 4.0Reference data
water+methylglyoxal+NADP(3-)2proton+NADPH(4-)+pyruvate
Reaction pageLeft to rightBalancedEC 1.2.1.49cytosol
Human-GEM MAR04360CC BY 4.0Reference data
methylglyoxalmethylglyoxal
Reaction pageReversibleBalancedcytosol, extracellular space
Human-GEM MAR05011CC BY 4.0Reference data
proton+methylglyoxal+NADPH(4-)hydroxyacetone+NADP(3-)
Catalysed by AKR7A2 or AKR1B1 or AKR1A1
Reaction pageLeft to rightBalancedEC 1.1.1.21, 1.1.1.2cytosol
Human-GEM MAR08497CC BY 4.0Reference data
proton+hydroxyacetone+NADPH(4-)+dioxygen2water+methylglyoxal+NADP(3-)
Catalysed by CYP2E1
Reaction pageLeft to rightBalancedEC 1.14.14.1cytosol
Human-GEM MAR08499CC BY 4.0Reference data
proton+methylglyoxal+NADPH(4-)(R)-lactaldehyde+NADP(3-)
Catalysed by GRHPR
Reaction pageLeft to rightBalancedEC 1.1.1.79, 1.1.1.81cytosol
Human-GEM MAR08501CC BY 4.0Reference data
CHEBI:16108methylglyoxal+phosphate(3-)
Reaction pageLeft to rightBalancedcytosol
Human-GEM MAR08516CC BY 4.0Reference data
CHEBI:29052methylglyoxal+phosphate(3-)
Reaction pageLeft to rightBalancedEC 4.2.3.3cytosol
Human-GEM MAR08517CC BY 4.0Reference data
methylglyoxal
Reaction pageReversibleBalance undeterminableextracellular space
Human-GEM MAR09375CC BY 4.0Reference data

Show the remaining 25

Other names

11 names

Resolves to: methylglyoxal

Also called: 1,2-propanedione2-Ketopropionaldehyde2-Oxopropanal2-oxopropionaldehydeacetylformaldehydeacetylformylalpha-ketopropionaldehydeCH3COCHOPyruvaldehydePyruvic aldehydeα-ketopropionaldehyde