methylglyoxal (CHEBI:17158)

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ChEBI Name	methylglyoxal

ChEBI ID	CHEBI:17158

Definition	A 2-oxo aldehyde derived from propanal.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:6875, CHEBI:11643, CHEBI:14599, CHEBI:25303

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

Wikipedia	License
In chemistry, cyanide (from Greek kyanos 'dark blue') is an inorganic chemical compound that contains a C≡N functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom. Ionic cyanides contain the cyanide anion −C≡N. This anion is extremely poisonous. Soluble cyanide salts such as sodium cyanide (NaCN), potassium cyanide (KCN) and tetraethylammonium cyanide ([(CH3CH2)4N]CN) are highly toxic. Covalent cyanides contain the −C≡N group, and are usually called nitriles if the group is linked by a single covalent bond to carbon atom. For example, in acetonitrile CH3−C≡N, the cyanide group is bonded to methyl −CH3. In tetracyanomethane C(−C≡N)4, four cyano groups are bonded to carbon. Although nitriles generally do not release cyanide ions, the cyanohydrins do and are thus toxic. The cyano group may be covalently bonded to atoms different than carbon, e.g., in cyanogen azide N3−C≡N, phosphorus tricyanide P(−C≡N)3 and trimethylsilyl cyanide (CH3)3Si−C≡N. Hydrogen cyanide, or H−C≡N, is a highly volatile toxic liquid that is produced on a large scale industrially. It is obtained by acidification of cyanide salts.
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Formula

C3H4O2

Net Charge

Average Mass

72.06266

Monoisotopic Mass

72.02113

InChI

InChI=1S/C3H4O2/c1-3(5)2-4/h2H,1H3

InChIKey

AIJULSRZWUXGPQ-UHFFFAOYSA-N

SMILES

[H]C(=O)C(C)=O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

ChEBI Ontology
Outgoing	methylglyoxal (CHEBI:17158) has role Escherichia coli metabolite (CHEBI:76971) methylglyoxal (CHEBI:17158) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) methylglyoxal (CHEBI:17158) has role human metabolite (CHEBI:77746) methylglyoxal (CHEBI:17158) has role mouse metabolite (CHEBI:75771) methylglyoxal (CHEBI:17158) is a 2-oxo aldehyde (CHEBI:27659) methylglyoxal (CHEBI:17158) is a propanals (CHEBI:26282)

Incoming	mitoguazone (CHEBI:43996) has functional parent methylglyoxal (CHEBI:17158)

IUPAC Name

2-oxopropanal

Last Modified

08 August 2018

General Comment
2011-01-26	Formed endogenously in numerous reactions, it modifies Arg and Lys residues in proteins, forming advanced glycation end-products which are associated with complications of diabetes and some neurodegenerative diseases.