4-Acetamidobutanal (also known as N-acetyl-γ-aminobutyraldehyde, N-acetyl-GABAL, or N-acetyl-GABA aldehyde) is an organic compound with the molecular formula C₆H₁₁NO₂ and a molecular weight of 129.16 g/mol. Its preferred IUPAC name is N-(4-oxobutyl)acetamide, and its SMILES representation is CC(=O)NCCCC=O.
Chemical Properties
The compound is classified as a monocarboxylic acid amide and an α-CH₂-containing aldehyde. It has a computed XLogP3-AA of −0.7, one hydrogen bond donor, two hydrogen bond acceptors, and four rotatable bonds. Its topological polar surface area is 46.2 Ų. It is a solid at standard conditions.
Biological Role
4-Acetamidobutanal is a metabolic intermediate in the biosynthesis of γ-aminobutyric acid (GABA) from putrescine. Other intermediates in this pathway include N-acetylputrescine and N-acetyl-γ-aminobutyric acid (N-acetyl-GABA). The enzymes involved in these transformations include putrescine acetyltransferase (PAT), monoamine oxidase B (MAO-B), aldehyde dehydrogenase (ALDH), and an unknown deacetylase enzyme.
While this pathway is a minor route for GABA synthesis compared to the main pathway in which GABA is synthesized from glutamate, it has been found to play an important physiological role in the brain, particularly in the production of GABA in the striatum and the resultant inhibition of dopaminergic neurons in that brain area.
Metabolite Status
4-Acetamidobutanal is recognized as a metabolite found in or produced by Saccharomyces cerevisiae (yeast) and has roles as both a mouse metabolite and a human metabolite. It is functionally related to butanal. The compound is indexed in PubChem (CID 440850), ChEBI (CHEBI:7386), the Human Metabolome Database (HMDB), KEGG, and has the CAS number 24431-54-7.
