N-nitroso-N-methyl-4-aminobutyric acid (CHEBI:176579)

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ChEBI Name	N-nitroso-N-methyl-4-aminobutyric acid

ChEBI ID	CHEBI:176579

ChEBI ASCII Name	N-nitroso-N-methyl-4-aminobutyric acid

Definition	A nitrosamine that has methyl and 3-carboxypropyl substituents. It is a tobacco-derived nitrosamino acid that is a known animal and potential human carcinogen. It induces bladder transitional cell carcinomas in rats and has recently been identified as a contaminant in certain blood pressure medications.

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

Submitter	Rob Nash

Supplier Information

Download	Molfile XML SDF

Formula

C5H10N2O3

Net Charge

Average Mass

146.146

Monoisotopic Mass

146.06914

InChI

InChI=1S/C5H10N2O3/c1-7(6-10)4-2-3-5(8)9/h2-4H2,1H3,(H,8,9)

InChIKey

SJLBIPLIGYWGJV-UHFFFAOYSA-N

SMILES

CN(CCCC(O)=O)N=O

Metabolite of Species	Details
Rattus norvegicus (NCBI:txid10116)	Found in urine (BTO:0001419). of strain F344 See: PubMed
Nicotiana sp. (NCBI:txid4094)	Identified in tobacco. See: PubMed

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	carcinogenic agent A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities. rat metabolite Any mammalian metabolite produced during a metabolic reaction in rat (Rattus norvegicus). xenobiotic metabolite Any metabolite produced by metabolism of a xenobiotic compound. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

ChEBI Ontology
Outgoing	N-nitroso-N-methyl-4-aminobutyric acid (CHEBI:176579) has role carcinogenic agent (CHEBI:50903) N-nitroso-N-methyl-4-aminobutyric acid (CHEBI:176579) has role plant metabolite (CHEBI:76924) N-nitroso-N-methyl-4-aminobutyric acid (CHEBI:176579) has role rat metabolite (CHEBI:86264) N-nitroso-N-methyl-4-aminobutyric acid (CHEBI:176579) has role xenobiotic metabolite (CHEBI:76206) N-nitroso-N-methyl-4-aminobutyric acid (CHEBI:176579) is a monocarboxylic acid (CHEBI:25384) N-nitroso-N-methyl-4-aminobutyric acid (CHEBI:176579) is a nitrosamine (CHEBI:35803)

IUPAC Name

4-[methyl(nitroso)amino]butanoic acid

Synonyms	Sources
4-(methylnitrosamino)butyric acid	SUBMITTER
4-(methylnitrosoamino)butanoic acid	ChEBI
4-(N-nitroso-N-methylamino)butyric acid	ChemIDplus
N-methyl-N-(3-carboxypropyl)nitrosamine	ChemIDplus
N-nitrosomethyl-3-carboxypropylamine	ChemIDplus
N-nitrosomethylaminobutyric acid	ChEBI
nitrosomethyl-3-carboxypropylamine	ChemIDplus
NMBA	SUBMITTER

Last Modified

23 June 2021