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

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

ChEBI ID	CHEBI:176579
ChEBI Name	N-nitroso-N-methyl-4-aminobutyric acid
Stars
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.
Last Modified	23 June 2021
Submitter	rnash
Downloads	Molfile

Formula	C5H10N2O3
Net Charge	0
Average Mass	146.146
Monoisotopic Mass	146.06914
SMILES	CN(CCCC(=O)O)N=O
InChI	InChI=1S/C5H10N2O3/c1-7(6-10)4-2-3-5(8)9/h2-4H2,1H3,(H,8,9)
InChIKey	SJLBIPLIGYWGJV-UHFFFAOYSA-N

Species of Metabolite	Component	Source	Comments
Nicotiana sp. (ncbitaxon:4094)	-	PubMed (2766465)	Identified in tobacco.
Rattus norvegicus (ncbitaxon:10116)	urine (BTO:0001419)	PubMed (3131281)	Strain: F344

Roles Classification

Chemical Role:

Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).

Biological Roles:

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 Relation(s)
	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	Source
4-(N-nitroso-N-methylamino)butyric acid	ChemIDplus
4-(methylnitrosamino)butyric acid	SUBMITTER
4-(methylnitrosoamino)butanoic acid	ChEBI
N-methyl-N-(3-carboxypropyl)nitrosamine	ChemIDplus
N-nitrosomethyl-3-carboxypropylamine	ChemIDplus
N-nitrosomethylaminobutyric acid	ChEBI

Manual Xrefs	Databases
39785	ChemSpider

Registry Numbers	Sources
Reaxys:2245230	Reaxys
CAS:61445-55-4	ChemIDplus

Citations