aspartame (CHEBI:2877)

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ChEBI Name	aspartame

ChEBI ID	CHEBI:2877

Definition	A dipeptide obtained by formal condensation of the α-carboxy group of L-aspartic acid with the amino group of methyl L-phenylalaninate. Commonly used as an artificial sweetener.

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

Secondary ChEBI IDs	CHEBI:45047

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Formula

C14H18N2O5

Net Charge

Average Mass

294.304

Monoisotopic Mass

294.12157

InChI

InChI=1S/C14H18N2O5/c1-21-14(20)11(7-9-5-3-2-4-6-9)16-13(19)10(15)8-12(17)18/h2-6,10-11H,7-8,15H2,1H3,(H,16,19)(H,17,18)/t10-,11-/m0/s1

InChIKey

IAOZJIPTCAWIRG-QWRGUYRKSA-N

SMILES

C(C[C@@H](C(N[C@@H](CC1=CC=CC=C1)C(=O)OC)=O)N)(=O)O

Roles Classification
Chemical Role(s):	environmental contaminant Any minor or unwanted substance introduced into the environment that can have undesired effects. Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	sweetening agent Substance that sweeten food, beverages, medications, etc. micronutrient Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions. apoptosis inhibitor Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms. EC 3.1.3.1 (alkaline phosphatase) inhibitor An EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor that interferes with the action of alkaline phosphatase (EC 3.1.3.1). xenobiotic A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.

Application(s):	sweetening agent Substance that sweeten food, beverages, medications, etc. nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.

ChEBI Ontology
Outgoing	aspartame (CHEBI:2877) has functional parent L-aspartic acid (CHEBI:17053) aspartame (CHEBI:2877) has functional parent methyl L-phenylalaninate (CHEBI:49339) aspartame (CHEBI:2877) has role apoptosis inhibitor (CHEBI:68494) aspartame (CHEBI:2877) has role EC 3.1.3.1 (alkaline phosphatase) inhibitor (CHEBI:63332) aspartame (CHEBI:2877) has role environmental contaminant (CHEBI:78298) aspartame (CHEBI:2877) has role micronutrient (CHEBI:27027) aspartame (CHEBI:2877) has role nutraceutical (CHEBI:50733) aspartame (CHEBI:2877) has role sweetening agent (CHEBI:50505) aspartame (CHEBI:2877) has role xenobiotic (CHEBI:35703) aspartame (CHEBI:2877) is a carboxylic acid (CHEBI:33575) aspartame (CHEBI:2877) is a dipeptide (CHEBI:46761) aspartame (CHEBI:2877) is a methyl ester (CHEBI:25248) aspartame (CHEBI:2877) is tautomer of aspartame zwitterion (CHEBI:195544)

Incoming	aspartame zwitterion (CHEBI:195544) is tautomer of aspartame (CHEBI:2877)

IUPAC Name

methyl L-α-aspartyl-L-phenylalaninate

Synonyms	Sources
1-methyl N-L-α-aspartyl-L-phenylalanate	ChemIDplus
3-Amino-N-(α-carboxyphenethyl)succinamic acid N-methyl ester	ChemIDplus
3-Amino-N-(α-methoxycarbonylphenethyl) succinamic acid	ChemIDplus
Asp-phe-ome	ChemIDplus
Aspartame	KEGG COMPOUND
Aspartylphenylalanine methyl ester	ChemIDplus
E 951	HMDB
L-Aspartyl-L-phenylalanine methyl ester	ChemIDplus
NutraSweet	HMDB

Last Modified

11 August 2023

General Comment
2014-10-29	Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag