ChemFOnt: Showing chemical card for Aspartame (CFc000001262)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:51 UTC

Chemfont ID

CFc000001262

Molecule Identification

Common Name

Aspartame

Definition

Aspartame is the name for an artificial, non-carbohydrate sweetener, aspartyl-phenylalanine-1-methyl ester; i.e., the methyl ester of the dipeptide of the amino acids aspartic acid and phenylalanine. It is marketed under a number of trademark names, such as Equal, and Canderel, and is an ingredient of approximately 6,000 consumer foods and beverages sold worldwide. It is commonly used in diet soft drinks, and is often provided as a table condiment. It is also used in some brands of chewable vitamin supplements. In the European Union, it is also known under the E number (additive code) E951. Aspartame is also one of the sugar substitutes used by diabetics. Upon ingestion, aspartame breaks down into several constituent chemicals, including the naturally-occurring essential amino acid phenylalanine which is a health hazard to the few people born with phenylketonuria, a congenital inability to process phenylalanine. Aspartic acid is an amino acid commonly found in foods. Approximately 40% of aspartame (by mass) is broken down into aspartic acid. Because aspartame is metabolized and absorbed very quickly (unlike aspartic acid-containing proteins in foods), it is known that aspartame could spike blood plasma levels of aspartate. Aspartic acid is in a class of chemicals known as excitotoxins. Abnormally high levels of excitotoxins have been shown in hundreds of animals studies to cause damage to areas of the brain unprotected by the blood-brain barrier and a variety of chronic diseases arising out of this neurotoxicity.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Gold, hermesetas	MeSH
Hermesetas gold	MeSH
Canderel	MeSH
Aspartylphenylalanine, methyl	MeSH
Milisucre	MeSH
Tri-sweet	MeSH
Aspartylphenylalanine methyl ester	MeSH
Methyl ester, aspartylphenylalanine	MeSH
NutraSweet	MeSH
TriSweet	MeSH
Nozucar	MeSH
Goldswite	MeSH
Tri sweet	MeSH
Methyl aspartylphenylalanine	MeSH

Chemical Formula

C₁₄H₁₈N₂O₅

Average Molecular Weight

294.3031

Monoisotopic Molecular Weight

294.121571696

IUPAC Name

3-amino-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)-C-hydroxycarbonimidoyl]propanoic acid

Traditional Name

NutraSweet

CAS Registry Number

22839-47-0

SMILES

COC(=O)C(CC1=CC=CC=C1)N=C(O)C(N)CC(O)=O

InChI Identifier

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)

InChI Key

IAOZJIPTCAWIRG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
Phenylalanine or derivatives
Aspartic acid or derivatives
Alpha-amino acid ester
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Amphetamine or derivatives
Fatty acid ester
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty amide
N-acyl-amine
Fatty acyl
Benzenoid
Methyl ester
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Amino acid
Carboxylic acid
Organic oxygen compound
Primary amine
Organic oxide
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Amine
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Brain (HMDB: HMDB0001894)

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 12097436)

Source

Exogenous

Exogenous (HMDB: HMDB0001894)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.44 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-1.7	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.14	ChemAxon
pKa (Strongest Basic)	9.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.21 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	73.74 m³·mol⁻¹	ChemAxon
Polarizability	29.37 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000569

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C11045

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Aspartame

METLIN ID

Not Available

PubChem Compound

2242

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Fuganti, Claudio; Grasselli, Piero; Malpezzi, Luciana; Casati, Paolo. Synthesis of aspartame via asymmetric hydrogenation of N-protected (Z)-N-a-L-aspartyl-D-phenylalanine methyl ester. Journal of Organic Chemistry (1986), 51(7), 1126-8.

Showing chemical card for Aspartame (CFc000001262)

MOL for CFc000001262 (Aspartame)

3D MOL for CFc000001262 (Aspartame)

3D SDF for CFc000001262 (Aspartame)

3D-SDF for CFc000001262 (Aspartame)

PDB for CFc000001262 (Aspartame)

3D PDB for CFc000001262 (Aspartame)

SMILES for CFc000001262 (Aspartame)

INCHI for CFc000001262 (Aspartame)

Structure for CFc000001262 (Aspartame)

3D Structure for CFc000001262 (Aspartame)