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25548-16-7 molecular structure
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3-amino-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl]propanoic acid

ChemBase ID: 53
Molecular Formular: C14H18N2O5
Molecular Mass: 294.30312
Monoisotopic Mass: 294.12157169
SMILES and InChIs

SMILES:
O(C(=O)C(NC(=O)C(N)CC(=O)O)Cc1ccccc1)C
Canonical SMILES:
COC(=O)C(NC(=O)C(CC(=O)O)N)Cc1ccccc1
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)
InChIKey:
IAOZJIPTCAWIRG-UHFFFAOYSA-N

Cite this record

CBID:53 http://www.chembase.cn/molecule-53.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
3-amino-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl]propanoic acid
IUPAC Traditional name
aspartame
aminosweet
Brand Name
Canderel
Equal
Nutrasweet
Tri-sweet
Aminosweet
Synonyms
Aspartam [INN-French]
Asp-phe-ome
Aspartame [USAN:BAN:INN]
APM
Aspartamo [INN-Spanish]
Aspartamum [INN-Latin]
Aspartylphenylalanine methyl ester
1-Methyl N-L-alpha-aspartyl-L-phenylalanate
3-Amino-N-(alpha-methoxycarbonylphenethyl) succinamic acid
3-Amino-N-(alpha-carboxyphenethyl)succinamic acid N-methyl ester, stereoisomer
3-Amino-N-(alpha-carboxyphenethyl)succinamic acid N-methyl ester
1-Methyl N-L-alpha-aspartyl-L-phenylalanine
N-L-alpha-Aspartyl-L-phenylalanine 1-methyl ester
Methyl N-L-alpha-aspartyl-L-phenylalaninate
Methyl L-aspartyl-L-phenylalanine
Methyl L-alpha-aspartyl-L-phenylalanate
Methyl aspartylphenylalanate
L-Aspartyl-L-phenylalanine methyl ester
Dipeptide sweetener
Sweet dipeptide
Aspartame
3-amino-4-[(1-benzyl-2-methoxy-2-oxoethyl)amino]-4-oxobutanoic acid
Asp-Phe methyl ester
CAS Number
25548-16-7
22839-47-0
MDL Number
MFCD00002724
MFCD00176858
PubChem SID
160963516
PubChem CID
2242

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.525723  H Acceptors
H Donor LogD (pH = 5.5) -2.2199712 
LogD (pH = 7.4) -2.2454615  Log P -2.2182105 
Molar Refractivity 73.2182 cm3 Polarizability 29.14675 Å3
Polar Surface Area 118.72 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -1.18  LOG S -2.65 
Solubility (Water) 6.52e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Product Information Bioassay(PubChem)
Solubility
The solubility of aspartame in water is dependent on pH and temperature, the maximum solubility is reached at pH 2.2 (20 mg/mL at 25oC) and the minimum solubility at pH 5.2 (pHi) is 13.5 mg/mL at 25oC. expand Show data source
Hydrophobicity(logP)
-0.1 expand Show data source
Purity
97% expand Show data source
98% expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00168 external link
Item Information
Drug Groups approved; nutraceutical
Description Flavoring agent sweeter than sugar, metabolized as phenylalanine and aspartic acid. [PubChem]
Indication Used as a diet supplement and sugar substitute.
Pharmacology Aspartame (L-alpha-aspartyl-L-phenylalanine methyl ester) is a low-calorie sweetener used to sweeten a wide variety of low- and reduced-calorie foods and beverages, including low-calorie tabletop sweeteners. Aspartame is composed of two amino acids, aspartic acid and phenylalanine, as the methyl ester. Aspartic acid and phenylalanine are also found naturally in protein containing foods, including meats, grains and dairy products. Methyl esters are also found naturally in many foods such as fruits and vegetable and their juices. Upon digestion, aspartame breaks down into three components (aspartic acid, phenylalanine and methanol), which are then absorbed into the blood and used in normal body processes. Neither aspartame nor its components accumulates in the body. These components are used in the body in the same ways as when they are derived from common foods.
Toxicity Mild gastrointestinal side effects including diarrhea have been reported.
Affected Organisms
Humans and other mammals
Biotransformation Approximately 10% of aspartame (by weight) is broken down into methanol in the small intestine. Most of the methanol is absorbed and quickly converted into formaldehyde. Approximately 50% of aspartame (by weight) is broken down into phenylalanine. Approximately 40% of aspartame (by mass) is broken down into aspartic acid.
Absorption Absorbed in the small intestine, aspartame is metabolized and absorbed very quickly.
Half Life At room temperature, aspartame is most stable at pH 4.3, where its half-life is nearly 300 days. At pH 7 however, its half-life is only a few days.
External Links
Wikipedia

REFERENCES

REFERENCES

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PATENTS

PATENTS

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