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: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-amino-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl]propanoic acid
• IUPAC Traditional name: aminosweet; aspartame
• Brand Name: Canderel; Equal; Nutrasweet; Tri-sweet; Aminosweet
• Synonyms: Asp-Phe methyl ester; 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

Database IDs

• CAS Number: 22839-47-0; 25548-16-7
• MDL Number: MFCD00002724; MFCD00176858
• PubChem SID: 160963516
• PubChem CID: 2242

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.525723
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.2199712
• LogD (pH = 7.4): -2.2454615
• Log P: -2.2182105
• Molar Refractivity: 73.2182 cm^3
• Polarizability: 29.14675 Å^3
• Polar Surface Area: 118.72 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.18
• LOG S: -2.65
• Solubility (Water): 6.52e-01 g/l

PROPERTIES

Physical Property

• 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.
• Hydrophobicity(logP): -0.1

Product Information

• Purity: 97%; 98%

DETAILS

DrugBank - DB00168

• 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