(3S)-3-amino-3-{[(2S)-1-(2H3)methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl}propanoic acid

• ChemBase ID: 160845
• Molecular Formular: C14H18N2O5
• Molecular Mass: 294.30312
• Monoisotopic Mass: 294.12157169
• SMILES: C([C@@H](C(=O)N[C@H](C(=O)OC)Cc1ccccc1)N)C(=O)O
• Canonical SMILES: COC(=O)[C@@H](NC(=O)[C@H](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)/t10-,11-/m0/s1
• InChIKey: IAOZJIPTCAWIRG-QWRGUYRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-amino-3-{[(2S)-1-(^2H₃)methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl}propanoic acid
• IUPAC Traditional name: (3S)-3-amino-3-{[(2S)-1-(^2H₃)methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl}propanoic acid
• Synonyms: L-α-Aspartyl-L-phenylalanine 2-(Methyl-d3) Ester; Canderel-d3; Dipeptide-d3 Sweetener; E 951; Equal-d3; Finn-d3; L-Aspartame-d3; NutraSweet-d3; Pal Sweet-d3; Palsweet Diet-d3; Sweet Dipeptide-d3; Zero-Cal-d3; α-Aspartame-d3; α-L-Aspartyl-L-phenylalanine (Methyl-d3) Ester; α-Sweet-d3; Aspartame-d3

Database IDs

• CAS Number: 1356841-28-5
• PubChem SID: 162254980
• PubChem CID: 46780483

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 217-219°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A790017

A labelled dipeptide ester about 160 times sweeter than sucrose in aqueous solution. A non-nutritive sweetener.

REFERENCES

• Cloninger, B., et al.: Science, 170, 81 (1970)
• Oppermann, et al.: J. Nutr., 103, 1454 (1970)