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

• ChemBase ID: 175006
• Molecular Formular: C20H30N2O5
• Molecular Mass: 378.4626
• Monoisotopic Mass: 378.21547207
• SMILES: C([C@@H](C(=O)N[C@H](C(=O)OC)Cc1ccccc1)NCCC(C)(C)C)C(=O)O
• Canonical SMILES: COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(=O)O)NCCC(C)(C)C
• InChI: InChI=1S/C20H30N2O5/c1-20(2,3)10-11-21-15(13-17(23)24)18(25)22-16(19(26)27-4)12-14-8-6-5-7-9-14/h5-9,15-16,21H,10-13H2,1-4H3,(H,22,25)(H,23,24)/t15-,16-/m0/s1
• InChIKey: HLIAVLHNDJUHFG-HOTGVXAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(3,3-dimethylbutyl)amino]-3-{[(2S)-1-(^2H₃)methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl}propanoic acid
• IUPAC Traditional name: (3S)-3-[(3,3-dimethylbutyl)amino]-3-{[(2S)-1-(^2H₃)methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl}propanoic acid
• Synonyms: N-(3,3-Dimethylbutyl)-L-α-aspartyl-L-phenylalanine 2-(Methyl-d3) Ester; Neotame-d3

Database IDs

• PubChem SID: 164230916
• PubChem CID: 46782468

CALCULATED PROPERTIES

• Acid pKa: 3.6017694
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.08625246
• LogD (pH = 7.4): -0.087601945
• Log P: -0.08332551
• Molar Refractivity: 100.8901 cm^3
• Polarizability: 40.14354 Å^3
• Polar Surface Area: 104.73 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 99-104°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N390062

A labelled alkylated dipeptide reported to be 6000 to 10000 times sweeter than sucrose; structurally related to Aspartame. A non-nutritive sweetener.

REFERENCES

• Ranney, R., et al.: J. Toxicol. Environ. Health, 2, 441 (1976)
• Padden, B.E., et al.: Anal. Chem., 71, 3325 (1976)
• Arai, H., et al.: Metabolism, 56, 115 (1976)