(2Z)-3-amino-3-phenylprop-2-enoic acid

• ChemBase ID: 165679
• Molecular Formular: C9H9NO2
• Molecular Mass: 163.17326
• Monoisotopic Mass: 163.06332853
• SMILES: c1cccc(c1)/C(=C/C(=O)O)/N
• Canonical SMILES: N/C(=C\C(=O)O)/c1ccccc1
• InChI: InChI=1S/C9H9NO2/c10-8(6-9(11)12)7-4-2-1-3-5-7/h1-6H,10H2,(H,11,12)/b8-6-
• InChIKey: TZAGBUCWNWFIOZ-VURMDHGXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-3-amino-3-phenylprop-2-enoic acid
• IUPAC Traditional name: (2Z)-3-amino-3-phenylprop-2-enoic acid
• Synonyms: 2-Amino-3-phenyl-2-propenoic Acid; α-Aminocinnamic Acid; Dehydro Phenylalanine(cis/trans Mixture)

Database IDs

• CAS Number: 7060-39-1
• PubChem SID: 162259812
• PubChem CID: 21465617

CALCULATED PROPERTIES

• Acid pKa: 3.2246678
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.781819
• LogD (pH = 7.4): -2.3431036
• Log P: -0.34234515
• Molar Refractivity: 46.6097 cm^3
• Polarizability: 17.326612 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D229995

The α,β-dehydro analog for the corresponding natural amino acid Phenylalanine. It is used for stabilization of unusual structures in peptides.

REFERENCES

• Porter, D.J.T., et al.: J. Biol. Chem., 262, 9154 (1987)