(2S)-2-[(2S)-3-(4-hydroxyphenyl)-2-(phenylformamido)propanamido]propanoic acid

• ChemBase ID: 161312
• Molecular Formular: C19H20N2O5
• Molecular Mass: 356.3725
• Monoisotopic Mass: 356.13722175
• SMILES: c1c(ccc(c1)C[C@@H](C(=O)N[C@@H](C)C(=O)O)NC(=O)c1ccccc1)O
• Canonical SMILES: O=C([C@@H](NC(=O)c1ccccc1)Cc1ccc(cc1)O)N[C@H](C(=O)O)C
• InChI: InChI=1S/C19H20N2O5/c1-12(19(25)26)20-18(24)16(11-13-7-9-15(22)10-8-13)21-17(23)14-5-3-2-4-6-14/h2-10,12,16,22H,11H2,1H3,(H,20,24)(H,21,23)(H,25,26)/t12-,16-/m0/s1
• InChIKey: PSRCBRUPIDLBSA-LRDDRELGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-3-(4-hydroxyphenyl)-2-(phenylformamido)propanamido]propanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-3-(4-hydroxyphenyl)-2-(phenylformamido)propanamido]propanoic acid
• Synonyms: N-Bz-Tyr-Ala-OH; N-Benzoyl-L-tyrosyl-L-alanine; N-(N-Benzoyl-L-tyrosyl)-L-alanine

Database IDs

• CAS Number: 76264-09-0
• PubChem SID: 162255447
• PubChem CID: 46780674

CALCULATED PROPERTIES

• Acid pKa: 3.5426958
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -0.040088404
• LogD (pH = 7.4): -1.4550251
• Log P: 1.9105518
• Molar Refractivity: 94.5089 cm^3
• Polarizability: 36.172024 Å^3
• Polar Surface Area: 115.73 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B209850

Used in the enzymic production of peptide.

REFERENCES

• Steinke, D., et al.: Angewandte Chemie, 102, 1204 (1990)