(2S)-2-(2,2-dimethylpropanamido)-3-(4-hydroxyphenyl)propanoic acid

• ChemBase ID: 176819
• Molecular Formular: C14H19NO4
• Molecular Mass: 265.30496
• Monoisotopic Mass: 265.13140809
• SMILES: N(C(=O)C(C)(C)C)[C@@H](Cc1ccc(cc1)O)C(=O)O
• Canonical SMILES: OC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)C(C)(C)C
• InChI: InChI=1S/C14H19NO4/c1-14(2,3)13(19)15-11(12(17)18)8-9-4-6-10(16)7-5-9/h4-7,11,16H,8H2,1-3H3,(H,15,19)(H,17,18)/t11-/m0/s1
• InChIKey: SUQCHHVYBPOPTR-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(2,2-dimethylpropanamido)-3-(4-hydroxyphenyl)propanoic acid
• IUPAC Traditional name: (2S)-2-(2,2-dimethylpropanamido)-3-(4-hydroxyphenyl)propanoic acid
• Synonyms: N-(2,2-Dimethyl-1-oxopropyl)-L-tyrosine; N-Pivaloyl-L-tyrosine

Database IDs

• CAS Number: 33019-85-1
• PubChem SID: 164232729
• PubChem CID: 29893621

CALCULATED PROPERTIES

• Acid pKa: 3.8983352
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 0.78507984
• LogD (pH = 7.4): -0.82540274
• Log P: 2.3924327
• Molar Refractivity: 70.2434 cm^3
• Polarizability: 27.412823 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P551500

Used in peptide N-terminal amino acid determination.

REFERENCES

• Prota, G., et al.: Biochimie, 53, 51 (1971)