(2S)-3-(3-acetyl-4-hydroxyphenyl)-2-aminopropanoic acid

• ChemBase ID: 159515
• Molecular Formular: C11H13NO4
• Molecular Mass: 223.22522
• Monoisotopic Mass: 223.0844579
• SMILES: c1(c(ccc(c1)C[C@H](N)C(=O)O)O)C(=O)C
• Canonical SMILES: N[C@H](C(=O)O)Cc1ccc(c(c1)C(=O)C)O
• InChI: InChI=1S/C11H13NO4/c1-6(13)8-4-7(2-3-10(8)14)5-9(12)11(15)16/h2-4,9,14H,5,12H2,1H3,(H,15,16)/t9-/m0/s1
• InChIKey: QORSWSUKHPLZDP-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-(3-acetyl-4-hydroxyphenyl)-2-aminopropanoic acid
• IUPAC Traditional name: (2S)-3-(3-acetyl-4-hydroxyphenyl)-2-aminopropanoic acid
• Synonyms: 3-Acetyl-L-tyrosine

Database IDs

• CAS Number: 32483-30-0
• PubChem SID: 162253650
• PubChem CID: 155971

CALCULATED PROPERTIES

• Acid pKa: 1.6714762
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.280827
• LogD (pH = 7.4): -1.2873229
• Log P: -1.2808852
• Molar Refractivity: 57.5 cm^3
• Polarizability: 22.27349 Å^3
• Polar Surface Area: 100.62 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A189750

3-Acetyl-L-tyrosine is an acetylated L-Tyrosine derivative. 3-Acetyl-L-tyrosine can potentially be used in the preparation and modification of non-natural protein containing non-natural amino acids. An impurity of Levodopa (D533751).

REFERENCES

• Tamilarasu, N. et al.: BIconj. Chem., 12, 135 (2001)
• Song, Y.-L. et al.: J. Med. Chem., 49, 1585 (2001)