(2S)-2-[2-(2-aminoacetamido)acetamido]-3-(4-hydroxyphenyl)propanoic acid

• ChemBase ID: 169699
• Molecular Formular: C13H17N3O5
• Molecular Mass: 295.29118
• Monoisotopic Mass: 295.11682066
• SMILES: N(C(=O)CNC(=O)CN)[C@@H](Cc1ccc(cc1)O)C(=O)O
• Canonical SMILES: NCC(=O)NCC(=O)N[C@H](C(=O)O)Cc1ccc(cc1)O
• InChI: InChI=1S/C13H17N3O5/c14-6-11(18)15-7-12(19)16-10(13(20)21)5-8-1-3-9(17)4-2-8/h1-4,10,17H,5-7,14H2,(H,15,18)(H,16,19)(H,20,21)/t10-/m0/s1
• InChIKey: INLIXXRWNUKVCF-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[2-(2-aminoacetamido)acetamido]-3-(4-hydroxyphenyl)propanoic acid
• IUPAC Traditional name: (2S)-2-[2-(2-aminoacetamido)acetamido]-3-(4-hydroxyphenyl)propanoic acid
• Synonyms: N-(N-Glycylglycyl)-L-tyrosine; N-(N-Glycylglycyl)tyrosine; Glycylglycyltyrosine; NSC 334194; Glycylglycyl-L-tyrosine

Database IDs

• CAS Number: 17343-07-6
• PubChem SID: 162263831
• PubChem CID: 6992499

CALCULATED PROPERTIES

• Acid pKa: 3.3567164
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.700991
• LogD (pH = 7.4): -3.8262978
• Log P: -3.7033494
• Molar Refractivity: 72.7042 cm^3
• Polarizability: 28.396263 Å^3
• Polar Surface Area: 141.75 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - G718500

Fungal tyrosinases and their capability to oxidize peptide-bound tyrosine residues is important in a view of applicability of tyrosinases.

REFERENCES

• Bowness, J., et al.: Biochem. J., 53, 620 (1953)
• Cuff, M., et al.: J. Mol. Biol., 278, 855 (1953)
• Kubo, I., et al.: Bioorg. Med. Chem., 12, 5349 (1953)