(2S)-2-amino-3-(2-hydroxyphenyl)propanoic acid

• ChemBase ID: 179368
• Molecular Formular: C9H11NO3
• Molecular Mass: 181.18854
• Monoisotopic Mass: 181.07389322
• SMILES: c1cccc(c1C[C@H](N)C(=O)O)O
• Canonical SMILES: OC(=O)[C@H](Cc1ccccc1O)N
• InChI: InChI=1S/C9H11NO3/c10-7(9(12)13)5-6-3-1-2-4-8(6)11/h1-4,7,11H,5,10H2,(H,12,13)/t7-/m0/s1
• InChIKey: WRFPVMFCRNYQNR-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(2-hydroxyphenyl)propanoic acid
• IUPAC Traditional name: 2-hydroxyphenylalanine
• Synonyms: 2-Hydroxy-L-phenylalanine; (-)-o-Tyrosine; L-3-(2-Hydroxyphenyl)alanine; L-o-Hydroxyphenylalanine; o-L-Tyrosine; L-o-Tyrosine

Database IDs

• CAS Number: 7423-92-9
• PubChem SID: 164235278
• PubChem CID: 6950574

CALCULATED PROPERTIES

• Acid pKa: 2.0057738
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.4882036
• LogD (pH = 7.4): -1.501613
• Log P: -1.4883343
• Molar Refractivity: 47.0972 cm^3
• Polarizability: 18.512674 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 237-244°C dec.

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T899990

A metabolite of Phenylalanine (P319415).

REFERENCES

• Baynes, J., et al.: Diabetes, 40, 405 (1991)
• Fu, S., et al.: J. Biol .Chem., 273, 28603 (1991)
• Magsino, C., et al.: Metabolism, 49, 799 (1991)