methyl (2S)-2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoate

• ChemBase ID: 173610
• Molecular Formular: C11H15NO4
• Molecular Mass: 225.2411
• Monoisotopic Mass: 225.10010797
• SMILES: c1c(c(ccc1C[C@H](N)C(=O)OC)O)OC
• Canonical SMILES: COC(=O)[C@H](Cc1ccc(c(c1)OC)O)N
• InChI: InChI=1S/C11H15NO4/c1-15-10-6-7(3-4-9(10)13)5-8(12)11(14)16-2/h3-4,6,8,13H,5,12H2,1-2H3/t8-/m0/s1
• InChIKey: OSGOAQVFZXVPBZ-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoate
• IUPAC Traditional name: methyl (2S)-2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoate
• Synonyms: 3-Methoxy-L-tyrosine Methyl Ester; 3-O-Methyl-L-DOPA Methyl Ester

Database IDs

• CAS Number: 78148-37-5
• PubChem SID: 164229520
• PubChem CID: 14104959

CALCULATED PROPERTIES

• Acid pKa: 9.944875
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.71268123
• LogD (pH = 7.4): 0.62339306
• Log P: 0.76227254
• Molar Refractivity: 58.3295 cm^3
• Polarizability: 23.133768 Å^3
• Polar Surface Area: 81.78 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Grey Solid

DETAILS

Toronto Research Chemicals - M303820

Protected 3-O-Methyl-L-DOPA (M303815). 3-O-Methyl-L-DOPA is the major metabolite of L-DOPA via catechol O-methyltransferase (COMT). 3-Methoxy-L-tyrosine is neither a substrate for nor an inhibitor of L-amino acid decarboxylase activity. Inhibition of COMT

REFERENCES

• Soares-da Silva, P., et al.: Brain Res., 863, 293 (2000)
• Deleu, D., et al.: Clin. Pharmacokinet., 41, 261 (2000)