(2S)-2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoic acid hydrate

• ChemBase ID: 173609
• Molecular Formular: C10H15NO5
• Molecular Mass: 229.2298
• Monoisotopic Mass: 229.09502259
• SMILES: c1c(c(ccc1C[C@H](N)C(=O)O)O)OC.O
• Canonical SMILES: COc1cc(ccc1O)C[C@@H](C(=O)O)N.O
• InChI: InChI=1S/C10H13NO4.H2O/c1-15-9-5-6(2-3-8(9)12)4-7(11)10(13)14;/h2-3,5,7,12H,4,11H2,1H3,(H,13,14);1H2/t7-;/m0./s1
• InChIKey: IDRRCKUGGXLORG-FJXQXJEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoic acid hydrate
• IUPAC Traditional name: 3-methoxytyrosine hydrate
• Synonyms: 3-Methoxy-L-tyrosine Monohydrate; 3-Methoxy-4-hydroxyphenylalanine Monohydrate; 3-Methoxy-DOPA Monohydrate; 3-O-Methyldopa Monohydrate; L-3-Methoxy-4-hydroxyphenylalanine Monohydrate; L-3-O-Methyl-DOPA Monohydrate; L-4-Hydroxy-3-methoxyphenylalanine Monohydrate; 3-O-Methyl-L-DOPA Monohydrate

Database IDs

• CAS Number: 200630-46-2
• PubChem SID: 164229519
• PubChem CID: 46782236

CALCULATED PROPERTIES

• Acid pKa: 1.7533966
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.6461834
• LogD (pH = 7.4): -1.6509163
• Log P: -1.646272
• Molar Refractivity: 53.5604 cm^3
• Polarizability: 21.057919 Å^3
• Polar Surface Area: 92.78 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Brown Solid
• Melting Point: 223-225°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - 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 enhances the anti-Parkinson activity o

REFERENCES

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