2-amino-3-[4-hydroxy-3-(2H3)methoxyphenyl]propanoic acid

• ChemBase ID: 173608
• Molecular Formular: C10H13NO4
• Molecular Mass: 211.21452
• Monoisotopic Mass: 211.0844579
• SMILES: c1c(c(ccc1CC(N)C(=O)O)O)OC
• Canonical SMILES: COc1cc(ccc1O)CC(C(=O)O)N
• InChI: InChI=1S/C10H13NO4/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)
• InChIKey: PFDUUKDQEHURQC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-[4-hydroxy-3-(^2H₃)methoxyphenyl]propanoic acid
• IUPAC Traditional name: 2-amino-3-[4-hydroxy-3-(^2H₃)methoxyphenyl]propanoic acid
• Synonyms: 3-Methoxytyrosine-d3; 3-(4-Hydroxy-3-methoxy-d3-phenyl)alanine; 3-(Methoxy-d3)-dl-tyrosine; 4-Hydroxy-3-(methoxy-d3)phenylalanine; DL-3-(Methoxy-d3)-4-hydroxyphenylalanine; DL-3-(Methoxy-d3)tyrosine; DL-3-O-(Methyl-d3)dopa; NSC 122476-d3; rac 3-O-Methyl DOPA-d3

Database IDs

• PubChem SID: 164229518
• PubChem CID: 46782235

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: 21.058882 Å^3
• Polar Surface Area: 92.78 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M303807

The major labelled metabolite of L-DOPA. A useful marker that can be used to screen for the absense of Aromatic L-amino acid decarboxylase (AADC).

REFERENCES

• Tabar, et al.: Pharmacol. Biochem. Behav., 33, 139 (1989)
• De Souza Silva, et al.: J. Neurochem., 68, 233 (1989)
• Feigin, A., et al.: Neurology, 57, 2083 (1989)
• Perera, A., et al.: J. Labelled Comp. Radiopharm., 46, 389 (1989)