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

• ChemBase ID: 109719
• Molecular Formular: C10H13NO4
• Molecular Mass: 211.21452
• Monoisotopic Mass: 211.0844579
• SMILES: COc1cc(C[C@H](N)C(=O)O)ccc1O
• Canonical SMILES: COc1cc(ccc1O)C[C@@H](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)/t7-/m0/s1
• InChIKey: PFDUUKDQEHURQC-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoic acid
• IUPAC Traditional name: 3-methoxytyrosine
• Synonyms: 3-METHOXY-L-TYROSINE; 4-Hydroxy-3-methoxy-L-phenylalanine; L-3-O-Methyl-DOPA; 3-Methoxy-L-tyrosine monohydrate

Database IDs

• CAS Number: 300-48-1; 200630-46-2
• MDL Number: MFCD00150495
• PubChem SID: 162089237; 24896916
• PubChem CID: 9307

CALCULATED PROPERTIES

• 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
• Acid pKa: 1.7533966
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.6461834
• LogD (pH = 7.4): -1.6509163

PROPERTIES

Physical Property

• Apperance: powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

DETAILS

MP Biomedicals - 05212326

MP Biomedicals Rare Chemical collection

Sigma Aldrich - M4255

Biochem/physiol Actions
3-Methoxy-L-tyrosine is a metabolite of L-Dopa.
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 of L-DOPA.