(2S)-3-(3,4-dihydroxyphenyl)-2-(methylamino)propanoic acid

• ChemBase ID: 173612
• Molecular Formular: C10H13NO4
• Molecular Mass: 211.21452
• Monoisotopic Mass: 211.0844579
• SMILES: c1(c(ccc(c1)C[C@H](NC)C(=O)O)O)O
• Canonical SMILES: CN[C@H](C(=O)O)Cc1ccc(c(c1)O)O
• InChI: InChI=1S/C10H13NO4/c1-11-7(10(14)15)4-6-2-3-8(12)9(13)5-6/h2-3,5,7,11-13H,4H2,1H3,(H,14,15)/t7-/m0/s1
• InChIKey: QZIWDCLHLOADPK-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-(3,4-dihydroxyphenyl)-2-(methylamino)propanoic acid
• IUPAC Traditional name: (2S)-3-(3,4-dihydroxyphenyl)-2-(methylamino)propanoic acid
• Synonyms: 3-Hydroxy-N-methyl-L-tyrosine; 3-(3,4-Dihydroxyphenyl)-N-methylalanine; β-(3,4-Dihydroxyphenyl)-N-methylalanine; N-Methyldopa; N-Methyl-L-DOPA

Database IDs

• CAS Number: 70152-53-3
• PubChem SID: 164229522
• PubChem CID: 23620856

CALCULATED PROPERTIES

• Acid pKa: 1.3350147
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.5685006
• LogD (pH = 7.4): -1.5744572
• Log P: -1.5685015
• Molar Refractivity: 53.8527 cm^3
• Polarizability: 20.989399 Å^3
• Polar Surface Area: 89.79 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M303825

N-Methyl-L-DOPA is a methylated L-DOPA that can act as a potential alternative substrate or competitive inhibitor of tyrosinase.

REFERENCES

• Passi, S. et al.: Br. J. Dermatol., 104, 659 (1981)