(2R)-3-(4-hydroxyphenyl)-2-(methylamino)propanoic acid

• ChemBase ID: 174462
• Molecular Formular: C10H13NO3
• Molecular Mass: 195.21512
• Monoisotopic Mass: 195.08954328
• SMILES: c1c(ccc(c1)C[C@H](C(=O)O)NC)O
• Canonical SMILES: CN[C@@H](C(=O)O)Cc1ccc(cc1)O
• InChI: InChI=1S/C10H13NO3/c1-11-9(10(13)14)6-7-2-4-8(12)5-3-7/h2-5,9,11-12H,6H2,1H3,(H,13,14)/t9-/m1/s1
• InChIKey: AXDLCFOOGCNDST-SECBINFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-(4-hydroxyphenyl)-2-(methylamino)propanoic acid
• IUPAC Traditional name: (2R)-3-(4-hydroxyphenyl)-2-(methylamino)propanoic acid
• Synonyms: Surinamine; (+)-N-Methyltyrosine; Andirine; Andrine; N-Methyl-L-tyrosine; N-Methyltyrosine; Ratanhin; Ratanhine; Surinamin; N-Methyl-L-tyrosine

Database IDs

• CAS Number: 537-49-5
• PubChem SID: 164230372
• PubChem CID: 7010357

CALCULATED PROPERTIES

• Acid pKa: 1.6689992
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.2649099
• LogD (pH = 7.4): -1.26855
• Log P: -1.2649757
• Molar Refractivity: 51.8718 cm^3
• Polarizability: 20.346928 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous acid; Aqueous Base
• Apperance: White to Off-White Solid
• Melting Point: 253-256°C (dec.)

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M332720

A tyrosine hydroxylase inhibitor. An antihypertensive in pheochromocytoma. N-Methyl-L-tyrosine from seeds of Combretum zeyheri.

REFERENCES

• Itokawa, H., et al.: Phytochemistry, 28, 1667 (1989)
• Itokawa, H., et al.: Chem. Pharm. Bull., 38, 701 (1989)
• Silva, R., et al.: J. Pharm. Pharmacol., 53, 535 (1989)