(2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid

• ChemBase ID: 174460
• Molecular Formular: C10H13NO3
• Molecular Mass: 195.21512
• Monoisotopic Mass: 195.08954328
• SMILES: c1cc(ccc1C[C@](C)(N)C(=O)O)O
• Canonical SMILES: Oc1ccc(cc1)C[C@@](C(=O)O)(N)C
• InChI: InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)/t10-/m0/s1
• InChIKey: NHTGHBARYWONDQ-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
• IUPAC Traditional name: metyrosine
• Synonyms: (S)-2-(4-Hydroxybenzyl)-2-aminopropanoic Acid; (S)-α-Methyltyrosine; Demser; L(-)-Metyrosine; L-Metyrosine; L-α-MT; L-α-Methyl-p-tyrosine; L-α-Methyltyrosine; MK 781; Metirosine; Metyrosine; α-Methyl-L-tyrosine

Database IDs

• CAS Number: 672-87-7
• PubChem SID: 164230370
• PubChem CID: 441350

CALCULATED PROPERTIES

• Acid pKa: 2.0631347
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.0558071
• LogD (pH = 7.4): -1.0610021
• Log P: -1.0558642
• Molar Refractivity: 51.8105 cm^3
• Polarizability: 20.34689 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Boiling Methanol; Water
• Apperance: White Solid
• Melting Point: >300°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M332700

A tyrosine hydroxylase inhibitor. An antihypertensive in pheochromocytoma.

REFERENCES

• Espin, J., et al.: Biochem. J., 331, 547 (1998)
• Espin, J., et al.: J. Agric. Food Chem., 47, 3495 (1998)
• Espin, J., et al.: Eur. J. Biochem., 267, 1270 (1998)
• Battaini, G., et al.: J. Biol. Chem., 277, 44606 (1998)