methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoate hydrochloride

• ChemBase ID: 173607
• Molecular Formular: C11H16ClNO4
• Molecular Mass: 261.70204
• Monoisotopic Mass: 261.07678568
• SMILES: c1c(c(ccc1C[C@@](N)(C)C(=O)OC)O)O.Cl
• Canonical SMILES: COC(=O)[C@](Cc1ccc(c(c1)O)O)(N)C.Cl
• InChI: InChI=1S/C11H15NO4.ClH/c1-11(12,10(15)16-2)6-7-3-4-8(13)9(14)5-7;/h3-5,13-14H,6,12H2,1-2H3;1H/t11-;/m0./s1
• InChIKey: OGIAQNHFLNCESH-MERQFXBCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoate hydrochloride
• IUPAC Traditional name: methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoate hydrochloride
• Synonyms: 3-Hydroxy-α-methyl-L-tyrosine Hydrate; (-)-α-Methyldopa Hydrate; (-)-Methyldopa Hydrate; (S)-α-Methyldopa Hydrate; α-Methyl-L-3,4-dihydroxyphenylalanine Hydrate; L-α-Methyl DOPA Hydrate; 3-Hydroxy-α-methyl-L-tyrosine Methyl Ester Hydrochloride; L-α-Methyl DOPA Methyl Ester Hydrochloride

Database IDs

• CAS Number: 41372-08-1; 115054-62-1
• PubChem SID: 164229517
• PubChem CID: 13589971

CALCULATED PROPERTIES

• Acid pKa: 9.288523
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.6657065
• LogD (pH = 7.4): 0.82067055
• Log P: 1.0491444
• Molar Refractivity: 58.5605 cm^3
• Polarizability: 23.064346 Å^3
• Polar Surface Area: 92.78 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M303795

Antihypertensive agent.

Toronto Research Chemicals - M303810

Methyldopa angiotensin II analog.

REFERENCES

• Beckett, et al.: J. Pharm. Pharmacol., 7, 433 (1955)
• Sletzinger, et al.: J. Med. Chem., 6, 101 (1955)
• Karle, I., et al.: Biochemistry, 29, 6747 (1990)
• Biron, E., et al.: Bioorg. Med. Chem., 12, 1279 (1990)