(2R)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid

• ChemBase ID: 173606
• Molecular Formular: C10H13NO4
• Molecular Mass: 211.21452
• Monoisotopic Mass: 211.0844579
• SMILES: c1c(c(ccc1C[C@](N)(C)C(=O)O)O)O
• Canonical SMILES: OC(=O)[C@@](Cc1ccc(c(c1)O)O)(N)C
• InChI: InChI=1S/C10H13NO4/c1-10(11,9(14)15)5-6-2-3-7(12)8(13)4-6/h2-4,12-13H,5,11H2,1H3,(H,14,15)/t10-/m1/s1
• InChIKey: CJCSPKMFHVPWAR-SNVBAGLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid
• IUPAC Traditional name: (-)-methyldopa
• Synonyms: 3-Hydroxy-α-methyl-D-tyrosine; D-3-(3,4-Dihydroxyphenyl)-2-methylalanine; (+)-α-Methyldopa; D-(3,4-Dihydroxyphenyl)-2-methylalanine; D-Methyldopa; D-α-Methyl DOPA

Database IDs

• CAS Number: 2799-15-7
• PubChem SID: 164229516
• PubChem CID: 721860

CALCULATED PROPERTIES

• Acid pKa: 1.7286927
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.3594157
• LogD (pH = 7.4): -1.3670306
• Log P: -1.3594803
• Molar Refractivity: 53.7914 cm^3
• Polarizability: 20.989363 Å^3
• Polar Surface Area: 103.78 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Solid
• Melting Point: >250°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M303790

Antihypertensive agent.Product reacts with methanol to form methyl ester very fast.

REFERENCES

• Beckett, et al.: J. Pharm. Pharmacol., 7, 433 (1955)
• Sletzinger, et al.: J. Med. Chem., 6, 101 (1955)