(2R)-2-acetamido-3-(4-hydroxy-3-iodophenyl)propanamide

• ChemBase ID: 159329
• Molecular Formular: C11H13IN2O3
• Molecular Mass: 348.13699
• Monoisotopic Mass: 347.99709029
• SMILES: c1c(c(cc(c1)C[C@H](C(=O)N)NC(=O)C)I)O
• Canonical SMILES: CC(=O)N[C@@H](C(=O)N)Cc1ccc(c(c1)I)O
• InChI: InChI=1S/C11H13IN2O3/c1-6(15)14-9(11(13)17)5-7-2-3-10(16)8(12)4-7/h2-4,9,16H,5H2,1H3,(H2,13,17)(H,14,15)/t9-/m1/s1
• InChIKey: WEEJPQQOBNMRHS-SECBINFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-acetamido-3-(4-hydroxy-3-iodophenyl)propanamide
• IUPAC Traditional name: (2R)-2-acetamido-3-(4-hydroxy-3-iodophenyl)propanamide
• Synonyms: (S)-α-(Acetylamino)-4-hydroxy-3-iodo-benzenepropanamide; N-Acetyl-3-iodo-L-tyrosine Amide

Database IDs

• CAS Number: 59302-19-1
• PubChem SID: 162253464
• PubChem CID: 29970927

CALCULATED PROPERTIES

• Log P: 0.7148982
• Molar Refractivity: 71.7257 cm^3
• Polarizability: 27.87534 Å^3
• Polar Surface Area: 92.42 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 8.372677
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.7143202
• LogD (pH = 7.4): 0.6712579

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 219-221°C

DETAILS

Toronto Research Chemicals - A179410

Used in the synthesis of 3-iodo-L-thyronine and its iodinated derivatives.

REFERENCES

• Block, P., et al.: J. Med. Chem., 19, 1067 (1976)