ethyl (2R)-2-acetamido-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate

• ChemBase ID: 159505
• Molecular Formular: C19H17I4NO5
• Molecular Mass: 846.95986
• Monoisotopic Mass: 846.72856465
• SMILES: c1(c(cc(cc1I)Oc1c(cc(cc1I)C[C@H](C(=O)OCC)NC(=O)C)I)I)O
• Canonical SMILES: CCOC(=O)[C@@H](Cc1cc(I)c(c(c1)I)Oc1cc(I)c(c(c1)I)O)NC(=O)C
• InChI: InChI=1S/C19H17I4NO5/c1-3-28-19(27)16(24-9(2)25)6-10-4-14(22)18(15(23)5-10)29-11-7-12(20)17(26)13(21)8-11/h4-5,7-8,16,26H,3,6H2,1-2H3,(H,24,25)/t16-/m1/s1
• InChIKey: HXNJCVUANVPHHP-MRXNPFEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2R)-2-acetamido-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate
• IUPAC Traditional name: ethyl (2R)-2-acetamido-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate
• Synonyms: N-Acetyl-O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine Ethyl Ester; N-Acetyl-(S)-thyroxine Ethyl Ester; N-Acetyl L-Thyroxine Ethyl Ester

Database IDs

• CAS Number: 30804-52-5
• PubChem SID: 162253640
• PubChem CID: 71313012

CALCULATED PROPERTIES

• Acid pKa: 7.430795
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 6.306638
• LogD (pH = 7.4): 6.0286455
• Log P: 6.3116636
• Molar Refractivity: 145.7495 cm^3
• Polarizability: 57.65018 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dimethylformamide; DMSO; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - A188900

Protected Thyroxine (H963600).

REFERENCES

• Hao, Y., et al.: Endocrinol., 88, 81 (1971)
• Safran, M., et al.: J. Biol. Chem., 268, 14224 (1971)