ethyl (2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate

• ChemBase ID: 178610
• Molecular Formular: C17H15I4NO4
• Molecular Mass: 804.92318
• Monoisotopic Mass: 804.71799997
• SMILES: c1(c(cc(cc1I)Oc1c(cc(cc1I)C[C@H](N)C(=O)OCC)I)I)O
• Canonical SMILES: CCOC(=O)[C@H](Cc1cc(I)c(c(c1)I)Oc1cc(I)c(c(c1)I)O)N
• InChI: InChI=1S/C17H15I4NO4/c1-2-25-17(24)14(22)5-8-3-12(20)16(13(21)4-8)26-9-6-10(18)15(23)11(19)7-9/h3-4,6-7,14,23H,2,5,22H2,1H3/t14-/m0/s1
• InChIKey: LSSGNEFHGVQOPA-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 76353-71-4
• PubChem SID: 164234520
• PubChem CID: 54050781

CALCULATED PROPERTIES

• Acid pKa: 7.5547547
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.0535145
• LogD (pH = 7.4): 6.097481
• Log P: 6.100211
• Molar Refractivity: 136.3057 cm^3
• Polarizability: 54.211002 Å^3
• Polar Surface Area: 81.78 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T425620

An analog of Thyroxine (L425600) with stimulatory effects on human red blood cell membrane Ca2+-activated ATPase. It is a potential inactivator of iodothyronine deiodinase type II.

REFERENCES

• Davis, F.B. et al.: J. Biol. Chem., 258, 12373 (1983)
• Safran, M. et al.: J. Biol. Chem., 268, 14224 (1983)