(2S)-3-{4-[4-hydroxy-3,5-diiodo(1,2,3,4,5,6-13C6)phenoxy]-3,5-diiodophenyl}-2-formamidopropanoic acid

• ChemBase ID: 169436
• Molecular Formular: C16H11I4NO5
• Molecular Mass: 810.83604903
• Monoisotopic Mass: 810.70174349
• SMILES: [13c]1([13c]([13cH][13c]([13cH][13c]1I)Oc1c(cc(cc1I)C[C@H](NC=O)C(=O)O)I)I)O
• Canonical SMILES: O=CN[C@H](C(=O)O)Cc1cc(I)c(c(c1)I)O[13c]1[13cH][13c](I)[13c]([13c]([13cH]1)I)O
• InChI: InChI=1S/C16H11I4NO5/c17-9-4-8(5-10(18)14(9)23)26-15-11(19)1-7(2-12(15)20)3-13(16(24)25)21-6-22/h1-2,4-6,13,23H,3H2,(H,21,22)(H,24,25)/t13-/m0/s1/i4+1,5+1,8+1,9+1,10+1,14+1
• InChIKey: DNRNTTVIRGKKSQ-GBLPCCAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-{4-[4-hydroxy-3,5-diiodo(1,2,3,4,5,6-^1^3C₆)phenoxy]-3,5-diiodophenyl}-2-formamidopropanoic acid
• IUPAC Traditional name: (2S)-3-{4-[4-hydroxy-3,5-diiodo(1,2,3,4,5,6-^1^3C₆)phenoxy]-3,5-diiodophenyl}-2-formamidopropanoic acid
• Synonyms: N-Formyl-O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine-13C6; N-Formyl Thyroxine-13C6

Database IDs

• PubChem SID: 162263568
• PubChem CID: 71316965

CALCULATED PROPERTIES

• Acid pKa: 2.034509
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.559649
• LogD (pH = 7.4): 1.954284
• Log P: 5.7602625
• Molar Refractivity: 131.7413 cm^3
• Polarizability: 52.1333 Å^3
• Polar Surface Area: 95.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F701302

Labelled Thyroxine derivative which showed less thyroid activity than Thyroxine Sodium (T425601).

REFERENCES

• Basil, B., et al.: Br. J. Pharmacol. Chemother., 5, 315 (1950)