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

• ChemBase ID: 159504
• Molecular Formular: C17H13I4NO5
• Molecular Mass: 824.86262903
• Monoisotopic Mass: 824.71739355
• SMILES: [13c]1([13c]([13cH][13c]([13cH][13c]1I)Oc1c(cc(cc1I)C[C@@H](NC(=O)C)C(=O)O)I)I)O
• Canonical SMILES: OC(=O)[C@@H](Cc1cc(I)c(c(c1)I)O[13c]1[13cH][13c](I)[13c]([13c]([13cH]1)I)O)NC(=O)C
• InChI: InChI=1S/C17H13I4NO5/c1-7(23)22-14(17(25)26)4-8-2-12(20)16(13(21)3-8)27-9-5-10(18)15(24)11(19)6-9/h2-3,5-6,14,24H,4H2,1H3,(H,22,23)(H,25,26)/t14-/m1/s1/i5+1,6+1,9+1,10+1,11+1,15+1
• InChIKey: NERGVJCCFAPEMR-NAUDCQFPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-acetamido-3-{4-[4-hydroxy-3,5-diiodo(1,2,3,4,5,6-^1^3C₆)phenoxy]-3,5-diiodophenyl}propanoic acid
• IUPAC Traditional name: (2R)-2-acetamido-3-{4-[4-hydroxy-3,5-diiodo(1,2,3,4,5,6-^1^3C₆)phenoxy]-3,5-diiodophenyl}propanoic acid
• Synonyms: N-Acetyl-L-thyroxine-13C6; N-Acetylthyroxine-13C6; N-Acetyl L-Thyroxine-13C6; N-Acetyl-O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine-13C6

Database IDs

• PubChem SID: 162253639
• PubChem CID: 71313011

CALCULATED PROPERTIES

• Acid pKa: 2.1265204
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.6601942
• LogD (pH = 7.4): 2.00445
• Log P: 5.8089614
• Molar Refractivity: 136.2318 cm^3
• Polarizability: 53.897144 Å^3
• Polar Surface Area: 95.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A188892

Labelled Thyroxine (T425600) analogue, a thyroid hormone for use in diagnosing and treating diabetes.

REFERENCES

• Gonzales, M., et al.: J. Biol. Chem., 272, 11288 (1997)
• de Wolf, F., et al.: Pharm. Rev., 52, 207 (1997)
• Waner, M., et al.: Biophys. J., 87, 2701 (1997)