(2S)-2-amino-3-{4-[3,5-diiodo-4-(sulfooxy)phenoxy]-3,5-diiodophenyl}propanoic acid

• ChemBase ID: 178613
• Molecular Formular: C15H11I4NO7S
• Molecular Mass: 856.93322
• Monoisotopic Mass: 856.6435147
• SMILES: c1(c(cc(cc1I)Oc1c(cc(cc1I)C[C@H](N)C(=O)O)I)I)OS(=O)(=O)O
• Canonical SMILES: N[C@H](C(=O)O)Cc1cc(I)c(c(c1)I)Oc1cc(I)c(c(c1)I)OS(=O)(=O)O
• InChI: InChI=1S/C15H11I4NO7S/c16-8-1-6(3-12(20)15(21)22)2-9(17)13(8)26-7-4-10(18)14(11(19)5-7)27-28(23,24)25/h1-2,4-5,12H,3,20H2,(H,21,22)(H,23,24,25)/t12-/m0/s1
• InChIKey: QYXIJUZWSSQICT-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-{4-[3,5-diiodo-4-(sulfooxy)phenoxy]-3,5-diiodophenyl}propanoic acid
• IUPAC Traditional name: thyroxine sulfic acid
• Synonyms: O-[3,5-Diiodo-4-(sulfooxy)phenyl]-3,5-diiodo-L-tyrosine; Thyroxine Hydrogen Sulfate; Thyroxine Sulfate; Thyroxine 4'-O-Sulfate

Database IDs

• CAS Number: 77074-49-8
• PubChem SID: 164234523
• PubChem CID: 131742

CALCULATED PROPERTIES

• Acid pKa: -2.9610977
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.88622564
• LogD (pH = 7.4): 0.872132
• Log P: 4.3136983
• Molar Refractivity: 136.7798 cm^3
• Polarizability: 55.503963 Å^3
• Polar Surface Area: 136.15 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T425635

Thyroxine 4-O-Sulfate is a metabolite and sulfoconjugated derivative of Thyroxine (T425600).

REFERENCES

• Huang, W.S. et al.: Endocrine J., 44, 467 (1997)
• Debaveye, Y. et al.: Endocrinology, 149, 4218 (1997)
• Hays, M.T. et al.: Endocrine Res., 14, 51 (1997)