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

• ChemBase ID: 179151
• Molecular Formular: C15H12I3NO7S
• Molecular Mass: 731.03669
• Monoisotopic Mass: 730.74686673
• SMILES: c1(c(cc(cc1)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)Oc1ccc(c(c1)I)OS(=O)(=O)O
• InChI: InChI=1S/C15H12I3NO7S/c16-9-6-8(1-2-13(9)26-27(22,23)24)25-14-10(17)3-7(4-11(14)18)5-12(19)15(20)21/h1-4,6,12H,5,19H2,(H,20,21)(H,22,23,24)/t12-/m0/s1
• InChIKey: XBQYQXVJBNDCGY-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-{3,5-diiodo-4-[3-iodo-4-(sulfooxy)phenoxy]phenyl}propanoic acid
• IUPAC Traditional name: triiodothyronine sulfate
• Synonyms: 3-[4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenyl]-L-alanine Hydrogen Sulfate; Triiodothyronine Hydrogen Sulfate; Liothyronine Sulfate; T3 Sulfate; 3,3',5-Triiodo-L-thyronine 4'-O-Sulfate; Triiodothyronine Sulfate; 3,5-Diiodo-O-[3-iodo-4-(sulfooxy)phenyl]-L-tyrosine

Database IDs

• CAS Number: 31135-55-4
• PubChem SID: 164235061
• PubChem CID: 122196

CALCULATED PROPERTIES

• Acid pKa: -2.913364
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.042008925
• LogD (pH = 7.4): -0.056802575
• Log P: 3.3947623
• Molar Refractivity: 123.4173 cm^3
• Polarizability: 49.92854 Å^3
• Polar Surface Area: 136.15 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T795395

3,3’,5-Triiodo-L-thyronine 4’-O-Sulfate is the sulfoconjugated metabolite of 3,3’,5-Triiodo-L-thyronine (T795380).

REFERENCES

• Rooda, S.J. et al.: J. Clin. Endocrinol. Metab., 69, 552 (1989)
• Everts, M. E. et al.: Metab. Clin. Exp., 43, 1282 (1989)
• Pinna, G. et al.: Endocrinology, 143, 1789 (1989)