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

• ChemBase ID: 178607
• Molecular Formular: C15H10I4NNaO4
• Molecular Mass: 798.85185
• Monoisotopic Mass: 798.66864409
• SMILES: c1(c(cc(cc1I)Oc1c(cc(cc1I)C[C@H](N)C(=O)[O-])I)I)O.[Na+]
• Canonical SMILES: [O-]C(=O)[C@H](Cc1cc(I)c(c(c1)I)Oc1cc(I)c(c(c1)I)O)N.[Na+]
• InChI: InChI=1S/C15H11I4NO4.Na/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23;/h1-2,4-5,12,21H,3,20H2,(H,22,23);/q;+1/p-1/t12-;/m0./s1
• InChIKey: YDTFRJLNMPSCFM-YDALLXLXSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate
• IUPAC Traditional name: sodium levothyroxine(1-)
• Synonyms: O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine Sodium; (-)-Thyroxine Sodium; 3,3',5,5'-Tetraiodo-L-thyronine Sodium; Henning Sodium; L-T4 Sodium; L-Thyroxin Sodium; Levothyroxine Sodium; NSC 36397-Sodium; T4 Sodium; Thyrax Sodium; Thyreoideum Sodium; Thyroxin Sodium; Thyroxinal Sodium; Thyroxine Sodium Salt

Database IDs

• CAS Number: 55-03-8
• PubChem SID: 164234517
• PubChem CID: 23666112

CALCULATED PROPERTIES

• Acid pKa: 0.27336746
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.722463
• LogD (pH = 7.4): 3.4409168
• Log P: 3.727307
• Molar Refractivity: 137.6251 cm^3
• Polarizability: 50.34098 Å^3
• Polar Surface Area: 95.61 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 215-218°C (dec.)

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T425601

One of the thyroid hormones involved in the maintenance of metabolic homeostasis. Synthesized and stored as amino acid residues of thyroglobulin, the major protein component of the thyroid follicular colloid. Synthesis and secretion are regulated by the p

REFERENCES

• Post, A., et al.: Anal. Profiles Drug Subs., 5, 225 (1976)
• Nelson, J.C., et al.: Clin. Chem., 34, 1737 (1976)
• Fischer, D.A., et al.: Clin. Chem., 42, 135 (1976)
• Cavalieri, R.R., et al.: Thyroid, 7, 177 (1976)