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

• ChemBase ID: 178608
• Molecular Formular: C15H11I4NO4
• Molecular Mass: 782.82594903
• Monoisotopic Mass: 782.70682887
• SMILES: [13c]1([13c]([13cH][13c]([13cH][13c]1I)Oc1c(cc(cc1I)C[C@H](N)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)N
• InChI: InChI=1S/C15H11I4NO4/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)/t12-/m0/s1/i4+1,5+1,7+1,8+1,9+1,13+1
• InChIKey: XUIIKFGFIJCVMT-DOEZJOBUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-{4-[4-hydroxy-3,5-diiodo(1,2,3,4,5,6-^1^3C₆)phenoxy]-3,5-diiodophenyl}propanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-{4-[4-hydroxy-3,5-diiodo(1,2,3,4,5,6-^1^3C₆)phenoxy]-3,5-diiodophenyl}propanoic acid
• Synonyms: O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine; (-)-Thyroxine; 3,3',5,5'-Tetraiodo-L-thyronine; Henning; L-T4; L-Thyroxin; Levothyroxine; NSC 36397; T4; T4 (hormone); Thyrax; Thyreoideum; Thyroxin; Thyroxinal; Thyroxine-13C6

Database IDs

• PubChem SID: 164234518
• PubChem CID: 46783077

CALCULATED PROPERTIES

• Acid pKa: 0.27336746
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.722463
• LogD (pH = 7.4): 3.4409168
• Log P: 3.727307
• Molar Refractivity: 126.788 cm^3
• Polarizability: 50.46104 Å^3
• Polar Surface Area: 92.78 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: >175°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T425602

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)