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

• ChemBase ID: 179149
• Molecular Formular: C15H12I3NO4
• Molecular Mass: 656.92941903
• Monoisotopic Mass: 656.8101809
• SMILES: [13c]1([13c]([13cH][13c]([13cH][13cH]1)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][13cH][13c]([13c]([13cH]1)I)O)N
• InChI: InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1/i1+1,2+1,6+1,8+1,9+1,13+1
• InChIKey: AUYYCJSJGJYCDS-DGAVPSMWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-{4-[4-hydroxy-3-iodo(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-iodo(1,2,3,4,5,6-^1^3C₆)phenoxy]-3,5-diiodophenyl}propanoic acid
• Synonyms: O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine-13C6; Liothyronine-13C6; T3; L-T3-13C6; 3,3’,5-Triiodothyronine-13C6; T3 (Hormone)-13C6; Tresitope-13C6; Triiodothyronine-13C6; 3,3',5-Triiodo-L-thyronine-13C6

Database IDs

• PubChem SID: 164235059
• PubChem CID: 46783186

CALCULATED PROPERTIES

• Acid pKa: 0.30246884
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.798151
• LogD (pH = 7.4): 2.7648876
• Log P: 2.798505
• Molar Refractivity: 113.4255 cm^3
• Polarizability: 44.90148 Å^3
• Polar Surface Area: 92.78 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 237-239°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T795382

One of the hormones produced by the thyroid gland that is involved in the maintenance of metabolic homeostasis. Also produced in peripheral tissues as the active metabolite of Thyroxine.

REFERENCES

• Gross, J., et al.: Lancet I, 439 (1952)
• Roche, J., et al.: Biochim. Biophys. Acta, 11, 215 (1952)
• Chacon, M.A., et al.: J. Pediatr., 99, 758 (1952)
• Chopra, I.J., et al.: Thyroid, 6, 255 (1952)