(2R)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid

• ChemBase ID: 111726
• Molecular Formular: C15H11I4NO4
• Molecular Mass: 776.87002
• Monoisotopic Mass: 776.68669984
• SMILES: N[C@H](Cc1cc(I)c(Oc2cc(I)c(O)c(I)c2)c(I)c1)C(=O)O
• Canonical SMILES: OC(=O)[C@@H](Cc1cc(I)c(c(c1)I)Oc1cc(I)c(c(c1)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-/m1/s1
• InChIKey: XUIIKFGFIJCVMT-GFCCVEGCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid
• IUPAC Traditional name: D-thyroxine; dextrothyroxine
• Synonyms: D-THYROXINE; 3,3′,5,5′-Tetraiodo-D-thyronine; 3-[4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]-D-alanine; D-Thyroxine; O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-D-tyrosine; 3,3',5,5'-Tetraiodo-D-thyronine; Dextrothyroxine; 3,3′,5,5′-四碘代-D-甲状腺原氨酸; 3-[4-(4-羟基-3,5-二碘苯氧基)-3,5-二碘苯基]-D-丙氨酸; D-甲状腺素

Database IDs

• CAS Number: 51-49-0
• MDL Number: MFCD00063056
• Beilstein Number: 2954910
• PubChem SID: 162098118
• PubChem CID: 8730

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: Methanol
• Apperance: Tan Solid
• Melting Point: ~235 °C (dec.); >210°C (dec.)

Safety Information

• Storage Condition: Refrigerator

Product Information

• Purity: 99%
• Empirical Formula (Hill Notation): C15H11I4NO4

DETAILS

MP Biomedicals - 05220578

MP Biomedicals Rare Chemical collection

Toronto Research Chemicals - T425605

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)