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

• ChemBase ID: 168798
• Molecular Formular: C16H13I4NO4
• Molecular Mass: 790.8966
• Monoisotopic Mass: 790.7023499
• SMILES: c1(c(cc(cc1I)Oc1c(cc(cc1I)CC(C(=O)O)(N)C)I)I)O
• Canonical SMILES: OC(=O)C(Cc1cc(I)c(c(c1)I)Oc1cc(I)c(c(c1)I)O)(N)C
• InChI: InChI=1S/C16H13I4NO4/c1-16(21,15(23)24)6-7-2-11(19)14(12(20)3-7)25-8-4-9(17)13(22)10(18)5-8/h2-5,22H,6,21H2,1H3,(H,23,24)
• InChIKey: XVWORJPLTFZBFO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]-2-methylpropanoic acid
• IUPAC Traditional name: 2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]-2-methylpropanoic acid
• Synonyms: O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-α-methyl-tyrosine; α-Methyl-DL-thyroxine; Etiroxate Carboxylic Acid

Database IDs

• CAS Number: 3414-34-4
• PubChem SID: 162262930
• PubChem CID: 20311799

CALCULATED PROPERTIES

• Acid pKa: 0.3375862
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 4.1552477
• LogD (pH = 7.4): 3.8753173
• Log P: 4.160061
• Molar Refractivity: 131.5013 cm^3
• Polarizability: 52.226864 Å^3
• Polar Surface Area: 92.78 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Aqueous Sodium Hydroxide
• Apperance: Beige Solid

DETAILS

Toronto Research Chemicals - E932985

Thyroxin derivative inhibiting glutamate dehydrogenase, isocitrate dehydrogenase, alcohol dehydrogenase, rat liver mitochondrial phosphorylation and electron transfer. Administration also induces hypothyroid state.

REFERENCES

• Blank, B., et al.: J. Med. Chem., 9, 10 (1966)
• Zenker, N., et al.: Biochem. Pharmacol., 25, 1757 (1966)