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

• ChemBase ID: 178611
• Molecular Formular: C16H13I4NO4
• Molecular Mass: 790.8966
• Monoisotopic Mass: 790.7023499
• SMILES: c1(c(cc(cc1I)Oc1c(cc(cc1I)C[C@H](N)C(=O)OC)I)I)O
• Canonical SMILES: COC(=O)[C@H](Cc1cc(I)c(c(c1)I)Oc1cc(I)c(c(c1)I)O)N
• InChI: InChI=1S/C16H13I4NO4/c1-24-16(23)13(21)4-7-2-11(19)15(12(20)3-7)25-8-5-9(17)14(22)10(18)6-8/h2-3,5-6,13,22H,4,21H2,1H3/t13-/m0/s1
• InChIKey: ZTSGDCMQRKBJKC-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate
• IUPAC Traditional name: methyl (2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate
• Synonyms: O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine Methyl Ester; L-Thyroxine Methyl Ester; Thyroxine Methyl Ester

Database IDs

• CAS Number: 32180-11-3
• PubChem SID: 164234521
• PubChem CID: 13911218

CALCULATED PROPERTIES

• Acid pKa: 7.5548363
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.696409
• LogD (pH = 7.4): 5.7406006
• Log P: 5.7432623
• Molar Refractivity: 131.5571 cm^3
• Polarizability: 52.44041 Å^3
• Polar Surface Area: 81.78 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T425625

The methyl ester analog of Thyroxine (T425600) with high cross reactivity with thyroxine-specific monoclonal antibodies of humans and lab animals. It is an inhibitor of malate dehydrogenase.

REFERENCES

• Mpoko, C.N. et al.: Clin. Chim. Acta, 146, 215 (1985)
• Maggio, E.T. et al.: Biochim. Biophys. Acta Enzymol., 522, 284 (1985)