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

• ChemBase ID: 171370
• Molecular Formular: C15H11I4NO5
• Molecular Mass: 798.82534903
• Monoisotopic Mass: 798.70174349
• SMILES: [13c]1([13c]([13cH][13c]([13cH][13c]1I)Oc1c(cc(cc1I)C([C@H](N)C(=O)O)O)I)I)O
• Canonical SMILES: OC(=O)[C@H](C(c1cc(I)c(c(c1)I)O[13c]1[13cH][13c](I)[13c]([13c]([13cH]1)I)O)O)N
• InChI: InChI=1S/C15H11I4NO5/c16-7-3-6(4-8(17)13(7)22)25-14-9(18)1-5(2-10(14)19)12(21)11(20)15(23)24/h1-4,11-12,21-22H,20H2,(H,23,24)/t11-,12?/m0/s1/i3+1,4+1,6+1,7+1,8+1,13+1
• InChIKey: QIFVILYTCIFAPL-IUJKBILGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-hydroxy-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-hydroxy-3-{4-[4-hydroxy-3,5-diiodo(1,2,3,4,5,6-^1^3C₆)phenoxy]-3,5-diiodophenyl}propanoic acid
• Synonyms: β-[3,5-Diiodo-4-(3,5-diiodo-4-hydroxyphenoxy)phenyl]serine-3C6; β-Hydroxy Thyroxine-13C6

Database IDs

• PubChem SID: 164227280
• PubChem CID: 71749374

CALCULATED PROPERTIES

• Acid pKa: 0.20749103
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 2.8033478
• LogD (pH = 7.4): 2.5118718
• Log P: 2.8083267
• Molar Refractivity: 127.9955 cm^3
• Polarizability: 51.204464 Å^3
• Polar Surface Area: 113.01 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H963602

Labelled β-Hydroxy Thyroxine (H963600). It has been prepared for testing as possible antithyroid. It showed some thyromimetic activity.

REFERENCES

• Wawzone, S., et al.: J. Med. Chem., 6, 442 (1963)