(2S)-2-amino-3-[4-(4-hydroxyphenoxy)-3-iodophenyl]propanoic acid

• ChemBase ID: 171701
• Molecular Formular: C15H14INO4
• Molecular Mass: 399.18043
• Monoisotopic Mass: 398.99675593
• SMILES: c1cc(ccc1Oc1ccc(cc1I)C[C@H](N)C(=O)O)O
• Canonical SMILES: OC(=O)[C@H](Cc1ccc(c(c1)I)Oc1ccc(cc1)O)N
• InChI: InChI=1S/C15H14INO4/c16-12-7-9(8-13(17)15(19)20)1-6-14(12)21-11-4-2-10(18)3-5-11/h1-7,13,18H,8,17H2,(H,19,20)/t13-/m0/s1
• InChIKey: SXQVOFSDWXYIRP-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-[4-(4-hydroxyphenoxy)-3-iodophenyl]propanoic acid
• IUPAC Traditional name: 3-iodothyronine
• Synonyms: O-(4-Hydroxyphenyl)-3-iodo-L-tyrosine; 3-[4-(p-Hydroxyphenoxy)-3-iodophenyl]-L-alanine; 3-Monoiodothyronine; 3-Iodo-L-thyronine

Database IDs

• CAS Number: 10468-90-3
• PubChem SID: 164227611
• PubChem CID: 112117

CALCULATED PROPERTIES

• Acid pKa: 0.7901647
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 0.94063115
• LogD (pH = 7.4): 0.934783
• Log P: 0.9406672
• Molar Refractivity: 86.7005 cm^3
• Polarizability: 34.003178 Å^3
• Polar Surface Area: 92.78 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Hot 2N Hydrochloric Acid; Sodium Hydroxide (aq.),
• Apperance: Tan-to-Light Brown Solid
• Melting Point: 191-193°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - I721500

A metabolite of thyroid hormone. Of interest for the early detection and treatment of congenital or drug-induced hypothyroidism in the developing human fetus.

REFERENCES

• Block, P.: J. Med. Chem., 19, 1067 (1976)
• Lum, S., et al.: J. Clin. Invest., 73, 570 (1976)
• St Germain, D., et al.: Thyroid, 7, 655 (1976)
• Soukhova, N., et al.: Clin. Chim. Acta., 343, 185 (1976)