(2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3-iodophenyl]propanoic acid

• ChemBase ID: 129252
• Molecular Formular: C15H12I3NO4
• Molecular Mass: 650.97349
• Monoisotopic Mass: 650.79005187
• SMILES: c1cc(c(cc1C[C@@H](C(=O)O)N)I)Oc1cc(c(c(c1)I)O)I
• Canonical SMILES: OC(=O)[C@H](Cc1ccc(c(c1)I)Oc1cc(I)c(c(c1)I)O)N
• InChI: InChI=1S/C15H12I3NO4/c16-9-3-7(4-12(19)15(21)22)1-2-13(9)23-8-5-10(17)14(20)11(18)6-8/h1-3,5-6,12,20H,4,19H2,(H,21,22)/t12-/m0/s1
• InChIKey: HZCBWYNLGPIQRK-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3-iodophenyl]propanoic acid
• IUPAC Traditional name: 3,3,5-triiodothyronine
• Synonyms: Reverse triiodothyronine; 3,3',5'-Triiodo-L-thyronine; Reverse T3; rT(3); 3,3′,5′-Triiodo-L-thyronine

Database IDs

• CAS Number: 5817-39-0
• MDL Number: MFCD00036864
• PubChem SID: 162223546; 24899878
• PubChem CID: 22069; 644280
• MeSH Name: Reverse+triiodothyronine
• Wikipedia Title: Reverse_triiodothyronine

CALCULATED PROPERTIES

• Acid pKa: 0.7172853
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.79367
• LogD (pH = 7.4): 2.5180905
• Log P: 2.7982569
• Molar Refractivity: 113.4255 cm^3
• Polarizability: 44.901867 Å^3
• Polar Surface Area: 92.78 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 50 mg/mL in 4N Ammonia in Methanol gives a Yellow-Orange Solution
• Apperance: Beige Powder
• Melting Point: 180-185°C (dec.)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Empirical Formula (Hill Notation): C15H12I3NO4

DETAILS

Sigma Aldrich - T0281

Biochem/physiol Actions
rT3 inhibits the increase of sodium current generated by other thyroid hormone analogs in neonatal rat myocytes.1 The ratio of triiodothryonine (T3) to rT3 has been investigated as in indicator of insulin resistance.2

Toronto Research Chemicals - T795350

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(8)
• 1067-1069 (8)
• Shiba, T., & Cahmann, H.J.: J.O.C., 29, 1652-1653 (1964)