sodium (2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoate

• ChemBase ID: 133323
• Molecular Formular: C15H11I3NNaO4
• Molecular Mass: 672.95532
• Monoisotopic Mass: 672.77199612
• SMILES: c1cc(c(cc1Oc1c(cc(cc1I)C[C@@H](C(=O)[O-])N)I)I)O.[Na+]
• Canonical SMILES: [O-]C(=O)[C@H](Cc1cc(I)c(c(c1)I)Oc1ccc(c(c1)I)O)N.[Na+]
• InChI: InChI=1S/C15H12I3NO4.Na/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22;/h1-4,6,12,20H,5,19H2,(H,21,22);/q;+1/p-1/t12-;/m0./s1
• InChIKey: SBXXSUDPJJJJLC-YDALLXLXSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoate
• IUPAC Traditional name: sodium liothyronine(1-)
• Synonyms: T3; 3,3′,5-Triiodo-L-thyronine sodium salt; 3-[4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenyl]-L-alanine Monosodium Salt; Basoprocin; Cynomel; Cyomel; Cytobin; Cytomel; Cytomel sodium; Cytomine; Ibiothyron; L-Triiodothyronine Sodium Salt; Sodium Triiodo-L-thyronine; Sodium Triiodothyronine; T3 Sodium Salt; Tertroxin; Triiodothyronine Sodium Salt; Triostat; Triothyrone; 3,3',5-Triiodo-L-thyronine Sodium Salt; Liothyronine; O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine sodium salt; O-(4-羟基-3-碘苯基)-3,5-二碘-L-酪氨酸 钠盐; 碘塞罗宁; 3,3′,5-三碘-L-甲状腺原氨酸 钠盐

Database IDs

• CAS Number: 55-06-1
• EC Number: 200-223-5
• MDL Number: MFCD00002594
• Beilstein Number: 8179867
• PubChem SID: 24900071; 24889594; 24900372; 162227600; 24900290
• PubChem CID: 23666110

CALCULATED PROPERTIES

• Acid pKa: 0.30246884
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.798151
• LogD (pH = 7.4): 2.7648876
• Log P: 2.798505
• Molar Refractivity: 124.2626 cm^3
• Polarizability: 44.781998 Å^3
• Polar Surface Area: 95.61 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 4 M NH4OH in methanol: soluble125 g/5mL, clear, yellow-brown; DMSO
• Apperance: Light Purple Solid; powder
• Melting Point: 196-197°C (dec.)
• Optical Rotation: [α]20/D +21±2°, c = 1% in ethanol/1 M HCl (2:1)

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Gene Information: human ... THRA(7067), THRB(7068)rat ... Thra(81812), Thrb(24831)

Product Information

• Purity: ≥95%; ≥95% (HPLC); ≥98.0% (sum of enantiomers, HPLC)
• Potency: 0.02-50 ng/mL; 0.02-50 μg/mL
• Suitability: suitable for cell culture
• Sterility: γ-irradiated
• Empirical Formula (Hill Notation): C15H11I3NNaO4

DETAILS

Sigma Aldrich - T6397

Biochem/physiol Actions
T3 is a thyroid hormone that increases rates of proteins synthesis, stimulates the breakdown of cholesterol, and effects embryonic development. In cell culture, T3 regulates cell differentiation and protein expression.
Reconstitution
To prepare 20 μg/ml stock solution: add 1ml 1N NaOH per mg 3,3′, 5-triiodo-L-thyronine; gently swirl to dissolve. To this, add 49 ml sterile medium per ml 1N NaOH added.
Physical form
powder-0 °C; stock-frozen in working aliquots, avoid repeated freeze/thaw, solution stable 2-8 °C, 30 days

Sigma Aldrich - T5516

Biochem/physiol Actions
T3 是一种甲状腺激素，可加快蛋白质的合成，促进胆固醇的降解，影响胚胎的发育。在细胞培养中，T3 可调控细胞分化和蛋白质表达。
Reconstitution
制备 20μg/mL 储存液：加入 1mL 1N NaOH；缓缓搅拌溶解；加入 49mL 无菌培养基。
Physical form
0°C 下为粉末状；分成小份冻存，以避免使用时重复冰冻/解冻，溶液在 2-8°C 下可稳定 30 天

Sigma Aldrich - 92010

Application
Literature see 3,5,3′-Triodo-L-thyronine, 91990

Toronto Research Chemicals - T795385

One of the hormones produced by the thyroid gland that is involved in the maintenance of metabolic homeostasis. Also produced in peripheral tissues as the active metabolite of Thyroxine.

REFERENCES

• McLaughlin, C., et al.: Clin. Endocrinol., 69, 169 (2008)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2008)
• Lee, J., et al.: Thyroid, 20, 173 (2008)