(2S,3S,4S,5R,6S)-6-{[(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 179150
• Molecular Formular: C21H20I3NO10
• Molecular Mass: 827.09761
• Monoisotopic Mass: 826.82213985
• SMILES: c1(c(cc(cc1)Oc1c(cc(cc1I)C[C@H](N)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)I)I)O
• Canonical SMILES: O=C([C@H](Cc1cc(I)c(c(c1)I)Oc1ccc(c(c1)I)O)N)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H20I3NO10/c22-9-6-8(1-2-13(9)26)33-17-10(23)3-7(4-11(17)24)5-12(25)20(32)35-21-16(29)14(27)15(28)18(34-21)19(30)31/h1-4,6,12,14-16,18,21,26-29H,5,25H2,(H,30,31)/t12-,14-,15-,16+,18-,21-/m0/s1
• InChIKey: LQMBVWCQWFEPFK-DKBYMCRTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: Liothyronine Acyl Glucuronide; T3 Acyl Glucuronide; O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo- L-Tyrosine 1-ester with β-D-Glucopyranuronic Acid; Triiodothyronine Acyl Glucuronide; Glucuronic Acid 1-Ester with 3-[4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenyl]alanine; 3,3',5-Triiodo-L-thyronine Acyl β-D-Glucuronide

Database IDs

• CAS Number: 910907-23-2
• PubChem SID: 164235060
• PubChem CID: 71752794

CALCULATED PROPERTIES

• Acid pKa: 2.9230678
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): 0.8424885
• LogD (pH = 7.4): 0.30464607
• Log P: 0.8505227
• Molar Refractivity: 145.7241 cm^3
• Polarizability: 58.9188 Å^3
• Polar Surface Area: 189.0 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T795390

3,3’,5-Triiodo-L-thyronine Acyl β-D-Glucuronide is the acyl glucuronidated metabolite of 3,3’,5-Triiodo-L-thyronine (T795380).

REFERENCES

• Tong, Z. et al.: Drug Metab. Dispos., 35, 2203 (2007)
• Beraud, T. et al.: Acta Endocrinol., 35, 324 (2007)