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

• ChemBase ID: 178609
• Molecular Formular: C21H19I4NO10
• Molecular Mass: 952.99414
• Monoisotopic Mass: 952.71878781
• SMILES: c1(c(cc(cc1I)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)Oc1cc(I)c(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/C21H19I4NO10/c22-8-4-7(5-9(23)13(8)27)34-17-10(24)1-6(2-11(17)25)3-12(26)20(33)36-21-16(30)14(28)15(29)18(35-21)19(31)32/h1-2,4-5,12,14-16,18,21,27-30H,3,26H2,(H,31,32)/t12-,14-,15-,16+,18-,21-/m0/s1
• InChIKey: HMTFXPJOBPIOIN-DKBYMCRTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[(2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-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-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: Thyroxine Glucuronoside; O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine β-D-Glucopyranuronosyl Ester; Levothyroxine Acyl Glucuronide; Thyroxine Acyl-β-D-Glucuronide

Database IDs

• CAS Number: 909880-81-5
• PubChem SID: 164234519
• PubChem CID: 71752554

CALCULATED PROPERTIES

• Acid pKa: 2.9230242
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): 1.7671051
• LogD (pH = 7.4): 0.9809129
• Log P: 1.7783023
• Molar Refractivity: 159.0866 cm^3
• Polarizability: 64.469185 Å^3
• Polar Surface Area: 189.0 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T425610

Thyroxine Acyl-β-D-Glucuronide is a major metabolite and glucuronide conjugate of Thyroxine (T425600) formed via the glucuronidation of the carboxyl group.

REFERENCES

• Tong, Z. et al.: Drug Metab. Dispos., 35, 2203 (2007)
• West, C.D. et al.: J. Clin. INvest., 42, 1134 (2007)