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

• ChemBase ID: 178612
• 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)I)I)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)Cc1cc(I)c(c(c1)I)Oc1cc(I)c(c(c1)I)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H19I4NO10/c22-8-1-6(3-12(26)19(30)31)2-9(23)16(8)34-7-4-10(24)17(11(25)5-7)35-21-15(29)13(27)14(28)18(36-21)20(32)33/h1-2,4-5,12-15,18,21,27-29H,3,26H2,(H,30,31)(H,32,33)/t12-,13-,14-,15+,18-,21+/m0/s1
• InChIKey: RGHRJBIKIYUHEV-OBOXGAGSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-(4-{4-[(2S)-2-amino-2-carboxyethyl]-2,6-diiodophenoxy}-2,6-diiodophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-(4-{4-[(2S)-2-amino-2-carboxyethyl]-2,6-diiodophenoxy}-2,6-diiodophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 4-[4-[(2S)-2-Amino-2-carboxyethyl]-2,6-diiodophenoxy]-2,6-diiodophenyl β-D-Glucopyranosiduronic Acid; Levothyroxine Phenolic Glucuronide; (S)-4-[4-(2-Amino-2-carboxyethyl)-2,6-diiodophenoxy]-2,6-diiodophenyl β-D-Glucopyranosiduronic Acid; L-Thyroxine Glucuronide; Thyroxine Glucuronide; Thyroxine 4'-O-β-D-Glucuronide

Database IDs

• CAS Number: 21462-56-6
• PubChem SID: 164234522
• PubChem CID: 71752555

CALCULATED PROPERTIES

• Acid pKa: 0.26069057
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -1.3949548
• LogD (pH = 7.4): -1.7466991
• Log P: 1.6902351
• Molar Refractivity: 158.7998 cm^3
• Polarizability: 64.31464 Å^3
• Polar Surface Area: 189.0 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T425630

Thyroxine 4-O-β-D-Glucuronide is a major metabolite and glucuronide conjugate of Thyroxine (T425600) formed via the glucuronidation of the phenyl hydroxyl group.

REFERENCES

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