(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[2-(4-hydroxyphenyl)(2H6)propan-2-yl]phenoxy}oxane-2-carboxylic acid

• ChemBase ID: 162389
• Molecular Formular: C21H24O8
• Molecular Mass: 404.41046
• Monoisotopic Mass: 404.14711773
• SMILES: c1(C(c2ccc(cc2)O)(C)C)ccc(cc1)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: Oc1ccc(cc1)C(c1ccc(cc1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)(C)C
• InChI: InChI=1S/C21H24O8/c1-21(2,11-3-7-13(22)8-4-11)12-5-9-14(10-6-12)28-20-17(25)15(23)16(24)18(29-20)19(26)27/h3-10,15-18,20,22-25H,1-2H3,(H,26,27)/t15-,16-,17+,18-,20+/m0/s1
• InChIKey: KHZOXXYQSBJDHB-HBWRTXEVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[2-(4-hydroxyphenyl)(^2H₆)propan-2-yl]phenoxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[2-(4-hydroxyphenyl)(^2H₆)propan-2-yl]phenoxy}oxane-2-carboxylic acid
• Synonyms: 4-[1-(4-Hydroxyphenyl)-1-methylethyl-d6]phenyl β-D-Glucopyranosiduronic Acid; Bisphenol A-d6 β-D-Glucuronide

Database IDs

• PubChem SID: 162256524
• PubChem CID: 71314103

CALCULATED PROPERTIES

• Acid pKa: 3.2542336
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.12902485
• LogD (pH = 7.4): -1.3391258
• Log P: 2.0971818
• Molar Refractivity: 111.2869 cm^3
• Polarizability: 40.127068 Å^3
• Polar Surface Area: 136.68 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Gray Solid
• Melting Point: 105-108°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B519512

A labelled metabolite of Bisphenol A.

REFERENCES

• Zalko, D., et al.: Drug Metab. Dispos., 26, 28 (1998)
• Matthews, J., et al.: Chem. Res. Toxico., 14, 149 (1998)
• Kinjo, J., et al.: Biol. Pharm. Bull., 27, 185 (1998)
• Murata, M., et al.: Biochemistry, 43, 2569 (1998)