trisodium 3-(sulfonatooxy)-5-[(E)-2-[4-(sulfonatooxy)phenyl]ethenyl]phenyl sulfate

• ChemBase ID: 177410
• Molecular Formular: C14H9Na3O12S3
• Molecular Mass: 534.37837
• Monoisotopic Mass: 533.89492157
• SMILES: c1(cc(cc(c1)/C=C/c1ccc(cc1)OS(=O)(=O)[O-])OS(=O)(=O)[O-])OS(=O)(=O)[O-].[Na+].[Na+].[Na+]
• Canonical SMILES: [O-]S(=O)(=O)Oc1ccc(cc1)/C=C/c1cc(cc(c1)OS(=O)(=O)[O-])OS(=O)(=O)[O-].[Na+].[Na+].[Na+]
• InChI: InChI=1S/C14H12O12S3.3Na/c15-27(16,17)24-12-5-3-10(4-6-12)1-2-11-7-13(25-28(18,19)20)9-14(8-11)26-29(21,22)23;;;/h1-9H,(H,15,16,17)(H,18,19,20)(H,21,22,23);;;/q;3*+1/p-3/b2-1+
• InChIKey: FHTZEDSDNIFGEW-YOTINIEPSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium 3-(sulfonatooxy)-5-[(E)-2-[4-(sulfonatooxy)phenyl]ethenyl]phenyl sulfate
• IUPAC Traditional name: trisodium 3-(sulfonatooxy)-5-[(E)-2-[4-(sulfonatooxy)phenyl]ethenyl]phenyl sulfate
• Synonyms: 5-[(1E)-2-[4-(Sulfooxy)phenyl]ethenyl]-1,3-benzenediol 1,3-Bis(hydrogen sulfate) Trisodium Salt; trans Resveratrol-3,4',5-trisulfate Trisodium Salt

Database IDs

• PubChem SID: 164233320
• PubChem CID: 71752001

CALCULATED PROPERTIES

• Acid pKa: -2.9083648
• H Acceptors: 9
• H Donor: 0
• LogD (pH = 5.5): -5.1527405
• LogD (pH = 7.4): -5.1527452
• Log P: 1.9764508
• Molar Refractivity: 94.0658 cm^3
• Polarizability: 39.525375 Å^3
• Polar Surface Area: 199.29 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: >255°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - R149995

A novel metabolite of Resveratrol in human plasma.

REFERENCES

• Banerjee, S., et al.: Cancer Res., 62, 4945 (2002)
• Wang, L., et al.: J. Pharm. Sci., 93, 2448 (2002)
• Provinciali, M., et al.: Int. J. Cancer, 115, 36 (2002)
• Lancon, A., et al.: Drug Metab. Dispos., 35, 699 (2002)