5-[(Z)-2-(3,4-dihydroxyphenyl)ethenyl]benzene-1,3-diol

• ChemBase ID: 176473
• Molecular Formular: C14H12O4
• Molecular Mass: 244.24268
• Monoisotopic Mass: 244.07355886
• SMILES: c1(cc(cc(c1)/C=C\c1ccc(c(c1)O)O)O)O
• Canonical SMILES: Oc1cc(/C=C\c2ccc(c(c2)O)O)cc(c1)O
• InChI: InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1-
• InChIKey: CDRPUGZCRXZLFL-UPHRSURJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(Z)-2-(3,4-dihydroxyphenyl)ethenyl]benzene-1,3-diol
• IUPAC Traditional name: 5-[(Z)-2-(3,4-dihydroxyphenyl)ethenyl]benzene-1,3-diol
• Synonyms: 4-[(1Z)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,2-benzenediol; cis-Piceatannol

Database IDs

• CAS Number: 106325-86-4
• PubChem SID: 164232383
• PubChem CID: 6603962

CALCULATED PROPERTIES

• Acid pKa: 8.905793
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 3.098656
• LogD (pH = 7.4): 3.0854614
• Log P: 3.0988255
• Molar Refractivity: 69.4364 cm^3
• Polarizability: 25.926823 Å^3
• Polar Surface Area: 80.92 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P436295

The cis isomer of human metabolite of Resveratrol (R150000).

REFERENCES

• Athar, M., et al.: Toxicol. Appl. Pharmacol., 224, 274 (2007)
• Bernhardt, R., et al.: J. Biotechnol., 124, 128 (2007)
• Fairman, D.A., et al.: Drug Metab. Dispos., 35, 2159 (2007)