Showing Metabocard for piceatannol (BASm0001605)
| Common Name | Piceatannol |
|---|---|
| Description | 3,3',4'5-Tetrahydroxystilbene (or Piceatannol) is a phenolic stilbenoid. It is a metabolite of resveratrol found in red wine. A viral protein-tyrosine kinase (LMP2A) implicated in leukemia, non-Hodgkin's lymphoma and other diseases associated with Epstein-Barr virus, was recently found to be blocked by picetannol in vitro (PMID 2590224 ). Therefore there is research interest in piceatannol as an anti-cancer and anti-EBV drug. Piceatannol can also act as an agonist for estrogen receptor alpha in human breast cancer cells (PMID: 16216908 ). |
| Structure | |
| Molecular Formula | C14H12O4 |
| Average Mass | 244.24600 |
| Monoisotopic Mass | 244.07356 |
| IUPAC Name | 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol |
| Traditional Name | Piceatannol |
| CAS Registry Number | 10083-24-6 |
| SMILES | Oc1cc(O)cc(/C=C/c2ccc(O)c(O)c2)c1 |
| InChI Identifier | 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+ |
| InChI Key | CDRPUGZCRXZLFL-OWOJBTEDSA-N |
| CHEBI ID | CHEBI:28814 |
| HMDB ID | HMDB0004215 |
| State | Not Available |
| Water Solubility | 9.70e-02 g/l |
| logP | 2.12 |
| logS | -3.40 |
| pKa (Strongest Acidic) | 8.91 |
| pKa (Strongest Basic) | -5.68 |
| Hydrogen Acceptor Count | 4 |
| Hydrogen Donor Count | 4 |
| Polar Surface Area | 80.92 Ų |
| Rotatable Bond Count | 2 |
| Physiological Charge | 0 |
| Formal Charge | 0 |
| Refractivity | 69.44 m³·mol⁻¹ |
| Polarizability | 25.46 |