1.0 2011-09-21 00:28:16 UTC 2025-11-19 02:43:47 UTC FDB023335 3,3',4'5-Tetrahydroxystilbene 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). [HMDB] 3-Hydroxyresveratol 3,4,3',5'-tetrahydroxy-trans-stilbene 3,5,3',4'-Tetrahydroxystilbene 4-[(e)-2-(3,5-Dihydroxyphenyl)vinyl]benzene-1,2-diol C14H12O4 244.246 244.073558866 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol 10083-24-6 OC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(O)=C1 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+ CDRPUGZCRXZLFL-OWOJBTEDSA-N belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Stilbenes Organic compounds Phenylpropanoids and polyketides Stilbenes Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Catechols Hydrocarbon derivatives Organooxygen compounds Resorcinols Styrenes 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Benzenoid Catechol Hydrocarbon derivative Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol Resorcinol Stilbene Styrene Diphenyl ethers, biphenyls, dibenzyls and stilbenes Diphenyl ethers, biphenyls, dibenzyls and stilbenes Stilbenes stilbenol Solid logp 2.12 ALOGPS logs -3.40 ALOGPS solubility 9.70e-02 g/l ALOGPS logp 3.1 ChemAxon pka_strongest_acidic 8.41 ChemAxon pka_strongest_basic -6.2 ChemAxon iupac 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol ChemAxon average_mass 244.246 ChemAxon mono_mass 244.073558866 ChemAxon smiles OC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(O)=C1 ChemAxon formula C14H12O4 ChemAxon 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+ ChemAxon inchikey CDRPUGZCRXZLFL-OWOJBTEDSA-N ChemAxon polar_surface_area 80.92 ChemAxon refractivity 69.44 ChemAxon polarizability 25.46 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 2010 Specdb::CMs 2164 Specdb::CMs 3353 Specdb::CMs 31513 Specdb::CMs 31514 Specdb::CMs 38731 Specdb::CMs 132606 Specdb::CMs 140340 Specdb::MsMs 179991 Specdb::MsMs 179992 Specdb::MsMs 179993 Specdb::MsMs 182325 Specdb::MsMs 182326 Specdb::MsMs 182327 Specdb::MsMs 2241952 Specdb::MsMs 2754007 Specdb::MsMs 2754008 Specdb::MsMs 2754009 Specdb::MsMs 2951262 Specdb::MsMs 2951263 Specdb::MsMs 2951264 HMDB04215 28814 PIT #<Reference:0x000055ce3225bc18> #<Reference:0x000055ce3225ba38> #<Reference:0x000055ce3225b650> #<Reference:0x000055ce3225b470> Almond Type 1 specific Prunus dulcis 3755 Anatidae Type 1 specific Anatidae 8830 Arabica coffee Type 1 specific Coffea arabica 13443 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Black tea Type 1 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Coffee Type 1 generic Coffea 13442 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Deerberry Type 1 specific Vaccinium stamineum 176259 Dessert wine Type 2 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Fruit juice Type 2 specific Garden rhubarb Type 1 specific Rheum rhabarbarum 3621 Green tea Type 1 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Milk (Cow) Type 2 specific Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Red champagne Type 1 Red tea Type 1 Red wine Type 2 Robusta coffee Type 1 specific Coffea canephora 49390 Rock ptarmigan Type 1 specific Lagopus muta 64668 Rosé wine Type 2 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 White champagne Type 1 White wine Type 2 Wild boar Type 1 specific Sus scrofa 9823