resveratrol   Click here for help

GtoPdb Ligand ID: 8741

Synonyms: 3,4',5-stilbenetriol | 3,5,4'-trihydroxystilbene | trans-resveratrol
PDB Ligand Immunopharmacology Ligand
Comment: Resveratrol is a natural product found in the skins of grapes and some other berries used predominantly as an antioxidant dietery supplement [9,14-15]. The compound exists as a mixture of trans- (shown here) and cis- (PubChem CID 1548910) conformations. Resveratrol has been investigated for its various roles in complex biological processes [2,5,7,12-13,18,20]. It has some activity as a cyclooxygenase inhibitor/antiinflammatory agent.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 0
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 60.69
Molecular weight 228.08
XLogP 3.44
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Oc1ccc(cc1)C=Cc1cc(O)cc(c1)O
Isomeric SMILES Oc1ccc(cc1)/C=C/c1cc(O)cc(c1)O
InChI InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1+
InChI Key LUKBXSAWLPMMSZ-OWOJBTEDSA-N
No information available.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Resveratrol is believed to be anti-atherogenic, by promoting apoA-1 and HDL-mediated efflux in addition to regulating the expression of proteins important for cholesterol transport [19]. These actions of resveratrol appear to involve PPARγ and α2A-adrenoceptor pathways. Resveratrol is also reported to protect lung epithelial cells [10] and coronary arterial endothelial cells [17] from oxidative damage via a Nrf2 (nuclear factor (erythroid-derived 2)-like 2; NFE2L2)-dependent mechanism.