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.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: resveratrol

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Bioactivity Comments
The highest affinity target of resveratrol identified so far is the oxidoreductase enzyme quinone reductase 2 (NQO2; P16083). The Ki for this inhibition is 88nM [16].
Selectivity at nuclear hormone receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Peroxisome proliferator-activated receptor-γ Hs Antagonist Antagonist 5.8 pKd - 4
pKd 5.8 (Kd 1.4x10-6 M) [4]
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
COX-2 Hs Inhibitor Inhibition 6.1 pIC50 - 8
pIC50 6.1 (IC50 7.5x10-7 M) [8]