resveratrol   Click here for help

GtoPdb Ligand ID: 8741

Synonyms: 3,4',5-stilbenetriol | 3,5,4'-trihydroxystilbene | trans-resveratrol
PDB Ligand Immunopharmacology Ligand
Compound class: Natural product
Comment: Resveratrol is a natural product found in the skins of grapes and some other berries used predominantly as an antioxidant dietery supplement [9,14,16]. 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 [2,5,7,12-13,19,21]. It has some activity as a cyclooxygenase inhibitor/antiinflammatory agent.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: resveratrol

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Bariani MV, Correa F, Leishman E, Domínguez Rubio AP, Arias A, Stern A, Bradshaw HB, Franchi AM. (2017)
Resveratrol protects from lipopolysaccharide-induced inflammation in the uterus and prevents experimental preterm birth.
Mol Hum Reprod, 23 (8): 571-581. [PMID:28810692]
2. Britton RG, Kovoor C, Brown K. (2015)
Direct molecular targets of resveratrol: identifying key interactions to unlock complex mechanisms.
Ann N Y Acad Sci, 1348 (1): 124-33. [PMID:26099829]
3. Buhrmann C, Popper B, Aggarwal BB, Shakibaei M. (2017)
Resveratrol downregulates inflammatory pathway activated by lymphotoxin α (TNF-β) in articular chondrocytes: Comparison with TNF-α.
PLoS ONE, 12 (11): e0186993. [PMID:29095837]
4. Calleri E, Pochetti G, Dossou KS, Laghezza A, Montanari R, Capelli D, Prada E, Loiodice F, Massolini G, Bernier M et al.. (2014)
Resveratrol and its metabolites bind to PPARs.
Chembiochem, 15 (8): 1154-60. [PMID:24796862]
5. Fu W, Zhuang W, Zhou S, Wang X. (2015)
Plant-derived neuroprotective agents in Parkinson's disease.
Am J Transl Res, 7 (7): 1189-202. [PMID:26328004]
6. Gong WH, Zhao N, Zhang ZM, Zhang YX, Yan L, Li JB. (2017)
The inhibitory effect of resveratrol on COX-2 expression in human colorectal cancer: a promising therapeutic strategy.
Eur Rev Med Pharmacol Sci, 21 (5): 1136-1143. [PMID:28338176]
7. Han G, Xia J, Gao J, Inagaki Y, Tang W, Kokudo N. (2015)
Anti-tumor effects and cellular mechanisms of resveratrol.
Drug Discov Ther, 9 (1): 1-12. [PMID:25788047]
8. Hoshino J, Park EJ, Kondratyuk TP, Marler L, Pezzuto JM, van Breemen RB, Mo S, Li Y, Cushman M. (2010)
Selective synthesis and biological evaluation of sulfate-conjugated resveratrol metabolites.
J Med Chem, 53 (13): 5033-43. [PMID:20527891]
9. Kelsey NA, Wilkins HM, Linseman DA. (2010)
Nutraceutical antioxidants as novel neuroprotective agents.
Molecules, 15 (11): 7792-814. [PMID:21060289]
10. Kode A, Rajendrasozhan S, Caito S, Yang SR, Megson IL, Rahman I. (2008)
Resveratrol induces glutathione synthesis by activation of Nrf2 and protects against cigarette smoke-mediated oxidative stress in human lung epithelial cells.
Am J Physiol Lung Cell Mol Physiol, 294 (3): L478-88. [PMID:18162601]
11. Kong F, Zhang R, Zhao X, Zheng G, Wang Z, Wang P. (2017)
Resveratrol raisesin vitroanticancer effects of paclitaxel in NSCLC cell line A549 through COX-2 expression.
Korean J Physiol Pharmacol, 21 (5): 465-474. [PMID:28883751]
12. Ma T, Tan MS, Yu JT, Tan L. (2014)
Resveratrol as a therapeutic agent for Alzheimer's disease.
Biomed Res Int, 2014: 350516. [PMID:25525597]
13. Park EJ, Pezzuto JM. (2015)
The pharmacology of resveratrol in animals and humans.
Biochim Biophys Acta, 1852 (6): 1071-113. [PMID:25652123]
14. Rizvi SI, Pandey KB. (2010)
Activation of the erythrocyte plasma membrane redox system by resveratrol: a possible mechanism for antioxidant properties.
Pharmacol Rep, 62 (4): 726-32. [PMID:20885013]
15. Roland WS, van Buren L, Gruppen H, Driesse M, Gouka RJ, Smit G, Vincken JP. (2013)
Bitter taste receptor activation by flavonoids and isoflavonoids: modeled structural requirements for activation of hTAS2R14 and hTAS2R39.
J Agric Food Chem, 61 (44): 10454-66. [PMID:24117141]
16. Speciale A, Chirafisi J, Saija A, Cimino F. (2011)
Nutritional antioxidants and adaptive cell responses: an update.
Curr Mol Med, 11 (9): 770-89. [PMID:21999148]
17. St John SE, Jensen KC, Kang S, Chen Y, Calamini B, Mesecar AD, Lipton MA. (2013)
Design, synthesis, biological and structural evaluation of functionalized resveratrol analogues as inhibitors of quinone reductase 2.
Bioorg Med Chem, 21 (19): 6022-37. [PMID:23953689]
18. Ungvari Z, Bagi Z, Feher A, Recchia FA, Sonntag WE, Pearson K, de Cabo R, Csiszar A. (2010)
Resveratrol confers endothelial protection via activation of the antioxidant transcription factor Nrf2.
Am J Physiol Heart Circ Physiol, 299 (1): H18-24. [PMID:20418481]
19. Vahid F, Zand H, Nosrat-Mirshekarlou E, Najafi R, Hekmatdoost A. (2015)
The role dietary of bioactive compounds on the regulation of histone acetylases and deacetylases: a review.
Gene, 562 (1): 8-15. [PMID:25701602]
20. Voloshyna I, Hai O, Littlefield MJ, Carsons S, Reiss AB. (2013)
Resveratrol mediates anti-atherogenic effects on cholesterol flux in human macrophages and endothelium via PPARγ and adenosine.
Eur J Pharmacol, 698 (1-3): 299-309. [PMID:23041272]
21. Zordoky BN, Robertson IM, Dyck JR. (2015)
Preclinical and clinical evidence for the role of resveratrol in the treatment of cardiovascular diseases.
Biochim Biophys Acta, 1852 (6): 1155-77. [PMID:25451966]