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
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. 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]
16. 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]
17. 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]
18. 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]
19. 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]
20. 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]