Structure Database (LMSD)
Common Name
Resveratrol
Systematic Name
Synonyms
- 3,4',5-trihydroxystilbene
3D model of Resveratrol
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
trans-Resveratrol is a polyphenol that has been found in grapes and has diverse biological activities.1,2 It inhibits the cyclooxygenase and hydroperoxidase activities of COX-1 (EC50s = 15 and 3.7 μM, respectively) but not COX-2 (EC50s = >100 μM and 85 μM, respectively).1 trans-Resveratrol (200 μM) also activates sirtuin 1 (SIRT1), as well as inhibits a variety of targets including ERK1, JNK1, Src, PKCα, aromatase/CYP19, and DNA polymerases α and δ (IC50s = 37, 50, 20, <10, 25, 3.3, and 5 μM, respectively) in vitro.3,2 It inhibits free radical formation induced by phorbol 12-myristate 13-acetate (TPA) in HL-60 cells and reduces the tumor incidence and number of tumors in a two-stage mouse model of skin cancer induced by TPA and 7,12-dimethyl-benz[a]anthracene (DMBA). trans-Resveratrol (3 and 8 mg/kg) inhibits carrageenan-induced paw edema in mice. Intravaginal administration of trans-resveratrol (12.5% v/v) inhibits herpes simplex virus 1 (HSV-1) and HSV-2 replication and delays the development of extravaginal disease in mouse models of vaginal HSV infection.4 It also prolongs lifespan in model organisms including C. elegans, D. melanogaster, and mice.2
This information has been provided by Cayman Chemical
References
1. Docherty, J.J., Fu, M.M., Hah, J.M., et al. Effect of resveratrol on herpes simplex virus vaginal infection in the mouse. Antiviral Res. 67(3), 155-162 (2005).
2. Pirola, L., and Fröjdö, S. Resveratrol: One molecule, many targets. IUMBM Life 60(5), 323-332 (2008).
3. Borra, M.T., Smith, B.C., and Denu, J.M. Mechanism of human SIRT1 activation by resveratrol. J. Biol. Chem. 280(17), 17187-17195 (2005).
String Representations
InChiKey (Click to copy)
LUKBXSAWLPMMSZ-OWOJBTEDSA-N
InChi (Click to copy)
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+
SMILES (Click to copy)
C1=C(O)C=C(/C=C/C2=CC=C(O)C=C2)C=C1O
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
17
Rings
2
Aromatic Rings
2
Rotatable Bonds
2
Van der Waals Molecular Volume
212.13
Topological Polar Surface Area
60.69
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
3
logP
2.97
Molar Refractivity
66.81
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Updated at
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