Structure Database (LMSD)

Common Name
Resveratrol
Systematic Name
Synonyms
  • 3,4',5-trihydroxystilbene
LM ID
LMPK13090005
Formula
Exact Mass
Calculate m/z
228.078645
Status
Curated




Classification

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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