Structure Database (LMSD)

Common Name
Oxyresveratrol
Systematic Name
Synonyms
LM ID
LMPK13090011
Formula
Exact Mass
Calculate m/z
244.07356
Status
Curated


Classification

Biological Context

Resveratrol is a potent phenolic antioxidant found in the skin of grapes and red wine that has anti-proliferative, anti-inflammatory, and cardioprotective properties.1 Oxyresveratrol is a naturally occurring analog of resveratrol found in mulberry wood. It effectively scavenges H2O2, NO (IC50 = 45.3 μM), and the artificial free radical 2,2-diphenyl-l-picrylhydrazyl (IC50 = 28.9 μM).2 At 10 mg/kg, oxyresveratrol acts as a neuroprotectant, reducing brain infarct volume and reducing cytochrome c release and caspase-3 activation in an in vivo model of stroke.3 Oxyresveratrol also has depigmenting effects by effectively inhibiting tyrosinase activity, which catalyzes the rate-limiting step in synthesizing melanin pigments (IC50s = 1.2 and 52.7 μM in mushroom and mouse melanoma B-16 cells, respectively).4 It is 32-fold more potent than kojic acid, a depigmenting agent used in cosmetic materials with skin-whitening effects and medical agents used to treat hyperpigmentation disorders.4

This information has been provided by Cayman Chemical

References

2. Andrabi, S.A., Spina, M.G., Lorenz, P., et al. Oxyresveratrol (trans-2,3',4,5'-tetrahydroxystilbene) is neuroprotective and inhibits the apoptotic cell death in transient cerebral ischemia. Brain Res. 1017, 98-107 (2004).
4. Kim, Y.M., Yun, J., Lee, C.K., et al. Oxyresveratrol and hydroxystilbene compounds. Inhbitory effect on tyrosinase and mechanism of action. The Journal of Biological Chemisty 277(18), 16340-16344 (2002).

String Representations

InChiKey (Click to copy)
PDHAOJSHSJQANO-OWOJBTEDSA-N
InChi (Click to copy)
InChI=1S/C14H12O4/c15-11-4-3-10(14(18)8-11)2-1-9-5-12(16)7-13(17)6-9/h1-8,15-18H/b2-1+
SMILES (Click to copy)
C1=C(O)C=C(/C=C/C2=CC=C(O)C=C2O)C=C1O

Other Databases

KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID

Calculated Physicochemical Properties

Heavy Atoms 18
Rings 2
Aromatic Rings 2
Rotatable Bonds 2
Van der Waals Molecular Volume 220.92
Topological Polar Surface Area 80.92
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 4
logP 2.68
Molar Refractivity 68.47

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Updated at
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