Structure Database (LMSD)
Common Name
Pterostilbene
Systematic Name
Synonyms
3D model of Pterostilbene
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
Pterostilbene is a polyketide synthase-derived stilbene originally isolated from P. santalinus that has diverse biological activities.1,2,3,4,5 It reduces photooxidative leakage induced by the herbicide acifluorfen in C. sativus cotyledon disks when used at a concentration of 30 µg/ml.2 Pterostilbene (25 and 50 µM) inhibits invasion and migration of HepG2 hepatoma cells induced by 12-O-tetradecanoylphorbol 13-acetate (TPA).3 It inhibits the production of nitric oxide (NO) and prostaglandin E2 (PGE2) in LPS-stimulated RAW 264.7 macrophages when used at concentrations of 10 and 20 µM.4 Pterostilbene (100 and 300 µM) activates peroxisome proliferator-activated receptor α (PPARα) in H4IIEC3 rat hepatoma cells.5 It decreases plasma glucose and LDL levels and increases plasma levels of HDL in a hamster model of hypercholesterolemia induced by a high-fat diet when administered in the diet at 25 ppm.
This information has been provided by Cayman Chemical
References
3. Pan, M.-H., Chiou, Y.-S., Chen, W.-J., et al. Pterostilbene inhibited tumor invasion via suppressing multiple signal transduction pathways in human hepatocellular carcinoma cells. Carcinogenesis 30(7), 1234-1242 (2009).
4. Rimando, A.M., Nagmani, R., Feller, D.R., et al. Pterostilbene, a new agonist for the peroxisome proliferator-activated receptor α-isoform, lowers plasma lipoproteins and cholesterol in hypercholesterolemic hamsters. J. Agric. Food Chem. 53(9), 3403-3407 (2005).
5. Austin, M.B., and Noel, J.P. The chalcone synthase superfamily of type III polyketide synthases. Nat. Prod. Rep. 20(1), 79-110 (2003).
String Representations
InChiKey (Click to copy)
VLEUZFDZJKSGMX-ONEGZZNKSA-N
InChi (Click to copy)
InChI=1S/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11,17H,1-2H3/b4-3+
SMILES (Click to copy)
C1=C(OC)C=C(/C=C/C2=CC=C(O)C=C2)C=C1OC
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
19
Rings
2
Aromatic Rings
2
Rotatable Bonds
4
Van der Waals Molecular Volume
246.73
Topological Polar Surface Area
38.69
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
3
logP
3.58
Molar Refractivity
76.58
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Updated at
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