Structure Database (LMSD)
Common Name
Dihydroresveratrol
Systematic Name
Synonyms
3D model of Dihydroresveratrol
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
Dihydroresveratrol is a polyketide synthase-derived bibenzyl that has been found in C. sativa and has diverse biological activities.1,2,3,4 It is also an active metabolite of resveratrol that is formed by gut microbiota.5 Dihydroresveratrol inhibits DNA polymerase α but not DNA polymerase δ (Kis =29.3 and >100 µM, respectively) and the formation of thiobarbituric acid reactive substances (TBARS) in rat liver microsomes (EC50 = 1.57 µM).2 It stimulates the proliferation of hormone-sensitive MCF-7 breast cancer cells but not hormone-resistant MDA-MB-231 and BT474 breast cancer cells when used at concentrations ranging from 0.01 pM to 100 nM.3 Dihydroresveratrol decreases interalveolar septal thickness and alveolar hemorrhage in a rat model of lung injury induced by cerulein- and LPS-stimulated pancreatitis when administered at a dose of 50 mg/kg.4
This information has been provided by Cayman Chemical
References
1. Stivala, L.A., Savio, M., Carafoli, F., et al. Specific structural determinants are responsible for the antioxidant activity and the cell cycle effects of resveratrol. The Journal of Biological Chemisty 276(25), 22586-22594 (2001).
3. Boddington, K.F., Soubeyrand, E., Van Gelder, K., et al. Bibenzyl synthesis in Cannabis sativa L. Plant J. 109(3), 693-707 (2022).
String Representations
InChiKey (Click to copy)
HITJFUSPLYBJPE-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C14H14O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h3-9,15-17H,1-2H2
SMILES (Click to copy)
C1=C(O)C=C(CCC2=CC=C(O)C=C2)C=C1O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
17
Rings
2
Aromatic Rings
2
Rotatable Bonds
3
Van der Waals Molecular Volume
214.77
Topological Polar Surface Area
60.69
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
3
logP
2.59
Molar Refractivity
65.29
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