Structure Database (LMSD)

Common Name
Dihydroresveratrol
Systematic Name
Synonyms
LM ID
LMPK13090035
Formula
Exact Mass
Calculate m/z
230.094295
Status
Curated



Classification

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

KEGG ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID

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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Updated at
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