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@ARTICLE{Buczek:1043732,
      author       = {Buczek, Aneta and Rzepiela, Kacper and Broda, Małgorzata
                      A. and Kupka, Teobald and Strodel, Birgit and Fatafta,
                      Hebah},
      title        = {{W}ater modulated influence of intramolecular
                      hydrogen-bonding on the conformational properties of
                      {C}annabidiol ({CBD})},
      journal      = {Journal of molecular liquids},
      volume       = {423},
      issn         = {0167-7322},
      address      = {New York, NY [u.a.]},
      publisher    = {Elsevier},
      reportid     = {FZJ-2025-03014},
      pages        = {127033 -},
      year         = {2025},
      abstract     = {Cannabidiol (CBD), a non-psychoactive phytocannabinoid from
                      Cannabis sativa, has gained significant attention due to its
                      diverse therapeutic properties, including anti-inflammatory,
                      antioxidant, and anxiolytic effects. However, its clinical
                      application is hindered by poor water solubility, which
                      limits its bioavailability. The aim of this study is to
                      deepen our understanding of the conformational properties of
                      CBD, and investigate how these properties affect its
                      solubility. Using Density Functional Theory (DFT)
                      calculations, we analyzed the axial and equatorial positions
                      of substituents on the limonene ring and the arrangement of
                      both hydroxyl groups. Our findings indicate that the most
                      stable conformation of CBD involves diequatorial
                      substitution on the limonene ring, stabilized by specific
                      –OH⋯π hydrogen bonding interactions. All-atom Molecular
                      Dynamics (MD) simulations in an aqueous environment revealed
                      that while single CBD molecules maintain their conformation,
                      multiple CBD molecules tend to cluster. These insights
                      provide a comprehensive understanding of the molecular
                      interactions that underlies CBD’s low aqueous solubility
                      and suggests potential strategies for enhancing its
                      bioavailability, which could optimize its therapeutic
                      potential.},
      cin          = {IBI-7},
      ddc          = {540},
      cid          = {I:(DE-Juel1)IBI-7-20200312},
      pnm          = {5241 - Molecular Information Processing in Cellular Systems
                      (POF4-524)},
      pid          = {G:(DE-HGF)POF4-5241},
      typ          = {PUB:(DE-HGF)16},
      doi          = {10.1016/j.molliq.2025.127033},
      url          = {https://juser.fz-juelich.de/record/1043732},
}