Hydrogen Bond Acceptor and Donor Factors, Ca and Cd: New QSAR Descriptors

  • James W. McFarland
  • Oleg A. Raevsky
  • Wendell W. Wilkerson


Hydrogen bonding has been widely recognized as an important contributor to the forces binding a drug to its receptor, and also as one of the physical properties associated with lipophilicity and cell permeability. Until lately, H-bonding ability mainly has been described in QSAR problems by the use of indicator variables, e.g. the presence or absence of a H-bond donor (1 or 0). Over the past two decades, Raevsky and coworkers1 have prepared a large database (>12,000 entries) of thermodynamic measurements on H-bonding systems. From these data, the Russian team developed a method to estimate the H-bond acceptor and donor strengths of various chemical moieties. Both the thermodynamic database and the method are available as software called HYBOT (HYdrogen BOnd Thermodynamics).


Skin Penetration Donor Factor Donor Strength Pomona College Cyclic Urea 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


  1. 1.
    O.A Raevsky, V. Grigor’ev, E. Mednikova, QSAR H-bonding descriptions, in: Trends in QSAR and Molecular Modelling 92, C.G Wermuth, ed., ESCOM, Leiden, (1993).Google Scholar
  2. 2.
    R.L Scheuplein, R.L Bronaugh, in: Biochemistry and Physiology of the Skin, L.A. Goldsmith, ed., Oxford University Press, Oxford (1983), p. 1255 ff.Google Scholar
  3. 3.
    W.W. Wilkerson, E. Akamike, W.W. Cheatham, A.Y. Hollis, R.D. Collins, I. DeLucca, P.Y.S Lam, Y. Ru, HIV Protease Inhibitory Bis-benzamide Cyclic Ureas: A Quantitative Structure-Activity Relationship Analysis, J Med. Chem., 39: 4299 (1996).CrossRefGoogle Scholar
  4. 4.
    E.J. Lien, C-QSAR Program, BioByte Corp. 201 West 4th St., Suite 204, Claremont, CA 91711, USA, Dataset name: BIO_1700.Google Scholar
  5. 5.
    H. van de Waterbeemd, G. Camenisch, G. Folkers, O.A. Raevsky, Estimation of Caco-2 Cell Permeability using Calculated Molecular Descriptors. Quant. Struct.-Act. Relat.,15:480 (1996), and references therein.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2000

Authors and Affiliations

  • James W. McFarland
    • 1
  • Oleg A. Raevsky
    • 2
  • Wendell W. Wilkerson
    • 3
  1. 1.reckon.dat consultingOld LymeUSA
  2. 2.The Institute of Physiologically Active Compounds of the Russian Academy of SciencesChernogolovkaRussia
  3. 3.Dextron CorporationBearUSA

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