Abstract
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).
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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).
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.
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).
E.J. Lien, C-QSAR Program, BioByte Corp. 201 West 4th St., Suite 204, Claremont, CA 91711, USA, Dataset name: BIO_1700.
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.
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McFarland, J.W., Raevsky, O.A., Wilkerson, W.W. (2000). Hydrogen Bond Acceptor and Donor Factors, Ca and Cd: New QSAR Descriptors. In: Gundertofte, K., Jørgensen, F.S. (eds) Molecular Modeling and Prediction of Bioactivity. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4141-7_40
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DOI: https://doi.org/10.1007/978-1-4615-4141-7_40
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