31 Steroids Binding to the Corticosteroid Binding Globulin (CBG) Receptor

Introduction

This dataset was first compiled by Cramer et al.1 for the presentation of the CoMFA method. A subset of the data containing the first 21 steroids is distributed with the Sybyl program package.2 Richards et al.3 used the same data for similarity calculations; it is distributed as an example file with the ASP program package.4 Comparison of all these printed or computer-coded versions of the dataset shows several errors in structure coding. Thus, the dataset was carefully recompiled by returning to the original literature.5 The 3D coordinates were calculated by the 3D structure generator CORINA.

This dataset was used in our group to model the corticosteroid binding globulin receptor activity with autocorrelation of molecular surface properties and neural networks.6 The dataset has been extensively studied by different methods in several research groups. A critical appraisal of all this work and fthi dataset is given in 7.

References

  1. Cramer, R.D., III; Patterson, D.E.; Bunce, J.D.,
    J. Am. Chem. Soc., 1988, 110, 5959-5967.
  2. Sybyl, Tripos Associates Inc.: St. Louis, MO, USA.
  3. Good, A.C.; So, S.; Richards, W.G.,
    J. Med. Chem., 1993, 36, 433-438.
  4. Automated Similarity Package, Oxford Molecular Ltd.: Oxford, UK.
  5. (a) Dunn, J.F.; Nisula, B.C.; Rodbard, D.,
    J. Crin. Endocrin. Metab., 1981, 53, 58-68.
    (b) Mickelson, K.E.; Forsthoefel, J.; Westphal, U.,
    Biochemistry, 1981, 20, 6211-6218.
  6. Wagener, M.; Sadowski, J.; Gasteiger, J.,
    J. Am. Chem. Soc., 1995, 117, 7769-7775.
  7. Anzali, S.; Gasteiger, J.; Holzgrabe, U.; Polanski, J.; Sadowski, J.; Teckentrup, A.; Wagener, M.,
    The Use of Self-Organizing Neural Networks in Drug Design.
    in 3D QSAR in Drug Design, Vol. 2,
    Kubinyi, H.; Folkers, G.; Martin, Y. C. (Ed.); Kluwer/ESCOM, Dordrecht, NL, 1998, p. 273-299.

The Structures

aldosterone

androstanediol

5-androstenediol

4-androstenedione

androsterone

corticosterone

cortisol

cortisone

dehydroepiandrosterone

11-deoxycorticosterone

11-deoxycortisol

dihydrotestosterone

estradiol

estriol

estrone

etiocholanolone

pregnenolone

17a-hydroxypregnenolone

progesterone

17a-hydroxyprogesterone

testosterone

prednisolone

cortisolacetat

4-pregnene-3,11,20-trione

epicorticosterone

19-nortestosterone

16a,17a-dihydroxyprogesterone

16a-methylprogesterone

19-norprogesterone

2a-methylcortisol

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2a-methyl-9a-fluoro-cortisol



Download

The complete dataset as 3D MDL SDFile

The biological activity data (CBG binding affinity)

Contact

In case of any problems please contact Christof H. Schwab