Merck chemical structure information

Brown and others [12] describe the Merck, Sharp, and Dohme chemical structure information system which utilizes this approach. 

Brown, H. D., Marianne Costlow, Frank A. Cutler, Albert N. DeMott, Walter B. Gall, David P. Jacobus, and Charles J. Miller, "The Computer-Based Chemical Structure Information System of Merck, Sharp and Dohme Research Laboratories," Journal of Chemical Information and Computer Sciences, 16(1), 5-10 (1976). 

The system, still operating to this date, is based on the approach used at the Walter Reed Army Institute of Research in Washington, D.C. The system was extensively enhanced to meet the specific needs of the Merck Sharp and Dohme Research Laboratories (MSDRL) and the Chemical Data Department (CDD) which is responsible for processing chemical structure information at Merck and Co., Inc. 

Brown, H.D. Costlow, M. Cutler, F.A. Jr. DeMott, A.N. Gall, W.B. Jacobus, D.P. Miller, C.J. The Computer-Based Chemical Structure Information System of Merck Sharp and Dohme Research Laboratories . J. Chem. Inf. Comput. Sci. 1976,16, 5-10. 

Quality control is performed at the moment of data entry, in particular, with respect to errors present in publications. Chemical structures are checked for structural consistency by matching the molecular weight (MW) and chemical formula with the ones available in the experimental section and/or supporting information - whenever available, and by comparison to prior publications. Whenever in doubt, we also use other sources, such as the Merck Index [20] and free Internet resources. In the instances... 

A second, more sophisticated clustering technique for alphanumeric information proceeds as follows The data base can be imagined as a collection ot items which are described by a set ot properties. Again, our properties in the Merck Index data base are chemical structures as names, and medical use. Each item in the data base is assigned a vector whose column elements indicate whether the item has a given set ot properties or whether it does not. For example, a 1 indicates the presence ot the property and a zero indicates the absence ot the property (Table III). 

Textual names have the advantage of being machine-readable, but many chemical compound names are derived in the absence of structural information. Common or trivial names were frequently given to compounds based on their properties or methods of extraction (because their structural information was originally an unknown). For example, mandelic acid was extracted from bitter almonds, and its name is derived from Mandel, the German word for almond (Merck 1989). 

The information for each chemical entry is given as it is relevant to polymeric materials. Individual chemical species (e.g., ethanol) were taken from the CRC Handbook of Chemistry and Physics (2004), the Merck Index and other reference materials. The reader may refer to these references for additional physical properties and written chemical formulae. Extensive use was made of ChemDraw , CambridgeSoft Corporation for naming and drawing chemical structures (conversion of structure to name and vice versa), which are included with each chemical entry where possible. Special attention was given to the lUPAC name that is often given with the common name for the convenience of the reader. 

The examples from SciFinder and the Merck Index are not intended to question the quality of these products, which we consider to be outstanding. They are invaluable resources to many chemists worldwide, and the error rate in these two databases is insignificant if one takes into account the enormous volume of indexed data. One of us has published a structure-activity paper on HIV-protease inhibitors [31] where a modified peptide was present in both the training set and the test set. Al Leo of Pomona College has recently [32] detected 100 chemical and name errors in the printed version of the sixth edition of Burger s Medicinal Chemistry [33], errors that will be corrected in the on-line edition [34]. One can never be too careful in verifying the available information, in particular if one is to invest a significant amount of resources in that area. 

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