SYNLIB

RECCAS, available from Molecular Design Ltd, Hayward, California. P. A. Zurer (1985). Chem. Eng. News, 63,21 SYNLIB will be available from Distributed Graphics Ltd, J. Haggin (i 983). Chem. Eng. News, 61, 7. 

Borkent, J.H., Oukes, F., and Noordik, J.H. 1988. Chemical reaction searching compared in REACCS, SYNLIB and ORAC. Journal of Chemical Information and Computer Science, 28(3) 148-150. 

In-house chemical information management systems began to emerge at some of the larger chemical and pharmaceutical firms. These included CONTRAST and SOCRATES at Pfizer, SYNLIB at SmithKline, COUSIN at Upjohn, MSDRL/CSIS at Merck, and CROSSBOW at ICI (27). The Chemical Abstracts database was made available online in 1967 (28). In 1980 this became CAS ONLINE. A compre-... 

To make the Macintosh compatible with MACCS, we use the Versaterm Pro software package, which allows the Macintosh to emulate the Tektronix 4105, one of the acceptable terminal types. By this same package, the Macintosh can emulate the Tektronix 4014 and VT-100, which allow the chemists to use other applications programs, such as SYNLIB for chemical reaction literature and of course, all the standard non-graphics applications such as electronic mail. 

The Macintosh can be hooked up to a high quality laserprinter (the Apple LaserWriter) via the AppleTalk network software, or when used as a terminal, it can direct output from systems such as MACCS or SYNLIB to a local laserprinter. (The Figures in this Chapter were done on the Macintosh and printed on the LaserWriter.) Another deciding factor in the choice of the Macintosh was the availability of quality software. 

For chemical reaction literature, chemists use the SYNLIB database from Distributed Chemical Graphics. SYNLIB is a well-documented, user-friendly system, designed for end user browsing. Figure 6 shows sample SYNLIB printed output, two records to the page. For chemical supplier information, the Fine Chemicals Directory from Fraser Williams (Scientific Systems) Ltd. is available through MACCS, as is an internally developed database of chemicals available in our Chemical Stockroom. 

A number of commercial systems that were available at the time were evaluated. Several failed to meet all criteria, due to a lack of U.S. installations and/or U.S.-based system support groups. Those that failed were DARC/Questel, Telesystemes, Paris, France the NIH-EPA Chemical Information System CHEMPIX, developed by Moreaux of Roussel-Uclaf and marketed by Chemical Information Management Inc. and SYNLIB, marketed by Smith Kline Beckman. The Upjohn COUSIN system, developed by Dr J Howe, was not commercially available. Chemical Abstracts Service (CAS) private file support was considered too expensive. Security with the CAS file was also a concern of MSDRL since it could not be brought in-house. 

The major commercially available reaction indexing programs are REACCS (Molecular Design Limited), SYNLIB (started by Clark Still, developed by Smith, Kline and French and now sold by Dan Chodosh), ORAC (developed at the University of Leeds) and DARC-RMS (Telelsystemes). Pfizer s in-house system CONTRAST is noteworthy but is not available outside Pfizer. The release of CASREACT by Chemical Abstracts is awaited with interest. 

Definitions of Reaction Site. There are three ways of looking at this. The graphical reaction site consists of all the bonds which have undergone a change and the atoms attached to those bonds. The chemical reaction site (as used in ORAC) extends the graphical reaction site by the addition of those functional groups which are absolutely essential for the reaction to proceed. The subjective reaction site (as used in SYNLIB) consists of those atoms and bonds the inputter considers significant. 

REACCS can currently offer about 100,000 reactions, SYNLIB 35,000 and ORAC 30,000. The author confidently expects ORAC to offer 110,000 by mid-1988. 

The next step is to find all reactions in the other ORAC databases that correspond to a CASP synthesis proposal or to a CASP transform in general. For this purpose CASP can deliver the reactant and product substructures with corresponding differences and put them into a query file for ORAC to search. The detected cross references can be stored in the CASP transform library for quick retrieval. Doing this manually so far for our ongoing transform work we found that many transforms have no corresponding ORAC (or SYNLIB) reactions. It seems that some classical chemistry is not yet represented therein. 

This technique can be used to search the public literature, to retrieve the "hesV literature precedents for a desired reaction. The search question can be generally formulated as Which possibilities are available to convert starting material P into target material T Systems to answer this question are SYNLIB, ORAC and REACCS. 

Reaction-oriented searching can also be used as an in-house tool to store and retrieve company reactions. The DARC-RMS and MACCS/REACCS systems are typical examples of this usage, although SYNLIB and ORAC could alsobe used for this purpose. 

On the other hand, the data in the base file may be converted into an SMD file (Standardised Molecular Data) which is used by the companies of the CASP pool in Europe for interchanging substance and reaction data. Interfaces to commercially available reaction retrieval systems, using the SMD data structure, exist or are being developed. In this way, in-house versions of the database to be used with REACCS, ORAC, SYNLIB, etc., will be made available. 

SYNLIB, see Software appendix) and a combination of synthesis-planning software with literature reaction retrieval software is a powerful tool for synthetic chemistry. 

Example 10.4 shows the implementations for MULT UNS OP. Information about modules, operators and the implementations available can be obtained by executing the report synlib command. The synthetic operator MULT UNS OP is defined in the standard.sldb synthetic library. MULT UNS OP may be mapped to multiple synthetic modules which may have more than one implementation. The synthetic module DW02 mult has among other bindings, one binding b3 to MULT UNS OP. 

This could be due to the fact that the user does not have a Ucense for SynLib-Seq. This part can however, be evaluated and timing and area reports obtained from it by setting the variable... 

FIZ Chemie = Fachinformation.szentrum Cheniie ISl = institute for Scientific Information IRDAS = ISIS reaction database access system ISIS = integrated scientific information system JSM = Journal of Synthetic Methods MACCS = molecule access system MOS = Metlwd.s in Organic Synthesis, ORAC = Organic Reaction Acce.ss by Computer REACCS = Reaction Access System SMD = standard molecular data SPORE = Solid Phase Organic Reactions, STN = Scientific and Technical Information Network SYNLIB = Synthesis Library. 

SYNLIB is a very special reaction retrieval system, which differs significantly from other systems in terms of the underlying philosophy and functionality. It has a built-in fuzziness, such that usually not the entire (sub)structures entered are matched in the database, but only those parts of the query that the user declared as target (Figure 10). Target centers are usually reaction centers plus some parts of the environment . " ... 

---