SECS—simulation and evaluation of chemical

SECS—Simulation and Evaluation of Chemical Synthesis Strategy and Planning 

CHOPLIN, and W. SIEBER Board of Studies in Chemistry, University of California, Santa Cruz, Calif. 95064 

Our goal, given target T, is to generate good syntheses by working backward from the target toward simpler compounds (problem type III). This paper is concerned mainly with this 

ACS Symposium Series American Chemical Society Washington, DC, 1977. 

Our goal state, the target molecule, is a specific organization of atomic nuclei and electrons. The target molecule is connected by chemical transformations to many other states which we call precursors. Some of the precursors are more complicated than the target (i.e., more difficult to synthesize than the target) and others are simpler than the target (see Fig. 1). 

---

Plan Representation in SECS. The SECS Simulation and Evaluation of Chemical Synthesis program explicitly represents its plans(2) as a list structure of goal instructions with logical connectives. A goal instruction can specify one of the following ... 

Wipke, W. T. Braun, H. Smith, G. Choplin, F. Sieber, W. "SECS — Simulation and Evaluation of Chemical Synthesis Strategy and Planning American Chemical Society Vol. 61,... 

Wipke, W. T., Brown, H., Smith, G., Choplin, F., Seber, W. SECS-Simulation and evaluation of chemical synthesis strategy and planning , ACS 61, 1977... 

Corey EJ, Wipke WT, Cramer RD, Howe WJ (1972) Computer-assisted synthetic analysis. Facile man-machine communication of chemical structure by interactive computer graphics, J Am Chem Soc 94/2 421 Wipke WT, Braun H, Smith G, Choplin F, SieberW (1977) SECS — Simulation and evaluation of chemical synthesis Strategy and planning, in Computer-assisted organic synthesis, Wipke WT, Howe WJ ed, ACS Symposium Series, p 98... 

W. T. Wipke, H. Braun, G. Smith, F. Choplin, and W. Sieber. in SECS - Simulation and Evaluation of Chemical Synthesis in Computer Assisted Organic Synthesis, eds. W. T, Wipke... 

The evolution of molecular graphics (7) is described in an earlier ACS Symposium Series book (77) which acts as an interesting precursor to this present volume. Chemical reaction systems such as LHASA (Logic and Heuristics Applied to Synthetic Analysis) 18) and SECS (Simulation and Evaluation of Chemical Synthesis) (79) had long used graphics but it was some time before the first in-house, proprietary system appeared, attracting much interest in the chemical and pharmaceutical industries. This was Upjohn s Compound Information System, COUSIN 20-21). 

Simulation and Evaluation of Chemical Synthesis (SECS) was developed by Wipke and uses heuristic methods similar to LHASA but puts special emphasis on stereochemistry, topology, and energy minimization [112]. 

Wipke, W.T., Ouchi, G.I., and Krishnan, S., Simulation and Evaluation of Chemical Synthesis — SECS — Application of Artificial Intelligence Techniques, Artif. IntelL, 11, 173, 1978. 

For a synthesizer, we are reimplementing the Simulation and Evaluation of Chemical Synthesis (SECS) program on our IBM computer in collaboration with Professor Wipke, Once the program is running at Merck, we will instruct the chemists in program operation, and then ask them to code and test transforms. 

The Standard Molecular Data (SMD) format is designed to provide such an integration tool on the basis of a file format. It has been developed in the course of the CASP project (Computer Assisted Synthesis Planning) which is run by a consortium of seven German and Swiss Chemical Companies (BASF, Bayer, Ciba-Geigy, Hoechst, E Merck, Hoffmann La Roche and Sandoz). The basis of this development was the Molfile format of the earlier SECS program (4) (Simulation and Evaluation of Chemical Synthesis). 

---