Rule‐based mass spectrum prediction and ranking: Applications to structure elucidation of novel marine sterols

A novel, computer aided approach to the interpretation of mass spectra is documented by its application to a series of recently isolated marine sterols. The method consists of construction of biosynthetically plausible candidate structures, prediction of their major mass spectral fragmentation paths using class-specific rules derived from a training set of known compounds, and a system of ranking candidate structures based on a comparison of the predicted and observed spectra.

[1]  B. Buchanan,et al.  Computerized mass spectrum prediction and ranking , 1980 .

[2]  C. Djerassi,et al.  Isolation of two new c30 sterols, ( 24e )-24-n-propylidenecholesterol and 24ξ-n-propylcholesterol, from a cultured marine chrysophyte , 1980, Steroids.

[3]  C. Djerassi,et al.  Mass spectrometry in structural and stereochemical problems. 252. Structural and stereochemical applications of mass spectrometry in the marine sterol field. Synthesis and electron impact induced mass spectral fragmentation of .DELTA.24- and .DELTA.24(28)-3.beta.-hydroxy-.DELTA.5-sterols , 1979 .

[4]  C. Djerassi,et al.  Minor and Trace Sterols in Marine Invertebrates. XII. Occurrence of 24 (R + S)‐isopropenylcholesterol, 24 (R + S)‐methylcholesta‐5, 25‐dien‐3β‐ol, and 24 (R + S)‐methylcholesta‐7, 25‐dien‐3β‐ol in the caribbean sponge, Verongia cauliformis , 1979 .

[5]  C. Djerassi,et al.  Minor and trace sterols in marine invertebrates. 8. Isolation, structure elucidation, and partial synthesis of two novel sterols - stelliferasterol and isostelliferasterol , 1978 .

[6]  C. Djerassi,et al.  Minor and trace sterols in marine invertebrates. 24-Ethyl-.DELTA.5,24(28),28-cholestatrien-3.beta.-ol - a naturally occurring allenic marine sterol , 1978 .

[7]  Tomas H. Varkony,et al.  Computer-Assisted Simulation of Chemical Reaction Sequences. Applications to Problems of Structure Elucidation , 1978, J. Chem. Inf. Comput. Sci..

[8]  Dennis H. Smith,et al.  Computer-assisted structure manipulation : Studies in the biosynthesis of natural products , 1978 .

[9]  Carl Djerassi,et al.  Recent advances in the mass spectrometry of steroids , 1978 .

[10]  S. Wyllie,et al.  Electron impact induced fragmentation of cholesterol and related C-5 unsaturated steroids. , 1977, The Journal of organic chemistry.

[11]  E. Feigenbaum,et al.  Applications of artificial intelligence for chemical inference. 22. Automatic rule formation in mass spectrometry by means of the meta-DENDRAL program , 1976 .

[12]  Gail M. Pesyna,et al.  2 – Computerized Structure Retrieval and Interpretation of Mass Spectra , 1976 .

[13]  Dennis H. Smith,et al.  Applications of artificial intelligence for chemical inference. XVII. Approach to computer-assisted elucidation of molecular structure , 1975 .

[14]  L. Mayol,et al.  Calysterol: A C29 cyclopropene-containing marine sterol from the sponge Calyx nicaensis , 1975 .

[15]  N. Gray,et al.  Programs for spectrum classification and screening of gas chromotographic-mass spectrometric data on a laboratory computer , 1975 .

[16]  Allan B. Delfino,et al.  Heuristic programming as an ion generator in mass spectrometry. II—Generation of primary ions from simple cyclic structures† , 1974 .

[17]  Jerry Ray Dias,et al.  Mass spectrometry in structural and stereo‐chemical problems—CCXXIV: Fragmentation of cyclopropanes , 1973 .

[18]  E. Feigenbaum,et al.  Applications of artificial intelligence for chemical inference—X , 1973 .

[19]  Dennis H. Smith.  Compound classifier based on computer analysis of low-resolution mass spectral data. Geochemical and environmental applications , 1972 .

[20]  J. D. Morrison,et al.  Computer methods in analytical mass spectrometry. Development of programs for analysis of low-resolution mass spectra , 1971 .

[21]  C. Djerassi,et al.  Mass spectrometry in structural and stereochemical problems. CXLVI. Mass spectrometric fragmentations typical of sterols wit unsaturated side chains , 1968 .