Biochemical Systematics and Ecology 31 (2003) 25–43 www.elsevier.com/locate/biochemsyseco A program for terpenoid skeleton prediction based on botanical information M.J.P. Ferreira a , S.A.V. Alvarenga b , P.A.T. Macari c , G.V. Rodrigues d , V.P. Emerenciano a,* a Instituto de Quı ´mica, Universidade de Sa ˜o Paulo, Caixa Postal 26077, 0551-3-970 Sa ˜o Paulo, SP, Brazil b Faculdade de Engenharia de Guaratingueta ´, Universidade Estadual Paulista, 12516-410 Guaratingueta ´, SP, Brazil c Faculdade de Cie ˆncias Exatas e Experimentais, Universidade Mackenzie, 01239-902 Sa ˜o Paulo, SP, Brazil d Departamento de Quı ´mica, ICEx, Universidade Federal de Minas Gerais, 30161-000 Belo Horizonte, MG, Brazil Received 23 May 2001; accepted 13 February 2002 Abstract This paper describes a new program developed to the SISTEMAT expert system, the SISOC- BOT program. This program employs the botanical data analysis and predicts, at the end of analysis, the probable skeleton of a compound based on the input of family or genus names. The SISOCBOT program was tested with 78 samples involving 302 substances, pertaining to 38 carbon skeletons, and showed a high hit index on skeleton prediction, thus emphasizing the potential importance of these data for structural determination of natural products.  2002 Elsevier Science Ltd. All rights reserved. Keywords: Terpenoids; Natural products; Botanical information; Skeleton prediction; Expert system 1. Introduction Structural elucidation in general is seen as a process consisting of various stages. It involves collections and interpretation of the results from chemical and spectroscopy * Corresponding author. Fax: +55-11-3-815-5579. E-mail address: vdpemere@quim.iq.usp.br (V.P. Emerenciano). 0305-1978/02/$ - see front matter  2002 Elsevier Science Ltd. All rights reserved. PII:S0305-1978(02)00066-2