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Ashlar Vellum is a CAD package for mechanical engineers and designers, that includes the ability to intelligently predict where the user wants to connect the next object. There were both "2D" and "3D" versions.
The Official Guide to Netscape Navigator, from Personal Training Systems, is an interactive training tool for teaching new users the ins and outs of using Netscape Navigator to access information on the Internet.
VideoWorks is a Macintosh animation program that eventually became Macromedia/Adobe Director.