The invention provides for the evaluation of semantic closeness of a source data file relative to candidate data files. The system includes an artificial neural network and processing intelligence that derives a property vector from extractable measurable properties of a data file. The property vector is mapped to related semantic properties for that same data file and such that, during ANN training, pairwise similarity/dissimilarity in property is mapped, during towards corresponding pairwise semantic similarity/dissimilarity in semantic space to preserve semantic relationships. Based on comparisons between generated property vectors in continuous multi-dimensional property space, the system and method assess, rank, and then recommend and/or filter semantically close or semantically disparate candidate files from a query from a user that includes the data file. Applications of the categorization and recommendation system apply to search tools, including identification of illicit materials or logically progressive associations between disparate files.