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This article proposes a novel methodology to detect malicious uniform resource locators (URLs) using simulated expert (SE) and knowledge-base system (KBS). The proposed study not only efficiently detects known malicious URLs but also adapts countermeasure against the newly generated malicious URLs. Moreover, this article also explored which lexical features are contributing more in final decision using a factor analysis method, and thus help in avoiding the involvement of human experts. Furthermore, we apply the following state-of-the-art machine learning (ML) algorithms, i.e., naïve Bayes (NB), decision tree (DT), gradient boosted trees (GBT), generalized linear model (GLM), logistic regression (LR), deep learning (DL), and random rest (RF), and evaluate the performance of these algorithms on a large-scale real data set of data-driven Web applications. The experimental results clearly demonstrate the …