A system includes a computing platform having a hardware processor, and a system memory storing a software code and a content labeling predictive model. The hardware processor is configured to execute the software code to scan a database to identify content assets stored in the database, parse metadata stored in the database to identify labels associated with the content assets, and generate a graph by creating multiple first links linking each of the content assets to its corresponding label or labels. The hardware processor is configured to further execute the software code to train, using the graph, the content labeling predictive model, to identify, using the trained content labeling predictive model, multiple second links among the content assets and the labels, and to annotate the content assets based on the second links.