As machine learning is used to make strides in med- ical diagnostics, few methods provide heuristics from which human doctors can learn directly. This work introduces a method for leveraging human observable structures, such as macro scale vascular formations, for producing assessments of medical conditions with rela- tively few training cases, and uncovering patterns that are potential diagnostic aids. The approach draws on shape grammars, a rule-based technique, pioneered in design and architecture, and accelerated through a re- cursive sub-graph mining algorithm. The distribution of rule instances in the data from which they are in- duced is then used as an intermediary representation en- abling common classification and anomaly detection ap- proaches to identify indicative rules with relatively small data sets. The method is applied to 7 Tesla time-of- flight (TOF) angiography MRI (n = 54) of human brain vasculature. The data were segmented and induced to generate representative grammar rules. Ensembles of rules were isolated to implicate vascular conditions reli- ably. This application demonstrates the power of auto- mated structured intermediary representations for as- sessing nuanced biological form relationships, and the strength of shape grammars, in particular for identify- ing indicative patterns in complex vascular networks.