To better understand of the role of ortho substituents in the chiroptical sensing of g-stereogenic alcohols, we next focused on the selection, synthesis, and evaluation of aldehydes 10l -10p (Figure ). Boronic acid precursors 13l -13p were selected using the ML-based selection workflow described in Figure (13l -13p depicted with orange diamonds, Figure ). It should be noted that this selection protocol focused on a narrower region of chemical space (ortho-functionalized compounds only) and that this is reflected by the close grouping of 13l and 13n -13p on the UMAP plot. The resultant assemblies 12l -12p were then evaluated via CD spectroscopy. As was anticipated from the MLR model shown above, ortho-functionalized assemblies 12j -12p tended to give comparatively higher CD intensities than 12a -12i (Figure ). Nevertheless, the varied substituents in the aldehyde structures provided meaningful trends difficult to ascertain by simple inspection. Once more, we turned to statistical modeling to assess assemblies 12a -12p (Figure ). The best model obtained was able to adequately account for both assemblies 12a and 12b suggesting common NCIs intrinsic to the biaryl motif are similarly important whether alcohol 11a or 11b are used. The model featured a good correlation (R 2 = 0.91) and robust internal validation measures (Q 2 = 0.85 and 4-fold = 0.84). Furthermore, an external validation was prepared by initially partitioning the data into training and test set (80/20 split, see SI for details) and then evaluating the ability of the model to predict the test set data points. It was found that the model reliably predicted the CD signals of the test set (test R 2 = 0.91).