Circling back to the association process, our sorgoleone aggregate was the slowest to penetrate the membrane, when compared with other small molecules along the synthesis pathway (Figure ). While we do not have nearly enough statistics to make definitive conclusions, retarding sorgoleone reentry into the membrane once in root exudates would certainly be useful to minimize autotoxicity, and may require further study. Furthermore, analysis of Figure also demonstrates that sorgoleone, despite having the shortest membrane residence time, switches leaflets most frequently compared with the other precursors. We quantify this movement by counting the number of times the different small molecules switch leaflets during these equilibrium simulations (Table ). Sorgoleone transits between membrane leaflets more than its precursors by almost an order of magnitude, which would be a positive indicator for a high potential flux out of the cell. Chemically speaking, the increased mobility for sorgoleone appears tied to its propensity to hydrogen bond differently than the other compounds in the study. Quantifying hydrogen bonds where our molecules of interest are either a donor or acceptor (Figure ), we find that the number of times that the molecules act as hydrogen bond acceptors is relatively consistent across molecules (Figure ), despite the varied functional groups presence and quantity in the precursors (Figure ). However, sorgoleone is the worst hydrogen bond donor (Figure ), as its only hydroxyl group is adjacent to the hydrophobic tail, relatively inaccessible to other potential hydrogen bond partners. Since phospholipid head groups have more hydrogen bond acceptors than donors, a poor proton donor like sorgoleone will have fewer interactions with the headgroup. With fewer interactions tethering the compound to a single leaflet, interleaflet transfer for sorgoleone is accelerated.