Friday, June 14, 2019

Comparison of SMILES-, DeepSMILES-, SELFIES-, and graph-based genetic algorithms Part 2

This post is a follow up to this post. There are two changes:

In that post I generated the data for the string based methods using my graph-based GA (GB-GA) code interfaced with new, string-based, crossover and mutation code. However, this involves going back and forth between graph and string-based representations which could potentially change the atom order. To make sure that doesn't happen I have now written a stand alone string-based GA code, where strings only are converted to graphs when computing the score and graphs are never converted back to strings.

I also had a another look at Brown et al.'s GA code and noticed that they remove duplicates from the population for each generation, which my code didn't. So implemented that as well for both the graph- and string-based methods. In the table below I list the best results, where the original implementation that does not remove duplicates are indicated by a "*".

For GB the removal of duplicates only improves results for celecoxib, where it is now rediscovered 8 times instead of 4. Tiotixene is not rediscovered and troglitazone is only found once with GB-GA, when duplicates are removed.

The new string-based implementation improves results for SMILES and DeepSMILES, with the exception of SMILES for troglitazone, which is discovered once using the old implementation. For SELFIES the new implementation is a little bit worse, but I would say the difference is within the statistical uncertainty. 

GB still tends to outperform string based methods, though they all perform much better than I had expected. Amazingly, DeepSMILES and SELFIES do not appear to offer a clear advantage over SMILES with the exception of troglitazone, where DeepSMILES performs significantly better.

Here are the high scoring molecules found with string based methods. Some of the molecules have radical centers (red boxes) due to misplaced chiral centers.


This work is licensed under a Creative Commons Attribution 4.0

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