Pavel Karpov

Pavel Karpov, Guillaume Godin, Igor V. Tetko

We present SMILES-embeddings derived from the internal encoder state of a Transformer [1] model trained to canonize SMILES as a Seq2Seq problem. Using a CharNN [2] architecture upon the embeddings results in higher quality interpretable QSAR/QSPR models on diverse benchmark datasets including regression and classification tasks. The proposed Transformer-CNN method uses SMILES augmentation for training and inference, and thus the prognosis is based on an internal consensus. That both the augmentation and transfer learning are based on embeddings allows the method to provide good results for small datasets. We discuss the reasons for such effectiveness and draft future directions for the development of the method. The source code and the embeddings needed to train a QSAR model are available on https://github.com/bigchem/transformer-cnn. The repository also has a standalone program for QSAR prognosis which calculates individual atoms contributions, thus interpreting the model's result. OCHEM [3] environment (https://ochem.eu) hosts the on-line implementation of the method proposed.

Pavel Karpov, Ilya Petrenkov, Ruslan Raiman

Clinical laboratory results are ubiquitous in any diagnosis making. Predicting abnormal values of not prescribed tests based on the results of performed tests looks intriguing, as it would be possible to make early diagnosis available to everyone. The special place is taken by the Common Blood Count (CBC) test, as it is the most widely used clinical procedure. Combining routine biochemical panels with CBC presents a set of test-value pairs that varies from patient to patient, or, in common settings, a table with missing values. Here we formulate a tabular modeling problem as a set translation problem where the source set comprises pairs of GPT-like label column embedding and its corresponding value while the target set consists of the same type embeddings only. The proposed approach can effectively deal with missing values without implicitly estimating them and bridges the world of LLM with the tabular domain. Applying this method to clinical laboratory data, we achieve an improvement up to 8% AUC for joint predictions of high uric acid, glucose, cholesterol, and low ferritin levels.

Igor V. Tetko, Pavel Karpov, Ruud Van Deursen et al.

We investigated the effect of different training scenarios on predicting the (retro)synthesis of chemical compounds using a text-like representation of chemical reactions (SMILES) and Natural Language Processing neural network Transformer architecture. We showed that data augmentation, which is a powerful method used in image processing, eliminated the effect of data memorization by neural networks, and improved their performance for the prediction of new sequences. This effect was observed when augmentation was used simultaneously for input and the target data simultaneously. The top-5 accuracy was 84.8% for the prediction of the largest fragment (thus identifying principal transformation for classical retro-synthesis) for the USPTO-50k test dataset and was achieved by a combination of SMILES augmentation and a beam search algorithm. The same approach provided significantly better results for the prediction of direct reactions from the single-step USPTO-MIT test set. Our model achieved 90.6% top-1 and 96.1% top-5 accuracy for its challenging mixed set and 97% top-5 accuracy for the USPTO-MIT separated set. It also significantly improved results for USPTO-full set single-step retrosynthesis for both top-1 and top-10 accuracies. The appearance frequency of the most abundantly generated SMILES was well correlated with the prediction outcome and can be used as a measure of the quality of reaction prediction.