All SMILES Variational Autoencoder

30 May 2019  ·  Zaccary Alperstein, Artem Cherkasov, Jason Tyler Rolfe ·

Variational autoencoders (VAEs) defined over SMILES string and graph-based representations of molecules promise to improve the optimization of molecular properties, thereby revolutionizing the pharmaceuticals and materials industries. However, these VAEs are hindered by the non-unique nature of SMILES strings and the computational cost of graph convolutions. To efficiently pass messages along all paths through the molecular graph, we encode multiple SMILES strings of a single molecule using a set of stacked recurrent neural networks, pooling hidden representations of each atom between SMILES representations, and use attentional pooling to build a final fixed-length latent representation. By then decoding to a disjoint set of SMILES strings of the molecule, our All SMILES VAE learns an almost bijective mapping between molecules and latent representations near the high-probability-mass subspace of the prior. Our SMILES-derived but molecule-based latent representations significantly surpass the state-of-the-art in a variety of fully- and semi-supervised property regression and molecular property optimization tasks.

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Results from the Paper


 Ranked #1 on Molecular Graph Generation on ZINC (QED Top-3 metric)

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Task Dataset Model Metric Name Metric Value Global Rank Benchmark
Drug Discovery Tox21 SSVAE with multiple SMILES AUC 0.871 # 3
Molecular Graph Generation ZINC All SMILES VAE Validty 98.5 # 9
QED Top-3 0.948, 0.948, 0.948 # 1
PlogP Top-3 29.80, 29.76, 29.11 # 1
function evaluations 250500 # 14
Uniqueness 100 # 1
Novelty 99.96 # 3

Methods