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SMILES Transformer: Pre-trained Molecular Fingerprint for Low Data Drug Discovery

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arxiv 1911.04738 v1 pith:2I6QUHYT submitted 2019-11-12 cs.LG stat.ML

classification cs.LGstat.ML
keywords molecularsmilestransformeralgorithmsfingerprintslanguagemoleculesdata
verification ladder T0 review T1 audit T2 compute T3 formal
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In drug-discovery-related tasks such as virtual screening, machine learning is emerging as a promising way to predict molecular properties. Conventionally, molecular fingerprints (numerical representations of molecules) are calculated through rule-based algorithms that map molecules to a sparse discrete space. However, these algorithms perform poorly for shallow prediction models or small datasets. To address this issue, we present SMILES Transformer. Inspired by Transformer and pre-trained language models from natural language processing, SMILES Transformer learns molecular fingerprints through unsupervised pre-training of the sequence-to-sequence language model using a huge corpus of SMILES, a text representation system for molecules. We performed benchmarks on 10 datasets against existing fingerprints and graph-based methods and demonstrated the superiority of the proposed algorithms in small-data settings where pre-training facilitated good generalization. Moreover, we define a novel metric to concurrently measure model accuracy and data efficiency.

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Cited by 6 Pith papers

Reviewed papers in the Pith corpus that reference this work. Sorted by Pith novelty score. Full citation record

  1. TopoFormer: Topology Meets Attention for Graph Learning

    cs.LG 2026-07 conditional novelty 6.0 of 10

    Sliding-window interlevel Betti sequences (Topo-Scan) plus Transformers match or beat strong GNN and TDA baselines on graph classification and molecular property tasks while avoiding full persistence diagrams.

  2. MS-GPT: Rethinking MS/MS De Novo Structure Elucidation as Spectrum-Induced Posterior Querying of a Molecule-Language Model

    cs.LG 2026-07 accept novelty 6.0 of 10

    Querying a fingerprint-conditioned molecule-language model with a calibrated band of spectrum-induced posteriors beats point-threshold fingerprint decoding on NPLIB1 and MassSpecGym.

  3. Hypothesis-and-Refinement Learning of Organic Structures from Multimodal Spectroscopic Data

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    A two-stage AI pipeline — spectral hypothesis generation followed by mass-constrained molecular refinement — reconstructs organic structures from multimodal spectra, with 93.8% top-1 accuracy on simulated QM9 data and...

  4. SIGMA: Semantic Identifier Grouping for Molecular Autoregression

    cs.LG 2026-03 reject novelty 6.0 of 10

    A same-suffix contrastive objective makes autoregressive molecular-string models more invariant to how a molecule is written, improving generation fidelity on the reported ZINC benchmark.

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    SmilesT5 shows that pretraining a T5 model to reconstruct Murcko scaffolds and predict molecular fragments beats masked-language pretraining on six molecular property classification benchmarks.

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