File size: 2,689 Bytes
551b635
5728221
 
50a049b
 
 
 
 
5728221
50a049b
5728221
50a049b
 
5728221
0987158
 
50a049b
 
 
 
0987158
50a049b
f81de2d
 
50a049b
f81de2d
 
50a049b
f81de2d
 
 
 
0987158
50a049b
 
 
 
 
 
 
 
551b635
5728221
 
 
b740481
5728221
 
 
b740481
5728221
 
 
972b98a
5728221
b740481
5728221
 
b740481
5728221
 
 
 
 
 
 
 
 
5534637
5728221
 
 
 
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
72
73
74
---
license: cc-by-4.0
tags:
- chemistry
- molecules
- reactions
- smiles
- cheminformatics
size_categories:
- 1M<n<10M
task_categories:
- text-generation
- fill-mask
pretty_name: Reaction SMILES Dataset
dataset_info:
  features:
  - name: smiles
    dtype: string
  - name: source_id
    dtype: int64
  splits:
  - name: train
    num_bytes: 747528582
    num_examples: 2752563
  - name: validation
    num_bytes: 93440971
    num_examples: 344070
  - name: test
    num_bytes: 93441242
    num_examples: 344071
  download_size: 406610470
  dataset_size: 934410795
configs:
- config_name: default
  data_files:
  - split: train
    path: data/train-*
  - split: validation
    path: data/validation-*
  - split: test
    path: data/test-*
---

# Reaction SMILES Dataset

A collated dataset of 3.4M unique chemical reaction SMILES strings compiled from multiple public sources for use in pre-training and fine-tuning chemical language models.

Reaction SMILES (Simplified Molecular Input Line Entry System) extend the standard SMILES notation to represent complete chemical reactions. They encode reactants, reagents/catalysts, and products in a single text string using the `>` delimiter:

```text
reactants>reagents>products
```

For example: `CC(=O)O.CCO>[H+]>CC(=O)OCC.O` represents the esterification of acetic acid with ethanol to form ethyl acetate.

## Dataset Features

- **smiles**: The reaction SMILES string
- **source_id**: Original data source identifier

## Data Sources

| Source ID | Source URL                                                                                                                             |
| --------- | -------------------------------------------------------------------------------------------------------------------------------------- |
| 1         | [US Patents 1976-Sep2016 Grants](https://figshare.com/articles/dataset/Chemical_reactions_from_US_patents_1976-Sep2016_/5104873)       |
| 2         | [US Patents 2001-Sep2016 Applications](https://figshare.com/articles/dataset/Chemical_reactions_from_US_patents_1976-Sep2016_/5104873) |
| 3         | [CRD 1.37M Dataset (2024)](https://figshare.com/articles/dataset/Reaction_SMILES_b_CRD_b_1_37M_dataset/28230053/1)                     |
| 4         | [USPTO Year 2023](https://figshare.com/articles/dataset/Reaction_SMILES_USPTO_year_2023/24921555)                                      |
| 5         | [Reaction SMILES Dataset (2023)](https://figshare.com/articles/dataset/Reaction_SMILES_dataset/22491730)                               |

## License

This dataset aggregates publicly available reaction data. Please refer to the individual source links for specific licensing terms.