ncsw-data-source 2025.9.2

The computer-assisted chemical synthesis data source research project.

Data Source

Welcome to the computer-assisted chemical synthesis data source research project !!!

Over the past decade, computer-assisted chemical synthesis has re-emerged as a prominent research subject. Even though the idea of utilizing computers to assist chemical synthesis has existed for nearly as long as computers themselves, the inherent complexity repeatedly exceeded the available resources. However, recent machine learning approaches have exhibited the potential to break this tendency. The performance of such approaches is dependent on data that frequently suffer from limited quantity, quality, visibility, and accessibility, posing significant challenges to potential scientific breakthroughs. Consequently, the primary objective of the Data Source research project is to systematically curate and facilitate access to relevant open computer-assisted chemical synthesis data sources.

Utilization Instructions

The utilization instructions of this repository are structured as follows:

• Installation of the Package
• Utilization of the Package
• Utilization of the Scripts

Installation of the Package

The data_source package can be installed in an existing environment using the pip command as follows:

pip install ncsw-data-source

A local environment can be created using the git and conda commands as follows:

git clone https://github.com/neo-chem-synth-wave/data-source.git

cd data-source

conda env create -f environment.yaml

conda activate data-source-env

pip install .

Utilization of the Package

The data_source package supports three alternatives for the downloading, extraction, and formatting of a specific version of computer-assisted chemical synthesis data from a specific source. The first alternative is by importing and utilizing the individual data source utility classes:

from data_source.compound.zinc.utility import (
    ZINCCompoundDatabaseDownloadUtility,
    ZINCCompoundDatabaseExtractionUtility,
    ZINCCompoundDatabaseFormattingUtility
)

ZINCCompoundDatabaseDownloadUtility.download_v_building_block(
    version="v_building_block_bb_30",
    output_directory_path="/path/to/the/directory_a"
)

ZINCCompoundDatabaseExtractionUtility.extract_v_building_block(
    version="v_building_block_bb_30",
    input_directory_path="/path/to/the/directory_a",
    output_directory_path="/path/to/the/directory_b"
)

ZINCCompoundDatabaseFormattingUtility.format_v_building_block(
    version="v_building_block_bb_30",
    input_directory_path="/path/to/the/directory_b",
    output_directory_path="/path/to/the/directory_c"
)

The second alternative is by importing and utilizing the individual data source classes:

from data_source.compound.zinc import ZINCCompoundDatabase

zinc_compound_db = ZINCCompoundDatabase()

zinc_compound_db.get_supported_versions()

zinc_compound_db.download(
    version="v_building_block_bb_30",
    output_directory_path="/path/to/the/directory_a"
)

zinc_compound_db.extract(
    version="v_building_block_bb_30",
    input_directory_path="/path/to/the/directory_a",
    output_directory_path="/path/to/the/directory_b"
)

zinc_compound_db.format(
    version="v_building_block_bb_30",
    input_directory_path="/path/to/the/directory_b",
    output_directory_path="/path/to/the/directory_c"
)

The third alternative is by importing and utilizing the data source category classes:

from data_source.compound import CompoundDataSource

compound_data_source = CompoundDataSource()

compound_data_source.get_names_of_supported_data_sources()

compound_data_source.get_supported_versions(
    name="zinc"
)

compound_data_source.download(
    name="zinc",
    version="v_building_block_bb_30",
    output_directory_path="/path/to/the/directory_a"
)

compound_data_source.extract(
    name="zinc",
    version="v_building_block_bb_30",
    input_directory_path="/path/to/the/directory_a",
    output_directory_path="/path/to/the/directory_b"
)

compound_data_source.format(
    name="zinc",
    version="v_building_block_bb_30",
    input_directory_path="/path/to/the/directory_b",
    output_directory_path="/path/to/the/directory_c"
)

Utilization of the Scripts

The purpose of the scripts directory is to illustrate how to utilize the data_source package to download, extract, and format a specific version of computer-assisted chemical synthesis data from a specific source. The download_extract_and_format_data script can be utilized as follows:

# Get the chemical reaction data source name information.
python scripts/download_extract_and_format_data.py \
  --data_source_category "reaction" \
  --get_data_source_name_information

# Get the USPTO chemical reaction dataset version information.
python scripts/download_extract_and_format_data.py \
  --data_source_category "reaction" \
  --data_source_name "uspto" \
  --get_data_source_version_information

# Download, extract, and format the data from the USPTO chemical reaction dataset.
python scripts/download_extract_and_format_data.py \
  --data_source_category "reaction" \
  --data_source_name "uspto" \
  --data_source_version "v_50k_by_20171116_coley_c_w_et_al" \
  --output_directory_path "/path/to/the/output/directory"

The full list of script arguments is as follows:

• --data_source_category or -dsc → The category of the data source. (i.e., compound, compound_pattern, reaction, or reaction_pattern)
• --get_data_source_name_information or -gdsni → The indicator of whether to get the data source name information.
• --data_source_name or -dsn → The name of the data source. (i.e., chembl, crd, miscellaneous, ord, rdkit, retro_rules, rhea, uspto, or zinc)
• --get_data_source_version_information or -gdsvi → The indicator of whether to get the data source version information.
• --data_source_version or -dsv → The version of the data source.
• --output_directory_path or -odp → The path to the output directory where the data should be downloaded, extracted, and formatted.
• --number_of_processes or -nop → The number of processes, if relevant.

Supported Data Sources

The following data sources are supported:

• Chemical Compounds
• Chemical Compound Patterns
• Chemical Reactions
• Chemical Reaction Patterns

Chemical Compounds

The following chemical compound data sources are supported:

• ZINC
• ChEMBL
• COCONUT
• Miscellaneous Chemical Compound Data Sources

The chemical compound data source relationships can be illustrated as follows:

ZINC

The following ZINC ^{[1, 2, 3]} chemical compound database versions are supported:

Version	DOI	Status
v_building_block_{building_block_subset_name} [2]	10.1021/acs.jcim.0c00675	:green_circle:
v_catalog_{catalog_subset_name} [2]	10.1021/acs.jcim.0c00675	:green_circle:

_{:green_circle: Completely Implemented}

ChEMBL

The following ChEMBL ^[4] chemical compound database versions are supported:

Version	DOI	Status
v_release_{release_number ≥ 25} [4]	10.6019/CHEMBL.database.{release_number}	:green_circle:

_{:green_circle: Completely Implemented}

COCONUT

The following COCONUT ^{[5, 6]} chemical compound database versions are supported:

Version	DOI	Status
v_2_0_by_20241126_chandrasekhar_v_et_al [6]	10.5281/zenodo.13382750	:green_circle:
v_2_0_complete_by_20241126_chandrasekhar_v_et_al [6]	10.5281/zenodo.13382750	:green_circle:

_{:green_circle: Completely Implemented}

Miscellaneous Chemical Compound Data Sources

The following miscellaneous chemical compound data sources are supported:

Version	DOI	Status
v_moses_by_20201218_polykovskiy_d_et_al [7]	10.3389/fphar.2020.565644	:green_circle:

_{:green_circle: Completely Implemented}

Chemical Compound Patterns

The following chemical compound pattern data sources are supported:

• RDKit

The chemical compound pattern data source relationships can be illustrated as follows:

RDKit

The following RDKit ^[8] chemical compound pattern dataset versions are supported:

Version	DOI	Status
v_htl_by_20080307_brenk_r_et_al [9]	10.1002/cmdc.200700139	:green_circle:
v_pains_by_20100204_baell_j_b_and_holloway_g_a [10]	10.1021/jm901137j	:green_circle:

_{:green_circle: Completely Implemented}

Chemical Reactions

The following chemical reaction data sources are supported:

• United States Patent and Trademark Office (USPTO)
• Open Reaction Database (ORD)
• Chemical Reaction Database (CRD)
• Rhea
• Miscellaneous Chemical Reaction Data Sources

The chemical reaction data source relationships can be illustrated as follows:

United States Patent and Trademark Office (USPTO)

The following United States Patent and Trademark Office (USPTO) ^[11] chemical reaction dataset versions are supported:

Version	DOI	Status
v_1976_to_2013_rsmi_by_20121009_lowe_d_m [11]	10.6084/m9.figshare.12084729.v1	:green_circle:
v_50k_by_20141226_schneider_n_et_al [12]	10.1021/ci5006614	:green_circle:
v_50k_by_20161122_schneider_n_et_al [13]	10.1021/acs.jcim.6b00564	:green_circle:
v_15k_by_20170418_coley_c_w_et_al [14]	10.1021/acscentsci.7b00064	:green_circle:
v_1976_to_2016_cml_by_20121009_lowe_d_m [11]	10.6084/m9.figshare.5104873.v1	:yellow_circle:
v_1976_to_2016_rsmi_by_20121009_lowe_d_m [11]	10.6084/m9.figshare.5104873.v1	:green_circle:
v_50k_by_20170905_liu_b_et_al [15]	10.1021/acscentsci.7b00303	:green_circle:
v_50k_by_20171116_coley_c_w_et_al [16]	10.1021/acscentsci.7b00355	:green_circle:
v_480k_or_mit_by_20171204_jin_w_et_al [17]	10.48550/arXiv.1709.04555	:green_circle:
v_480k_or_mit_by_20180622_schwaller_p_et_al [18]	10.1039/C8SC02339E	:green_circle:
v_stereo_by_20180622_schwaller_p_et_al [18]	10.1039/C8SC02339E	:green_circle:
v_lef_by_20181221_bradshaw_j_et_al [19]	10.48550/arXiv.1805.10970	:green_circle:
v_1k_tpl_by_20210128_schwaller_p_et_al [20]	10.1038/s42256-020-00284-w	:green_circle:
v_1976_to_2016_remapped_by_20210407_schwaller_p_et_al [21]	10.1126/sciadv.abe4166	:green_circle:
v_1976_to_2016_remapped_by_20240313_chen_s_et_al [22]	10.6084/m9.figshare.25046471.v1	:green_circle:
v_50k_remapped_by_20240313_chen_s_et_al [22]	10.6084/m9.figshare.25046471.v1	:green_circle:
v_mech_31k_by_20240810_chen_s_et_al [23]	10.6084/m9.figshare.24797220.v2	:green_circle:

_{:green_circle: Completely Implemented
:yellow_circle: Partially Implemented (Limited to Reaction SMILES Strings)}

Open Reaction Database (ORD)

The following Open Reaction Database (ORD) ^[24] versions are supported:

Version	DOI	Status
v_release_0_1_0 [24]	10.1021/jacs.1c09820	:yellow_circle:
v_release_main [24]	10.1021/jacs.1c09820	:yellow_circle:

_{:green_circle: Completely Implemented
:yellow_circle: Partially Implemented (Limited to Reaction SMILES Strings)}

Chemical Reaction Database (CRD)

The following Chemical Reaction Database (CRD) ^[25] versions are supported:

Version	DOI	Status
v_reaction_smiles_2001_to_2021 [25]	10.6084/m9.figshare.20279733.v1	:green_circle:
v_reaction_smiles_2001_to_2023 [25]	10.6084/m9.figshare.22491730.v1	:green_circle:
v_reaction_smiles_2023 [25]	10.6084/m9.figshare.24921555.v1	:green_circle:
v_reaction_smiles_1976_to_2024 [25]	10.6084/m9.figshare.28230053.v1	:green_circle:

_{:green_circle: Completely Implemented}

Rhea

The following Rhea ^[26] chemical reaction database versions are supported:

Version	DOI	Status
v_release_{release_number ≥ 126} [26]	10.1093/nar/gkab1016	:green_circle:

_{:green_circle: Completely Implemented}

Miscellaneous Chemical Reaction Data Sources

The following miscellaneous chemical reaction data sources are supported:

Version	DOI	Status
v_20131008_kraut_h_et_al [27]	10.1021/ci400442f	:green_circle:
v_20161014_wei_j_n_et_al [28]	10.1021/acscentsci.6b00219	:green_circle:
v_20200508_grambow_c_et_al [29]	10.5281/zenodo.3581266	:green_circle:
v_add_on_by_20200508_grambow_c_et_al [29]	10.5281/zenodo.3731553	:green_circle:
v_golden_dataset_by_20211102_lin_a_et_al [30]	10.1002/minf.202100138	:green_circle:
v_rdb7_by_20220718_spiekermann_k_et_al [31]	10.5281/zenodo.5652097	:green_circle:
v_orderly_condition_by_20240422_wigh_d_s_et_al [32]	10.6084/m9.figshare.23298467.v4	:green_circle:
v_orderly_forward_by_20240422_wigh_d_s_et_al [32]	10.6084/m9.figshare.23298467.v4	:green_circle:
v_orderly_retro_by_20240422_wigh_d_s_et_al [32]	10.6084/m9.figshare.23298467.v4	:green_circle:

_{:green_circle: Completely Implemented}

Chemical Reaction Patterns

The following chemical reaction pattern data sources are supported:

• RetroRules
• Miscellaneous Chemical Reaction Pattern Data Sources

The chemical reaction pattern data source relationships can be illustrated as follows:

RetroRules

The following RetroRules ^[33] chemical reaction pattern database versions are supported:

Version	DOI	Status
v_release_rr01_rp2_hs [33]	10.5281/zenodo.5827427	:green_circle:
v_release_rr02_rp2_hs [33]	10.5281/zenodo.5828017	:green_circle:
v_release_rr02_rp3_hs [33]	10.5281/zenodo.5827977	:green_circle:
v_release_rr02_rp3_nohs [33]	10.5281/zenodo.5827969	:green_circle:

_{:green_circle: Completely Implemented}

Miscellaneous Chemical Reaction Pattern Data Sources

The following miscellaneous chemical reaction pattern data sources are supported:

Version	DOI	Status
v_retro_transform_db_by_20180421_avramova_s_et_al [34]	10.5281/zenodo.1209312	:green_circle:
v_dingos_by_20190701_button_a_et_al [35]	10.24433/CO.6930970.v1	:green_circle:
v_auto_template_by_20240627_chen_l_and_li_y [36]	10.1186/s13321-024-00869-2	:green_circle:

_{:green_circle: Completely Implemented}

Data

The purpose of the data directory is to archive and backup the data sources that are hosted on GitHub, GitLab, and CodeOcean repositories.

License Information

The contents of this repository are published under the MIT license. Please refer to the individual references for more details regarding the license information of external resources utilized within the repository.

Contact

If you are interested in contributing to this research project by submitting bugs, questions, and feedback or contributing to the code and data, please refer to the contribution guidelines.

References

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[34] Avramova, S. et al. RetroTransformDB: A Dataset of Generic Transforms for Retrosynthetic Analysis. Data, 2018, 3, 14.

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