From 19ced79387a033f0be52bad436da90573cfb5783 Mon Sep 17 00:00:00 2001
From: Samuel Genheden <samuel.genheden@astrazeneca.com>
Date: Mon, 21 Nov 2022 09:16:15 +0000
Subject: [PATCH] Public release 1.2.0

---
 .pre-commit-config.yaml                     |   4 +-
 CHANGELOG.md                                |   7 +
 docs/conf.py                                |   2 +-
 poetry.lock                                 | 610 ++++++--------------
 pyproject.toml                              |   4 +-
 rxnutils/chem/reaction.py                   |  67 ++-
 rxnutils/pipeline/actions/reaction_props.py | 234 +++++++-
 tests/data/example_ring_reactions.csv       |   3 +
 tests/test_reaction.py                      |  26 +
 tests/test_reaction_props_actions.py        |  46 ++
 10 files changed, 544 insertions(+), 459 deletions(-)
 create mode 100644 tests/data/example_ring_reactions.csv

diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
index d9172bb..8fd4652 100644
--- a/.pre-commit-config.yaml
+++ b/.pre-commit-config.yaml
@@ -14,7 +14,7 @@ repos:
     -   id: check-added-large-files
     -   id: check-merge-conflict
 -   repo: https://github.com/psf/black
-    rev: 20.8b1
+    rev: 22.0.0
     hooks:
     -   id: black
-# We should add some linter to here at some point
\ No newline at end of file
+# We should add some linter to here at some point
diff --git a/CHANGELOG.md b/CHANGELOG.md
index e917381..90568fa 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,12 @@
 # CHANGELOG
 
+## Version 1.2.0 - 2022-11-21
+
+### Features
+
+- Adding pipeline actions for identifying RingBreaker reactions
+- Adding support for extracting new type of RingBreaker templates
+
 ## Version 1.1.1 - 2022-08-31
 
 ### Trival changes
diff --git a/docs/conf.py b/docs/conf.py
index 809c67c..7bea246 100644
--- a/docs/conf.py
+++ b/docs/conf.py
@@ -6,7 +6,7 @@
 project = "ReactionUtils"
 copyright = "2022, Molecular AI group"
 author = "Molecular AI group"
-release = "1.1.1"
+release = "1.2.0"
 
 extensions = [
     "sphinx.ext.autodoc",
diff --git a/poetry.lock b/poetry.lock
index 17ff11e..4399764 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -6,14 +6,6 @@ category = "main"
 optional = false
 python-versions = "*"
 
-[[package]]
-name = "appdirs"
-version = "1.4.4"
-description = "A small Python module for determining appropriate platform-specific dirs, e.g. a \"user data dir\"."
-category = "dev"
-optional = false
-python-versions = "*"
-
 [[package]]
 name = "appnope"
 version = "0.1.3"
@@ -24,7 +16,7 @@ python-versions = "*"
 
 [[package]]
 name = "astroid"
-version = "2.12.5"
+version = "2.12.10"
 description = "An abstract syntax tree for Python with inference support."
 category = "main"
 optional = false
@@ -55,10 +47,10 @@ optional = false
 python-versions = ">=3.5"
 
 [package.extras]
-dev = ["cloudpickle", "coverage[toml] (>=5.0.2)", "furo", "hypothesis", "mypy (>=0.900,!=0.940)", "pre-commit", "pympler", "pytest (>=4.3.0)", "pytest-mypy-plugins", "sphinx", "sphinx-notfound-page", "zope.interface"]
-docs = ["furo", "sphinx", "sphinx-notfound-page", "zope.interface"]
-tests = ["cloudpickle", "coverage[toml] (>=5.0.2)", "hypothesis", "mypy (>=0.900,!=0.940)", "pympler", "pytest (>=4.3.0)", "pytest-mypy-plugins", "zope.interface"]
-tests_no_zope = ["cloudpickle", "coverage[toml] (>=5.0.2)", "hypothesis", "mypy (>=0.900,!=0.940)", "pympler", "pytest (>=4.3.0)", "pytest-mypy-plugins"]
+dev = ["coverage[toml] (>=5.0.2)", "hypothesis", "pympler", "pytest (>=4.3.0)", "mypy (>=0.900,!=0.940)", "pytest-mypy-plugins", "zope.interface", "furo", "sphinx", "sphinx-notfound-page", "pre-commit", "cloudpickle"]
+docs = ["furo", "sphinx", "zope.interface", "sphinx-notfound-page"]
+tests = ["coverage[toml] (>=5.0.2)", "hypothesis", "pympler", "pytest (>=4.3.0)", "mypy (>=0.900,!=0.940)", "pytest-mypy-plugins", "zope.interface", "cloudpickle"]
+tests_no_zope = ["coverage[toml] (>=5.0.2)", "hypothesis", "pympler", "pytest (>=4.3.0)", "mypy (>=0.900,!=0.940)", "pytest-mypy-plugins", "cloudpickle"]
 
 [[package]]
 name = "babel"
@@ -81,25 +73,25 @@ python-versions = "*"
 
 [[package]]
 name = "black"
-version = "20.8b1"
+version = "22.8.0"
 description = "The uncompromising code formatter."
 category = "dev"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.6.2"
 
 [package.dependencies]
-appdirs = "*"
-click = ">=7.1.2"
+click = ">=8.0.0"
 mypy-extensions = ">=0.4.3"
-pathspec = ">=0.6,<1"
-regex = ">=2020.1.8"
-toml = ">=0.10.1"
-typed-ast = ">=1.4.0"
-typing-extensions = ">=3.7.4"
+pathspec = ">=0.9.0"
+platformdirs = ">=2"
+tomli = {version = ">=1.1.0", markers = "python_full_version < \"3.11.0a7\""}
+typing-extensions = {version = ">=3.10.0.0", markers = "python_version < \"3.10\""}
 
 [package.extras]
 colorama = ["colorama (>=0.4.3)"]
-d = ["aiohttp (>=3.3.2)", "aiohttp-cors"]
+d = ["aiohttp (>=3.7.4)"]
+jupyter = ["ipython (>=7.8.0)", "tokenize-rt (>=3.2.0)"]
+uvloop = ["uvloop (>=0.15.2)"]
 
 [[package]]
 name = "bleach"
@@ -115,18 +107,18 @@ webencodings = "*"
 
 [package.extras]
 css = ["tinycss2 (>=1.1.0,<1.2)"]
-dev = ["Sphinx (==4.3.2)", "black (==22.3.0)", "build (==0.8.0)", "flake8 (==4.0.1)", "hashin (==0.17.0)", "mypy (==0.961)", "pip-tools (==6.6.2)", "pytest (==7.1.2)", "tox (==3.25.0)", "twine (==4.0.1)", "wheel (==0.37.1)"]
+dev = ["build (==0.8.0)", "flake8 (==4.0.1)", "hashin (==0.17.0)", "pip-tools (==6.6.2)", "pytest (==7.1.2)", "Sphinx (==4.3.2)", "tox (==3.25.0)", "twine (==4.0.1)", "wheel (==0.37.1)", "black (==22.3.0)", "mypy (==0.961)"]
 
 [[package]]
 name = "boto3"
-version = "1.24.63"
+version = "1.24.83"
 description = "The AWS SDK for Python"
 category = "main"
 optional = false
 python-versions = ">= 3.7"
 
 [package.dependencies]
-botocore = ">=1.27.63,<1.28.0"
+botocore = ">=1.27.83,<1.28.0"
 jmespath = ">=0.7.1,<2.0.0"
 s3transfer = ">=0.6.0,<0.7.0"
 
@@ -135,7 +127,7 @@ crt = ["botocore[crt] (>=1.21.0,<2.0a0)"]
 
 [[package]]
 name = "botocore"
-version = "1.27.63"
+version = "1.27.83"
 description = "Low-level, data-driven core of boto 3."
 category = "main"
 optional = false
@@ -170,7 +162,7 @@ cffi = ">=1.0.0"
 
 [[package]]
 name = "certifi"
-version = "2022.6.15"
+version = "2022.9.24"
 description = "Python package for providing Mozilla's CA Bundle."
 category = "main"
 optional = false
@@ -231,7 +223,7 @@ colorama = {version = "*", markers = "platform_system == \"Windows\""}
 
 [[package]]
 name = "cloudpickle"
-version = "2.1.0"
+version = "2.2.0"
 description = "Extended pickling support for Python objects"
 category = "main"
 optional = false
@@ -247,7 +239,7 @@ python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*"
 
 [[package]]
 name = "coverage"
-version = "6.4.4"
+version = "6.5.0"
 description = "Code coverage measurement for Python"
 category = "dev"
 optional = false
@@ -261,7 +253,7 @@ toml = ["tomli"]
 
 [[package]]
 name = "dask"
-version = "2022.8.1"
+version = "2022.9.1"
 description = "Parallel PyData with Task Scheduling"
 category = "main"
 optional = false
@@ -279,11 +271,11 @@ toolz = ">=0.8.2"
 
 [package.extras]
 array = ["numpy (>=1.18)"]
-complete = ["bokeh (>=2.4.2)", "distributed (==2022.8.1)", "jinja2", "numpy (>=1.18)", "pandas (>=1.0)"]
+complete = ["bokeh (>=2.4.2)", "distributed (==2022.9.1)", "jinja2", "numpy (>=1.18)", "pandas (>=1.0)"]
 dataframe = ["numpy (>=1.18)", "pandas (>=1.0)"]
 diagnostics = ["bokeh (>=2.4.2)", "jinja2"]
-distributed = ["distributed (==2022.8.1)"]
-test = ["pandas", "pre-commit", "pytest", "pytest-rerunfailures", "pytest-xdist"]
+distributed = ["distributed (==2022.9.1)"]
+test = ["pandas", "pytest", "pytest-rerunfailures", "pytest-xdist", "pre-commit"]
 
 [[package]]
 name = "debugpy"
@@ -313,7 +305,7 @@ python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*"
 wrapt = ">=1.10,<2"
 
 [package.extras]
-dev = ["PyTest (<5)", "PyTest-Cov (<2.6)", "bump2version (<1)", "configparser (<5)", "importlib-metadata (<3)", "importlib-resources (<4)", "pytest", "pytest-cov", "sphinx (<2)", "sphinxcontrib-websupport (<2)", "tox", "zipp (<2)"]
+dev = ["tox", "bump2version (<1)", "sphinx (<2)", "importlib-metadata (<3)", "importlib-resources (<4)", "configparser (<5)", "sphinxcontrib-websupport (<2)", "zipp (<2)", "PyTest (<5)", "PyTest-Cov (<2.6)", "pytest", "pytest-cov"]
 
 [[package]]
 name = "dill"
@@ -375,7 +367,7 @@ testing = ["covdefaults (>=2.2)", "coverage (>=6.4.2)", "pytest (>=7.1.2)", "pyt
 
 [[package]]
 name = "fsspec"
-version = "2022.8.0"
+version = "2022.8.2"
 description = "File-system specification"
 category = "main"
 optional = false
@@ -386,7 +378,7 @@ abfs = ["adlfs"]
 adl = ["adlfs"]
 arrow = ["pyarrow (>=1)"]
 dask = ["dask", "distributed"]
-dropbox = ["dropbox", "dropboxdrivefs", "requests"]
+dropbox = ["dropboxdrivefs", "requests", "dropbox"]
 entrypoints = ["importlib-metadata"]
 fuse = ["fusepy"]
 gcs = ["gcsfs"]
@@ -395,7 +387,7 @@ github = ["requests"]
 gs = ["gcsfs"]
 gui = ["panel"]
 hdfs = ["pyarrow (>=1)"]
-http = ["aiohttp (!=4.0.0a0,!=4.0.0a1)", "requests"]
+http = ["requests", "aiohttp (!=4.0.0a0,!=4.0.0a1)"]
 libarchive = ["libarchive-c"]
 oci = ["ocifs"]
 s3 = ["s3fs"]
@@ -406,7 +398,7 @@ tqdm = ["tqdm"]
 
 [[package]]
 name = "identify"
-version = "2.5.3"
+version = "2.5.5"
 description = "File identification library for Python"
 category = "dev"
 optional = false
@@ -417,7 +409,7 @@ license = ["ukkonen"]
 
 [[package]]
 name = "idna"
-version = "3.3"
+version = "3.4"
 description = "Internationalized Domain Names in Applications (IDNA)"
 category = "main"
 optional = false
@@ -443,9 +435,9 @@ python-versions = ">=3.7"
 zipp = ">=0.5"
 
 [package.extras]
-docs = ["jaraco.packaging (>=9)", "rst.linker (>=1.9)", "sphinx"]
+docs = ["sphinx", "jaraco.packaging (>=9)", "rst.linker (>=1.9)"]
 perf = ["ipython"]
-testing = ["flufl.flake8", "importlib-resources (>=1.3)", "packaging", "pyfakefs", "pytest (>=6)", "pytest-black (>=0.3.7)", "pytest-checkdocs (>=2.4)", "pytest-cov", "pytest-enabler (>=1.3)", "pytest-flake8", "pytest-mypy (>=0.9.1)", "pytest-perf (>=0.9.2)"]
+testing = ["pytest (>=6)", "pytest-checkdocs (>=2.4)", "pytest-flake8", "pytest-cov", "pytest-enabler (>=1.3)", "packaging", "pyfakefs", "flufl.flake8", "pytest-perf (>=0.9.2)", "pytest-black (>=0.3.7)", "pytest-mypy (>=0.9.1)", "importlib-resources (>=1.3)"]
 
 [[package]]
 name = "iniconfig"
@@ -465,7 +457,7 @@ python-versions = "*"
 
 [[package]]
 name = "ipykernel"
-version = "6.15.2"
+version = "6.16.0"
 description = "IPython Kernel for Jupyter"
 category = "main"
 optional = false
@@ -485,7 +477,7 @@ tornado = ">=6.1"
 traitlets = ">=5.1.0"
 
 [package.extras]
-test = ["flaky", "ipyparallel", "pre-commit", "pytest (>=6.0)", "pytest-cov", "pytest-timeout"]
+test = ["flaky", "ipyparallel", "pre-commit", "pytest-cov", "pytest-timeout", "pytest (>=6.0)"]
 
 [[package]]
 name = "ipython"
@@ -514,14 +506,14 @@ doc = ["Sphinx (>=1.3)"]
 kernel = ["ipykernel"]
 nbconvert = ["nbconvert"]
 nbformat = ["nbformat"]
-notebook = ["ipywidgets", "notebook"]
+notebook = ["notebook", "ipywidgets"]
 parallel = ["ipyparallel"]
 qtconsole = ["qtconsole"]
-test = ["ipykernel", "nbformat", "nose (>=0.10.1)", "numpy (>=1.17)", "pygments", "requests", "testpath"]
+test = ["nose (>=0.10.1)", "requests", "testpath", "pygments", "nbformat", "ipykernel", "numpy (>=1.17)"]
 
 [[package]]
 name = "ipywidgets"
-version = "8.0.1"
+version = "8.0.2"
 description = "Jupyter interactive widgets"
 category = "main"
 optional = false
@@ -546,10 +538,10 @@ optional = false
 python-versions = ">=3.6.1,<4.0"
 
 [package.extras]
-colors = ["colorama (>=0.4.3,<0.5.0)"]
 pipfile_deprecated_finder = ["pipreqs", "requirementslib"]
+requirements_deprecated_finder = ["pipreqs", "pip-api"]
+colors = ["colorama (>=0.4.3,<0.5.0)"]
 plugins = ["setuptools"]
-requirements_deprecated_finder = ["pip-api", "pipreqs"]
 
 [[package]]
 name = "jedi"
@@ -606,7 +598,7 @@ tornado = ">=6.2"
 traitlets = "*"
 
 [package.extras]
-doc = ["ipykernel", "myst-parser", "sphinx (>=1.3.6)", "sphinx-rtd-theme", "sphinxcontrib-github-alt"]
+doc = ["ipykernel", "myst-parser", "sphinx-rtd-theme", "sphinx (>=1.3.6)", "sphinxcontrib-github-alt"]
 test = ["codecov", "coverage", "ipykernel (>=6.5)", "ipython", "mypy", "pre-commit", "pytest", "pytest-asyncio (>=0.18)", "pytest-cov", "pytest-timeout"]
 
 [[package]]
@@ -626,7 +618,7 @@ test = ["ipykernel", "pre-commit", "pytest", "pytest-cov", "pytest-timeout"]
 
 [[package]]
 name = "jupyterlab-widgets"
-version = "3.0.2"
+version = "3.0.3"
 description = "Jupyter interactive widgets for JupyterLab"
 category = "main"
 optional = false
@@ -689,7 +681,7 @@ python-versions = ">=3.6"
 
 [[package]]
 name = "metaflow"
-version = "2.7.7"
+version = "2.7.12"
 description = "Metaflow: More Data Science, Less Engineering"
 category = "main"
 optional = false
@@ -731,8 +723,8 @@ optional = false
 python-versions = ">=3.6"
 
 [package.extras]
-check = ["check-manifest", "flake8", "flake8-black", "isort (>=5.0.3)", "pygments", "readme-renderer", "twine"]
-test = ["coverage[toml] (>=5.2)", "coveralls (>=2.1.1)", "hypothesis", "pyannotate", "pytest", "pytest-cov"]
+check = ["check-manifest", "flake8", "flake8-black", "readme-renderer", "pygments", "isort (>=5.0.3)", "twine"]
+test = ["pytest", "pytest-cov", "pyannotate", "coverage[toml] (>=5.2)", "coveralls (>=2.1.1)", "hypothesis"]
 type = ["mypy", "mypy-extensions"]
 
 [[package]]
@@ -761,7 +753,7 @@ python-versions = "*"
 
 [[package]]
 name = "nest-asyncio"
-version = "1.5.5"
+version = "1.5.6"
 description = "Patch asyncio to allow nested event loops"
 category = "main"
 optional = false
@@ -777,7 +769,7 @@ python-versions = ">=2.7,!=3.0.*,!=3.1.*,!=3.2.*,!=3.3.*,!=3.4.*,!=3.5.*,!=3.6.*
 
 [[package]]
 name = "numpy"
-version = "1.23.2"
+version = "1.23.3"
 description = "NumPy is the fundamental package for array computing with Python."
 category = "main"
 optional = false
@@ -796,7 +788,7 @@ pyparsing = ">=2.0.2,<3.0.5 || >3.0.5"
 
 [[package]]
 name = "pandas"
-version = "1.4.4"
+version = "1.5.0"
 description = "Powerful data structures for data analysis, time series, and statistics"
 category = "main"
 optional = false
@@ -804,16 +796,14 @@ python-versions = ">=3.8"
 
 [package.dependencies]
 numpy = [
-    {version = ">=1.18.5", markers = "platform_machine != \"aarch64\" and platform_machine != \"arm64\" and python_version < \"3.10\""},
-    {version = ">=1.19.2", markers = "platform_machine == \"aarch64\" and python_version < \"3.10\""},
-    {version = ">=1.20.0", markers = "platform_machine == \"arm64\" and python_version < \"3.10\""},
     {version = ">=1.21.0", markers = "python_version >= \"3.10\""},
+    {version = ">=1.20.3", markers = "python_version < \"3.10\""},
 ]
 python-dateutil = ">=2.8.1"
 pytz = ">=2020.1"
 
 [package.extras]
-test = ["hypothesis (>=5.5.3)", "pytest (>=6.0)", "pytest-xdist (>=1.31)"]
+test = ["pytest-xdist (>=1.31)", "pytest (>=6.0)", "hypothesis (>=5.5.3)"]
 
 [[package]]
 name = "parso"
@@ -840,11 +830,11 @@ locket = "*"
 toolz = "*"
 
 [package.extras]
-complete = ["blosc", "numpy (>=1.9.0)", "pandas (>=0.19.0)", "pyzmq"]
+complete = ["blosc", "pyzmq", "pandas (>=0.19.0)", "numpy (>=1.9.0)"]
 
 [[package]]
 name = "pathspec"
-version = "0.10.0"
+version = "0.10.1"
 description = "Utility library for gitignore style pattern matching of file paths."
 category = "dev"
 optional = false
@@ -890,8 +880,8 @@ optional = false
 python-versions = ">=3.7"
 
 [package.extras]
-docs = ["furo (>=2021.7.5b38)", "proselint (>=0.10.2)", "sphinx (>=4)", "sphinx-autodoc-typehints (>=1.12)"]
-test = ["appdirs (==1.4.4)", "pytest (>=6)", "pytest-cov (>=2.7)", "pytest-mock (>=3.6)"]
+docs = ["furo (>=2021.7.5b38)", "proselint (>=0.10.2)", "sphinx-autodoc-typehints (>=1.12)", "sphinx (>=4)"]
+test = ["appdirs (==1.4.4)", "pytest-cov (>=2.7)", "pytest-mock (>=3.6)", "pytest (>=6)"]
 
 [[package]]
 name = "pluggy"
@@ -923,7 +913,7 @@ virtualenv = ">=20.0.8"
 
 [[package]]
 name = "prompt-toolkit"
-version = "3.0.30"
+version = "3.0.31"
 description = "Library for building powerful interactive command lines in Python"
 category = "main"
 optional = false
@@ -934,14 +924,14 @@ wcwidth = "*"
 
 [[package]]
 name = "psutil"
-version = "5.9.1"
+version = "5.9.2"
 description = "Cross-platform lib for process and system monitoring in Python."
 category = "main"
 optional = false
 python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*"
 
 [package.extras]
-test = ["enum34", "ipaddress", "mock", "pywin32", "wmi"]
+test = ["ipaddress", "mock", "enum34", "pywin32", "wmi"]
 
 [[package]]
 name = "ptyprocess"
@@ -980,10 +970,10 @@ texttable = "*"
 zipfile-deflate64 = ">=0.2.0"
 
 [package.extras]
-check = ["check-manifest", "flake8", "flake8-black", "flake8-deprecated", "isort (>=5.0.3)", "mypy (>=0.940)", "mypy-extensions (>=0.4.1)", "pygments", "readme-renderer", "twine"]
+check = ["mypy (>=0.940)", "mypy-extensions (>=0.4.1)", "check-manifest", "flake8", "flake8-black", "flake8-deprecated", "isort (>=5.0.3)", "pygments", "readme-renderer", "twine"]
 debug = ["pytest", "pytest-leaks", "pytest-profiling"]
-docs = ["docutils", "sphinx (>=5.0)", "sphinx-a4doc", "sphinx-py3doc-enhanced-theme"]
-test = ["coverage[toml] (>=5.2)", "coveralls (>=2.1.1)", "py-cpuinfo", "pyannotate", "pytest", "pytest-benchmark", "pytest-cov", "pytest-remotedata", "pytest-timeout"]
+docs = ["sphinx (>=5.0)", "sphinx-py3doc-enhanced-theme", "sphinx-a4doc", "docutils"]
+test = ["pytest", "pytest-benchmark", "pytest-cov", "pytest-remotedata", "pytest-timeout", "pyannotate", "py-cpuinfo", "coverage[toml] (>=5.2)", "coveralls (>=2.1.1)"]
 test_compat = ["libarchive-c"]
 
 [[package]]
@@ -995,8 +985,8 @@ optional = false
 python-versions = ">=3.6"
 
 [package.extras]
-check = ["check-manifest", "flake8 (<5)", "flake8-black", "flake8-colors", "flake8-isort", "flake8-pyi", "flake8-typing-imports", "mypy (>=0.812)", "mypy-extensions (>=0.4.3)", "pygments", "readme-renderer"]
-test = ["coverage[toml] (>=5.2)", "hypothesis", "pytest (>=6.0)", "pytest-cov"]
+test = ["coverage[toml] (>=5.2)", "hypothesis", "pytest-cov", "pytest (>=6.0)"]
+check = ["pygments", "readme-renderer", "flake8-typing-imports", "flake8-pyi", "flake8-isort", "flake8-colors", "flake8-black", "flake8 (<5)", "check-manifest", "mypy-extensions (>=0.4.3)", "mypy (>=0.812)"]
 
 [[package]]
 name = "pycparser"
@@ -1027,14 +1017,14 @@ plugins = ["importlib-metadata"]
 
 [[package]]
 name = "pylint"
-version = "2.15.0"
+version = "2.15.3"
 description = "python code static checker"
 category = "main"
 optional = false
 python-versions = ">=3.7.2"
 
 [package.dependencies]
-astroid = ">=2.12.4,<=2.14.0-dev0"
+astroid = ">=2.12.10,<=2.14.0-dev0"
 colorama = {version = ">=0.4.5", markers = "sys_platform == \"win32\""}
 dill = ">=0.2"
 isort = ">=4.2.5,<6"
@@ -1057,7 +1047,7 @@ optional = false
 python-versions = ">=3.6.8"
 
 [package.extras]
-diagrams = ["jinja2", "railroad-diagrams"]
+diagrams = ["railroad-diagrams", "jinja2"]
 
 [[package]]
 name = "pyppmd"
@@ -1068,10 +1058,10 @@ optional = false
 python-versions = ">=3.6"
 
 [package.extras]
-check = ["check-manifest", "flake8", "flake8-black", "isort (>=5.0.3)", "mypy (>=0.812)", "mypy-extensions (>=0.4.3)", "pygments", "readme-renderer"]
+check = ["mypy (>=0.812)", "mypy-extensions (>=0.4.3)", "check-manifest", "flake8", "flake8-black", "readme-renderer", "pygments", "isort (>=5.0.3)"]
 docs = ["sphinx (>=2.3)", "sphinx-rtd-theme"]
 fuzzer = ["atheris", "hypothesis"]
-test = ["coverage[toml] (>=5.2)", "hypothesis", "pytest (>=6.0)", "pytest-benchmark", "pytest-cov", "pytest-timeout"]
+test = ["pytest (>=6.0)", "pytest-benchmark", "pytest-cov", "pytest-timeout", "hypothesis", "coverage[toml] (>=5.2)"]
 
 [[package]]
 name = "pytest"
@@ -1120,7 +1110,7 @@ coverage = {version = ">=5.2.1", extras = ["toml"]}
 pytest = ">=4.6"
 
 [package.extras]
-testing = ["fields", "hunter", "process-tests", "pytest-xdist", "six", "virtualenv"]
+testing = ["fields", "hunter", "process-tests", "six", "pytest-xdist", "virtualenv"]
 
 [[package]]
 name = "pytest-datadir"
@@ -1147,7 +1137,7 @@ pytest = ">=5.4.0"
 
 [[package]]
 name = "pytest-mock"
-version = "3.8.2"
+version = "3.9.0"
 description = "Thin-wrapper around the mock package for easier use with pytest"
 category = "dev"
 optional = false
@@ -1157,7 +1147,7 @@ python-versions = ">=3.7"
 pytest = ">=5.0"
 
 [package.extras]
-dev = ["pre-commit", "pytest-asyncio", "tox"]
+dev = ["pre-commit", "tox", "pytest-asyncio"]
 
 [[package]]
 name = "python-dateutil"
@@ -1196,7 +1186,7 @@ python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*, !=3.5.*"
 
 [[package]]
 name = "pyzmq"
-version = "23.2.1"
+version = "24.0.1"
 description = "Python bindings for 0MQ"
 category = "main"
 optional = false
@@ -1234,14 +1224,6 @@ python-versions = "*"
 numpy = "*"
 Pillow = "*"
 
-[[package]]
-name = "regex"
-version = "2022.8.17"
-description = "Alternative regular expression module, to replace re."
-category = "dev"
-optional = false
-python-versions = ">=3.6"
-
 [[package]]
 name = "requests"
 version = "2.28.1"
@@ -1292,7 +1274,7 @@ python-versions = "*"
 
 [[package]]
 name = "sphinx"
-version = "5.1.1"
+version = "5.2.2"
 description = "Python documentation generator"
 category = "main"
 optional = false
@@ -1300,16 +1282,16 @@ python-versions = ">=3.6"
 
 [package.dependencies]
 alabaster = ">=0.7,<0.8"
-babel = ">=1.3"
-colorama = {version = ">=0.3.5", markers = "sys_platform == \"win32\""}
+babel = ">=2.9"
+colorama = {version = ">=0.4.5", markers = "sys_platform == \"win32\""}
 docutils = ">=0.14,<0.20"
-imagesize = "*"
-importlib-metadata = {version = ">=4.4", markers = "python_version < \"3.10\""}
-Jinja2 = ">=2.3"
-packaging = "*"
-Pygments = ">=2.0"
+imagesize = ">=1.3"
+importlib-metadata = {version = ">=4.8", markers = "python_version < \"3.10\""}
+Jinja2 = ">=3.0"
+packaging = ">=21.0"
+Pygments = ">=2.12"
 requests = ">=2.5.0"
-snowballstemmer = ">=1.1"
+snowballstemmer = ">=2.0"
 sphinxcontrib-applehelp = "*"
 sphinxcontrib-devhelp = "*"
 sphinxcontrib-htmlhelp = ">=2.0.0"
@@ -1319,8 +1301,8 @@ sphinxcontrib-serializinghtml = ">=1.1.5"
 
 [package.extras]
 docs = ["sphinxcontrib-websupport"]
-lint = ["docutils-stubs", "flake8 (>=3.5.0)", "flake8-bugbear", "flake8-comprehensions", "isort", "mypy (>=0.971)", "sphinx-lint", "types-requests", "types-typed-ast"]
-test = ["cython", "html5lib", "pytest (>=4.6)", "typed-ast"]
+lint = ["flake8 (>=3.5.0)", "flake8-comprehensions", "flake8-bugbear", "flake8-simplify", "isort", "mypy (>=0.981)", "sphinx-lint", "docutils-stubs", "types-typed-ast", "types-requests"]
+test = ["pytest (>=4.6)", "html5lib", "typed-ast", "cython"]
 
 [[package]]
 name = "sphinxcontrib-applehelp"
@@ -1331,7 +1313,7 @@ optional = false
 python-versions = ">=3.5"
 
 [package.extras]
-lint = ["docutils-stubs", "flake8", "mypy"]
+lint = ["flake8", "mypy", "docutils-stubs"]
 test = ["pytest"]
 
 [[package]]
@@ -1343,7 +1325,7 @@ optional = false
 python-versions = ">=3.5"
 
 [package.extras]
-lint = ["docutils-stubs", "flake8", "mypy"]
+lint = ["flake8", "mypy", "docutils-stubs"]
 test = ["pytest"]
 
 [[package]]
@@ -1355,8 +1337,8 @@ optional = false
 python-versions = ">=3.6"
 
 [package.extras]
-lint = ["docutils-stubs", "flake8", "mypy"]
-test = ["html5lib", "pytest"]
+lint = ["flake8", "mypy", "docutils-stubs"]
+test = ["pytest", "html5lib"]
 
 [[package]]
 name = "sphinxcontrib-jsmath"
@@ -1367,7 +1349,7 @@ optional = false
 python-versions = ">=3.5"
 
 [package.extras]
-test = ["flake8", "mypy", "pytest"]
+test = ["pytest", "flake8", "mypy"]
 
 [[package]]
 name = "sphinxcontrib-qthelp"
@@ -1378,7 +1360,7 @@ optional = false
 python-versions = ">=3.5"
 
 [package.extras]
-lint = ["docutils-stubs", "flake8", "mypy"]
+lint = ["flake8", "mypy", "docutils-stubs"]
 test = ["pytest"]
 
 [[package]]
@@ -1390,7 +1372,7 @@ optional = false
 python-versions = ">=3.5"
 
 [package.extras]
-lint = ["docutils-stubs", "flake8", "mypy"]
+lint = ["flake8", "mypy", "docutils-stubs"]
 test = ["pytest"]
 
 [[package]]
@@ -1440,7 +1422,7 @@ python-versions = ">=3.7"
 
 [[package]]
 name = "tomlkit"
-version = "0.11.4"
+version = "0.11.5"
 description = "Style preserving TOML library"
 category = "main"
 optional = false
@@ -1464,7 +1446,7 @@ python-versions = ">= 3.7"
 
 [[package]]
 name = "tqdm"
-version = "4.64.0"
+version = "4.64.1"
 description = "Fast, Extensible Progress Meter"
 category = "main"
 optional = false
@@ -1481,7 +1463,7 @@ telegram = ["requests"]
 
 [[package]]
 name = "traitlets"
-version = "5.3.0"
+version = "5.4.0"
 description = ""
 category = "main"
 optional = false
@@ -1515,13 +1497,13 @@ optional = false
 python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*, !=3.5.*, <4"
 
 [package.extras]
-brotli = ["brotli (>=1.0.9)", "brotlicffi (>=0.8.0)", "brotlipy (>=0.6.0)"]
-secure = ["certifi", "cryptography (>=1.3.4)", "idna (>=2.0.0)", "ipaddress", "pyOpenSSL (>=0.14)", "urllib3-secure-extra"]
+brotli = ["brotlicffi (>=0.8.0)", "brotli (>=1.0.9)", "brotlipy (>=0.6.0)"]
+secure = ["pyOpenSSL (>=0.14)", "cryptography (>=1.3.4)", "idna (>=2.0.0)", "certifi", "urllib3-secure-extra", "ipaddress"]
 socks = ["PySocks (>=1.5.6,!=1.5.7,<2.0)"]
 
 [[package]]
 name = "virtualenv"
-version = "20.16.4"
+version = "20.16.5"
 description = "Virtual Python Environment builder"
 category = "dev"
 optional = false
@@ -1554,7 +1536,7 @@ python-versions = "*"
 
 [[package]]
 name = "widgetsnbextension"
-version = "4.0.2"
+version = "4.0.3"
 description = "Jupyter interactive widgets for Jupyter Notebook"
 category = "main"
 optional = false
@@ -1611,31 +1593,24 @@ optional = false
 python-versions = ">=3.7"
 
 [package.extras]
-docs = ["jaraco.packaging (>=9)", "jaraco.tidelift (>=1.4)", "rst.linker (>=1.9)", "sphinx"]
-testing = ["func-timeout", "jaraco.itertools", "pytest (>=6)", "pytest-black (>=0.3.7)", "pytest-checkdocs (>=2.4)", "pytest-cov", "pytest-enabler (>=1.3)", "pytest-flake8", "pytest-mypy (>=0.9.1)"]
+docs = ["sphinx", "jaraco.packaging (>=9)", "rst.linker (>=1.9)", "jaraco.tidelift (>=1.4)"]
+testing = ["pytest (>=6)", "pytest-checkdocs (>=2.4)", "pytest-flake8", "pytest-cov", "pytest-enabler (>=1.3)", "jaraco.itertools", "func-timeout", "pytest-black (>=0.3.7)", "pytest-mypy (>=0.9.1)"]
 
 [metadata]
 lock-version = "1.1"
 python-versions = "^3.8"
-content-hash = "1fb0f5ca043cd74d137f0805c882be8a360bad468668ba02aa6983f9aa24d275"
+content-hash = "e881ff3af94dbd9abc01646d1d5263ec3a55e0b2c1c0b6abb9a8116429228db4"
 
 [metadata.files]
 alabaster = [
     {file = "alabaster-0.7.12-py2.py3-none-any.whl", hash = "sha256:446438bdcca0e05bd45ea2de1668c1d9b032e1a9154c2c259092d77031ddd359"},
     {file = "alabaster-0.7.12.tar.gz", hash = "sha256:a661d72d58e6ea8a57f7a86e37d86716863ee5e92788398526d58b26a4e4dc02"},
 ]
-appdirs = [
-    {file = "appdirs-1.4.4-py2.py3-none-any.whl", hash = "sha256:a841dacd6b99318a741b166adb07e19ee71a274450e68237b4650ca1055ab128"},
-    {file = "appdirs-1.4.4.tar.gz", hash = "sha256:7d5d0167b2b1ba821647616af46a749d1c653740dd0d2415100fe26e27afdf41"},
-]
 appnope = [
     {file = "appnope-0.1.3-py2.py3-none-any.whl", hash = "sha256:265a455292d0bd8a72453494fa24df5a11eb18373a60c7c0430889f22548605e"},
     {file = "appnope-0.1.3.tar.gz", hash = "sha256:02bd91c4de869fbb1e1c50aafc4098827a7a54ab2f39d9dcba6c9547ed920e24"},
 ]
-astroid = [
-    {file = "astroid-2.12.5-py3-none-any.whl", hash = "sha256:d612609242996c4365aeb0345e61edba34363eaaba55f1c0addf6a98f073bef6"},
-    {file = "astroid-2.12.5.tar.gz", hash = "sha256:396c88d0a58d7f8daadf730b2ce90838bf338c6752558db719ec6f99c18ec20e"},
-]
+astroid = []
 atomicwrites = [
     {file = "atomicwrites-1.4.1.tar.gz", hash = "sha256:81b2c9071a49367a7f770170e5eec8cb66567cfbbc8c73d20ce5ca4a8d71cf11"},
 ]
@@ -1651,21 +1626,13 @@ backcall = [
     {file = "backcall-0.2.0-py2.py3-none-any.whl", hash = "sha256:fbbce6a29f263178a1f7915c1940bde0ec2b2a967566fe1c65c1dfb7422bd255"},
     {file = "backcall-0.2.0.tar.gz", hash = "sha256:5cbdbf27be5e7cfadb448baf0aa95508f91f2bbc6c6437cd9cd06e2a4c215e1e"},
 ]
-black = [
-    {file = "black-20.8b1.tar.gz", hash = "sha256:1c02557aa099101b9d21496f8a914e9ed2222ef70336404eeeac8edba836fbea"},
-]
+black = []
 bleach = [
     {file = "bleach-5.0.1-py3-none-any.whl", hash = "sha256:085f7f33c15bd408dd9b17a4ad77c577db66d76203e5984b1bd59baeee948b2a"},
     {file = "bleach-5.0.1.tar.gz", hash = "sha256:0d03255c47eb9bd2f26aa9bb7f2107732e7e8fe195ca2f64709fcf3b0a4a085c"},
 ]
-boto3 = [
-    {file = "boto3-1.24.63-py3-none-any.whl", hash = "sha256:719bfafbe4e076055aa1a51269ffdbe9c61446679b67f31d61c237976661154c"},
-    {file = "boto3-1.24.63.tar.gz", hash = "sha256:0e6ef4b5e47b6073887961028201ecfc2024198125f20fbe5f5c00234f124543"},
-]
-botocore = [
-    {file = "botocore-1.27.63-py3-none-any.whl", hash = "sha256:8567dee549430a53210c6b898dea3a8fc8ee9d7934ec1df7545c547cacbb2b8f"},
-    {file = "botocore-1.27.63.tar.gz", hash = "sha256:b97e17c930a7f45b50f94956a4474c1cd7b828e3dcd8a84dd0e3306ca6189335"},
-]
+boto3 = []
+botocore = []
 brotli = [
     {file = "Brotli-1.0.9-cp27-cp27m-macosx_10_9_x86_64.whl", hash = "sha256:268fe94547ba25b58ebc724680609c8ee3e5a843202e9a381f6f9c5e8bdb5c70"},
     {file = "Brotli-1.0.9-cp27-cp27m-manylinux1_i686.whl", hash = "sha256:c2415d9d082152460f2bd4e382a1e85aed233abc92db5a3880da2257dc7daf7b"},
@@ -1762,10 +1729,7 @@ brotlicffi = [
     {file = "brotlicffi-1.0.9.2-pp37-pypy37_pp73-win32.whl", hash = "sha256:7e72978f4090a161885b114f87b784f538dcb77dafc6602592c1cf39ae8d243d"},
     {file = "brotlicffi-1.0.9.2.tar.gz", hash = "sha256:0c248a68129d8fc6a217767406c731e498c3e19a7be05ea0a90c3c86637b7d96"},
 ]
-certifi = [
-    {file = "certifi-2022.6.15-py3-none-any.whl", hash = "sha256:fe86415d55e84719d75f8b69414f6438ac3547d2078ab91b67e779ef69378412"},
-    {file = "certifi-2022.6.15.tar.gz", hash = "sha256:84c85a9078b11105f04f3036a9482ae10e4621616db313fe045dd24743a0820d"},
-]
+certifi = []
 cffi = [
     {file = "cffi-1.15.1-cp27-cp27m-macosx_10_9_x86_64.whl", hash = "sha256:a66d3508133af6e8548451b25058d5812812ec3798c886bf38ed24a98216fab2"},
     {file = "cffi-1.15.1-cp27-cp27m-manylinux1_i686.whl", hash = "sha256:470c103ae716238bbe698d67ad020e1db9d9dba34fa5a899b5e21577e6d52ed2"},
@@ -1845,10 +1809,7 @@ click = [
     {file = "click-8.1.3-py3-none-any.whl", hash = "sha256:bb4d8133cb15a609f44e8213d9b391b0809795062913b383c62be0ee95b1db48"},
     {file = "click-8.1.3.tar.gz", hash = "sha256:7682dc8afb30297001674575ea00d1814d808d6a36af415a82bd481d37ba7b8e"},
 ]
-cloudpickle = [
-    {file = "cloudpickle-2.1.0-py3-none-any.whl", hash = "sha256:b5c434f75c34624eedad3a14f2be5ac3b5384774d5b0e3caf905c21479e6c4b1"},
-    {file = "cloudpickle-2.1.0.tar.gz", hash = "sha256:bb233e876a58491d9590a676f93c7a5473a08f747d5ab9df7f9ce564b3e7938e"},
-]
+cloudpickle = []
 colorama = [
     {file = "colorama-0.4.5-py2.py3-none-any.whl", hash = "sha256:854bf444933e37f5824ae7bfc1e98d5bce2ebe4160d46b5edf346a89358e99da"},
     {file = "colorama-0.4.5.tar.gz", hash = "sha256:e6c6b4334fc50988a639d9b98aa429a0b57da6e17b9a44f0451f930b6967b7a4"},
@@ -1905,18 +1866,9 @@ filelock = [
     {file = "filelock-3.8.0-py3-none-any.whl", hash = "sha256:617eb4e5eedc82fc5f47b6d61e4d11cb837c56cb4544e39081099fa17ad109d4"},
     {file = "filelock-3.8.0.tar.gz", hash = "sha256:55447caa666f2198c5b6b13a26d2084d26fa5b115c00d065664b2124680c4edc"},
 ]
-fsspec = [
-    {file = "fsspec-2022.8.0-py3-none-any.whl", hash = "sha256:d1b4850f659bbb63366f3aeee45c4f638ef68847692a614a71e834f6837947fc"},
-    {file = "fsspec-2022.8.0.tar.gz", hash = "sha256:85f46cfe0750b96f8c18cb7cdc0edb9ab7fb7ab0dbc7e38cb400039fc4fb426c"},
-]
-identify = [
-    {file = "identify-2.5.3-py2.py3-none-any.whl", hash = "sha256:25851c8c1370effb22aaa3c987b30449e9ff0cece408f810ae6ce408fdd20893"},
-    {file = "identify-2.5.3.tar.gz", hash = "sha256:887e7b91a1be152b0d46bbf072130235a8117392b9f1828446079a816a05ef44"},
-]
-idna = [
-    {file = "idna-3.3-py3-none-any.whl", hash = "sha256:84d9dd047ffa80596e0f246e2eab0b391788b0503584e8945f2368256d2735ff"},
-    {file = "idna-3.3.tar.gz", hash = "sha256:9d643ff0a55b762d5cdb124b8eaa99c66322e2157b69160bc32796e824360e6d"},
-]
+fsspec = []
+identify = []
+idna = []
 imagesize = [
     {file = "imagesize-1.4.1-py2.py3-none-any.whl", hash = "sha256:0d8d18d08f840c19d0ee7ca1fd82490fdc3729b7ac93f49870406ddde8ef8d8b"},
     {file = "imagesize-1.4.1.tar.gz", hash = "sha256:69150444affb9cb0d5cc5a92b3676f0b2fb7cd9ae39e947a5e11a36b4497cd4a"},
@@ -1933,18 +1885,12 @@ invoke = [
     {file = "invoke-1.7.1-py3-none-any.whl", hash = "sha256:2dc975b4f92be0c0a174ad2d063010c8a1fdb5e9389d69871001118b4fcac4fb"},
     {file = "invoke-1.7.1.tar.gz", hash = "sha256:7b6deaf585eee0a848205d0b8c0014b9bf6f287a8eb798818a642dff1df14b19"},
 ]
-ipykernel = [
-    {file = "ipykernel-6.15.2-py3-none-any.whl", hash = "sha256:59183ef833b82c72211aace3fb48fd20eae8e2d0cae475f3d5c39d4a688e81ec"},
-    {file = "ipykernel-6.15.2.tar.gz", hash = "sha256:e7481083b438609c9c8a22d6362e8e1bc6ec94ba0741b666941e634f2d61bdf3"},
-]
+ipykernel = []
 ipython = [
     {file = "ipython-7.34.0-py3-none-any.whl", hash = "sha256:c175d2440a1caff76116eb719d40538fbb316e214eda85c5515c303aacbfb23e"},
     {file = "ipython-7.34.0.tar.gz", hash = "sha256:af3bdb46aa292bce5615b1b2ebc76c2080c5f77f54bda2ec72461317273e7cd6"},
 ]
-ipywidgets = [
-    {file = "ipywidgets-8.0.1-py3-none-any.whl", hash = "sha256:fc0744df3a964ecfd68a6d2debe547fe89db252b8d7bb3db5740aba72edb0e6c"},
-    {file = "ipywidgets-8.0.1.tar.gz", hash = "sha256:1a296094203309e834f2781a275214d255ac5d266bbfa602f9f6915e1806614c"},
-]
+ipywidgets = []
 isort = [
     {file = "isort-5.10.1-py3-none-any.whl", hash = "sha256:6f62d78e2f89b4500b080fe3a81690850cd254227f27f75c3a0c491a1f351ba7"},
     {file = "isort-5.10.1.tar.gz", hash = "sha256:e8443a5e7a020e9d7f97f1d7d9cd17c88bcb3bc7e218bf9cf5095fe550be2951"},
@@ -1969,10 +1915,7 @@ jupyter-core = [
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     {file = "jupyter_core-4.11.1.tar.gz", hash = "sha256:2e5f244d44894c4154d06aeae3419dd7f1b0ef4494dc5584929b398c61cfd314"},
 ]
-jupyterlab-widgets = [
-    {file = "jupyterlab_widgets-3.0.2-py3-none-any.whl", hash = "sha256:98303a281f4004670cdcea2ef4aecba19c580adc297664c593f967025625c8c5"},
-    {file = "jupyterlab_widgets-3.0.2.tar.gz", hash = "sha256:47ab54cd165aa0cb3bcef1232d77471580cd2c36bbe2153fc5ba31e26ad87320"},
-]
+jupyterlab-widgets = []
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-    {file = "regex-2022.8.17-cp39-cp39-musllinux_1_1_x86_64.whl", hash = "sha256:a25d251546acb5edb1635631c4ae0e330fa4ec7c6316c01d256728fbfb9bbff2"},
-    {file = "regex-2022.8.17-cp39-cp39-win32.whl", hash = "sha256:fac611bde2609a46fcbd92da7171286faa2f5c191f84d22f61cd7dc27213f51d"},
-    {file = "regex-2022.8.17-cp39-cp39-win_amd64.whl", hash = "sha256:ccb986e80674c929f198464bce55e995178dea26833421e2479ff04a6956afac"},
-    {file = "regex-2022.8.17.tar.gz", hash = "sha256:5c77eab46f3a2b2cd8bbe06467df783543bf7396df431eb4a144cc4b89e9fb3c"},
-]
 requests = [
     {file = "requests-2.28.1-py3-none-any.whl", hash = "sha256:8fefa2a1a1365bf5520aac41836fbee479da67864514bdb821f31ce07ce65349"},
     {file = "requests-2.28.1.tar.gz", hash = "sha256:7c5599b102feddaa661c826c56ab4fee28bfd17f5abca1ebbe3e7f19d7c97983"},
@@ -2852,10 +2579,7 @@ snowballstemmer = [
     {file = "snowballstemmer-2.2.0-py2.py3-none-any.whl", hash = "sha256:c8e1716e83cc398ae16824e5572ae04e0d9fc2c6b985fb0f900f5f0c96ecba1a"},
     {file = "snowballstemmer-2.2.0.tar.gz", hash = "sha256:09b16deb8547d3412ad7b590689584cd0fe25ec8db3be37788be3810cbf19cb1"},
 ]
-sphinx = [
-    {file = "Sphinx-5.1.1-py3-none-any.whl", hash = "sha256:309a8da80cb6da9f4713438e5b55861877d5d7976b69d87e336733637ea12693"},
-    {file = "Sphinx-5.1.1.tar.gz", hash = "sha256:ba3224a4e206e1fbdecf98a4fae4992ef9b24b85ebf7b584bb340156eaf08d89"},
-]
+sphinx = []
 sphinxcontrib-applehelp = [
     {file = "sphinxcontrib-applehelp-1.0.2.tar.gz", hash = "sha256:a072735ec80e7675e3f432fcae8610ecf509c5f1869d17e2eecff44389cdbc58"},
     {file = "sphinxcontrib_applehelp-1.0.2-py2.py3-none-any.whl", hash = "sha256:806111e5e962be97c29ec4c1e7fe277bfd19e9652fb1a4392105b43e01af885a"},
@@ -2895,10 +2619,7 @@ tomli = [
     {file = "tomli-2.0.1-py3-none-any.whl", hash = "sha256:939de3e7a6161af0c887ef91b7d41a53e7c5a1ca976325f429cb46ea9bc30ecc"},
     {file = "tomli-2.0.1.tar.gz", hash = "sha256:de526c12914f0c550d15924c62d72abc48d6fe7364aa87328337a31007fe8a4f"},
 ]
-tomlkit = [
-    {file = "tomlkit-0.11.4-py3-none-any.whl", hash = "sha256:25d4e2e446c453be6360c67ddfb88838cfc42026322770ba13d1fbd403a93a5c"},
-    {file = "tomlkit-0.11.4.tar.gz", hash = "sha256:3235a9010fae54323e727c3ac06fb720752fe6635b3426e379daec60fbd44a83"},
-]
+tomlkit = []
 toolz = [
     {file = "toolz-0.12.0-py3-none-any.whl", hash = "sha256:2059bd4148deb1884bb0eb770a3cde70e7f954cfbbdc2285f1f2de01fd21eb6f"},
     {file = "toolz-0.12.0.tar.gz", hash = "sha256:88c570861c440ee3f2f6037c4654613228ff40c93a6c25e0eba70d17282c6194"},
@@ -2917,13 +2638,10 @@ tornado = [
     {file = "tornado-6.2.tar.gz", hash = "sha256:9b630419bde84ec666bfd7ea0a4cb2a8a651c2d5cccdbdd1972a0c859dfc3c13"},
 ]
 tqdm = [
-    {file = "tqdm-4.64.0-py2.py3-none-any.whl", hash = "sha256:74a2cdefe14d11442cedf3ba4e21a3b84ff9a2dbdc6cfae2c34addb2a14a5ea6"},
-    {file = "tqdm-4.64.0.tar.gz", hash = "sha256:40be55d30e200777a307a7585aee69e4eabb46b4ec6a4b4a5f2d9f11e7d5408d"},
-]
-traitlets = [
-    {file = "traitlets-5.3.0-py3-none-any.whl", hash = "sha256:65fa18961659635933100db8ca120ef6220555286949774b9cfc106f941d1c7a"},
-    {file = "traitlets-5.3.0.tar.gz", hash = "sha256:0bb9f1f9f017aa8ec187d8b1b2a7a6626a2a1d877116baba52a129bfa124f8e2"},
+    {file = "tqdm-4.64.1-py2.py3-none-any.whl", hash = "sha256:6fee160d6ffcd1b1c68c65f14c829c22832bc401726335ce92c52d395944a6a1"},
+    {file = "tqdm-4.64.1.tar.gz", hash = "sha256:5f4f682a004951c1b450bc753c710e9280c5746ce6ffedee253ddbcbf54cf1e4"},
 ]
+traitlets = []
 typed-ast = [
     {file = "typed_ast-1.4.3-cp35-cp35m-manylinux1_i686.whl", hash = "sha256:2068531575a125b87a41802130fa7e29f26c09a2833fea68d9a40cf33902eba6"},
     {file = "typed_ast-1.4.3-cp35-cp35m-manylinux1_x86_64.whl", hash = "sha256:c907f561b1e83e93fad565bac5ba9c22d96a54e7ea0267c708bffe863cbe4075"},
@@ -2964,10 +2682,7 @@ urllib3 = [
     {file = "urllib3-1.26.12-py2.py3-none-any.whl", hash = "sha256:b930dd878d5a8afb066a637fbb35144fe7901e3b209d1cd4f524bd0e9deee997"},
     {file = "urllib3-1.26.12.tar.gz", hash = "sha256:3fa96cf423e6987997fc326ae8df396db2a8b7c667747d47ddd8ecba91f4a74e"},
 ]
-virtualenv = [
-    {file = "virtualenv-20.16.4-py3-none-any.whl", hash = "sha256:035ed57acce4ac35c82c9d8802202b0e71adac011a511ff650cbcf9635006a22"},
-    {file = "virtualenv-20.16.4.tar.gz", hash = "sha256:014f766e4134d0008dcaa1f95bafa0fb0f575795d07cae50b1bee514185d6782"},
-]
+virtualenv = []
 wcwidth = [
     {file = "wcwidth-0.2.5-py2.py3-none-any.whl", hash = "sha256:beb4802a9cebb9144e99086eff703a642a13d6a0052920003a230f3294bbe784"},
     {file = "wcwidth-0.2.5.tar.gz", hash = "sha256:c4d647b99872929fdb7bdcaa4fbe7f01413ed3d98077df798530e5b04f116c83"},
@@ -2976,10 +2691,7 @@ webencodings = [
     {file = "webencodings-0.5.1-py2.py3-none-any.whl", hash = "sha256:a0af1213f3c2226497a97e2b3aa01a7e4bee4f403f95be16fc9acd2947514a78"},
     {file = "webencodings-0.5.1.tar.gz", hash = "sha256:b36a1c245f2d304965eb4e0a82848379241dc04b865afcc4aab16748587e1923"},
 ]
-widgetsnbextension = [
-    {file = "widgetsnbextension-4.0.2-py3-none-any.whl", hash = "sha256:966bd61443926b6adcc0abef9f499c48bdeda181c333b0f49842d7385d440579"},
-    {file = "widgetsnbextension-4.0.2.tar.gz", hash = "sha256:07f0e8582f920b24316cef16490f1aeb498f2c875d48980540e5c5dbf0ff5e2d"},
-]
+widgetsnbextension = []
 wrapt = [
     {file = "wrapt-1.14.1-cp27-cp27m-macosx_10_9_x86_64.whl", hash = "sha256:1b376b3f4896e7930f1f772ac4b064ac12598d1c38d04907e696cc4d794b43d3"},
     {file = "wrapt-1.14.1-cp27-cp27m-manylinux1_i686.whl", hash = "sha256:903500616422a40a98a5a3c4ff4ed9d0066f3b4c951fa286018ecdf0750194ef"},
diff --git a/pyproject.toml b/pyproject.toml
index a65bc32..bc711a8 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -1,6 +1,6 @@
 [tool.poetry]
 name = "reaction_utils"
-version = "1.1.1"
+version = "1.2.0"
 description = "Utilities for working with reactions, reaction templates and template extraction"
 authors = ["Genheden, Samuel <samuel.genheden@astrazeneca.com>", "Kannas, Christos <christos.kannas@astrazeneca.com>"]
 license = "Apache-2.0"
@@ -33,7 +33,7 @@ pytest-mock = "^3.7.0"
 pytest-mccabe = "^2.0"
 pytest-black = "^0.3.12"
 pytest-cov = "^3.0.0"
-black = "^20.8b1"
+black = "^22.0.0"
 mypy = "^0.800"
 pre-commit = "^2.10.1"
 ipython = "^7.21.0"
diff --git a/rxnutils/chem/reaction.py b/rxnutils/chem/reaction.py
index b9990b6..d45bbf5 100644
--- a/rxnutils/chem/reaction.py
+++ b/rxnutils/chem/reaction.py
@@ -1,6 +1,6 @@
 """Module containing a class to handle chemical reactions"""
 import hashlib
-from typing import List, Tuple, Optional
+from typing import List, Tuple, Optional, Dict, Any
 
 import wrapt_timeout_decorator
 from rdkit import Chem
@@ -136,7 +136,10 @@ def rinchi_key_short(self) -> str:
         return self._rinchi_data.short_rinchikey
 
     def generate_reaction_template(
-        self, radius: int = 1
+        self,
+        radius: int = 1,
+        expand_ring: bool = False,
+        expand_hetero: bool = False,
     ) -> Tuple[ReactionTemplate, ReactionTemplate]:
         """
         Extracts the forward(canonical) and retro reaction template with the specified radius.
@@ -148,6 +151,8 @@ def generate_reaction_template(
         :param radius: the radius refers to the number of atoms away from the reaction
                        centre to be extracted (the enivronment) i.e. radius = 1 (default)
                        returns the first neighbours around the reaction centre
+        :param expand_ring: if True will include all atoms in the same ring as the reaction centre in the template
+        :param expand_hetero: if True will extend the template with all bonded hetero atoms
         :returns: the canonical and retrosynthetic templates
         """
         if not self.sanitization_check():
@@ -207,12 +212,26 @@ def generate_reaction_template(
                 sorted(list(set(extra_reactant_fragment.split("."))))
             )
 
+        extra_atoms = {}
+        if expand_ring:
+            ring_atom_maps = self._product_unique_ring_atoms()
+            for reactant in self.reactants:
+                extra_atoms.update(
+                    {
+                        str(atom.GetAtomMapNum()): atom
+                        for atom in reactant.GetAtoms()
+                        if atom.GetAtomMapNum() in ring_atom_maps
+                    }
+                )
+
         try:
             # Generate canonical reaction template with rdChiral
             canonical_smarts = self._generate_rdchiral_template(
                 reactants=reactants,
                 products=products,
                 radius=radius,
+                extra_atoms=extra_atoms,
+                expand_hetero=expand_hetero,
             )
             # Canonical ReactionTemplate
             self._canonical_template = ReactionTemplate(canonical_smarts)
@@ -244,7 +263,11 @@ def generate_reaction_template(
         exception_message="Timed out",
     )
     def _generate_rdchiral_template(
-        reactants: List[Chem.Mol], products: List[Chem.Mol], radius: int = 1
+        reactants: List[Chem.Mol],
+        products: List[Chem.Mol],
+        radius: int = 1,
+        extra_atoms: Dict[str, Any] = None,
+        expand_hetero: bool = False,
     ) -> str:
         """Generate a reaction template with rdChiral.
 
@@ -256,9 +279,22 @@ def _generate_rdchiral_template(
         :raises ReactionException: Template generation failed: Timed out
         :return: Canonical reaction template
         """
-        _, changed_atom_tags, err = extractor.get_changed_atoms(
+        changed_atoms, changed_atom_tags, err = extractor.get_changed_atoms(
             reactants=reactants, products=products
         )
+
+        if expand_hetero:
+            for atom in changed_atoms:
+                for atom2 in atom.GetNeighbors():
+                    if atom2.GetSymbol() not in ["C", "H"] and atom2.GetAtomMapNum():
+                        extra_atoms[str(atom2.GetAtomMapNum())] = atom2
+
+        old_tags = list(changed_atom_tags)
+        for atom_num, atom in extra_atoms.items():
+            if atom_num not in old_tags:
+                changed_atoms.append(atom)
+                changed_atom_tags.append(atom_num)
+
         if err:
             raise ReactionException(
                 "Template generation failed: could not obtained changed atoms"
@@ -520,6 +556,29 @@ def _join_components(self, list_: List[str]) -> str:
         """
         return ".".join([f"({item})" if "." in item else item for item in list_])
 
+    def _product_unique_ring_atoms(self) -> List[int]:
+        def find_ring_atom_maps(mol):
+            ring_atoms_sets = []
+            for ring in mol.GetRingInfo().AtomRings():
+                ring_atoms_sets.append(
+                    tuple(
+                        sorted(mol.GetAtomWithIdx(idx).GetAtomMapNum() for idx in ring)
+                    )
+                )
+            return ring_atoms_sets
+
+        reactant_ring_atom_sets = []
+        for reactant in self.reactants:
+            reactant_ring_atom_sets.extend(find_ring_atom_maps(reactant))
+
+        product_ring_atom_sets = []
+        for product in self.products:
+            for set_ in find_ring_atom_maps(product):
+                if set_ not in reactant_ring_atom_sets:
+                    product_ring_atom_sets.append(set_)
+
+        return [idx for ring_atoms in product_ring_atom_sets for idx in ring_atoms]
+
     def _split_reaction(self) -> None:
         """
         This function is used instead of `_clean_reaction` if cleaning is not required.
diff --git a/rxnutils/pipeline/actions/reaction_props.py b/rxnutils/pipeline/actions/reaction_props.py
index 9bd8475..162d406 100644
--- a/rxnutils/pipeline/actions/reaction_props.py
+++ b/rxnutils/pipeline/actions/reaction_props.py
@@ -3,12 +3,14 @@
 
 import json
 from collections import defaultdict
-from typing import ClassVar, Tuple, List
+from typing import ClassVar, Tuple, List, Set
 
 from dataclasses import dataclass
 import pandas as pd
 from rdkit import RDLogger
 from rdkit import Chem
+from rdkit.Chem.rdMolDescriptors import CalcNumRings
+from rdkit.Chem import Descriptors
 
 from rxnutils.pipeline.base import action, global_apply, ReactionActionMixIn
 from rxnutils.chem.utils import (
@@ -122,6 +124,95 @@ def _row_action(self, row: pd.Series) -> str:
         return "@" in smiles
 
 
+@action
+@dataclass
+class HasUnmappedRadicalAtom:
+    """Action for flagging if reaction has any unmapped radical atoms"""
+
+    pretty_name: ClassVar[str] = "hasunmappedradicalatom"
+    in_column: str
+    out_column: str = "HasUnmappedRadicalAtom"
+
+    def __call__(self, df: pd.DataFrame) -> pd.DataFrame:
+        smiles_col = global_apply(df, self._row_action, axis=1)
+        return df.assign(**{self.out_column: smiles_col})
+
+    def __str__(self) -> str:
+        return f"{self.pretty_name} (detect if there is an unmapped radical in the reaction SMILES)"
+
+    def _row_action(self, row: pd.Series) -> str:
+        reactants, _, product = row["rsmi_processed"].split(">")
+
+        react_mol = Chem.MolFromSmiles(reactants)
+        if Descriptors.NumRadicalElectrons(react_mol) == 0:
+            return False
+
+        prod_mol = Chem.MolFromSmiles(product)
+        unmapped_product_atom_element = None
+        for atom in prod_mol.GetAtoms():
+            if atom.GetAtomMapNum() == 0:
+                unmapped_product_atom_element = atom.GetAtomicNum()
+                break
+
+        if unmapped_product_atom_element is None:
+            return False
+
+        has_radical = False
+        for atom in react_mol.GetAtoms():
+            if (
+                atom.GetAtomMapNum() == 0
+                and atom.GetNumRadicalElectrons() > 0
+                and atom.GetAtomicNum() == unmapped_product_atom_element
+            ):
+                has_radical = True
+                break
+        return has_radical
+
+
+@action
+@dataclass
+class HasUnsanitizableReactants:
+    """Action for flagging if reaction has any unsanitizable reactants"""
+
+    pretty_name: ClassVar[str] = "unsanitizablereactants"
+    rsmi_column: str
+    bad_columns: List[str]
+    out_column: str = "HasUnsanitizableReactants"
+
+    def __call__(self, df: pd.DataFrame) -> pd.DataFrame:
+        smiles_col = global_apply(df, self._row_action, axis=1)
+        return df.assign(**{self.out_column: smiles_col})
+
+    def __str__(self) -> str:
+        return f"{self.pretty_name} (detect if there is unsanitizable reactants)"
+
+    def _row_action(self, row: pd.Series) -> str:
+        unsanitize_atom_map_num = set()
+        for column in self.bad_columns:
+            if not isinstance(row[column], str):
+                continue
+            unsanitize_atom_map_num |= self._process_bad_column(row[column])
+
+        if not unsanitize_atom_map_num:
+            return False
+
+        _, _, product = row[self.rsmi_column].split(">")
+        prod_atom_map_num = set(atom_mapping_numbers(product))
+        return bool(prod_atom_map_num.intersection(unsanitize_atom_map_num))
+
+    @staticmethod
+    def _process_bad_column(smiles_list: str) -> Set[int]:
+        unsanitize_atom_map_num = set()
+        for smiles in smiles_list.split(","):
+            mol = Chem.MolFromSmiles(smiles, sanitize=False)
+            if not mol:
+                continue
+            unsanitize_atom_map_num |= {
+                atom.GetAtomMapNum() for atom in mol.GetAtoms() if atom.GetAtomMapNum()
+            }
+        return unsanitize_atom_map_num
+
+
 @action
 @dataclass
 class ProductAtomMappingStats:
@@ -309,6 +400,147 @@ def _row_action(self, row: pd.Series) -> str:
         return reactant_atom_count
 
 
+@action
+@dataclass
+class RingNumberChange:
+    """
+    Action for calculating if reaction has change in number of rings
+
+    A positive number from this action implies that a ring was formed during the reaction
+    """
+
+    pretty_name: ClassVar[str] = "ringnumberchange"
+    in_column: str
+    out_column: str = "NRingChange"
+
+    def __call__(self, df: pd.DataFrame) -> pd.DataFrame:
+        smiles_col = global_apply(df, self._row_action, axis=1)
+        return df.assign(**{self.out_column: smiles_col})
+
+    def __str__(self) -> str:
+        return f"{self.pretty_name} (ring change based on number of rings)"
+
+    def _row_action(self, row: pd.Series) -> str:
+        reactants, _, products = row[self.in_column].split(">")
+        prod_mol = Chem.MolFromSmiles(products)
+
+        if not prod_mol:
+            return False
+
+        reactants_mols = [Chem.MolFromSmiles(smi) for smi in reactants.split(".")]
+        nrings_reactants = sum(CalcNumRings(mol) for mol in reactants_mols if mol)
+        nrings_product = CalcNumRings(prod_mol)
+        return nrings_product - nrings_reactants
+
+
+@action
+@dataclass
+class RingBondMade:
+    """Action for flagging if reaction has made a ring bond in the product"""
+
+    pretty_name: ClassVar[str] = "ringbondmade"
+    in_column: str
+    out_column: str = "RingBondMade"
+
+    def __call__(self, df: pd.DataFrame) -> pd.DataFrame:
+        smiles_col = global_apply(df, self._row_action, axis=1)
+        return df.assign(**{self.out_column: smiles_col})
+
+    def __str__(self) -> str:
+        return f"{self.pretty_name} (ring change based on ring bond made)"
+
+    def _row_action(self, row: pd.Series) -> str:
+        reactants, _, products = row[self.in_column].split(">")
+
+        prod_mol = Chem.MolFromSmiles(products)
+        if not prod_mol:
+            return False
+        ring_bonds = [
+            (bond.GetBeginAtom().GetAtomMapNum(), bond.GetEndAtom().GetAtomMapNum())
+            for bond in prod_mol.GetBonds()
+            if bond.IsInRing()
+        ]
+
+        for smiles in split_smiles_from_reaction(reactants):
+            reactant_mol = Chem.MolFromSmiles(smiles)
+            if not reactant_mol:
+                continue
+            r_mappings = self._mapping_to_index(reactant_mol)
+            for atom_map1, atom_map2 in ring_bonds:
+                if atom_map1 not in r_mappings and atom_map2 not in r_mappings:
+                    continue
+
+                # If not both of the atoms are in the same molecule the bond is new
+                if atom_map1 not in r_mappings and atom_map2 in r_mappings:
+                    return True
+                if atom_map2 not in r_mappings and atom_map1 in r_mappings:
+                    return True
+
+                atom_idx1 = r_mappings[atom_map1]
+                atom_idx2 = r_mappings[atom_map2]
+                bond = reactant_mol.GetBondBetweenAtoms(atom_idx1, atom_idx2)
+                if bond is None or not bond.IsInRing():
+                    return True
+        return False
+
+    @staticmethod
+    def _mapping_to_index(mol):
+        return {
+            atom.GetAtomMapNum(): atom.GetIdx()
+            for atom in mol.GetAtoms()
+            if atom.GetAtomMapNum()
+        }
+
+
+@action
+@dataclass
+class RingMadeSize:
+    """Action for computing the size of a newly formed ring"""
+
+    pretty_name: ClassVar[str] = "ringmadesize"
+    in_column: str
+    out_column: str = "RingMadeSize"
+
+    def __call__(self, df: pd.DataFrame) -> pd.DataFrame:
+        smiles_col = global_apply(df, self._row_action, axis=1)
+        return df.assign(**{self.out_column: smiles_col})
+
+    def __str__(self) -> str:
+        return f"{self.pretty_name} (largest ring made)"
+
+    def _row_action(self, row: pd.Series) -> str:
+        reactants, _, products = row[self.in_column].split(">")
+
+        prod_mol = Chem.MolFromSmiles(products)
+        if not prod_mol:
+            return None
+
+        reactant_rings = []
+        for smiles in split_smiles_from_reaction(reactants):
+            reactant_mol = Chem.MolFromSmiles(smiles)
+            if not reactant_mol:
+                continue
+
+            reactant_rings.extend(self._find_rings(reactant_mol))
+
+        largest_made_ring = 0
+        for ring in self._find_rings(prod_mol):
+            if ring not in reactant_rings:
+                largest_made_ring = max(largest_made_ring, len(ring))
+        return largest_made_ring
+
+    @staticmethod
+    def _find_rings(mol):
+        rings = []
+        for ring in mol.GetRingInfo().AtomRings():
+            ring_atoms = [mol.GetAtomWithIdx(idx).GetAtomMapNum() for idx in ring]
+            # Only consider at least partially atom-mapped rings
+            if set(ring_atoms) == {0}:
+                continue
+            rings.append(tuple(sorted(ring_atoms)))
+        return rings
+
+
 @action
 @dataclass
 class SmilesLength:
diff --git a/tests/data/example_ring_reactions.csv b/tests/data/example_ring_reactions.csv
new file mode 100644
index 0000000..c675111
--- /dev/null
+++ b/tests/data/example_ring_reactions.csv
@@ -0,0 +1,3 @@
+rsmi
+[CH3:1][C:2](=[O:3])[C:4]#[CH:15].[N-:5]=[N+:6]=[CH:7][C:8](=[O:9])[O:10][C:11]>>[CH3:1][C:2](=[O:3])[c:4]1[n:5][nH:6][c:7]([C:8](=[O:9])[O:10][C:11])[cH:15]1
+Br[CH2:9][CH2:10][CH2:11]Br.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]#[N:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([C:7]#[N:8])[CH2:9][CH2:10][CH2:11]1
\ No newline at end of file
diff --git a/tests/test_reaction.py b/tests/test_reaction.py
index bbdee6a..26a1591 100644
--- a/tests/test_reaction.py
+++ b/tests/test_reaction.py
@@ -245,3 +245,29 @@ def test_timedout_template_creation():
         ReactionException, match="Template generation failed with message: Timed out"
     ):
         rxn.generate_reaction_template()
+
+
+def test_ringbreaker_template_creation():
+    rsmi = (
+        "[Cl:2][C:4]#[CH:15].[N-:5]=[N+:6]=[CH:7][C:8](=[O:9])[O:10][CH3:11]>>"
+        "[Cl:2][c:4]1[n:5][nH:6][c:7]([C:8](=[O:9])[O:10][CH3:11])[cH:15]1"
+    )
+    rxn = ChemicalReaction(rsmi, clean_smiles=False)
+
+    _, retro_template = rxn.generate_reaction_template(
+        radius=0, expand_ring=True, expand_hetero=True
+    )
+    expected = (
+        "[Cl;H0;D1;+0:3]-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[c;H0;D3;+0:4]:[nH;D2;+0:5]:[n;H0;D2;+0:6]:1>>"
+        "[CH;D1;+0:1]#[C;H0;D2;+0:2]-[Cl;H0;D1;+0:3].[CH;D2;+0:4]=[N+;H0;D2:5]=[N-;H0;D1:6]"
+    )
+    assert retro_template.smarts == expected
+
+    _, retro_template = rxn.generate_reaction_template(
+        radius=0, expand_ring=True, expand_hetero=False
+    )
+    expected = (
+        "[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3]:[nH;D2;+0:4]:[n;H0;D2;+0:5]:1"
+        ">>[C;H0;D2;+0:1]#[CH;D1;+0:2].[CH;D2;+0:3]=[N+;H0;D2:4]=[N-;H0;D1:5]"
+    )
+    assert retro_template.smarts == expected
diff --git a/tests/test_reaction_props_actions.py b/tests/test_reaction_props_actions.py
index a57ea7e..facecdb 100644
--- a/tests/test_reaction_props_actions.py
+++ b/tests/test_reaction_props_actions.py
@@ -1,8 +1,11 @@
 import json
 
+import pandas as pd
+
 from rxnutils.pipeline.actions.reaction_props import (
     CountComponents,
     CountElements,
+    HasUnsanitizableReactants,
     ProductAtomMappingStats,
     ProductSize,
     PseudoReactionHash,
@@ -10,7 +13,11 @@
     ReactantSize,
     SmilesLength,
     SmilesSanitizable,
+    RingBondMade,
+    RingMadeSize,
+    RingNumberChange,
 )
+from rxnutils.pipeline.actions.reaction_mod import RemoveUnsanitizable
 from rxnutils.pipeline.base import global_apply
 
 global_apply.max_workers = 1
@@ -112,3 +119,42 @@ def test_smiles_sanitizable(make_reaction_dataframe):
     df2 = action(df)
 
     assert df2["SmilesSanitizable"].to_list() == [False, True]
+
+
+def test_unsanitizable_reactants(make_reaction_dataframe):
+    action1 = RemoveUnsanitizable(in_column="rsmi")
+    action2 = HasUnsanitizableReactants(
+        rsmi_column="rsmi", bad_columns=["BadMolecules"]
+    )
+    df = make_reaction_dataframe
+
+    df2 = action1(df)
+    df3 = action2(df2)
+
+    assert df3["HasUnsanitizableReactants"].to_list() == [False, False]
+
+
+def test_ring_actions(shared_datadir):
+    df = pd.read_csv(shared_datadir / "example_ring_reactions.csv")
+    action1 = RingBondMade(in_column="rsmi")
+    action2 = RingMadeSize(in_column="rsmi")
+    action3 = RingNumberChange(in_column="rsmi")
+
+    df2 = action3(action2(action1(df)))
+
+    assert df2["NRingChange"].to_list() == [1, 1]
+    assert df2["RingBondMade"].to_list() == [True, True]
+    assert df2["RingMadeSize"].to_list() == [5, 4]
+
+
+def test_ring_actions_no_rings(make_reaction_dataframe):
+    df = make_reaction_dataframe
+    action1 = RingBondMade(in_column="rsmi")
+    action2 = RingMadeSize(in_column="rsmi")
+    action3 = RingNumberChange(in_column="rsmi")
+
+    df2 = action3(action2(action1(df)))
+
+    assert df2["NRingChange"].to_list() == [0, 0]
+    assert df2["RingBondMade"].to_list() == [False, False]
+    assert df2["RingMadeSize"].to_list() == [0, 0]