MASSA-Algorithm 2.2.0__py3-none-any.whl → 2.2.2__py3-none-any.whl

{massa_algorithm-2.2.0.dist-info → massa_algorithm-2.2.2.dist-info}/METADATA

@@ -1,180 +1,183 @@
-Metadata-Version: 2.4
-Name: MASSA_Algorithm
-Version: 2.2.0
-Summary: MASSA Algorithm is a Python package to separate data sets of molecules into training and test sets, considering the diversity of structural, physicochemical and biological characteristics of these molecules.
-Home-page: https://github.com/gcverissimo/MASSA_Algorithm
-Author: Gabriel Corrêa Veríssimo
-Author-email: gcverissimo@outlook.com
-License: AGPLv3
-Keywords: chemoinformatics,training,test,training-test,dataset preparation,data set preparation,rdkit
-Classifier: Programming Language :: Python :: 3
-Classifier: Programming Language :: Python :: 3.8
-Classifier: Programming Language :: Python :: 3.9
-Classifier: Programming Language :: Python :: 3.10
-Classifier: Programming Language :: Python :: 3.11
-Classifier: License :: OSI Approved :: GNU Affero General Public License v3
-Classifier: Operating System :: OS Independent
-Classifier: Topic :: Scientific/Engineering :: Chemistry
-Requires-Python: >=3.8
-Description-Content-Type: text/markdown
-License-File: LICENSE
-Requires-Dist: numpy
-Requires-Dist: rdkit
-Requires-Dist: pandas
-Requires-Dist: matplotlib>=3.2
-Requires-Dist: scipy>=1.6
-Requires-Dist: scikit-learn>0.24
-Requires-Dist: kmodes>=0.10
-Dynamic: author
-Dynamic: author-email
-Dynamic: classifier
-Dynamic: description
-Dynamic: description-content-type
-Dynamic: home-page
-Dynamic: keywords
-Dynamic: license
-Dynamic: license-file
-Dynamic: requires-dist
-Dynamic: requires-python
-Dynamic: summary
-
-# MASSA Algorithm
-MASSA Algorithm: A tool for separating data sets of molecules into training and test sets. Developed with the objective of preparing data sets for the generation of prediction models in cheminformatics.
-
-
-## Version 1.0.0
-- Version 1.0.0 includes a code refactoring and adds the ability to split data into training, test, and validation subsets.
-
-## Version 2.0.0
-- Version 2.0.0 introduces algorithm changes to better handle large datasets. Specifically, for datasets with 10,000 molecules or more, Hierarchical Clustering Analysis (HCA) is automatically replaced by MiniBatch K-Means. This is the new default behavior, but it can be controlled using the flag -a / --large-datasets. Since dendrograms are generated from HCA, dendrogram plotting is disabled for large datasets. In such cases, the flag -f / --dendrogram-plot is automatically disabled, regardless of user input.
-
-- This version introduces the ability to call the MASSA Algorithm from any Python script using MASSA_Algorithm.pyMASSA.py_massa(). However, instructions and documentation for doing so will be provided in future updates.
-
-- Version 2.0.0 also addresses the "NaN/None values in y" error, which was caused by duplicate molecule names. In this version, molecules with identical names are detected and renamed by appending their original index as a suffix to ensure uniqueness.
-
-- MASSA now preserves the input order of molecules in its output. However, molecules with chemical errors are skipped and excluded from the process. 
-
-## Instalation
-MASSA Algorithm can be installed using pip:
-```
-pip install MASSA_Algorithm
-```
-To upgrade to the latest version (recommended), also use pip:
-```
-pip install --upgrade MASSA_Algorithm
-```
-Alternatively, you can build the latest development version from source:
-```
-git clone https://github.com/gcverissimo/MASSA_Algorithm.git
-cd MASSA_Algorithm
-python setup.py install
-```
-### Requirements
-* python: >= 3.8;
-* rdkit;
-* numpy;
-* pandas;
-* matplotlib: >= 3.2;
-* scipy: >= 1.6;
-* scikit-learn: > 0.24;
-* kmodes:¹ >= 0.10.
-
-NOTE: Also tested on: scikit-learn: 1.7.0, scipy: 1.16.1, numpy: 2.0.2, rdkit: 2025.03.5.
-
-## Usage
-Once installed, the program can be run directly from the command line:
-```
-MASSA_Algorithm -i <input_file>.sdf -o <output_file>.sdf
-```
-
-Required arguments:
-* **Input file**: ```-i``` or ```--input```.
-    * MASSA Algorithm accepts input files in the formats: .sdf, .mol, .mol2, .xlsx, .xls, and .csv. However, the .sdf format is preferred. Notes:
-        * .mol2 files have limitations in storing molecular properties and follow different saving patterns. Due to this, we only support .mol2 files that are generated by Discovery Studio Visualizer.
-        * For .xlsx, .xls, and .csv:
-            * MASSA will look for a column with smiles in the name and use it as the source of input molecules.
-            * MASSA will look for a column with one of the following names in the priority order: Molecule name, Name, Molecule ChEMBL ID, or ID. If none of these columns are found, it will use the molecule index.
-* **Output file**: ```-o``` or ```--output```.
-    * Enter the output file name or file path. Image files will be saved to a folder within the same directory as the output file.
-    * It is highly recommended to use an .sdf file to avoid errors.
-
-Optional arguments include:
-* **Splitting strategy**: ```-y``` or ```--splitting_strategy```.
-    * Defines the splitting strategy, either into training and test sets or into training, test, and validation sets.
-    * Options = 'tt', 'tt-val'.
-    * 'tt', means splitting into training and test sets. 'tt-val', means splitting into training, test, and validation sets.
-    * Default = 'tt'.
-* **Percentage of molecules in training set**: ```-p``` or ```--percentage_of_training```.
-    * Percentage of molecules in training set. Must be a number from 0 to 1.
-    * Default = 0.8.
-* **Number of biological activities for separation**: ```-b``` or ```--number_of_biological```.
-    * Number of biological activities that will be used to separate the set into training and test.
-    * Default = 1.
-* **Name of biological activities for separation**: ```-s``` or ```--the_biological_activities```.
-    * The biological activity(ies) or other y-property(ies) used for QSAR or machine learning modeling. The algorithm can handle one or more properties. Enter a list with the names of biological activities separated by commas and no spaces. These properties must be represented as either integers or floating-point numbers. If your dataset is represented in classes (e.g., active or inactive; soluble, partially soluble, or insoluble), you should represent them as integers (e.g., 0 or 1; 1, 2, or 3).
-    * Example: ```MASSA_Algorithm -i <input_file>.sdf -o <output_file>.sdf -s pIC50,pMIC```.
-    * Default = If not entered directly on the command line, it will be requested during algorithm execution.
-* **Number of principal components in PCA**: ```-n``` or ```--number_of_PCs```.
-    * Defines the number of principal components to reduce the dimensionality of variables related to biological, physicochemical and structural domains. If the value is a decimal between 0 and 1, the number of principal components is what explains for (```<input number>```* 100)% of the variance. If the value is greater than 1, the number of PCs will be exactly the input integer, but PAY ATTENTION:
-
-        1) If the number of PCs is an integer and equal to or greater than the number of physicochemical properties (7), the PCA step will be bypassed for this domain.
-        2) The same for the biological domain.
-        3) If the number of biological activities is less than 3, the PCA step will be bypassed for this domain.
-    * Default = 0.85.
-* **SVD solver parameter for PCA**: ```-v``` or ```--svd_solver_for_PCA```.
-    * See the sklearn.decomposition.PCA topic on https://scikit-learn.org/stable/modules/generated/sklearn.decomposition.PCA.html for more info.
-    * Default = full.
-* **HCA linkage method**: ```-l``` or ```--linkage_method```.
-    * The linkage criterion to use. The algorithm will merge the pairs of cluster that minimize this criterion.
-    * Options = complete, single, ward, average, weighted, centroid, median. For more info, see the scipy.cluster.hierarchy.linkage topic on https://docs.scipy.org/doc/scipy/reference/generated/scipy.cluster.hierarchy.linkage.html?highlight=linkage#scipy.cluster.hierarchy.linkage.
-    * Default = complete.
-* **Extension of image files**: ```-t``` or ```--image_type```.
-    * Extension of the image files that will be generated. Suggested = png or svg.
-    * Default = png.
-* **Font size for X-axis of dendrograms**: ```-d``` or ```--dendrogram_Xfont_size```.
-    * Sets the font size on the x-axis of the dendrogram (molecule labels).
-    * Default = 5.
-* **Font size for X-axis of bar plots**: ```-x``` or ```--barplot_Xfont_size```.
-    * Sets the font size on the x-axis of the bar plot (cluster labels).
-    * Default = 12.
-* **Enable Dendrogram plot**: ```-f``` or ```--dendrogram_plot```.
-    * Defines whether or not dendrogram images will be generated.
-	* Options = true (dendrogram will be generated), false (dendrogram will not be generated).
-    * Default = true.
-* **Ignore Errors**: ```-e``` or ```--drop_errors```.
-    * Ignore chemistry errors, saving only molecules without any errors.
-	* Options = true (ignore molecule errors and log them in the log file), false (treat molecule errors as fatal and fail the execution).
-    * Default = true.
-* **Large Dataset**: ```-a``` or ```--large_dataset```.
-    * Switch the MASSA algorithm from HCA to MiniBatch-KMeans to handle large datasets.
-    * Options = auto (switches to KMeans if ≥ 10,000 molecules), false = use HCA (for smaller datasets), true = use KMeans (for large datasets).
-    * Default = auto.
-
-#### Command line help
-A full description of the arguments can also be viewed directly from the command line using the command:
-```
-MASSA_Algorithm -h
-```
-or
-```
-MASSA_Algorithm --help
-```
-
-## Cite
-1. To ensure accurate citation, kindly include a reference to the MASSA article, accessible via the DOI:
-Veríssimo, G. C.; Panteleão, S. Q.; Fernandes, P. O.; Gertrudes, J. C.; Kronenberger, T.; Honorio, K. M.; Maltarollo; V. G. MASSA Algorithm: an automated rational sampling of training and test subsets for QSAR modeling. J. Comput. Aided Mol. Des. 2023, 37, 735–754. https://doi.org/10.1007/s10822-023-00536-y.
-
-2. Furthermore, please incorporate the program citation following the provided template:
-
-```
-@Misc{veríssimo2021,
-    author = {Gabriel Corrêa Veríssimo},
-    title = {MASSA Algorithm: Molecular data set sampling for training-test separation},
-    howpublished = {\url{https://github.com/gcverissimo/MASSA_Algorithm}},
-    year = {2021}
-  }
-```
-
-## References
-[1]: DE VOS, N. J. kmodes categorical clustering library. https://github.com/nicodv/kmodes. 2015-2021.
-
+Metadata-Version: 2.4
+Name: MASSA-Algorithm
+Version: 2.2.2
+Summary: MASSA Algorithm is a Python package to separate data sets of molecules into training and test sets, considering the diversity of structural, physicochemical and biological characteristics of these molecules.
+Home-page: https://github.com/gcverissimo/MASSA_Algorithm
+Author: Gabriel Corrêa Veríssimo
+Author-email: gcverissimo@outlook.com
+License: AGPLv3
+Keywords: chemoinformatics,training,test,training-test,dataset preparation,data set preparation,rdkit
+Classifier: Programming Language :: Python :: 3
+Classifier: Programming Language :: Python :: 3.8
+Classifier: Programming Language :: Python :: 3.9
+Classifier: Programming Language :: Python :: 3.10
+Classifier: Programming Language :: Python :: 3.11
+Classifier: Programming Language :: Python :: 3.12
+Classifier: Programming Language :: Python :: 3.13
+Classifier: License :: OSI Approved :: GNU Affero General Public License v3
+Classifier: Operating System :: OS Independent
+Classifier: Topic :: Scientific/Engineering :: Chemistry
+Requires-Python: >=3.8
+Description-Content-Type: text/markdown
+License-File: LICENSE
+Requires-Dist: numpy
+Requires-Dist: rdkit
+Requires-Dist: pandas
+Requires-Dist: matplotlib>=3.2
+Requires-Dist: scipy>=1.6
+Requires-Dist: scikit-learn>0.24
+Requires-Dist: kmodes>=0.10
+Dynamic: author
+Dynamic: author-email
+Dynamic: classifier
+Dynamic: description
+Dynamic: description-content-type
+Dynamic: home-page
+Dynamic: keywords
+Dynamic: license
+Dynamic: license-file
+Dynamic: requires-dist
+Dynamic: requires-python
+Dynamic: summary
+
+# MASSA Algorithm
+MASSA Algorithm: A tool for separating data sets of molecules into training and test sets. Developed with the objective of preparing data sets for the generation of prediction models in cheminformatics.
+
+
+## Version 1.0.0
+- Version 1.0.0 includes a code refactoring and adds the ability to split data into training, test, and validation subsets.
+
+## Version 2.0.0
+- Version 2.0.0 introduces algorithm changes to better handle large datasets. Specifically, for datasets with 10,000 molecules or more, Hierarchical Clustering Analysis (HCA) is automatically replaced by MiniBatch K-Means. This is the new default behavior, but it can be controlled using the flag -a / --large-datasets. Since dendrograms are generated from HCA, dendrogram plotting is disabled for large datasets. In such cases, the flag -f / --dendrogram-plot is automatically disabled, regardless of user input.
+
+- This version introduces the ability to call the MASSA Algorithm from any Python script using MASSA_Algorithm.pyMASSA.py_massa(). However, instructions and documentation for doing so will be provided in future updates.
+
+- Version 2.0.0 also addresses the "NaN/None values in y" error, which was caused by duplicate molecule names. In this version, molecules with identical names are detected and renamed by appending their original index as a suffix to ensure uniqueness.
+
+- MASSA now preserves the input order of molecules in its output. However, molecules with chemical errors are skipped and excluded from the process. 
+
+## Instalation
+MASSA Algorithm can be installed using pip:
+```
+pip install MASSA_Algorithm
+```
+To upgrade to the latest version (recommended), also use pip:
+```
+pip install --upgrade MASSA_Algorithm
+```
+Alternatively, you can build the latest development version from source:
+```
+git clone https://github.com/gcverissimo/MASSA_Algorithm.git
+cd MASSA_Algorithm
+python setup.py install
+```
+### Requirements
+* python: >= 3.8;
+* rdkit;
+* numpy;
+* pandas;
+* matplotlib: >= 3.2;
+* scipy: >= 1.6;
+* scikit-learn: > 0.24;
+* kmodes:¹ >= 0.10.
+
+NOTE: Also tested on: scikit-learn: 1.7.0, scipy: 1.16.1, numpy: 2.0.2, rdkit: 2025.03.5.
+
+## Usage
+Once installed, the program can be run directly from the command line:
+```
+MASSA_Algorithm -i <input_file>.sdf -o <output_file>.sdf
+```
+
+Required arguments:
+* **Input file**: ```-i``` or ```--input```.
+    * MASSA Algorithm accepts input files in the formats: .sdf, .mol, .mol2, .xlsx, .xls, .csv, and .smi. However, the .sdf format is preferred. Notes:
+        * .mol2 files have limitations in storing molecular properties and follow different saving patterns. Due to this, we only support .mol2 files that are generated by Discovery Studio Visualizer.
+        * For .xlsx, .xls, .smi, and .csv:
+            * MASSA will look for a column with smiles in the name and use it as the source of input molecules.
+            * MASSA will look for a column with one of the following names in the priority order: Molecule name, Name, Molecule ChEMBL ID, or ID. If none of these columns are found, it will use the molecule index.
+            * For .smi files, the first line must contain column headers.
+* **Output file**: ```-o``` or ```--output```.
+    * Enter the output file name or file path. Image files will be saved to a folder within the same directory as the output file.
+    * It is highly recommended to use an .sdf file to avoid errors.
+
+Optional arguments include:
+* **Splitting strategy**: ```-y``` or ```--splitting_strategy```.
+    * Defines the splitting strategy, either into training and test sets or into training, test, and validation sets.
+    * Options = 'tt', 'tt-val'.
+    * 'tt', means splitting into training and test sets. 'tt-val', means splitting into training, test, and validation sets.
+    * Default = 'tt'.
+* **Percentage of molecules in training set**: ```-p``` or ```--percentage_of_training```.
+    * Percentage of molecules in training set. Must be a number from 0 to 1.
+    * Default = 0.8.
+* **Number of biological activities for separation**: ```-b``` or ```--number_of_biological```.
+    * Number of biological activities that will be used to separate the set into training and test.
+    * Default = 1.
+* **Name of biological activities for separation**: ```-s``` or ```--the_biological_activities```.
+    * The biological activity(ies) or other y-property(ies) used for QSAR or machine learning modeling. The algorithm can handle one or more properties. Enter a list with the names of biological activities separated by commas and no spaces. These properties must be represented as either integers or floating-point numbers. If your dataset is represented in classes (e.g., active or inactive; soluble, partially soluble, or insoluble), you should represent them as integers (e.g., 0 or 1; 1, 2, or 3).
+    * Example: ```MASSA_Algorithm -i <input_file>.sdf -o <output_file>.sdf -s pIC50,pMIC```.
+    * Default = If not entered directly on the command line, it will be requested during algorithm execution.
+* **Number of principal components in PCA**: ```-n``` or ```--number_of_PCs```.
+    * Defines the number of principal components to reduce the dimensionality of variables related to biological, physicochemical and structural domains. If the value is a decimal between 0 and 1, the number of principal components is what explains for (```<input number>```* 100)% of the variance. If the value is greater than 1, the number of PCs will be exactly the input integer, but PAY ATTENTION:
+
+        1) If the number of PCs is an integer and equal to or greater than the number of physicochemical properties (7), the PCA step will be bypassed for this domain.
+        2) The same for the biological domain.
+        3) If the number of biological activities is less than 3, the PCA step will be bypassed for this domain.
+    * Default = 0.85.
+* **SVD solver parameter for PCA**: ```-v``` or ```--svd_solver_for_PCA```.
+    * See the sklearn.decomposition.PCA topic on https://scikit-learn.org/stable/modules/generated/sklearn.decomposition.PCA.html for more info.
+    * Default = full.
+* **HCA linkage method**: ```-l``` or ```--linkage_method```.
+    * The linkage criterion to use. The algorithm will merge the pairs of cluster that minimize this criterion.
+    * Options = complete, single, ward, average, weighted, centroid, median. For more info, see the scipy.cluster.hierarchy.linkage topic on https://docs.scipy.org/doc/scipy/reference/generated/scipy.cluster.hierarchy.linkage.html?highlight=linkage#scipy.cluster.hierarchy.linkage.
+    * Default = complete.
+* **Extension of image files**: ```-t``` or ```--image_type```.
+    * Extension of the image files that will be generated. Suggested = png or svg.
+    * Default = png.
+* **Font size for X-axis of dendrograms**: ```-d``` or ```--dendrogram_Xfont_size```.
+    * Sets the font size on the x-axis of the dendrogram (molecule labels).
+    * Default = 5.
+* **Font size for X-axis of bar plots**: ```-x``` or ```--barplot_Xfont_size```.
+    * Sets the font size on the x-axis of the bar plot (cluster labels).
+    * Default = 12.
+* **Enable Dendrogram plot**: ```-f``` or ```--dendrogram_plot```.
+    * Defines whether or not dendrogram images will be generated.
+	* Options = true (dendrogram will be generated), false (dendrogram will not be generated).
+    * Default = true.
+* **Ignore Errors**: ```-e``` or ```--drop_errors```.
+    * Ignore chemistry errors, saving only molecules without any errors.
+	* Options = true (ignore molecule errors and log them in the log file), false (treat molecule errors as fatal and fail the execution).
+    * Default = true.
+* **Large Dataset**: ```-a``` or ```--large_dataset```.
+    * Switch the MASSA algorithm from HCA to MiniBatch-KMeans to handle large datasets.
+    * Options = auto (switches to KMeans if ≥ 10,000 molecules), false = use HCA (for smaller datasets), true = use KMeans (for large datasets).
+    * Default = auto.
+
+#### Command line help
+A full description of the arguments can also be viewed directly from the command line using the command:
+```
+MASSA_Algorithm -h
+```
+or
+```
+MASSA_Algorithm --help
+```
+
+## Cite
+1. To ensure accurate citation, kindly include a reference to the MASSA article, accessible via the DOI:
+Veríssimo, G. C.; Panteleão, S. Q.; Fernandes, P. O.; Gertrudes, J. C.; Kronenberger, T.; Honorio, K. M.; Maltarollo; V. G. MASSA Algorithm: an automated rational sampling of training and test subsets for QSAR modeling. J. Comput. Aided Mol. Des. 2023, 37, 735–754. https://doi.org/10.1007/s10822-023-00536-y.
+
+2. Furthermore, please incorporate the program citation following the provided template:
+
+```
+@Misc{veríssimo2021,
+    author = {Gabriel Corrêa Veríssimo},
+    title = {MASSA Algorithm: Molecular data set sampling for training-test separation},
+    howpublished = {\url{https://github.com/gcverissimo/MASSA_Algorithm}},
+    year = {2021}
+  }
+```
+
+## References
+[1]: DE VOS, N. J. kmodes categorical clustering library. https://github.com/nicodv/kmodes. 2015-2021.
+

{massa_algorithm-2.2.0.dist-info → massa_algorithm-2.2.2.dist-info}/RECORD

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+massa_algorithm-2.2.2.dist-info/WHEEL,sha256=K260EYznzXsJYBQGqmI8VTxEdiZYNvDZwW9cBh9-_MA,91
+massa_algorithm-2.2.2.dist-info/entry_points.txt,sha256=oMtqswy07Di-w2uIYAEvenBKl0ovsr9AYm_yxn6LGtU,63
+massa_algorithm-2.2.2.dist-info/top_level.txt,sha256=IZyttJ20RSD8w9nAcaTHWAvkvxHV5FGaVGB7mDrw9Cc,16
+massa_algorithm-2.2.2.dist-info/RECORD,,

{massa_algorithm-2.2.0.dist-info → massa_algorithm-2.2.2.dist-info}/WHEEL

@@ -1,5 +1,5 @@
 Wheel-Version: 1.0
-Generator: setuptools (80.9.0)
+Generator: setuptools (83.0.0)
 Root-Is-Purelib: true
 Tag: py3-none-any