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BenchmarkFF

Language grade: Python DOI

README last updated: Nov 09 2020

About

Objective: Compare optimized geometries and energies from various force fields with respect to a QM reference.

This repository comprises code to extract molecule datasets from QCArchive, run energy minimizations with various force fields, and analyze the resulting geometries and energies with respect to QM reference data from QCArchive.

See our work in this preprint: Lim et. al.; Benchmark Assessment of Molecular Geometries and Energies from Small Molecule Force Fields. 2020.

Contents

Directories in this repo:

  • 01_setup: Extract molecules from QCArchive, convert to OpenEye mols, and standardize conformers and titles.
  • 02_calc: Run energy minimizations for various force fields.
  • 03_analysis: Analyze output energies and geometries.
  • examples: See this directory for example results and plots.
  • molecules: The molecule sets used in our benchmark analyses.
  • tools: A handful of helpful scripts (align structures for PDF output, find specific moieties, extract conformers by SD tag value).

File descriptions:

directory file description
01_setup extract_qcarchive_dataset.ipynb write out molecules from a QCArchive database which have completed QM calculations
01_setup combine_conformers.ipynb of the molecules from extract_qcarchive_dataset.ipynb, combine conformers that are labeled as different molecules
02_calc minimize_ffs.py minimize all molecules in an input SDF file with a specified force field
03_analysis color_by_moiety.py generate ddE vs TFD (or RMSD) scatter plots highglighting specific moieties by color
03_analysis compare_ffs.py compare FF-minimized molecules on their geometries and energies (no conformer matching)
03_analysis match_minima.py similar to compare_ffs of comparing geometries and energies but analyzing RMSD-matched structures
03_analysis probe_parameter.py find all molecules in a set that use certain specified parameter(s)
03_analysis reader.py reader for molecule sets and text input files called by the other analysis scripts
03_analysis tailed_parameters.py identify parameters that may be overrepresented in high RMSD/TFD tails for FFXML force fields

Python setup

Package dependencies

  • numpy, matplotlib, seaborn
  • OpenEye
  • RDKit (solely for TFD calculations)
  • OpenMM
  • OpenForceField
  • QCFractal, QCPortal

Conda setup

conda create -n parsley python=3.6 matplotlib numpy seaborn
conda activate parsley
conda install -c openeye -c conda-forge -c omnia rdkit openeye-toolkits qcfractal qcportal openforcefield cmiles openmm

The packages in VTL's conda environment is documented in this repo as parsley.yml.

Brief overview of usage

Setup

  1. Write out from a QCArchive database which have completed QM calculations, using extract_qcarchive_dataset.ipynb.
  2. Reorganize up the molecule set for conformers which are labeled as different molecules:
    1. Group all the same conformers together since they are separated by intervening molecules, using combine_conformers.ipynb.
    2. Of the full set, write out the good molecules that don't need conformer reorganization, using molextract.py* from OEChem.
    3. Combine the results of steps 2.1 and 2.2: cat whole_02_good.sdf whole_03_redosort.sdf > whole_04_combine.sdf
    4. Read in the whole set with proper conformers, and rename titles for numeric order, using combine_conformers.ipynb.
    5. (opt) Write out associated SMILES: awk '/SMILES/{getline; print}' whole_05_renew.sdf > whole_05_renew.smi
    6. (opt) Generate molecular structures in PDF format, using mols2pdf.py.

FF calculations

  1. (opt) Break up the full set into smaller chunks for managable computations, using molchunk.py.*
  2. Run the minimizations, using minimize_ffs.py.
  3. Remove the molecules that were unable to minimize (e.g., due to missing parameters) from all files, using cat_mols.py.*
  4. (opt) If the full set was broken up, concatenate all the constituent files back together, using cat or cat_mols.py.*

Analysis

  1. Analyze geometries and relative energies with compare_ffs.py.
    1. (opt) If some conformers (not full molecules) are outliers, can remove using get_by_tag.py.
    2. Mark certain moieties of interest in energy v. geometry scatter plots using color_by_moiety.py.
  2. Analyze energies of structurally similar conformers using match_minima.py.
  3. Explore parameters overrepresented in high TFD/RMSD regions using tailed_parameters.py and probe_parameter.py.

*The OEChem scripts referred to above are located here.

  • molextract.py
  • molchunk.py -- VTL modified to use OEAbsCanonicalConfTest

Note: Some of the analysis can take a long time for multiple force fields and many molecules (e.g. up to 2 hours on compare_ffs.py or 30-45 min on tailed_parameters.py). To explore the analyzed data, adjust plots, etc. without re-analyzing data, you can input the pickle file written out from the previously run analysis.

Contributors

  • Authors: Victoria T. Lim, David F. Hahn
  • Advising: David Mobley, Gary Tresadern, Chris Bayly
  • Code review: Jeffrey Wagner, Daniel Smith
  • Discussions: Jessica Maat, Caitlin Bannan, Hyesu Jang, Lee-Ping Wang

Big picture wish list / to do tasks

See more focused issues in the issue tracker.

  • Format code with YAPF/Black
  • Use logging module instead of print statements
  • Look into automatically serializable representations (e.g., Pydantic) instead of pickle
  • Use type hints for functions
  • Allow user to pass in dict for plotting parameters (i.e., talk or paper font sizes)
  • Generate plots with Plotly