Templates.h

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//
//  Copyright (C) 2023 Schrödinger, LLC
//
//   @@ All Rights Reserved @@
//  This file is part of the RDKit.
//  The contents are covered by the terms of the BSD license
//  which is included in the file license.txt, found at the root
//  of the RDKit source tree.
//
 
#ifndef RD_DEPICTOR_TEMPLATES_H
#define RD_DEPICTOR_TEMPLATES_H
 
#include <GraphMol/ROMol.h>
#include <GraphMol/SmilesParse/SmilesParse.h>
#include <GraphMol/MolOps.h>
 
#include "TemplateSmarts.h"
 
#include <fstream>
#include <unordered_map>
 
namespace RDDepict {
class RDKIT_DEPICTOR_EXPORT CoordinateTemplates {
 public:
  //! returns a reference to the singleton CoordinateTemplates
  /*
      \return a reference to the singleton CoordinateTemplates
 
      <b>Notes:</b>
        - if the singleton CoordinateTemplates has already been instantiated
          the singleton will be returned, otherwise the singleton will
          be constructed.
 
   */
  static CoordinateTemplates &getRingSystemTemplates() {
    static CoordinateTemplates template_mols;
    return template_mols;
  }
 
  bool hasTemplateOfSize(unsigned int atomCount) {
    if (m_templates.find(atomCount) != m_templates.end()) {
      return true;
    }
    return false;
  }
 
  const std::vector<std::shared_ptr<RDKit::ROMol>> &getMatchingTemplates(
      unsigned int atomCount) {
    return m_templates[atomCount];
  }
 
  void setRingSystemTemplates(const std::string &templatePath);
  void addRingSystemTemplates(const std::string &templatePath);
 
  //! check if a template is considered valid
  /*
      \param template mol
      \param smiles for logging
      \return whether the template is valid
 
      <b>A template is considered valid if it:</b>
        - has 2D coordinates
        - is a ring system (spiro'd ring systems are OK)
        - consists of only 1 fragment
 
   */
  static void assertValidTemplate(RDKit::ROMol &mol, const std::string &smiles);
 
  void loadDefaultTemplates() {
    clearTemplates();
    // load default templates into m_templates map by atom count
    for (const auto &smarts : TEMPLATE_SMARTS) {
      std::shared_ptr<RDKit::ROMol> mol(RDKit::SmartsToMol(smarts));
      if (!mol) {
        continue;
      }
      // Initialize ring info using symmetrizeSSSR to match depictor ring counting
      RDKit::VECT_INT_VECT arings;
      RDKit::MolOps::symmetrizeSSSR(*mol, arings);
      m_templates[mol->getNumAtoms()].push_back(mol);
    }
  }
 
 private:
  CoordinateTemplates() { loadDefaultTemplates(); }
  CoordinateTemplates(const CoordinateTemplates &) = delete;
  CoordinateTemplates &operator=(const CoordinateTemplates &) = delete;
 
  void clearTemplates() {
    for (auto &[atom_cout, romols] : m_templates) {
      romols.clear();
    }
    m_templates.clear();
  }
 
  ~CoordinateTemplates() { clearTemplates(); }
 
  void loadTemplatesFromPath(
      const std::string &templatePath,
      std::unordered_map<
          unsigned int, std::vector<std::shared_ptr<RDKit::ROMol>>> &templates);
 
  std::unordered_map<unsigned int, std::vector<std::shared_ptr<RDKit::ROMol>>>
      m_templates;
};
}  // namespace RDDepict
#endif  // RD_DEPICTOR_TEMPLATES_H