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//
// Copyright (C) 2018-2021 Susan H. Leung and other RDKit contributors
//
// @@ 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.
//
/*! \file Charge.h
\brief Defines the Reionizer class and Uncharger class.
*/
#include <RDGeneral/export.h>
#ifndef RD_CHARGE_H
#define RD_CHARGE_H
#include <utility>
#include "MolStandardize.h"
#include <Catalogs/Catalog.h>
#include <GraphMol/MolStandardize/AcidBaseCatalog/AcidBaseCatalogEntry.h>
#include <GraphMol/MolStandardize/AcidBaseCatalog/AcidBaseCatalogParams.h>
namespace RDKit {
class RWMol;
class ROMol;
namespace MolStandardize {
RDKIT_MOLSTANDARDIZE_EXPORT extern const CleanupParameters
defaultCleanupParameters;
typedef RDCatalog::HierarchCatalog<AcidBaseCatalogEntry, AcidBaseCatalogParams,
int>
AcidBaseCatalog;
struct RDKIT_MOLSTANDARDIZE_EXPORT ChargeCorrection {
std::string Name;
std::string Smarts;
int Charge;
ChargeCorrection(std::string name, std::string smarts, int charge)
: Name(std::move(name)), Smarts(std::move(smarts)), Charge(charge) {}
};
// The default list of ChargeCorrections.
RDKIT_MOLSTANDARDIZE_EXPORT extern std::vector<ChargeCorrection>
CHARGE_CORRECTIONS;
//! The reionizer class to fix charges and reionize a molecule such that the
/// strongest acids ionize first.
/*!
<b>Notes:</b>
-
*/
class RDKIT_MOLSTANDARDIZE_EXPORT Reionizer {
public:
Reionizer();
//! construct a Reionizer with a particular acidbaseFile
Reionizer(const std::string acidbaseFile);
//! construct a Reionizer with parameter data
Reionizer(const std::vector<std::tuple<std::string, std::string, std::string>>
&data);
//! construct a Reionizer with a particular acidbaseFile and charge
/// corrections
Reionizer(const std::string acidbaseFile,
const std::vector<ChargeCorrection> ccs);
//! construct a Reionizer with a particular acidbaseFile and charge
/// corrections
Reionizer(std::istream &acidbaseStream,
const std::vector<ChargeCorrection> ccs);
//! construct a Reionizer with parameter data and charge corrections
Reionizer(const std::vector<std::tuple<std::string, std::string, std::string>>
&data,
const std::vector<ChargeCorrection> ccs);
//! making Reionizer objects non-copyable
Reionizer(const Reionizer &other) = delete;
Reionizer &operator=(Reionizer const &) = delete;
~Reionizer();
//! Enforce charges on certain atoms, then perform competitive reionization.
ROMol *reionize(const ROMol &mol);
private:
AcidBaseCatalog *d_abcat;
std::vector<ChargeCorrection> d_ccs;
std::pair<unsigned int, std::vector<unsigned int>> *strongestProtonated(
const ROMol &mol,
const std::vector<std::pair<ROMOL_SPTR, ROMOL_SPTR>> &abpairs);
std::pair<unsigned int, std::vector<unsigned int>> *weakestIonized(
const ROMol &mol,
const std::vector<std::pair<ROMOL_SPTR, ROMOL_SPTR>> &abpairs);
}; // Reionizer class
// caller owns the returned pointer
inline Reionizer *reionizerFromParams(const CleanupParameters ¶ms) {
if (params.acidbaseData.empty()) {
return new Reionizer(params.acidbaseFile);
} else {
return new Reionizer(params.acidbaseData);
}
}
//! The Uncharger class for neutralizing ionized acids and bases.
/*!
<b>Notes:</b>
- This class uncharges molecules by adding and/or removing hydrogens.
- For zwitterions, hydrogens are moved to eliminate charges where
possible.
- In cases where there is a positive charge that is not neutralizable,
an attempt is made to also preserve the corresponding
negative charge.
*/
class RDKIT_MOLSTANDARDIZE_EXPORT Uncharger {
public:
Uncharger();
Uncharger(bool canonicalOrdering) : Uncharger() {
df_canonicalOrdering = canonicalOrdering;
}
Uncharger(const Uncharger &other);
~Uncharger();
ROMol *uncharge(const ROMol &mol);
private:
bool df_canonicalOrdering = true;
std::shared_ptr<ROMol> pos_h;
std::shared_ptr<ROMol> pos_noh;
std::shared_ptr<ROMol> neg;
std::shared_ptr<ROMol> neg_acid;
}; // Uncharger class
} // namespace MolStandardize
} // namespace RDKit
#endif
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