This is a class for storing and applying general chemical reactions. More...

#include <Reaction.h>

Inheritance diagram for RDKit::ChemicalReaction:

Public Member Functions
	ChemicalReaction ()
	ChemicalReaction (const std::string &binStr)
	construct a reaction from a pickle string
	ChemicalReaction (const ChemicalReaction &other)
ChemicalReaction &	operator= (const ChemicalReaction &other)
unsigned int	addReactantTemplate (ROMOL_SPTR mol)
	Adds a new reactant template.
unsigned int	addAgentTemplate (ROMOL_SPTR mol)
	Adds a new agent template.
unsigned int	addProductTemplate (ROMOL_SPTR mol)
	Adds a new product template.
void	removeUnmappedReactantTemplates (double thresholdUnmappedAtoms=0.2, bool moveToAgentTemplates=true, MOL_SPTR_VECT *targetVector=nullptr)
void	removeUnmappedProductTemplates (double thresholdUnmappedAtoms=0.2, bool moveToAgentTemplates=true, MOL_SPTR_VECT *targetVector=nullptr)
void	removeAgentTemplates (MOL_SPTR_VECT *targetVector=nullptr)
std::vector< MOL_SPTR_VECT >	runReactants (const MOL_SPTR_VECT reactants, unsigned int numProducts=1000) const
	Runs the reaction on a set of reactants.
std::vector< MOL_SPTR_VECT >	runReactant (ROMOL_SPTR reactant, unsigned int reactantTemplateIdx) const
	Runs a single reactant against a single reactant template.
bool	runReactant (RWMol &reactant, bool removeUnmatchedAtoms=true) const
	Runs a single reactant in place (the reactant is modified).
const MOL_SPTR_VECT &	getReactants () const
const MOL_SPTR_VECT &	getAgents () const
const MOL_SPTR_VECT &	getProducts () const
MOL_SPTR_VECT::const_iterator	beginReactantTemplates () const
MOL_SPTR_VECT::const_iterator	endReactantTemplates () const
MOL_SPTR_VECT::const_iterator	beginProductTemplates () const
MOL_SPTR_VECT::const_iterator	endProductTemplates () const
MOL_SPTR_VECT::const_iterator	beginAgentTemplates () const
MOL_SPTR_VECT::const_iterator	endAgentTemplates () const
MOL_SPTR_VECT::iterator	beginReactantTemplates ()
MOL_SPTR_VECT::iterator	endReactantTemplates ()
MOL_SPTR_VECT::iterator	beginProductTemplates ()
MOL_SPTR_VECT::iterator	endProductTemplates ()
MOL_SPTR_VECT::iterator	beginAgentTemplates ()
MOL_SPTR_VECT::iterator	endAgentTemplates ()
unsigned int	getNumReactantTemplates () const
unsigned int	getNumProductTemplates () const
unsigned int	getNumAgentTemplates () const
void	initReactantMatchers (bool silent=false)
	initializes our internal reactant-matching datastructures.
bool	isInitialized () const
bool	validate (unsigned int &numWarnings, unsigned int &numErrors, bool silent=false) const
bool	getImplicitPropertiesFlag () const
void	setImplicitPropertiesFlag (bool val)
const SubstructMatchParameters &	getSubstructParams () const
SubstructMatchParameters &	getSubstructParams ()
Public Member Functions inherited from RDKit::RDProps
	RDProps ()
	RDProps (const RDProps &rhs)
RDProps &	operator= (const RDProps &rhs)
	RDProps (RDProps &&o) noexcept=default
RDProps &	operator= (RDProps &&rhs) noexcept=default
void	clear ()
const Dict &	getDict () const
	gets the underlying Dictionary
Dict &	getDict ()
STR_VECT	getPropList (bool includePrivate=true, bool includeComputed=true) const
	returns a list with the names of our `properties`
template<typename T>
void	setProp (const std::string_view key, T val, bool computed=false) const
	sets a `property` value
template<typename T>
void	getProp (const std::string_view key, T &res) const
	allows retrieval of a particular property value
template<typename T>
T	getProp (const std::string_view key) const
	This is an overloaded member function, provided for convenience. It differs from the above function only in what argument(s) it accepts.
template<typename T>
bool	getPropIfPresent (const std::string_view key, T &res) const
bool	hasProp (const std::string_view key) const
	This is an overloaded member function, provided for convenience. It differs from the above function only in what argument(s) it accepts.
void	clearProp (const std::string_view key) const
	clears the value of a `property`
void	clearComputedProps () const
	clears all of our `computed` `properties`
void	updateProps (const RDProps &source, bool preserveExisting=false)
	update the properties from another

Friends
class	ReactionPickler

Additional Inherited Members
Protected Attributes inherited from RDKit::RDProps
Dict	d_props

Detailed Description

This is a class for storing and applying general chemical reactions.

basic usage will be something like:

ChemicalReaction rxn;
rxn.addReactantTemplate(r1);
rxn.addReactantTemplate(r2);
rxn.addProductTemplate(p1);
rxn.initReactantMatchers();

MOL_SPTR_VECT prods;
for(MOL_SPTR_VECT::const_iterator r1It=reactantSet1.begin();
    r1It!=reactantSet1.end();++r1It;){
  for(MOL_SPTR_VECT::const_iterator r2It=reactantSet2.begin();
      r2It!=reactantSet2.end();++r2It;){
    MOL_SPTR_VECT rVect(2);
    rVect[0] = *r1It;
    rVect[1] = *r2It;

    std::vector<MOL_SPTR_VECT> lprods;
    lprods = rxn.runReactants(rVect);
    for(std::vector<MOL_SPTR_VECT>::const_iterator lpIt=lprods.begin();
       lpIt!=lprods.end();++lpIt){
       // we know this is a single-product reaction:
       prods.push_back((*lpIt)[0]);
    }
  }
}

NOTES:

to allow more control over the reaction, it is possible to flag reactant atoms as being protected by setting the common_properties::_protected property on those atoms. Here's an example:

       std::string smi="[O:1]>>[N:1]";
       ChemicalReaction *rxn = RxnSmartsToChemicalReaction(smi);
       rxn->initReactantMatchers();

       MOL_SPTR_VECT reacts;
       reacts.clear();
       smi = "OCO";
       ROMol *mol = SmilesToMol(smi);
       reacts.push_back(ROMOL_SPTR(mol));
       std::vector<MOL_SPTR_VECT> prods;
       prods = rxn->runReactants(reacts);
       // here prods has two entries, because there are two Os in the
       // reactant.

       reacts[0]->getAtomWithIdx(0)->setProp(common_properties::_protected,1);
       prods = rxn->runReactants(reacts);
       // here prods only has one entry, the reaction at atom 0
       // has been blocked by the _protected property

Definition at line 122 of file Reaction.h.

Constructor & Destructor Documentation

◆ ChemicalReaction() [1/3]

RDKit::ChemicalReaction::ChemicalReaction ( )

inline

Definition at line 149 of file Reaction.h.

References RDKit::RDProps::RDProps().

Referenced by ChemicalReaction(), operator=(), and ReactionPickler.

◆ ChemicalReaction() [2/3]

RDKit::ChemicalReaction::ChemicalReaction ( const std::string & binStr )

construct a reaction from a pickle string

◆ ChemicalReaction() [3/3]

RDKit::ChemicalReaction::ChemicalReaction ( const ChemicalReaction & other )

inline

Definition at line 152 of file Reaction.h.

References ChemicalReaction(), and RDKit::RDProps::RDProps().

Member Function Documentation

◆ addAgentTemplate()

unsigned int RDKit::ChemicalReaction::addAgentTemplate ( ROMOL_SPTR mol )

inline

Adds a new agent template.

Returns: the number of agent

Definition at line 176 of file Reaction.h.

References rdcast.

◆ addProductTemplate()

unsigned int RDKit::ChemicalReaction::addProductTemplate ( ROMOL_SPTR mol )

inline

Adds a new product template.

Returns: the number of products

Definition at line 186 of file Reaction.h.

References rdcast.

◆ addReactantTemplate()

unsigned int RDKit::ChemicalReaction::addReactantTemplate ( ROMOL_SPTR mol )

inline

Adds a new reactant template.

Returns: the number of reactants

Definition at line 165 of file Reaction.h.

References rdcast.

◆ beginAgentTemplates() [1/2]

MOL_SPTR_VECT::iterator RDKit::ChemicalReaction::beginAgentTemplates ( )

inline

Definition at line 298 of file Reaction.h.

◆ beginAgentTemplates() [2/2]

MOL_SPTR_VECT::const_iterator RDKit::ChemicalReaction::beginAgentTemplates ( ) const

inline

Definition at line 277 of file Reaction.h.

◆ beginProductTemplates() [1/2]

MOL_SPTR_VECT::iterator RDKit::ChemicalReaction::beginProductTemplates ( )

inline

Definition at line 291 of file Reaction.h.

◆ beginProductTemplates() [2/2]

MOL_SPTR_VECT::const_iterator RDKit::ChemicalReaction::beginProductTemplates ( ) const

inline

Definition at line 270 of file Reaction.h.

◆ beginReactantTemplates() [1/2]

MOL_SPTR_VECT::iterator RDKit::ChemicalReaction::beginReactantTemplates ( )

inline

Definition at line 284 of file Reaction.h.

◆ beginReactantTemplates() [2/2]

MOL_SPTR_VECT::const_iterator RDKit::ChemicalReaction::beginReactantTemplates ( ) const

inline

Definition at line 263 of file Reaction.h.

◆ endAgentTemplates() [1/2]

MOL_SPTR_VECT::iterator RDKit::ChemicalReaction::endAgentTemplates ( )

inline

Definition at line 301 of file Reaction.h.

◆ endAgentTemplates() [2/2]

MOL_SPTR_VECT::const_iterator RDKit::ChemicalReaction::endAgentTemplates ( ) const

inline

Definition at line 280 of file Reaction.h.

◆ endProductTemplates() [1/2]

MOL_SPTR_VECT::iterator RDKit::ChemicalReaction::endProductTemplates ( )

inline

Definition at line 294 of file Reaction.h.

◆ endProductTemplates() [2/2]

MOL_SPTR_VECT::const_iterator RDKit::ChemicalReaction::endProductTemplates ( ) const

inline

Definition at line 273 of file Reaction.h.

◆ endReactantTemplates() [1/2]

MOL_SPTR_VECT::iterator RDKit::ChemicalReaction::endReactantTemplates ( )

inline

Definition at line 287 of file Reaction.h.

◆ endReactantTemplates() [2/2]

MOL_SPTR_VECT::const_iterator RDKit::ChemicalReaction::endReactantTemplates ( ) const

inline

Definition at line 266 of file Reaction.h.

◆ getAgents()

const MOL_SPTR_VECT & RDKit::ChemicalReaction::getAgents ( ) const

inline

Definition at line 260 of file Reaction.h.

◆ getImplicitPropertiesFlag()

bool RDKit::ChemicalReaction::getImplicitPropertiesFlag ( ) const

inline

returns whether or not the reaction uses implicit properties on the product atoms

This toggles whether or not unspecified atomic properties in the products are considered to be implicit and should be copied from the actual reactants. This is necessary due to a semantic difference between the "reaction SMARTS" approach and the MDL RXN approach: In "reaction SMARTS", this reaction: [C:1]-[Br:2].[O-:3]>>[C:1]-[O:3].[Br-:2] applied to [CH4+]Br should yield [CH4+]O Something similar drawn in an rxn file, and applied to [CH4+]Br should yield [CH3]O. In rxn there is no charge on the product C because nothing is specified in the rxn file; in "SMARTS" the charge from the actual reactants is not removed because no charge is specified in the reaction.

Definition at line 364 of file Reaction.h.

◆ getNumAgentTemplates()

unsigned int RDKit::ChemicalReaction::getNumAgentTemplates ( ) const

inline

Definition at line 310 of file Reaction.h.

References rdcast.

◆ getNumProductTemplates()

unsigned int RDKit::ChemicalReaction::getNumProductTemplates ( ) const

inline

Definition at line 307 of file Reaction.h.

References rdcast.

◆ getNumReactantTemplates()

unsigned int RDKit::ChemicalReaction::getNumReactantTemplates ( ) const

inline

Definition at line 304 of file Reaction.h.

References rdcast.

◆ getProducts()

const MOL_SPTR_VECT & RDKit::ChemicalReaction::getProducts ( ) const

inline

Definition at line 261 of file Reaction.h.

◆ getReactants()

const MOL_SPTR_VECT & RDKit::ChemicalReaction::getReactants ( ) const

inline

Definition at line 257 of file Reaction.h.

◆ getSubstructParams() [1/2]

SubstructMatchParameters & RDKit::ChemicalReaction::getSubstructParams ( )

inline

Definition at line 372 of file Reaction.h.

◆ getSubstructParams() [2/2]

const SubstructMatchParameters & RDKit::ChemicalReaction::getSubstructParams ( ) const

inline

Definition at line 369 of file Reaction.h.

◆ initReactantMatchers()

void RDKit::ChemicalReaction::initReactantMatchers ( bool silent = false )

initializes our internal reactant-matching datastructures.

This must be called after adding reactants and before calling runReactants.

Parameters

silent If this bool is true, no messages will be logged during the validation. By default, validation problems are reported to the warning and error logs depending on their severity.

◆ isInitialized()

bool RDKit::ChemicalReaction::isInitialized ( ) const

inline

Definition at line 325 of file Reaction.h.

◆ operator=()

ChemicalReaction & RDKit::ChemicalReaction::operator= ( const ChemicalReaction & other )

inline

Definition at line 153 of file Reaction.h.

References ChemicalReaction().

◆ removeAgentTemplates()

void RDKit::ChemicalReaction::removeAgentTemplates ( MOL_SPTR_VECT * targetVector = nullptr )

Removes the agent templates from a reaction if a pointer to a molecule vector is provided the agents are stored therein.

◆ removeUnmappedProductTemplates()

void RDKit::ChemicalReaction::removeUnmappedProductTemplates	(	double	thresholdUnmappedAtoms = 0.2,
		bool	moveToAgentTemplates = true,
		MOL_SPTR_VECT *	targetVector = nullptr )

Removes the product templates from a reaction if its atom mapping ratio is below a given threshold

By default the removed products templates were attached to the agent templates. An alternative will be to provide a pointer to a molecule vector where these products should be saved.

◆ removeUnmappedReactantTemplates()

void RDKit::ChemicalReaction::removeUnmappedReactantTemplates	(	double	thresholdUnmappedAtoms = 0.2,
		bool	moveToAgentTemplates = true,
		MOL_SPTR_VECT *	targetVector = nullptr )

Removes the reactant templates from a reaction if atom mapping ratio is below a given threshold

By default the removed reactant templates were attached to the agent templates. An alternative will be to provide a pointer to a molecule vector where these reactants should be saved.

◆ runReactant() [1/2]

std::vector< MOL_SPTR_VECT > RDKit::ChemicalReaction::runReactant	(	ROMOL_SPTR	reactant,
		unsigned int	reactantTemplateIdx ) const

Runs a single reactant against a single reactant template.

Parameters

reactant	The single reactant to use
reactantTemplateIdx	the reactant template to target in the reaction

◆ runReactant() [2/2]

bool RDKit::ChemicalReaction::runReactant	(	RWMol &	reactant,
		bool	removeUnmatchedAtoms = true ) const

Runs a single reactant in place (the reactant is modified).

This is only useable with reactions which have a single reactant and product and where no atoms are added in the product.

Parameters

reactant	The single reactant to use
removeUnmatchedAtoms	toggles whether or not atoms from the reactant which do not match template atoms are removed.

Returns: whether or not the reactant was actually modified

◆ runReactants()

std::vector< MOL_SPTR_VECT > RDKit::ChemicalReaction::runReactants	(	const MOL_SPTR_VECT	reactants,
		unsigned int	numProducts = 1000 ) const

Runs the reaction on a set of reactants.

Parameters

reactants	the reactants to be used. The length of this must be equal to this->getNumReactantTemplates()
maxProducts	if non zero, the maximum number of products to generate before stopping. If hit a warning will be generated.

Returns: a vector of vectors of products. Each subvector will be this->getNumProductTemplates() long.

We return a vector of vectors of products because each individual template may map multiple times onto its reactant. This leads to multiple possible result sets.

◆ setImplicitPropertiesFlag()

void RDKit::ChemicalReaction::setImplicitPropertiesFlag ( bool val )

inline

sets the implicit properties flag. See the documentation for getImplicitProertiesFlag() for a discussion of what this means.

Definition at line 367 of file Reaction.h.

◆ validate()

bool RDKit::ChemicalReaction::validate	(	unsigned int &	numWarnings,
		unsigned int &	numErrors,
		bool	silent = false ) const

validates the reactants and products to make sure the reaction seems "reasonable"

Returns: true if the reaction validates without errors (warnings do not stop validation)

Parameters

numWarnings	used to return the number of validation warnings
numErrors	used to return the number of validation errors
silent	If this bool is true, no messages will be logged during the validation. By default, validation problems are reported to the warning and error logs depending on their severity.

◆ ReactionPickler

friend class ReactionPickler

friend

Definition at line 123 of file Reaction.h.

References ChemicalReaction(), RDKit::RDProps::operator=(), and ReactionPickler.

Referenced by ReactionPickler.

The documentation for this class was generated from the following file:

Reaction.h

Public Member Functions

Friends

Additional Inherited Members

Detailed Description

Constructor & Destructor Documentation

◆ ChemicalReaction() [1/3]

◆ ChemicalReaction() [2/3]

◆ ChemicalReaction() [3/3]

Member Function Documentation

◆ addAgentTemplate()

◆ addProductTemplate()

◆ addReactantTemplate()

◆ beginAgentTemplates() [1/2]

◆ beginAgentTemplates() [2/2]

◆ beginProductTemplates() [1/2]

◆ beginProductTemplates() [2/2]

◆ beginReactantTemplates() [1/2]

◆ beginReactantTemplates() [2/2]

◆ endAgentTemplates() [1/2]

◆ endAgentTemplates() [2/2]

◆ endProductTemplates() [1/2]

◆ endProductTemplates() [2/2]

◆ endReactantTemplates() [1/2]

◆ endReactantTemplates() [2/2]

◆ getAgents()

◆ getImplicitPropertiesFlag()

◆ getNumAgentTemplates()

◆ getNumProductTemplates()

◆ getNumReactantTemplates()

◆ getProducts()

◆ getReactants()

◆ getSubstructParams() [1/2]

◆ getSubstructParams() [2/2]

◆ initReactantMatchers()

◆ isInitialized()

◆ operator=()

◆ removeAgentTemplates()

◆ removeUnmappedProductTemplates()

◆ removeUnmappedReactantTemplates()

◆ runReactant() [1/2]

◆ runReactant() [2/2]

◆ runReactants()

◆ setImplicitPropertiesFlag()

◆ validate()

Friends And Related Symbol Documentation

◆ ReactionPickler