// // Copyright (C) 2007-2013 Greg Landrum // // @@ 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 AtomPairs.h A few quick notes about fingerprint size and the way chirality is handled in these functions. By default the atom-pair and topologic-torsion fingerprints do not include any information about chirality; the atom invariants only include information about the atomic number, number of pi electrons, and degree. When chirality is included, two additional bits are added to the atom invariants to flag R/S/no chirality. These additional bits change the size of the atom invariants and either the size of the final fingerprint (atom pairs) or the maximum allowed path length (torsions). This means that even fingerprints for achiral molecules are different when includeChirality is true. */ #include #ifndef __RD_ATOMPAIRS_H__ #define __RD_ATOMPAIRS_H__ #include #include #include #include namespace RDKit { class Atom; namespace AtomPairs { const std::string atomPairsVersion = "1.1.0"; //! returns the atom-pair fingerprint for a molecule /*! The algorithm used is described here: R.E. Carhart, D.H. Smith, R. Venkataraghavan; "Atom Pairs as Molecular Features in Structure-Activity Studies: Definition and Applications" JCICS 25, 64-73 (1985). \param mol: the molecule to be fingerprinted \param minLength: minimum distance between atoms to be considered in a pair. Default is 1 bond. \param maxLength: maximum distance between atoms to be considered in a pair. Default is maxPathLen-1 bonds. \param fromAtoms: if provided, only atom pairs that involve the specified atoms will be included in the fingerprint \param ignoreAtoms: if provided, any atom pairs that include the specified atoms will not be included in the fingerprint \param atomInvariants: a list of invariants to use for the atom hashes note: only the first \c codeSize bits of each invariant are used. \param includeChirality: if set, chirality will be used in the atom invariants (note: this is ignored if atomInvariants are provided) \param use2D: if set, the 2D (topological) distance matrix is used. \param confId: the conformation to use if 3D distances are being used \return a pointer to the fingerprint. The client is responsible for calling delete on this. */ RDKIT_FINGERPRINTS_EXPORT SparseIntVect *getAtomPairFingerprint( const ROMol &mol, unsigned int minLength, unsigned int maxLength, const std::vector *fromAtoms = nullptr, const std::vector *ignoreAtoms = nullptr, const std::vector *atomInvariants = nullptr, bool includeChirality = false, bool use2D = true, int confId = -1); //! \overload RDKIT_FINGERPRINTS_EXPORT SparseIntVect *getAtomPairFingerprint( const ROMol &mol, const std::vector *fromAtoms = nullptr, const std::vector *ignoreAtoms = nullptr, const std::vector *atomInvariants = nullptr, bool includeChirality = false, bool use2D = true, int confId = -1); //! returns the hashed atom-pair fingerprint for a molecule /*! \param mol: the molecule to be fingerprinted \param nBits: the length of the fingerprint to generate \param minLength: minimum distance between atoms to be considered in a pair. Default is 1 bond. \param maxLength: maximum distance between atoms to be considered in a pair. Default is maxPathLen-1 bonds. \param fromAtoms: if provided, only atom pairs that involve the specified atoms will be included in the fingerprint \param ignoreAtoms: if provided, any atom pairs that include the specified atoms will not be included in the fingerprint \param atomInvariants: a list of invariants to use for the atom hashes note: only the first \c codeSize bits of each invariant are used. \param includeChirality: if set, chirality will be used in the atom invariants (note: this is ignored if atomInvariants are provided) \param use2D: if set, the 2D (topological) distance matrix is used. \return a pointer to the fingerprint. The client is responsible for calling delete on this. */ RDKIT_FINGERPRINTS_EXPORT SparseIntVect *getHashedAtomPairFingerprint( const ROMol &mol, unsigned int nBits = 2048, unsigned int minLength = 1, unsigned int maxLength = maxPathLen - 1, const std::vector *fromAtoms = nullptr, const std::vector *ignoreAtoms = nullptr, const std::vector *atomInvariants = nullptr, bool includeChirality = false, bool use2D = true, int confId = -1); //! returns the hashed atom-pair fingerprint for a molecule as a bit vector /*! \param mol: the molecule to be fingerprinted \param nBits: the length of the fingerprint to generate \param minLength: minimum distance between atoms to be considered in a pair. Default is 1 bond. \param maxLength: maximum distance between atoms to be considered in a pair. Default is maxPathLen-1 bonds. \param fromAtoms: if provided, only atom pairs that involve the specified atoms will be included in the fingerprint \param ignoreAtoms: if provided, any atom pairs that include the specified atoms will not be included in the fingerprint \param atomInvariants: a list of invariants to use for the atom hashes note: only the first \c codeSize bits of each invariant are used. \param nBitsPerEntry: number of bits to use in simulating counts \param includeChirality: if set, chirality will be used in the atom invariants (note: this is ignored if atomInvariants are provided) \param use2D: if set, the 2D (topological) distance matrix is used. \param confId: the conformation to use if 3D distances are being used \return a pointer to the fingerprint. The client is responsible for calling delete on this. */ RDKIT_FINGERPRINTS_EXPORT ExplicitBitVect * getHashedAtomPairFingerprintAsBitVect( const ROMol &mol, unsigned int nBits = 2048, unsigned int minLength = 1, unsigned int maxLength = maxPathLen - 1, const std::vector *fromAtoms = nullptr, const std::vector *ignoreAtoms = nullptr, const std::vector *atomInvariants = nullptr, unsigned int nBitsPerEntry = 4, bool includeChirality = false, bool use2D = true, int confId = -1); //! returns the topological-torsion fingerprint for a molecule /*! The algorithm used is described here: R. Nilakantan, N. Bauman, J. S. Dixon, R. Venkataraghavan; "Topological Torsion: A New Molecular Descriptor for SAR Applications. Comparison with Other Descriptors" JCICS 27, 82-85 (1987). \param mol: the molecule to be fingerprinted \param targetSize: the number of atoms to include in the "torsions" \param fromAtoms: if provided, only torsions that start or end at the specified atoms will be included in the fingerprint \param ignoreAtoms: if provided, any torsions that include the specified atoms will not be included in the fingerprint \param atomInvariants: a list of invariants to use for the atom hashes note: only the first \c codeSize bits of each invariant are used. \param includeChirality: if set, chirality will be used in the atom invariants (note: this is ignored if atomInvariants are provided) \return a pointer to the fingerprint. The client is responsible for calling delete on this. */ RDKIT_FINGERPRINTS_EXPORT SparseIntVect *getTopologicalTorsionFingerprint( const ROMol &mol, unsigned int targetSize = 4, const std::vector *fromAtoms = nullptr, const std::vector *ignoreAtoms = nullptr, const std::vector *atomInvariants = nullptr, bool includeChirality = false); //! returns a hashed topological-torsion fingerprint for a molecule /*! The algorithm used is described here: R. Nilakantan, N. Bauman, J. S. Dixon, R. Venkataraghavan; "Topological Torsion: A New Molecular Descriptor for SAR Applications. Comparison with Other Descriptors" JCICS 27, 82-85 (1987). \param mol: the molecule to be fingerprinted \param nBits: number of bits to include in the fingerprint \param targetSize: the number of atoms to include in the "torsions" \param fromAtoms: if provided, only torsions that start or end at the specified atoms will be included in the fingerprint \param ignoreAtoms: if provided, any torsions that include the specified atoms will not be included in the fingerprint \param atomInvariants: a list of invariants to use for the atom hashes note: only the first \c codeSize bits of each invariant are used. \param includeChirality: if set, chirality will be used in the atom invariants (note: this is ignored if atomInvariants are provided) \return a pointer to the fingerprint. The client is responsible for calling delete on this. */ RDKIT_FINGERPRINTS_EXPORT SparseIntVect * getHashedTopologicalTorsionFingerprint( const ROMol &mol, unsigned int nBits = 2048, unsigned int targetSize = 4, const std::vector *fromAtoms = nullptr, const std::vector *ignoreAtoms = nullptr, const std::vector *atomInvariants = nullptr, bool includeChirality = false); //! returns a hashed topological-torsion fingerprint for a molecule as a bit /// vector /*! \param mol: the molecule to be fingerprinted \param nBits: number of bits to include in the fingerprint \param targetSize: the number of atoms to include in the "torsions" \param fromAtoms: if provided, only torsions that start or end at the specified atoms will be included in the fingerprint \param ignoreAtoms: if provided, any torsions that include the specified atoms will not be included in the fingerprint \param atomInvariants: a list of invariants to use for the atom hashes note: only the first \c codeSize bits of each invariant are used. \param nBitsPerEntry: number of bits to use in simulating counts \param includeChirality: if set, chirality will be used in the atom invariants (note: this is ignored if atomInvariants are provided) \return a pointer to the fingerprint. The client is responsible for calling delete on this. */ RDKIT_FINGERPRINTS_EXPORT ExplicitBitVect * getHashedTopologicalTorsionFingerprintAsBitVect( const ROMol &mol, unsigned int nBits = 2048, unsigned int targetSize = 4, const std::vector *fromAtoms = nullptr, const std::vector *ignoreAtoms = nullptr, const std::vector *atomInvariants = nullptr, unsigned int nBitsPerEntry = 4, bool includeChirality = false); } // namespace AtomPairs } // namespace RDKit #endif