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NAME

ExtendedConnectivityFingerprints.pl - Generate extended connectivity fingerprints for SD files

SYNOPSIS

ExtendedConnectivityFingerprints.pl SDFile(s)...

ExtendedConnectivityFingerprints.pl [-a, --AtomIdentifierType AtomicInvariantsAtomTypes] [--AtomicInvariantsToUse ''AtomicInvariant,AtomicInvariant...''] [--FunctionalClassesToUse ''FunctionalClass1,FunctionalClass2...''] [--CompoundID DataFieldName or LabelPrefixString] [--CompoundIDLabel text] [--CompoundIDMode] [--DataFields ''FieldLabel1,FieldLabel2,...''] [-d, --DataFieldsMode All | Common | Specify | CompoundID] [-f, --Filter Yes | No] [--FingerprintsLabel text] [-h, --help] [-k, --KeepLargestComponent Yes | No] [-n, --NeighborhoodRadius number] [--OutDelim comma | tab | semicolon] [--output SD | text | both] [-o, --overwrite] [-q, --quote Yes | No] [-r, --root RootName] [-w, --WorkingDir dirname] SDFile(s)...

DESCRIPTION

Generate extended connectivity fingerprints [ Ref 48, Ref 52 ] for SDFile(s) and create appropriate SD or CSV/TSV text file(s) containing fingerprints vector strings corresponding to molecular fingerprints.

Multiple SDFile names are separated by spaces. The valid file extensions are .sdf and .sd. All other file names are ignored. All the SD files in a current directory can be specified either by *.sdf or the current directory name.

The current release of MayaChemTools supports generation of extended connectivity fingerprints corresponding to following -a, --AtomIdentifierTypes:

Based on values specified for -a, --AtomIdentifierType, --AtomicInvariantsToUse and --FunctionalClassesToUse, initial atom types are assigned to all non-hydrogen atoms in a molecule and these atom types strings are converted into initial atom identifier integers using TextUtil::HashCode function. The duplicate atom identifiers are removed.

For -n, --NeighborhoodRadius value of 0, the initial set of unique atom identifiers comprises the molecule fingerprints. Otherwise, atom neighborhoods are generated for each non-hydrogen atom up to specified -n, --NeighborhoodRadius value. For each non-hydrogen central atom at a specific radius, its neighbors at next radius level along with their bond orders and previously calculated atom identifiers are collected which in turn are used to generate a new integer atom identifier; the bond orders and atom identifier pairs list is first sorted by bond order followed by atom identifiers to make these values graph invariant.

After integer atom identifiers have been generated for all non-hydrogen atoms at all specified neighborhood radii, the duplicate integer atom identifiers corresponding to same hash code value generated using TextUtil::HashCode are removed by keeping the atom identifiers at lower radius. Additionally, all structurally duplicate integer atom identifiers at each specified radius are also removed by identifying equivalent atoms and bonds corresponding to substructures used for generating atom identifier and keeping integer atom identifier with lowest value.

The current release of MayaChemTools generates the following types of extended connectivity fingerprints vector strings:

OPTIONS

-a, --AtomIdentifierType AtomicInvariantsAtomTypes | FunctionalClassAtomTypes | DREIDINGAtomTypes | EStateAtomTypes | MMFF94AtomTypes | SLogPAtomTypes | SYBYLAtomTypes | TPSAAtomTypes | UFFAtomTypes

Specify atom identifier type to use for assignment of initial atom identifier to non-hydrogen atoms during calculation of extended connectivity fingerprints [ Ref 48, Ref 52]. Possible values in the current release are: AtomicInvariantsAtomTypes, FunctionalClassAtomTypes, DREIDINGAtomTypes, EStateAtomTypes, MMFF94AtomTypes, SLogPAtomTypes, SYBYLAtomTypes, TPSAAtomTypes, UFFAtomTypes. Default value: AtomicInvariantsAtomTypes.

--AtomicInvariantsToUse ''AtomicInvariant,AtomicInvariant...''

This value is used during AtomicInvariantsAtomTypes value of a, --AtomIdentifierType option. It's a list of comma separated valid atomic invariant atom types.

Possible values for atomic invarians are: AS, X, BO, LBO, SB, DB, TB, H, Ar, RA, FC, MN, SM. Default value [ Ref 24 ]: AS,X,BO,H,FC,MN.

The atomic invariants abbreviations correspond to:

AS = Atom symbol corresponding to element symbol

X<n> = Number of non-hydrogen atom neighbors or heavy atoms
BO<n> = Sum of bond orders to non-hydrogen atom neighbors or heavy atoms
LBO<n> = Largest bond order of non-hydrogen atom neighbors or heavy atoms
SB<n> = Number of single bonds to non-hydrogen atom neighbors or heavy atoms
DB<n> = Number of double bonds to non-hydrogen atom neighbors or heavy atoms
TB<n> = Number of triple bonds to non-hydrogen atom neighbors or heavy atoms
H<n> = Number of implicit and explicit hydrogens for atom
Ar = Aromatic annotation indicating whether atom is aromatic
RA = Ring atom annotation indicating whether atom is a ring
FC<+n/-n> = Formal charge assigned to atom
MN<n> = Mass number indicating isotope other than most abundant isotope
SM<n> = Spin multiplicity of atom. Possible values: 1 (singlet), 2 (doublet) or 3 (triplet)

Atom type generated by AtomTypes::AtomicInvariantsAtomTypes class corresponds to:

AS.X<n>.BO<n>.LBO<n>.<SB><n>.<DB><n>.<TB><n>.H<n>.Ar.RA.FC<+n/-n>.MN<n>.SM<n>

Except for AS which is a required atomic invariant in atom types, all other atomic invariants are optional. Atom type specification doesn't include atomic invariants with zero or undefined values.

In addition to usage of abbreviations for specifying atomic invariants, the following descriptive words are also allowed:

X : NumOfNonHydrogenAtomNeighbors or NumOfHeavyAtomNeighbors
BO : SumOfBondOrdersToNonHydrogenAtoms or SumOfBondOrdersToHeavyAtoms
LBO : LargestBondOrderToNonHydrogenAtoms or LargestBondOrderToHeavyAtoms
SB : NumOfSingleBondsToNonHydrogenAtoms or NumOfSingleBondsToHeavyAtoms
DB : NumOfDoubleBondsToNonHydrogenAtoms or NumOfDoubleBondsToHeavyAtoms
TB : NumOfTripleBondsToNonHydrogenAtoms or NumOfTripleBondsToHeavyAtoms
H : NumOfImplicitAndExplicitHydrogens
Ar : Aromatic
RA : RingAtom
FC : FormalCharge
MN : MassNumber
SM : SpinMultiplicity

AtomTypes::AtomicInvariantsAtomTypes module is used to assign atomic invariant atom types.

--FunctionalClassesToUse ''FunctionalClass1,FunctionalClass2...''

This value is used during FunctionalClassAtomTypes value of a, --AtomIdentifierType option. It's a list of comma separated valid functional classes.

Possible values for atom functional classes are: Ar, CA, H, HBA, HBD, Hal, NI, PI, RA. Default value [ Ref 24 ]: HBD,HBA,PI,NI,Ar,Hal.

The functional class abbreviations correspond to:

HBD: HydrogenBondDonor
HBA: HydrogenBondAcceptor
PI : PositivelyIonizable
NI : NegativelyIonizable
Ar : Aromatic
Hal : Halogen
H : Hydrophobic
RA : RingAtom
CA : ChainAtom

Functional class atom type specification for an atom corresponds to:

Ar.CA.H.HBA.HBD.Hal.NI.PI.RA

AtomTypes::FunctionalClassAtomTypes module is used to assign functional class atom types. It uses following definitions [ Ref 60-61, Ref 65-66 ]:

HydrogenBondDonor: NH, NH2, OH
HydrogenBondAcceptor: N[!H], O
PositivelyIonizable: +, NH2
NegativelyIonizable: -, C(=O)OH, S(=O)OH, P(=O)OH

--CompoundID DataFieldName or LabelPrefixString

This value is --CompoundIDMode specific and indicates how compound ID is generated.

For DataField value of --CompoundIDMode option, it corresponds to datafield label name whose value is used as compound ID; otherwise, it's a prefix string used for generating compound IDs like LabelPrefixString<Number>. Default value, Cmpd, generates compound IDs which look like Cmpd<Number>.

Examples for DataField value of --CompoundIDMode:

MolID
ExtReg

Examples for LabelPrefix or MolNameOrLabelPrefix value of --CompoundIDMode:

Compound

The value specified above generates compound IDs which correspond to Compound<Number> instead of default value of Cmpd<Number>.

--CompoundIDLabel text

Specify compound ID column label for CSV/TSV text file(s) used during CompoundID value of --DataFieldsMode option. Default: CompoundID.

--CompoundIDMode DataField | MolName | LabelPrefix | MolNameOrLabelPrefix

Specify how to generate compound IDs and write to CSV/TSV text file(s) along with generated fingerprints for text | both values of --output option: use a SDFile(s) datafield value; use molname line from SDFile(s); generate a sequential ID with specific prefix; use combination of both MolName and LabelPrefix with usage of LabelPrefix values for empty molname lines.

Possible values: DataField | MolName | LabelPrefix | MolNameOrLabelPrefix. Default: LabelPrefix.

For MolNameAndLabelPrefix value of --CompoundIDMode, molname line in SDFile(s) takes precedence over sequential compound IDs generated using LabelPrefix and only empty molname values are replaced with sequential compound IDs.

This is only used for CompoundID value of --DataFieldsMode option.

--DataFields ''FieldLabel1,FieldLabel2,...''

Comma delimited list of SDFiles(s) data fields to extract and write to CSV/TSV text file(s) along with generated fingerprints for text | both values of --output option.

This is only used for Specify value of --DataFieldsMode option.

Examples:

Extreg
MolID,CompoundName

-d, --DataFieldsMode All | Common | Specify | CompoundID

Specify how data fields in SDFile(s) are transferred to output CSV/TSV text file(s) along with generated fingerprints for text | both values of --output option: transfer all SD data field; transfer SD data files common to all compounds; extract specified data fields; generate a compound ID using molname line, a compound prefix, or a combination of both. Possible values: All | Common | specify | CompoundID. Default value: CompoundID.

-f, --Filter Yes | No

Specify whether to check and filter compound data in SDFile(s). Possible values: Yes or No. Default value: Yes.

By default, compound data is checked before calculating fingerprints and compounds containing atom data corresponding to non-element symbols or no atom data are ignored.

--FingerprintsLabel text

SD data label or text file column label to use for fingerprints string in output SD or CSV/TSV text file(s) specified by --output. Default value: ExtendedConnectivityFingerprints.

-h, --help

Print this help message.

-k, --KeepLargestComponent Yes | No

Generate fingerprints for only the largest component in molecule. Possible values: Yes or No. Default value: Yes.

For molecules containing multiple connected components, fingerprints can be generated in two different ways: use all connected components or just the largest connected component. By default, all atoms except for the largest connected component are deleted before generation of fingerprints.

-n, --NeighborhoodRadius number

Atomic neighborhood radius for generating extended connectivity neighborhoods. Default value: 4. Valid values: >= 0. Neighborhood radius of zero correspond to just the list of non-hydrogen atoms.

--OutDelim comma | tab | semicolon

Delimiter for output CSV/TSV text file(s). Possible values: comma, tab, or semicolon Default value: comma.

--output SD | text | both

Type of output files to generate. Possible values: SD, text, or both. Default value: text.

-o, --overwrite

Overwrite existing files.

-q, --quote Yes | No

Put quote around column values in output CSV/TSV text file(s). Possible values: Yes or No. Default value: Yes.

-r, --root RootName

New file name is generated using the root: <Root>.<Ext>. Default for new file names: <SDFileName><ExtendedConnectivityFP>.<Ext>. The file type determines <Ext> value. The sdf, csv, and tsv <Ext> values are used for SD, comma/semicolon, and tab delimited text files, respectively.This option is ignored for multiple input files.

-w, --WorkingDir DirName

Location of working directory. Default: current directory.

EXAMPLES

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using atomic invariants atom types in vector string format and create a SampleECAIFP.csv file containing sequential compound IDs along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using atomic invariants atom types in vector string format and create both SampleECAIFP.csv and SampleECAIFP.sdf files containing sequential compound IDs in CSV file along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using functional class atom types in vector string format and create a SampleECFCFP.csv file containing sequential compound IDs along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using DREIDING atom types in vector string format and create a SampleECFP.csv file containing sequential compound IDs along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using E-state atom types in vector string format and create a SampleECFP.csv file containing sequential compound IDs along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using MMFF94 atom types in vector string format and create a SampleECFP.csv file containing sequential compound IDs along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using SLogP atom types in vector string format and create a SampleECFP.csv file containing sequential compound IDs along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using SYBYL atom types in vector string format and create a SampleECFP.csv file containing sequential compound IDs along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using TPSA atom types in vector string format and create a SampleECFP.csv file containing sequential compound IDs along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using UFF atom types in vector string format and create a SampleECFP.csv file containing sequential compound IDs along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 6 using atomic invariants atom types in vector string format and create a SampleECAIFP.csv file containing sequential compound IDs along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 6 using functional class atom types in vector string format and create a SampleECFCFP.csv file containing sequential compound IDs along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using only AS,X atomic invariants atom types in vector string format and create a SampleECAIFP.csv file containing sequential compound IDs along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using only HBD,HBA functional class atom types in vector string format and create a SampleECFCFP.csv file containing sequential compound IDs along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using atomic invariants atom types in vector string format and create a SampleECAIFP.csv file containing compound ID from molecule name line along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using functional class atom types in vector string format and create a SampleECFCFP.csv file containing compound IDs using specified data field along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using atomic invariants atom types in vector string format and create a SampleECAIFP.tsv file containing compound ID using combination of molecule name line and an explicit compound prefix along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using functional class atom types in vector string format and create a SampleECFCFP.csv file containing specific data fields columns along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using atomic invariants atom types in vector string format and create a SampleECAIFP.tsv file containing common data fields columns along with fingerprints vector strings data, type:

To generate extended connectivity fingerprints corresponding to neighborhood radius up to 4 using functional class atom types in vector string format and create both SampleECFCFP.csv and SampleECFCFP.sdf files containing all data fields columns in CSV file along with fingerprints vector strings data, type:

AUTHOR

Manish Sud

SEE ALSO

InfoFingerprintsSDFiles.pl, InfoFingerprintsTextFiles.pl,  SimilarityMatrixSDFiles.pl, SimilarityMatrixTextFiles.pl, AtomNeighborhoodsFingerprints.pl,  MACCSKeysFingerprints.pl, PathLengthFingerprints.pl,  TopologicalAtomPairsFingerprints.pl, TopologicalAtomTorsionsFingerprints.pl,  TopologicalPharmacophoreAtomPairsFingerprints.pl, TopologicalPharmacophoreAtomTripletsFingerprints.pl

COPYRIGHT

Copyright (C) 2004-2010 Manish Sud. All rights reserved.

This file is part of MayaChemTools.

MayaChemTools is free software; you can redistribute it and/or modify it under the terms of the GNU Lesser General Public License as published by the Free Software Foundation; either version 3 of the License, or (at your option) any later version.