Structurechecker - The Command-line Tool of Structure Checker

Contents

• Structurechecker command-line tool
• Options
  • Commands
  • Checker actions
  • Fixer actions
• Usage
• Input
• Output
• Examples
• Links

Structurechecker command-line

Structure Checker is a chemical validation tool detecting and fixing common structural errors or special features that can be potential sources of problems. structurechecker is the command-line tool of Structure Checker.

Options

General options of structurechecker

  -h,  --help                        this help page
  -hc, --help-checker-action         help page of valid checker actions
  -hf, --help-fixer-action           help page of valid fixer actions
  -m, --mode <operationmode>         [check|fix]
                                     mode of the operation (default: check)
          check                      only check is executed, 
                                     does not modify molecules
          fix                        fix molecules containing structure errors 
                                     whenever possible
  -x                                 fix mode (deprecated, use --mode fix)
Input options:
  -c, --config <filepath|string>     action string configuration
                                     actions separated by "..",
Output options:
  -t, --output-type <output type>    [single|separated|accepted|discarded]
                                     set output type(default: single)           
          single                     both accepted and discarded structures are
                                     written to the <output path>
          separated                  accepted structures are written to the
                                     <output path>, discarded structures are
                                     written to the <discarded path>
          accepted                   only accepted structures are  
                                     written to the <output path>
          discarded                  only discarded structures are  
                                     written to the <discarded path>
  -o, --output <output path>         output file (default: standard output)
  -d, --discarded <discarded path>   write molecules with structure error to 
                                     a separate file (default:standard output)
  -f, --format <format>              output file format (default: smiles)
  -rf, --report-file <filepath>      write report to a file
  -rp, --report-property <propname>  write report to the property of the
                                     output, with the specified property name
  -rt, --report-pattern <pattern>    generate pattern based report file
  -re, --report-format <format>      file format of the molecules in report
  -l, --log <filepath>               write software-error log messages to file
  -ocr, --discard-scan-errors        discard incorrectly scanned molecules

Avaliable checker actions: structurechecker -hc

Valid checker actions (strings) are:
  3d                             detect atoms with 3D coordinates
  abbrevgroup                    detect all abbreviated groups
    :expanded=true               detect expanded abbreviated groups
    :contracted=true             detect contracted abbreviated groups
  absentchiralflag               detects absent chiral flag
  atropisomer                    detect atropisomers
  alias                          detect atoms with alias
  aromaticity                    detect aromaticity errors with the given
                                 aromatization type (default: general)
    :basic                       basic aromaticity errors
    :loose                       loose aromaticity errors
    :general                     general aromaticity errors
  atommap                        detect atoms with map number
  atomqueryproperty              detect all or specified atom query properties
    :H=[true|false]              hydrogen count
    :X=[true|false]              connection count
    :D=[true|false]              explicit connection count
    :R=[true|false]              ring count
    :h=[true|false]              implicit hydrogen count
    :r=[true|false]              smallest ring count
    :a=[true|false]              aromaticity
    :s=[true|false]              substitution count
    :u=[true|false]              unsaturation
    :rb=[true|false]             ring bond count
  atomvalue                      detect atoms with atom value
  attacheddata                   detect atoms with attached data
  bondangle                      detect unpreferred bond angles in 2d
  bondlength                     detect bonds that are too long or too short
  chiralflag                     detect incorrectly set chiral flag
  coordsystem                    detect invalid coordination systems
  covalentcounterion             detect covalent counterions
  crosseddoublebond              detect crossed double bonds
  empty                          detect items without atoms
  explicith                      detect all or specified explicit hydrogens
    :lonely=[true|false]         lonely explicit hydrogens
    :mapped[true|false]          mapped explicit hydrogens
    :charged=[true|false]        charged explicit hydrogens
    :isotopic=[true|false]       isotopic explicit hydrogens
    :radical=[true|false]        radical explicit hydrogens
    :wedged=[true|false]         wedged explicit hydrogens
    :hconnected=[true|false]     hydrogen connected to hydrogen atom
    :polymerendgroup=[true|false]hydrogen connected to a SRU S-group
    :sgroup=[true|false]         hydrogen which is the only atom in an S-group
    :sgroupend=[true|false]      hydrogen connected to a Superatom S-group
    :valenceerror=[true|false]   hydrogen connected to an atom which has
                                 valence error
    :bridgehead=[true|false]     hydrogen connected to a bridgehead atom
  explicitlp                     detect explicit lone pairs
  isotope                        detect isotopes
  metallocene                    detect incorrect metallocene representations
  missingatommap                 detect atoms without map numbers
  multicenter                    detect multicenters
  multicomponent                 detect molecules containing disconnected parts
  moleculecharge                 detect non-neutral molecules
  ocr                            detect drawings that originates from
                                 incorrect optical structure recognition
  overlappingAtoms               detect atoms that are too close to each other
  overlappingBonds               detect bonds that are too close to each other
  pseudoatom                     detect pseudo atoms
  queryatom                      detect query atoms
  querybond                      detect query bonds
  racemate                       detect asymmetric tetrahedral atoms without
                                 specific stereo configuration
  radical                        detect radical atoms
  ratom                          detect specified type of R-atoms
    :all=[true|false]            all type of R-atoms
    :disconnected=[true|false]   disconnected type of R-atoms
    :generic=[true|false]        generic type of R-atoms
    :linker=[true|false]         linker type of R-atoms
    :nested=[true|false]         nested type of R-atoms
  rare                           detect rare elements
  reactionmap                    detect reactions with invalid atom mapping
  rgroupattachmenterror          detect all R-group attachment errors
  rgroupreferenceerror           detect errors in R-group definitions
                                 DEPRECATED checker, please use
                                 missingrgroup
                                 unusedrgroup
                                 circularrgroup
                                 instead.
    :missingratom=[true|false]   missing R-atom definition
    :missingrgroup=[true|false]  missing R-group definition
    :selfreference=[true|false]  self reference errors in R-group definitions
  missingrgroup                  detects missing R-group definitions
  unusedrgroup                   detects unused R-group definitions
  circularrgroup                 detects circular R-group references
  ringstrainerror                detect small rings with trans or cumulative
                                 double bonds, or triple bond
  solvent                        detect common solvents appearing
                                 by a main component
  staratom                       detect star atoms
  substructure:[smarts]          detects the given SMARTS structure
                                 as a substructure in the original molecule
  unbalancedreaction             detect reactions with orphan atoms
  valence                        detect valence errors
  valenceproperty                detect atoms with all or specified
                                 valence properties
    :defaultvalence=true         default valence properties
    :nondefaultvalence=true      non-default valence properties
  wedge                          detect incorrect wedge bonds
  wigglydoublebond               detects non_stereo double bonds with wiggly
                                 representation connected to a double bond

Avaliable fixer actions: structurechecker -hf

Valid fixer actions (strings) are:
  aliastoatom               remove aliases from atoms
  aliastogroup              convert atoms with aliases to abbreviated groups 
                            if the alias is recognized
  aliastocarbon             remove alias values from atoms and 
                            convert the atom to a carbon
  clearabsstereo            remove the chiral flag
  clean                     calculate 2D coordinates
  contractgroup             contract all abbreviated groups
  converttoelementalform    convert isotopes into elemental atoms
  converttoionicform        convert covalent counterions to ionic form
  converttometalloceneform  convert non-standard metallocene representations 
                            into coordinated multicenter representation
  crosseddoublebond         convert non-stereo double bond represented by 
                            wiggly bond to crossed double bond representation
  crossedtowiggly           convert non-stereo double bond represented by 
                            crossed double bond to wiggly bond representation
  dearomatize               convert aromatic rings into Kekule form
  expandgroup               expand all abbreviated groups if it is possible
  fixrgroupattachment       add missing attachments points to members 
                            with single location
  fixvalence                correct valence problem by removing hydrogens
                            or setting charges
  mapmolecule               add atom maps to each atom of the molecule
  mapreaction               add atom maps to the reaction
  neutralize                remove charges from the molecule
  pseudotogroup             convert pseudo atoms to abbreviated groups
                            if pseudo label is a known abbreviated group
  removeexplicith           remove explicit hydrogens
  rearomatize               dearomatize the molecule and aromatize it again
  removealias               remove alias values from atoms
  removeatom                remove the problematic atoms from the molecule
  removeatommap             remove atom map numbers
  removeatomqueryproperty   remove atom query properties
  removeatomvalue           remove atom values
  removeattacheddata        remove data attached to atoms
  removebond                remove problematic bonds from the molecule
  removeradical             convert radicals to non_radical atoms
  removevalenceproperty     remove valence properties from atoms
  removezcoordinate         set the z-coordinates of atoms to zero
  ungroup                   ungroup all abbreviated groups
  wedgeclean                recalculate the orientation of the wedge bonds 

Usage

structurechecker  -c <config file> -m [mode] [<options>] [input list]

The command line parameter -c or --config is mandatory. This parameter specifies the configuration file path or a simple action string.

structurechecker -c config.xml or
structurechecker -c "atomqueryproperty"

The optional parameter -m or --mode specifies the operation mode. The following operation modes are available:

• check (default): searches for errors;
  structurechecker -c config.xml -m "check"
• fix: fixes automatically fixable errors.
  structurechecker -c config.xml -m "fix"

Note: The syntax of commands can be different under various command line shells (bash, tcsh, zsh, etc.).

Input

Structurechecker accepts most molecular file formats as input (Marvin Documents (MRV), MDL molfile, Sdfile, RXNfile, Rdfile, SMILES, etc.). The input can be specified as:

• input file(s),
• input string(s), or
• SMILES (default).

  structurechecker -c config.xml -m "check" input.mrv

structurechecker -c config.xml -m "check" "OCC(O)C1OC(=O)C(O)=C1O"

Output

Structurechecker's output contains the file(s) of the checked/fixed molecules and optionally a report of the results. The molecules are written to the output file(s). The format of the output file(s) can be specified by the -f or --format option (default format is: "smiles"). The type of output is defined by the -t or --output-type parameter. The possible values of the output type are the following:

• single (default): all molecules are written to the file defined by the --output parameter. If --output parameter is omitted, the result is written in the standard output (console). (--discarded parameter is ignored in this case.)
• separated: valid and invalid molecules are written to two different files. The --output parameter defines the output file of molecules with valid structures, and the --discarded parameter defines the output file of molecules with invalid structures (or in fix mode, those which cannot be fixed automatically).
  • If --discarded parameter is omitted, molecules with invalid structures are written to standard output;
  • If --output parameter is omitted, molecules with valid structures are written to standard output;

    Note: The indication of --output or --discarded parameter is mandatory. If none of these parameters are defined, the program stops.

• accepted: only molecules with valid structures are written to file defined by the --output parameter. If --output parameter is omitted, molecules with valid structures are written to the standard output. (--discarded parameter is ignored in this case)
• discarded: only molecules with invalid structures are written to the file defined by the --discarded parameter. If �-discarded parameter is omitted, molecules with valid structures are written to the standard output. (--output parameter is ignored in this case.)

Note: Not all molecules with structure errors are discarded. When fix mode is selected, molecules with automatically unfixable errors will be discarded only.

Usage examples

Below you can find the short descriptions of some examples.

1. structurechecker -c "metallocene"

   Executes a check with configuration metallocene on the molecule(s) defined in the standard input, and writes the result to the standard output (console);

2. structurechecker -c "bondLength" in.sdf

   Executes a check with configuration bondLength on the molecule(s) defined in the in.sdf file, and writes the result to the standard output (console);
3. structurechecker -c "isotope->converttoelementalform" in.sdf Executes a check with configuration isotope->converttoelementalform on the molecule(s) defined in the in.sdf file, and writes the result to the standard output (console);

4. structurechecker -c "aromaticity..valence" -m fix -f sdf -o out.sdf in.sdf

   Executes a fix with configuration aromaticity and valence on the molecule(s) defined in the in.sdf file, and writes the molecules with valid structures (including automatically fixed molecules) in sdf format to the out.sdf output file;

5. structurechecker -c config.xml -t separated -o out.sdf -d discarded.sdf

   Executes a check with configuration contained by the config.xml, and writes the molecules with valid structures to out.sdf, and writes the molecules with invalid structures to discarded.sdf.

   Note: The format of both outputs is SMILES(!) as --format (-f) is not defined;

6. structurechecker -c config.xml -m fix -t separated -d discarded.sdf Executes a fix with configuration contained by the config.xml, and writes the molecules with invalid structures to discarded.sdf, and writes molecules with valid structures to the standard output (console);
7. structurechecker -c config.xml -m fix -t discarded in.sdf Executes a fix with configuration contained by the config.xml, and writes the molecules with invalid structures to discarded.sdf, and omits molecules with valid structures.

Links

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