Jcsearch

Version 5.9.4

Introduction
Usage
Filtering expression syntax
R-group decomposition
Examples

Introduction

The jcsearch program is a command-line interface of the JChem chemical structure search. It is able to perform substructure, superstructure, full( formerly called exact), full fragment( formerly exact fragment), similarity, and duplicate( formerly perfect) searches, as well as match counts on the specified query and target molecules. These molecules can be specified as filenames, SMARTS/SMILES strings, or database tables (target only). A number of different molecular file formats are supported. Refer to the JChem Query Guide for a detailed description of search options and query features.

Note that the R-group decomposition functionality has been moved to a different script, the R-group Decomposition documentation contains specific information on this subject with examples.

Usage

For correct behaviour, please prepare the usage of the jcsearch script or batch file as described in Preparing the Usage of JChem Batch Files and Shell Scripts.

The program should be invoked in one of the following forms:

       jcsearch [options] [files...]
   or  jcsearch [options] DB:[table name]

With no file, or when file is -, it reads the standard input. When DB is specified, search is done in the database, using connection information saved by other JChem programs (e.g. jcman)

Options:

-h help message
-H help on output file formats
-q query SMARTS string or name of file that contains the query structure(s)
(More than one can be specified in non-database mode. Please see
options --and and --or.) For a detailed description about how
to formulate queries, see the JChem Query Guide.
In case of -t:p or --tautomer expects SMILES instead of SMARTS.
-t:type search type.
-t:s substructure search (default)
-t:f full search
-t:ff full fragment search
-t:d duplicate search
-t:i[:dissimilarity_threshold] similarity search
in case of mrv or sdf output the
dissimilarity value is stored as
molecule property.
-t:u superstructure search
(default for query tables)
-t:c count all hits
--hitColoring if the output format is MRV, colors the hits depending on
search type.
--hitColor in case of hitColoring specify color of hit atoms and bonds.
example: "#00FF00" means full green
examples: "red", "green", "blue"
--hitHomologyColor in case of hitColoring specify color of user defined homology
hit atoms and bonds.
example: "#00FF00" means full green
examples: "red", "green", "blue"
--nonHitColor in case of hitColoring specify color of hit atoms and bonds
example: "#00FF00" means full green
examples: "red", "green", "blue"
--nonHitColor3D in case of hitColoring in 3D molecules specify color of hit
atoms and bonds
example: "#00FF00" means full green
examples: "red", "green", "blue"
--removeUnusedDef in case of markush search remove unused R-group definitions.
Default value is y.
--markushScreening:y/n specify if screening should be used in case of markush search.
Default value is y.
--haltOnError:y/n specify how search should handle recoverable errors, stop
or log and continue if possible, default value is y
for normal structure searches and n for markush targets
--markushDisplayMode:o/r/rhg In case of markush searching and hit coloring
specifies the type of the resulting molecule.
Values:
o Default: The results is shown on the given target structure.
r Markush reduction to hit : The markush structure is reduced
according to the hit.
rhg Markush reduction to hit and the homology groups
are expanded according to the matching part of the query.
which can also be a single H atom or the empty set
--align align or template based clean hits if DB option
has been set, and output format is MRV.
--align:r rotate. If query molecule has 0 dimension, it
will be cleaned in 2d for alignment.
--align:p partial clean (template based clean). If query
molecule has 0 dimension, same as rotate.
--queryAbsoluteStereo:y/n All chiral atoms are absolute(y, default) or
consider chiral flag(n) in case of MDL mol files
w/o enhanced stereo labels. Has no effect in
database mode.
--targetAbsoluteStereo:y/n All chiral atoms are absolute(y, default) or
consider chiral flag(n) in case of MDL mol files
w/o enhanced stereo labels. Has no effect in
database mode.
--DBAbsoluteStereo:T/C/A In database mode, sets the above two
AbsoluteStereo flags.
T:(default) as set for table in database.
C: always check chiral flag(false)
A: always absolute stereo(true)
--orderSensitive Switches on order sensitive search
--tautomerSearch:d/y/n Tautomer search mode: d-default, y-on, n-off.
When set to d, tautomer search is off,
except in case of duplicate search in
a tautomer duplicate database table.
--tdf:y/n Use generic tautomers of query and target.
Effective only in case of duplicate search.
Default is n.
--exactAtomMatching:y/n Exact atom matching(y) or not(n). Default is n.
(Deprecated.)
--exactQueryAtomMatching:y/n Exact query atom matching(y) or not(n).
Default is n.
--exactRadicalMatching:y/n Exact radical matching(y) or not(n).
Default is n. (--radical is preferred instead.)
--exactIsotopeMatching:y/n Exact isotope matching(y) or not(n).
Default is n. (--isotope is preferred instead.)
--exactChargeMatching:y/n Exact charge matching(y) or not(n).
Default is n. (--charge is preferred instead.)
--charge:d/e/i Charge matching mode: d-default,
e-exact, i-ignore
--charge:i forces --implicitHMatching:i in case of
duplicate search
--isotope:d/e/i Isotope matching mode: d-default,
e-exact, i-ignore
--radical:d/e/i Radical matching mode: d-default,
e-exact, i-ignore
--valence:d/i Valence matching mode: d-default, i-ignore
--vagueBond:n/1/2/3/4 Vague handling of bond types:
n - off,
1 - handling of certain 5-membered ambiguous
aromatic rings like [C,N]1C=CC=C1 (default)
2 - all single and double ring bonds
match aromatic
3 - all single and double bonds
match aromatic
4 - ignore all bond types.
--completeHG:y/n Sets if only such structures can match on a
homology group that form an entire group. (e.g.
alkyl can't match on a cycloalkyl). default:y
--chekSpHyb Switch on sp hybridization checking.
--mix:d/i Handling of com, mix and for brackets: d-default,
i-ignore
--polymer:d/i Handling of polymer brackets: d-default,
i-ignore
--endGroupMatching:y/n Polymer end groups must match: y-yes,
n-no (default: yes)
--transformMonomer:y/n Polymer in their source based representation
are transformed to structure based : y-yes,
n-no (default: yes)
--phaseShift:y/n Polymers match the phase shifted variant:
y-yes, n-no (default: yes)
--copolymerMatching:y/n Polymers in copolymers can only be matched by
copolymers: y-yes, n-no (default: no)
--homologyHandling:y/n Homology pseudo atoms are matching on the
represented group: y-yes, n-no, only on pseudo
(default: yes)
--doubleBondStereo:N/M/A Double bond stereo Matching mode:None/Marked/All
Default is M.
--stereoSearchType:s/i/e/d Sets the stereo search type.
Possible values:
s - stereo specific searching (default),
i - ignore stereo,
e - exact stereo,
d - diastereomer search
--stereoModel:l/g/c Sets the used stereo model (for tetrahedral and
double bond stereo). Possible values:
l - local(default), g - global, c - comprehensive
--ignoreTetrahedralStereo:y/n Option for ignoring tetrahedral stereo
during searching: y-yes ignore, n-no
(default: no)
--ignoreDoubleBondStereo:y/n Option for ignoring double bond stereo
during searching: y-yes ignore, n-no
(default: no)
--ignoreAlleneStereo:y/n Option for ignoring allene stereo
during searching: y-yes ignore, n-no
(default: yes)
--ignoreAxialStereo:y/n Option for ignoring axial stereo
during searching: y-yes ignore, n-no
(default: yes)
--ignoreSynAntiStereo:y/n Option for ignoring syn-anti stereo
during searching: y-yes ignore, n-no
(default: yes)
--reactionUnpairedMap:All/unpairedOnly Option for matching unpaired maps in
reaction search:
All(default): match to any atom map,
unPairedOnly: match to unpaired map only.
--HCountMatching:G/E/A Hydrogen count query property interpretation.
Values:
G (greater or equal, mdl behaviour) target atom must have H-s
greater or equal to query H-s, in excess of explicit H-s.
H0 means no extra H other than explicitly drawn.
E (equal, daylight behaviour) target atom must have H-s equal to
H count number.
A automatically determine whether G or E should be used, from the
query source. (smiles and smarts source: E, all other: G).
--implicitHMatching:d/y/n/i Describes the matching of implicit and
explicit hydrogens.
Values:
d Default: its value is y in almost every cases.
There is only one exception: its value is n in case of duplicate
search against a query table in a database.
y Implicit and explicit hydrogens can match. In case of duplicate
searchThe sum of implicit and explicit hydrogens of the query atom
and the sum on the matched target atom must equal.
n Explicit hydrogens matches only on another explicit hydrogen. The
number of implicit hydrogens (of the matching atoms) are not checked.
i Implicit and explicit hydrogens are ignored. Hydrogens are excluded
from the matching.
For a more detailed explanation see: Search options apidoc.
--ssrType:s/c Describes the set of smallest rings to use for atom
property calculations.
Values:
s Smallest set of smallest rings(SSSR), may vary depending on atom orders.
c Complete set of smallest rings(CSSR).
--keepQueryOrder Does not rearrange the atoms of the query which
is done to achieve best search performance.
--markush:n/y Disable/enable special handling of
Markush targets. Default is n.
Enabling requires special license.
--hitIndexType:m/i For Markush targets returns hits for the
original Markush diagram (m - default) or for the
inner compiled representation (i)(See --allHits).
--hitOrdering:n/g Hit ordering type.
Possible values:
n - none (default),
g - undefined R-atom heavy group matching
takes precedence in order of R-group IDs.
--optimizeQueries:y/n Tries to speed up search when query molecule
contains special query features (atom lists,
bond lists) Default is y.
--distinctFirstAtomMatching:n/y Disable/enable special findAll algorithm.
If set, the hits must have different first atoms.
Default is n.
--attachedDataMatch Describes whether attached data
is compared.
Values:
i Default: ignores attached data when checks matching.
g general: if attached data is present in query, it must be
present in target as well.
e exact: existing attached data must match
both in query and target.
--attachedDataMatchPrefixes Comma separated list of name prefixes
(of attached data labels), that will be
compared. When not set or set to empty
string all attached data is checked.
Effective only when attachedDataMatch
is not set to 'i'.
--timeoutLimit The search timeouts reaching this number
of steps. Setting to -1 means no timeout
(Default 100000)
--exhaustiveModeLimit Upon reaching this number of steps, the
search switches to exhaustive mode from
fast mode. Setting to -1 means never.
(Default -1)

--undefinedRAtom:g/gh/ghe/a/u Describes the matching of an undefined
R-atom in query. Effective only when
--exactQueryAtomMatching is not set.
Values:
g Default: Undefined R-atom matches a group of
one or more connected atoms in target,
including at least one heavy atom.
gh Undefined R-atom matches a group of
one or more connected atoms in target,
which can also be a single H atom.
ghe Undefined R-atom matches a group of
one or more connected atoms in target,
which can also be a single H atom or the empty set
(empty set match is allowed for isolated or
one-attachment R-atoms only).
a Undefined R-atom matches any single atom in target.
u Undefined R-atom matches only an undefined R-atom in target.
--bridgingRAllowed:n/y Forbid/allow different R-atoms matching
the same group. Default is n.
--RLigandEqualityCheck:y/n Switch on/off the requirement that R-atoms
with the same R-group ID should match ligands
with the same structure. Default is y.
--maxResults:<n> Limits the number of molecules returned.
-f format output format (default: smiles). Run jcsearch -H for details.
-f :T<SDF field> write the value of the SDF field in matching targets
-f :Tname write the molecule names of matching targets
-f :M<SDF field1:...:SDF fieldn> write the specified field values to
the molecule as SDF feilds
-o file write output to file
-s SMILES read input from SMILES string
-v verbose
-vv very verbose, stack trace on error
-0 skip coordinate calculation for SMILES input
-d use Daylight-type aromatization (Huckel-rule) instead of
the standard one. (This flag overrides flags -S and --standardize!)
-2[:[On][e]] 2D coordinate calculation (useful if the input is SMILES)
-2 coordinate calculation with default options (O1)
-2:O0 no optimization -2:O1 optimize if needed
-2:O2 optimize -2:e make double either (cis/trans) bonds
-n List non-hits. For using with multiple targets, see options --and
and --or.
--and If two or more queries are present, all are required to match.
(Default) For DB targets, only the first query is considered.
If used together with option -n , a hit is returned if none of the
query molecules match.
--or If more than one queries are present, at least one is required to
match. For DB targets, only the first query is considered.
If used together with option -n , a hit is returned if at least
one query molecules does not match.
--allHits Instead of checking the existence of matching, all matchings of
the query molecule(s) are reported.
Symbols used in hit arrays in place of specific query atoms:
R - R-group
M - multicenter
U - unmapable (e.g. polymer star atom)
LP - lone pair
E - R-atom matching the empty set
EXCL - excluded query atom
-e "expression" | <file> A Chemical Terms filtering expression
or --expression "expression"|<file> for filtering hits. For syntax, see
Filtering expression syntax
-F "SQL statement" SQL query for filtering. The result should
or --filterQuery "SQL statement" contain the cd_id values. For syntax, see
filterQuery documentation
--ignoreCTExceptions:n/y If set to y, only syntactical exceptions
will be thrown during search. Those molecules
that return exception during evaluation
will be left out from hit list. Default is n.
-c config file Configuration xml file for Chemical Terms (optional)
or --config config file
-S, --standardize <file/string> standardize query and target
according to configuration file/string
See the Standardizer manual.
Default: -S 'aromatize'.
Set -S '' to skip standardization.
-g, --ignore-error continue with next molecule on error

Filtering expression syntax

Option -e or --expression requires an additional parameter, a filtering expression formulated in ChemAxon's Chemical Terms language. (It can also be the name of a file containing the filtering expression.) Only targets (and hits in case of the --allHits option) satisfying the filtering expression are reported. Note that the filter expression applies to all query molecules if more than one are specified (in case the filter expression uses the query molecule at all).

The expression syntax is described in the Chemical Terms Language Reference. Search specific functions contained in the search context provide access to the query and the target molecules, the search hit array and its elements:

mol(), target(): both refer to the search target molecule
query(): refers to the search query molecule
m(int i): refers to the query atom index with atom map i
hit(), h(): both refer to the search hit array
hit(int i), h(int i): both refer to the i-th element of the search hit array, this is the target atom index matching the query atom with atom index i
hm(int i): refers to the target atom index matching the query atom with atom map i (shorthand for h(m(i)))

The default input molecule is the target molecule (e.g. mass() is the same as mass(target()), both refer to the molecule mass of the target molecule).

In most cases the function and plugin definitions provided by the built-in evaluator.xml are sufficient, but it is possible to specify a user-defined configuration xml in the --config parameter. The user-defined configuration is added to the definitions contained in the built-in evaluator.xml. The syntax is described in the Chemical Terms Language Reference, which includes a set of search filter examples. The short reference tables give a summary of the functions and plugins provided by the built-in configuration. A set of working examples is also available.

Examples

Searching chlorobenzol in a SMILES file and sending the results to the standard output in SMILES format:
```
 jcsearch -q "c1ccccc1Cl" -f smiles input.smi
```
Searching molecules with chlorobenzol and bromine at the same time. Output: smiles and molecule name (which is stored in input.smi, separated from the smiles by spaces .)
```
 jcsearch -q "c1ccccc1Cl" --and -q "Br" -f smiles:Tfield_0 input.smi
```
Searching chlorobenzol in an SDfile file and writing the result (structures and all other data) into another SDfile:
```
 jcsearch -q "c1ccccc1Cl" -f sdf -o hits.sdf input.sdf
```
Like the above, but reading the query from a molfile and displaying the results using mview:
```
 jcsearch -q clbenz.mol -f sdf input.sdf | mview -f ID -
```
Like the above, but reading targets from a database table called molecules.
```
 jcsearch -q clbenz.mol -f sdf DB:molecules | mview -f ID -
```

Listing atom numbers with less than -0.3 partial charge in a specific molecule.

 jcsearch --allHits -e "charge(h(0)) < -0.3" -q '[*]' '[O-]C(=O)CCCCCC(=O)CCCC([O-])=O'

Listing carboxylic groups with acidic pK_a value on the carboxylic OH greater than 4.
```
 jcsearch --allHits -e "pka('acidic',hm(1)) > 4" -q "[H][O:1]C=[O:2]" target.mol
```
Filtering target molecules by both molecule mass and substructure search:
```
 jcsearch -e "mass() >= 250" -q query.mol targets.sdf
```
Similiarity search, threshold should be between 0 (very similar) to 1 (not similar):
```
 jcsearch -q "CC(C)(O)C#N" input.smi -t:i:0.4
```

Duplicate search, ignoring hydrogens:

 jcsearch -t:d --implicitHMatching:i -q Cc1c[nH]cn1 Cc1cnc[nH]1

Duplicate search, ignoring charge (which in turn implies --implicitHMatching:i):
```
 jcsearch -t:d --charge:i -q SC1=CC=CC=C1 [SH2+]C1=CC=CC=C1
```

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