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#!/usr/bin/perl
use strict;
use warnings;
use Chemistry::OpenSMILES qw( is_chiral mirror );
use File::Basename qw( basename );
use Getopt::Long::Descriptive;
use List::Util qw( none );
use SmilesScripts::Isomorphism;
my $basename = basename $0;
my( $opt, $usage ) = describe_options( <<"END" . 'OPTIONS',
USAGE
$basename [<args>] [<files>]
DESCRIPTION
$basename reads in files with SMILES descriptors and outputs whether
they qualify as racemates or not.
END
[ 'check-isomorphism',
'perform an extra isomorphism check on molecular entities detected ' .
'as isomorphic by comparing their canonical representations' ],
[],
[ 'help', 'print usage message and exit', { shortcircuit => 1 } ],
);
if( $opt->help ) {
print $usage->text;
exit;
}
my $pair_moieties_options = { check_isomorphism => $opt->check_isomorphism };
while( <> ) {
chomp;
my $additional_position = '';
if( s/\t([^\t]*)$// ) {
$additional_position = ' ' . $1;
}
local $SIG{__WARN__} = sub {
print STDERR "$basename: $ARGV($.)$additional_position: $_[0]"
};
my @moieties;
eval {
@moieties = @{ SmilesScripts::Isomorphism::parse_smiles( $_ ) };
};
print STDERR "$basename: $ARGV($.) $additional_position: $@" if $@;
my $total = scalar @moieties;
my $n_achiral = 0;
my $n_self_mirror = 0;
my $n_enantiomers = 0;
my $n_enantiopure = 0;
@moieties = grep { is_chiral( $_ ) } @moieties;
$n_achiral = $total - @moieties;
eval {
for my $moiety (@moieties) {
my @A;
my @B;
# Check for self-chiral moieties
@A = SmilesScripts::Isomorphism::copy_moiety( $moiety );
@B = SmilesScripts::Isomorphism::copy_moiety( $moiety );
mirror $B[0];
SmilesScripts::Isomorphism::pair_moieties( \@A, \@B, $pair_moieties_options );
if( !@A && !@B ) {
$n_self_mirror++;
next;
}
@A = @moieties;
@B = SmilesScripts::Isomorphism::copy_moiety( $moiety );
mirror $B[0];
SmilesScripts::Isomorphism::pair_moieties( \@A, \@B, $pair_moieties_options );
if( @B ) { # Mirrored moiety is not found among declared moieties
$n_enantiopure++;
} else {
$n_enantiomers++;
}
}
};
print STDERR "$basename: $ARGV($.) $additional_position: $@" if $@;
my @results;
push @results, "achiral ($n_achiral)" if $n_achiral;
push @results, "self-mirror ($n_self_mirror)" if $n_self_mirror;
push @results, "enantiomer ($n_enantiomers)" if $n_enantiomers;
push @results, "enantiopure ($n_enantiopure)" if $n_enantiopure;
print join( ' ', sort @results ), "\n";
}
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