From 8c973e16028cb95c978bb08cf79369a5c3520c31 Mon Sep 17 00:00:00 2001
From: Christoph Helma <helma@in-silico.ch>
Date: Sun, 28 Feb 2016 12:43:38 +0100
Subject: physchem feature class

---
 lib/physchem.rb | 138 ++++++++++++++++++++++++++++++++++++++++++++++++++++++++
 1 file changed, 138 insertions(+)
 create mode 100644 lib/physchem.rb

(limited to 'lib/physchem.rb')

diff --git a/lib/physchem.rb b/lib/physchem.rb
new file mode 100644
index 0000000..1126e69
--- /dev/null
+++ b/lib/physchem.rb
@@ -0,0 +1,138 @@
+module OpenTox
+
+  # Feature for physico-chemical descriptors
+  class PhysChem < NumericFeature
+
+    field :library, type: String
+    field :descriptor, type: String
+    field :description, type: String
+
+    JAVA_DIR = File.join(File.dirname(__FILE__),"..","java")
+    CDK_JAR = Dir[File.join(JAVA_DIR,"cdk-*jar")].last
+    JOELIB_JAR = File.join(JAVA_DIR,"joelib2.jar")
+    LOG4J_JAR = File.join(JAVA_DIR,"log4j.jar")
+    JMOL_JAR = File.join(JAVA_DIR,"Jmol.jar")
+
+    obexclude = ["cansmi","cansmiNS","formula","InChI","InChIKey","s","smarts","title","L5"]
+    OBDESCRIPTORS = Hash[OpenBabel::OBDescriptor.list_as_string("descriptors").split("\n").collect do |d|
+      name,description = d.split(/\s+/,2)
+      ["Openbabel."+name,description] unless obexclude.include? name
+    end.compact.sort{|a,b| a[0] <=> b[0]}]
+
+    cdkdescriptors = {}
+    CDK_DESCRIPTIONS = YAML.load(`java -classpath #{CDK_JAR}:#{JAVA_DIR}  CdkDescriptorInfo`)
+    CDK_DESCRIPTIONS.each do |d|
+      prefix="Cdk."+d[:java_class].split('.').last.sub(/Descriptor/,'')
+      d[:names].each { |name| cdkdescriptors[prefix+"."+name] = d[:description] }
+    end
+    CDKDESCRIPTORS = cdkdescriptors
+
+    # exclude Hashcode (not a physchem property) and GlobalTopologicalChargeIndex (Joelib bug)
+    joelibexclude = ["MoleculeHashcode","GlobalTopologicalChargeIndex"]
+    # strip Joelib messages from stdout
+    JOELIBDESCRIPTORS = Hash[YAML.load(`java -classpath #{JOELIB_JAR}:#{LOG4J_JAR}:#{JAVA_DIR}  JoelibDescriptorInfo | sed '0,/---/d'`).collect do |d|
+      name = d[:java_class].sub(/^joelib2.feature.types./,'')
+      ["Joelib."+name, "JOELIb does not provide meaningful descriptions, see java/JoelibDescriptors.java for details."] unless joelibexclude.include? name
+    end.compact.sort{|a,b| a[0] <=> b[0]}] 
+
+    DESCRIPTORS = OBDESCRIPTORS.merge(CDKDESCRIPTORS.merge(JOELIBDESCRIPTORS))
+
+    require_relative "unique_descriptors.rb"
+
+    def self.descriptors
+      DESCRIPTORS.collect do |name,description|
+        lib,desc = name.split('.',2)
+        self.find_or_create_by(:name => name, :library => lib, :descriptor => desc, :description => description, :measured => false, :calculated => true, :numeric => true, :nominal => false)
+      end
+    end
+
+    def self.unique_descriptors
+      udesc = []
+      UNIQUEDESCRIPTORS.each do |name|
+        lib,desc = name.split('.',2)
+        if lib == "Cdk"
+          CDK_DESCRIPTIONS.select{|d| desc == d[:java_class].split('.').last.sub('Descriptor','') }.first[:names].each do |n|
+            dname = "#{name}.#{n}"
+            description = DESCRIPTORS[dname]
+            udesc << self.find_or_create_by(:name => dname, :library => lib, :descriptor => desc, :description => description, :measured => false, :calculated => true, :numeric => true, :nominal => false)
+          end
+        else
+          description = DESCRIPTORS[name]
+          udesc << self.find_or_create_by(:name => name, :library => lib, :descriptor => desc, :description => description, :measured => false, :calculated => true, :numeric => true, :nominal => false)
+        end
+      end
+      udesc
+    end
+
+    # Description of available descriptors
+    def self.description descriptor
+      lib = descriptor.split('_').first
+      case lib
+      when "Openbabel"
+        OBDESCRIPTORS[descriptor]
+      when "Cdk"
+        name = descriptor.split('_')[0..-2].join('_')
+        CDKDESCRIPTORS[name]
+      when "Joelib"
+        JOELIBDESCRIPTORS[descriptor]
+      when "lookup"
+        "Read feature values from a dataset"
+      end
+    end
+
+    def calculate compound
+      result = send library.downcase,descriptor,compound
+      p result
+      result[self.name]
+    end
+
+    def openbabel descriptor, compound
+      obdescriptor = OpenBabel::OBDescriptor.find_type descriptor
+      obmol = OpenBabel::OBMol.new
+      obconversion = OpenBabel::OBConversion.new
+      obconversion.set_in_format 'smi'
+      obconversion.read_string obmol, compound.smiles
+      {"#{library.capitalize}.#{descriptor}" => fix_value(obdescriptor.predict(obmol))}
+    end
+
+    def cdk descriptor, compound
+      java_descriptor "cdk", descriptor, compound
+    end
+
+    def joelib descriptor, compound
+      java_descriptor "joelib", descriptor, compound
+    end
+
+    private
+
+    def java_descriptor lib, descriptor, compound
+
+      sdf_3d = "/tmp/#{SecureRandom.uuid}.sdf"
+      File.open(sdf_3d,"w+"){|f| f.print compound.sdf}
+      
+      # use java system call (rjb blocks within tasks)
+      # use Tempfiles to avoid "Argument list too long" error 
+      case lib
+      when "cdk"
+        `java -classpath #{CDK_JAR}:#{JAVA_DIR}  CdkDescriptors #{sdf_3d} #{descriptor}`
+      when "joelib"
+        `java -classpath #{JOELIB_JAR}:#{JMOL_JAR}:#{LOG4J_JAR}:#{JAVA_DIR}  JoelibDescriptors  #{sdf_3d} #{descriptor}`
+      end
+      result = YAML.load_file("#{sdf_3d}#{lib}.yaml").first
+      result.keys.each{|k| result[k] = result.delete(k)}
+      result
+    end
+
+    def fix_value val
+      val = val.first if val.is_a? Array and val.size == 1
+      val = nil if val == "NaN"
+      if val.numeric?
+        val = Float(val)
+        val = nil if val.nan? or val.infinite?
+      end
+      val
+    end
+
+  end
+
+end
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