Depth-First: Tag nametostruct

JRuby for Cheminformatics: Parsing IUPAC Nomenclature with OPSIN

Rich Apodaca — Fri, 12 Oct 2007 10:37:00 +0000

Recent articles have discussed the use of JRuby for cheminformatics. We've seen how to parse SMILES strings, and read or write InChIs. In this article, we'll see how easy it is to parse IUPAC nomenclature from JRuby using Peter Corbett's OPSIN library.

Installation

After installing JRuby, simply download the OPSIN jarfile and copy it to your JRuby lib directory. You're done.

A Simple Library

We can write a simple library to convert an IUPAC name into a CML document:

require 'jruby'

import 'uk.ac.cam.ch.wwmm.opsin.NameToStructure'

module IUPAC
  @@nts = NameToStructure.new

  def read_name name
    cml = @@nts.parse_to_cml(name)

    raise "Could not parse '#{name}'." unless cml

    cml.to_xml
  end
end

The read_name method accepts an iupac name as a string and returns a CML document as a string. If the input can't be parsed, an exception is raised.

Testing the Library

We can test the library by saving it as a file called iupac.rb and invoking jirb:

$ jirb
irb(main):001:0> require 'iupac'
=> true
irb(main):002:0> include IUPAC
=> Object
irb(main):003:0> read_name('4-iodobenzoic acid')

This returns the XML shown below, which has been re-formatted for clarity:

<cml xmlns="http://www.xml-cml.org/schema">
  <molecule id="m1">
    <atomArray>
      <atom id="a1" elementType="C">
        <label value="1" />
      </atom>
      <atom id="a2" elementType="C">
        <label value="2" />
      </atom>
      <atom id="a3" elementType="C">
        <label value="3" />
      </atom>
      <atom id="a4" elementType="C">
        <label value="4" />
      </atom>
      <atom id="a5" elementType="C">
        <label value="5" />
      </atom>
      <atom id="a6" elementType="C">
        <label value="6" />
      </atom>
      <atom id="a7" elementType="C" />
      <atom id="a8" elementType="O" />
      <atom id="a9" elementType="O" />
      <atom id="a10" elementType="I">
        <label value="1" />
      </atom>
    </atomArray>
    <bondArray>
      <bond atomRefs2="a1 a2" order="2" />
      <bond atomRefs2="a2 a3" order="1" />
      <bond atomRefs2="a3 a4" order="2" />
      <bond atomRefs2="a4 a5" order="1" />
      <bond atomRefs2="a5 a6" order="2" />
      <bond atomRefs2="a6 a1" order="1" />
      <bond atomRefs2="a7 a1" order="1" />
      <bond atomRefs2="a7 a8" order="2" />
      <bond atomRefs2="a7 a9" order="1" />
      <bond atomRefs2="a10 a4" order="1" />
    </bondArray>
  </molecule>
</cml>

This simple Ruby library has parsed the name '4-iodobenzoic acid' and has returned a string containing the CML representation for the molecule. If we had wanted the read_name method to return a traversable XML object model, we could have enabled that as well.

Conclusions

One of the objections raised whenever the issue of "new" programming languages comes up, regardless of their merit, is the age-old refrain "Yeah, but where's the software?" With JRuby, we bypass this question altogether. We can leverage the full scope of the massive Java development effort over the last ten years, which includes several excellent cheminformatics libraries. With virtually no effort, we have a working cheminformatics platform based on a widely-used, versatile and dynamic object-oriented scripting language. Future articles will discuss extensions to this platform and some applications.

From IUPAC Nomenclature to 2-D Structures With OPSIN

Rich Apodaca — Tue, 17 Oct 2006 13:57:00 +0000

A previous article introduced OPSIN, an Open Source Java library for decoding IUPAC chemical nomenclature. In this tutorial, you'll see how OPSIN can, when interfaced with freely-available chemical informatics software, generate 2-D structure diagrams from IUPAC names.

Prerequisites

This tutorial requires Ruby CDK (RCDK), which in turn requires Ruby, Java, and the Ruby Java Bridge. Tutorials detailing the installation of RCDK on both Windows and Linux platforms are available.

In addition, you'll need a copy of the standalone jarfile opsin-big-0.1.0.jar. Future versions of RCDK will integrate the OPSIN jarfile, making this step unnecessary.

Outlining the Problem and a Solution

We'd like to create a simple Ruby class with a method that accepts an IUPAC chemical name as input and produces a PNG image of the corresponding molecule as output. OPSIN accepts IUPAC names as input, but it only produces Chemical Markup Language (CML) as output. The CML output lacks 2-D coordinates, and OPSIN itself has no 2-D rendering capabilities.

We'll use RCDK to augment OPSIN's capabilities. Thanks to CDK's built-in CML support, RCDK can read CML and generate an AtomContainer representation. RCDK also supports the assignment of 2-D coordinates to an AtomContainer via CDK's StructureDiagramGenerator. To produce the PNG image, we'll use the 2-D rendering capability made possible through Structure-CDK, which is a built-in component of RCDK.

A Simple Ruby Library

Create a working directory and copy opsin-big-0.1.0.jar into it. Next, create a file called depictor.rb containing the following Ruby code:

require 'rubygems'
require_gem 'rcdk'
require 'rcdk'

Java::Classpath.add('opsin-big-0.1.0.jar')

require 'util'

# A simple IUPAC->2-D structure convertor.
class Depictor
  @@StringReader = import 'java.io.StringReader'
  @@NameToStructure = import 'uk.ac.cam.ch.wwmm.opsin.NameToStructure'
  @@CMLReader = import 'org.openscience.cdk.io.CMLReader'
  @@ChemFile = import 'org.openscience.cdk.ChemFile'

  def initialize
    @nts = @@NameToStructure.new
    @cml_reader = @@CMLReader.new
  end

  # Writes a <tt>width</tt> by <tt>height</tt> PNG to
  # <tt>filename</tt> for the molecule described by
  # <tt>iupac_name</tt>.
  def depict_png(iupac_name, filename, width, height)
    cml = @nts.parseToCML(iupac_name)

    throw("Can't parse name: #{iupac_name}") unless cml

    molfile = cml_to_molfile(cml)

    RCDK::Util::Image.molfile_to_png(molfile, filename, width, height)
  end

  private

  def cml_to_molfile(cml)
    string_reader = StringReader.new(cml.toXML)

    @cml_reader.setReader(string_reader)

    chem_file = @cml_reader.read(@@ChemFile.new)
    molecule = chem_file.getChemSequence(0).getChemModel(0).getSetOfMolecules.getMolecule(0)

    molecule = RCDK::Util::XY.coordinate_molecule(molecule)

    RCDK::Util::Lang.get_molfile(molecule)
  end
end

Testing, Testing

A short test will demonstrate the capabilities of the Depictor library. Add the following to a file called test.rb in your working directory (or enter it interactively with irb):

require 'depictor'

depictor = Depictor.new
name = '3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid' #Penicillin G

depictor.depict_png(name, 'out.png', 300, 300)

Running this test produces a 300x300 PNG image of Penicillin G, named out.png, in your working directory:

As you can see, this simple library and test code has:

correctly parsed the rather complex IUPAC name (3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2- carboxylic acid) to a valid CML representation
converted this representation to a CDK AtomContainer
assigned 2-D coordinates
rendered a PNG image in color

Notice how the thiaazabicyclo[3.2.0] system, complete with properly-placed substitutents, was flawlessly identified and parsed.

If you entered the above test code interactively via IRB, you may have noticed a multi-second delay in instantiating Depictor. This latency results from a sluggish NameToStructure constructor in OPSIN. A similar delay also occurs in OPSIN's pure-Java unit tests. Once Depictor is instantiated, however, image generation occurs relatively quickly.

The unususal orientation of the beta-lactam carbonyl group is determined by CDK's StructureDiagramGenerator. The source of this behavior will be explored in a future article.

More Examples

To illustrate some of the capabilities of the OPSIN-RCDK combination, a few more examples are provided below.

One of OPSIN's more surprising features is how well it handles heterocycles. For example, the IUPAC name for caffeine (1,3,7-trimethylpurine-2,6-dione) is translated to:

As another example, consider the tetrazole (1-[2-hydroxy-3-propyl-4-[3-(2H-tetrazol-5-yl)propoxy]phenyl]ethanone):

Highly substituted benzene rings and carboxylic acids are also translated accurately, as in 3-acetamido-5-(acetyl-methyl-amino)-2,4,6-triiodo-benzoic acid (Metrizoate):

How about a hairy-looking macrocycle name with multiple levels of morpheme nesting (3,6-diamino-N-[[15-amino-11-(2-amino-3,4,5,6-tetrahydropyrimidin-4-yl)-8- [(carbamoylamino)methylidene]-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo- 1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]hexanamide)? Not a problem:

Limitations

In my tests of the OPSIN library, one structure appeared to be incorrectly parsed - N-(5-chloro-2-methyl-phenyl)-2-methoxy-N-(2-oxooxazolidin-3-yl)acetamide:

There are actually two problems with the output. First, an oxygen atom and a methyl group are overlapping near the top of the diargram. This cosmetic issue is related to CDK's StructureDiagramGenerator. Second, the oxazolidine nitrogen atom is misplaced by OPSIN. The correct 2-D image of this molecule, obtained from PubChem, is shown below:

Conclusions

It's not common to find an early-development Open Source project with the sophistication of OPSIN. The smooth handling of nested morphemes, aromatic heterocycles, macrocycles, and a good fraction of what I threw at it leads me to belive that a well-designed and extensible nomenclature parsing engine lies at OPSIN's core. More on that later, though.

What could you do with a powerful Open Source IUPAC nomenclature parser? The answer to that one question could fill a three-volume series. Suffice it to say that OPSIN, in combination with other Open Source software, offers virtually limitless potential for indexing, collecting, repackaging, reprocessing, and mashing up vast amounts of chemical information. Because of its Open Source license, OPSIN can be extended and otherwise modified to fit your particular needs. Future articles will highlight some of the possibilities.

Decoding IUPAC Names With OPSIN

Rich Apodaca — Sat, 14 Oct 2006 14:39:00 +0000

IUPAC chemical nomenclature is everywhere. It can be found in journal articles, both new and old, on the Web, in databases, on Material Safety Data Sheets (MSDS), in chemical catalogs, and just about anywhere chemical information is found. The rules of this nomenclature are one of the first things taught in Organic Chemistry classes, and entire books are devoted to the subject. Although software for IUPAC nomenclature translation has been researched since the 1970s, it has only become widespread within the last ten years. As is typical, IUPAC nomenclature developer toolkits are closed, proprietary, very expensive, and not customizable - with one notable exception.

A little software package called OPSIN may be set to change this. Read on to see how you can use OPSIN to begin programatically decoding IUPAC chemical nomenclature today.

Meet OPSIN

OPSIN is an Open Source Java library for parsing IUPAC nomenclature. Despite its early development status, OPSIN can decode a variety of difficult features in basic IUPAC nomenclature, including bicyclo systems, nested substitution, saturated heterocycles, and a variety of arenes and heteroarenes. OPSIN currently doesn't handle stereochemistry, organometallics, or a variety of other advanced IUPAC nomenclature features.

Brief Background

OPSIN was written by Peter Corbett at the University of Cambridge. Until recently, OPSIN was an integral part of of the innovative chemical data checker OSCAR. One of the exciting uses of OSCAR is in the automated validation of experimental data.

Getting OPSIN

Recently, OPSIN was factored out of OSCAR. It can now be downloaded as two standalone packages from SourceForge:

Source Distribution: Contains the complete OPSIN source code, all library dependencies, all datasets, and an Ant build script.
Jarfile: A standalone jarfile containing all library dependencies and data files.

What OPSIN Does

OPSIN accepts an IUPAC name, encoded as a String object, as input and provides a Chemical Markup Language (CML) document object model as output. The main point of entry into the library is the NameToStructure class and its two overloaded parseToCML methods.

OPSIN's output is the root node in a XOM XML Element hierarchy. XOM's Element class provides a convenience method, toXML that conveniently prints the text-based XML representation for itself and all Elements below it.

Because its output is pure XML, OPSIN does not depend on any chemical informatics toolkit to do its job. This makes OPSIN ideal for use within larger chemical informatics systems. Provided your software can interpret CML, you should be able to manipulate OPSIN's output in a variety of useful ways.

What's Next?

Future articles will discuss OPSIN's capabilities and limitations in more detail. As has become customary for Depth-First's tutorials, Ruby and the excellent Ruby Java Bridge will be used to illustrate the important points.