So much to do, so little time

Trying to squeeze sense out of chemical data

Archive for the ‘cheminformatics’ tag

ChEMBL in RDF and Other Musings

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Earlier today, Egon announced the release of an RDF version of ChEMBL, hosted at Uppsala. A nice feature of this setup is that one can play around with the data via SPARQL queries as well as explore the classes and properties that the Uppsala folks have implemented. Having fiddled with SPARQL on and off, it was nice to play with ChEMBL since it contains such a wide array of data types. For example,  find articles referring to an assay (or experiment) run in mice targeting isomerases:

PREFIX  chembl:  <>
?protein chembl:hasKeyword "Isomerase" .
?x chembl:hasTarget ?protein .
?protein chembl:hasDescription ?pdesc .
?x chembl:organism  "Mus musculus" .
?x chembl:hasDescription ?DESC .
?x chembl:extractedFrom ?resource .
?resource <> ?pmid

I’ve been following the discussion on RDF and Semantic Web for some time. While I can see a number of benefits from this approach, I’ve never been fully convinced as to the utility. In too many cases, the use cases I’ve seen (such as the one above) could have been done relatively trivially via traditional SQL queries. There hasn’t been a really novel use case that leads to ‘Aha! So that’s what it’s good for’

Egons’ announcement today, led to a discussion on FriendFeed. I think I finally got the point that SPARQL queries are not magic and could indeed be replaced by traditional SQL. The primary value in RDF is the presence of linked data – which is slowly accumulating in the life sciences (cf. LODD and Bio2RDF).

Of the various features of RDF that I’ve heard about, the ability to define and use equivalence relationships seems very useful. I can see this being used to jump from domain to domain by recognizing properties that are equivalent across domains. Yet, as far as I can tell, this requires that somebody defines these equivalences manually. If we have to do that, one could argue that it’s not really different from defining a mapping table to link two RDBMS’s.

But I suppose in the end what I’d like to see is using all this RDF data to perform automated or semi-automated inferencing. In other words, what non-obvious relationships can be draw from a collection of facts and relationships? In absence of that, I am not necessarily pulling out a novel relationship (though I may be pulling out facts that I did not necessarily know) by constructing a SPARQL query. Is such inferencing even possible?

On those lines, I considered an interesting set of linked data – could we generate a geographically annotated version of PubMed. Essentially, identify a city and country for each PubMed ID. This could be converted to RDF and linked to other sources. One could start asking questions such as are people around me working on a certain topic? or what proteins are the focus of research in region X? Clearly, such a dataset does not require RDF per se. But given that geolocation data is qualitatively different from say UniProt ID’s and PubMed ID’s, it’d be interesting to see whether anything came of this. As a first step, here’s BioPython code to retrieve the Affiliation field from PubMed entries from 2009 and 2010.

from Bio import Entrez

startYear = 2009
endYear = 2010 = ""
h = Entrez.esearch(db='pubmed', term='%d:%d[dp]' % (startYear,endYear), retmax=1000000)
records =['IdList']
print 'Got %d records' % (len(records))
o = open('geo.txt', 'w')
for pmid in records:
    print 'Processing PMID %s' % (pmid)
    hf = Entrez.efetch(db='pubmed', id=pmid, retmode='xml', rettype='full')
    details =[0]
        aff = details['MedlineCitation']['Article']['Affiliation']
    except KeyError:
        print '%s had no affiliation' % (pmid)
        o.write('%s\t%s\n' % (pmid, aff.encode('latin-1')))
    except UnicodeEncodeError:
        'Cant encode for %s' % (pmid)

Using data from the National Geospatial Agency, it shouldn’t be too difficult to link PubMed ID’s to geography.

Written by Rajarshi Guha

February 10th, 2010 at 4:40 am

A GPL3 Oracle Cheminformatics Cartridge

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Sometime back I had mentioned a new cheminformatics toolkit, Indigo. Recently, Dmitry from SciTouch let me know that they had also developed Bingo, an Oracle cartridge based on Indigo, to perform cheminformatics operations in the database. This expands the current ecosystem of Open Source database cartridges (PGChem, MyChem, OrChem) which pretty much covers all the main RDBMSs (Postgres, MyQSL and Oracle). SciTouch have also provided a live instance of their database and associated cartridge, so you can play with it without requiring a local Oracle install. (It’d be useful to provide some details of the hardware that the DB is running on, so that timing numbers get some context)

Written by Rajarshi Guha

January 24th, 2010 at 2:35 pm

Posted in software

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Chemistry in Google Docs

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I met with Jean-Claude Bradley yesterday and we had a pretty useful hack session, allowing him to easily incorporate chemical and cheminformatics functionality into a GoogleDocs spreadsheet.

A common task that Jean-Claude wanted to automate was the calculation of milligrams (or milliliters) of a chemical required for a certain molarity.  So what we need for this calculation is the compound name, desired molarity, molecular weight and the density. Importantly, the people who’d like to use this will provide compound names and not a directly parseable SMILES.  So we’d also like to (optionally) get the SMILES. Finally, he wanted to be able to do this in a Google spreadsheet – rather than a specific web page or stand alone program.

It turns out that with a liberal helping of Python, a dash of ChemSpider and pinch of PubChem, all of this can be done in a half hour hack session.

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Written by Rajarshi Guha

December 10th, 2008 at 4:23 pm

AJAX’ified Pub3D

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Pub3D is a 3D version of PubChem, in which we have generated a single conformer for 99% of PubChem using the smi23d suite of programs. The structures are then stored in a PostgreSQL database along with their distance moment shape descriptors described by Ballester and Graham-Richards. This allows us to perform shape similarity queries against a user supplied 3D structure. By partitioning the database (thanks to the CGL folks at IU) and using a spatial index, performance is quite snappy. (I had briefly mentioned this in a presentation at the ACS meeting, last spring).

The database had been down for some time, so today I got it back up and running and AJAX’ified the interface, to make it look a little nicer.  jQuery rocks! (OK, the color scheme sucks)

There are obvious drawbacks to the current database – single conformer shape search is not very rigorous, especially since the stored structures are not necessarily the minimum energy conformer. However, we have started generating multiple conformers, so hopefully we’ll address this issue in time. The bigger issue is how this approach to shape similarity compares to other well known approaches such as ROCS. Clearly, a shape descriptor approach is lower resolution to a volumetric approach such as ROCS, so in that sense the results are ‘rougher’. However visual inspection of some searches seems to indicate that it isn’t too bad. The paper describing these shape descriptors didn’t do a rigorous comparison – that’s on our TODO list.

OK, the fun part (a.k.a, coding) is done for now – got to get back to the paper.

Written by Rajarshi Guha

October 3rd, 2008 at 5:33 am

Why Academic Cheminformatics is Important

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I’m in academia and I do cheminformatics. Recent collaborations, papers and funding issues in this field have made me think about the future of this research in this setting. This, and a thread discussing David Leahy’s talk on InkSpot Science at the Soton Open Science Workshop got me started on this post.

There are currently a number of groups and collaborations that are attempting to perform drug discovery without the large centralized infrastructure that is characteristic of this process. Examples of this include Jean Claude Bradley who runs the UsefulChem project and the Synaptic Leap as well as various academic labs. Also see Kozikowski et al

Cheminformatics plays a key role in drug discovery efforts at various stages. For example, identifying or prioritizing compounds from virtual libraries, predicting ADME profiles and side effects (e.g., hERG activation) and so on. I should stress that such computational methods don’t replace bench work – but they can certainly enhance it. More generally, we’re now faced with a deluge of data – and human eyeballs are not going to be able to handle this. And this is exactly the place that cheminformatics does it’s stuff.

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Written by Rajarshi Guha

September 1st, 2008 at 1:43 pm

Posted in research

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