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Friday, April 14, 2017

The ACS Spring disclosures of 2017 #1

At the American Chemical Society meetings drug companies disclose recent new drugs to the world. Normally, the chemical structures are already out in the open, often as part of patents. But because these patents commonly discuss many compounds, the disclosures are a big thing.

Now, these disclosure meetings are weird. You will not get InChIKeys (see doi:10.1186/s13321-015-0068-4) or something similar. No, people sit down with paper, manually redraw the structure. Like Carmen Drahl has done in the past. And Bethany Halford has taken over that role at some point. Great work from both! The Chemical & Engineering News has aggregated the tweets into this overview.

Of course, a drug structure disclosure is not complete if it does not lead to deposition in databases. The first thing is to convert the drawings into something machine readable. And thanks to the great work from John May on the Chemistry Development Kit and the OpenSMILES team, I'm happy with this being SMILES. So, we (Chris Southan and me) started a Google Spreadsheet with CCZero data:



I drew the structures in Bioclipse 2.6.2 (which has CDK 1.5.13) and copy-pasted the SMILES and InChIKey into the spreadsheet. Of course, it is essential to get the stereochemistry right. The stereochemistry of the compounds was discussed on Twitter, and we think we got it right. But we cannot be 100% sure. For that, it would have been hugely helpful if the disclosures included the InChIKeys!

As I wrote before, I see Wikidata as a central resource in a web of linked chemical data. So, using the same code I used previously to add disclosures to Wikidata, I created Wikidata items for these compounds, except for one that was already in the database (see the right image). The code also fetches PubChem compound IDs, which are also listed in this spreadsheet.

The Wikidata IDs link to the SQID interface, giving a friendly GUI, one that I actually brought up before too. That said, until people add more information, it may be a bit sparsely populated:


But others are working on this series of disclosures too, and keep an eye on this blog post, as others may follow up with further information!