Re: [Rdkit-discuss] Hankering after faster builds

On Fri, Dec 2, 2016 at 6:29 PM, Tim Dudgeon wrote: > But since I've been working with the Release_2016_09_2 release my Docker > image builds on Docker Hub [1] are timing out as they sometimes exceed > the 2 hour limit. If I try at a quiet time I can sometimes get them to >

Re: [Rdkit-discuss] Extracting SMILES from text

Hi Alexis, you may find also so some "novel" compounds by this approach :-). Whether your tuple solution improves performance strongly depends on the content of your text documents and how often they repeat the same words again - but my guess would be it will help. Probably the best way is even

[Rdkit-discuss] Extracting SMILES from text

Dear all, I am looking for a way to extract SMILES scattered in many text documents (thousands documents of several pages each). At the moment, I am thinking to scan each words from the text and try to make a mol object from them using Chem.MolFromSmiles() then store the words if they return a

Re: [Rdkit-discuss] Extracting SMILES from text

An initial start on some regexps that match SMILES is here: https://gist.github.com/lsauer/1312860/264ae813c2bd2c27a769d261c8c6b38da34e22fb that may also be useful On Fri, Dec 2, 2016 at 11:07 AM, Alexis Parenty < alexis.parenty.h...@gmail.com> wrote: > Hi Markus, > > > Yes! I might discover

Re: [Rdkit-discuss] Extracting SMILES from text

Hi, Alexis, if you should not track from which document SMILES come, you may just combine all words from all document in a list, take only unique words and try to test them. Thus, you should not store and check for valid/non-valid strings. That would reduce problem complexity as well.

Re: [Rdkit-discuss] Extracting SMILES from text

Hi Alexis, You may want to filter with some regex strings containing not valid characters (i.e. there is small subset of atoms that may be without brackets). See "Atoms" section: http://www.daylight.com/dayhtml/doc/theory/theory.smiles.html The set might grow pretty quick and may be inefficient,

Re: [Rdkit-discuss] Extracting SMILES from text

Hi Maciek, Thanks for your quick response. Excellent suggestions. I could filter out a lot of crap that way... Maybe I could also add a filter on word length to avoid having a lot of Ethane and Iodide false positives! This also made me think that I could transform the text into a set to avoid

Re: [Rdkit-discuss] Extracting SMILES from text

Hi Markus, Yes! I might discover novel compounds that way!! Would be interesting to see how they look like… Good suggestion to also store the words that were correctly identified as SMILES. I’ll add that to the script. I also like your “distribution of word” idea. I could safely skip any

Re: [Rdkit-discuss] Extracting SMILES from text

Dear Pavel And Greg, Thanks Greg for the regexps link. I’ll use that too. Pavel, I need to track on which document the SMILES are coming from, but I will indeed make a set of unique word for each document before looping. Thanks! Best, Alexis On 2 December 2016 at 11:21, Pavel

Re: [Rdkit-discuss] Extracting SMILES from text

I hacked a version of RDKit's smiles parser to compute heavy atom count, perhaps some version of this could be used to check smiles validity without making the actual molecule. >From a fun historical perspective: IBM had an expert system to find IUPAC names in documents. They ended up finding

Re: [Rdkit-discuss] Extracting SMILES from text

Hello Alexis, Depending on the size of your document, you could consider limit storing the already tested strings by word length and only memoize shorter words. SMILES tend to be longer, so everything above a given number of characters has a higher probability of being a SMILES. Large words

[Rdkit-discuss] Hankering after faster builds

Of course builds from source are never fast enough, and the RDKit one is pretty big. So far I've lived with this and made cups of coffee. But since I've been working with the Release_2016_09_2 release my Docker image builds on Docker Hub [1] are timing out as they sometimes exceed the 2 hour

Re: [Rdkit-discuss] Extracting SMILES from text

This was why they started using the dictionary lookup as I recall :). The iupac system they ended up using was Roger's when at OpenEye. Brian Kelley > On Dec 2, 2016, at 12:33 PM, Igor Filippov wrote: > > I could be wrong but I believe IBM system had a

Re: [Rdkit-discuss] Extracting SMILES from text

I could be wrong but I believe IBM system had a preprocessing step which removed all known dictionary words - which would get rid of "submarine" etc. I also believe this problem has been solved multiple times in the past, NextMove software comes to mind, chemical tagger -

Re: [Rdkit-discuss] Extracting SMILES from text

I think Alexis was referring to converting actual SMILES strings found in random text. Chemical entity recognition and name to structure conversion is another story altogether and nowadays one can quickly go a long way with open tools such as OSCAR + OPSIN in KNIME or with something like this:

Re: [Rdkit-discuss] Extracting SMILES from text

George, My point was actually parsing the words as IUPAC/SMILES is surprisingly effective as opposed to an ai or rule based system. Without sanitization, Rdkit is about 60,000/second for smiles parsing on my laptop. This is much faster when not making molecules, but I don't have the number

Re: [Rdkit-discuss] Extracting SMILES from text

Here is a very old version of Andrew's parser in code form: http://frowns.cvs.sourceforge.net/viewvc/frowns/frowns/smiles_parsers/Smiles.py?revision=1.1.1.1=text%2Fplain that I used in frowns more than a decade ago. It was fairy well tested on the sigma catalog back in the day. It might be

Re: [Rdkit-discuss] Extracting SMILES from text

Here's a pragmatic idea: If Alexis wants to search for valid SMILES strings representing typical *organic *molecules among text of plain English words, would it not be safe to assume that *any *word containing more than 4 'C' or 'c' characters would only be a SMILES string? This simple filter

Re: [Rdkit-discuss] Extracting SMILES from text

On Dec 2, 2016, at 11:11 AM, Greg Landrum wrote: > An initial start on some regexps that match SMILES is here: > https://gist.github.com/lsauer/1312860/264ae813c2bd2c27a769d261c8c6b38da34e22fb > > that may also be useful I've put together a more gnarly regular expression to find possible

Re: [Rdkit-discuss] Extracting SMILES from text

On Dec 2, 2016, at 10:12 PM, George Papadatos wrote: > If Alexis wants to search for valid SMILES strings representing typical > organic molecules among text of plain English words, would it not be safe to > assume that any word containing more than 4 'C' or 'c' characters would only > be a

Re: [Rdkit-discuss] Extracting SMILES from text

On Dec 2, 2016, at 10:05 PM, Brian Kelley wrote: > Here is a very old version of Andrew's parser in code form: ... It was fairy > well tested on the sigma catalog back in the day. It might be fun to > resurrect use it in some form. There's also my OpenSMILES parser written for Ragel:

Re: [Rdkit-discuss] Extracting SMILES from text

On 12/02/2016 03:12 PM, George Papadatos wrote: > Here's a pragmatic idea: ... would it not be safe to > assume that *any *word containing more than 4 'C' or 'c' characters would > only be a SMILES string? pneumonoultramicroscopicsilicovolcanoconiosis -- Dimitri Maziuk Programmer/sysadmin

Re: [Rdkit-discuss] Extracting SMILES from text

:) George. Sent from my giPhone > On 2 Dec 2016, at 22:11, Dimitri Maziuk wrote: > >> On 12/02/2016 03:12 PM, George Papadatos wrote: >> Here's a pragmatic idea: > ... would it not be safe to >> assume that *any *word containing more than 4 'C' or 'c' characters would