SMILES strings and on-line tutorials

[C Anthony Lewis]

Dear Colleagues,

Recently, I have been playing with the CS ChemDraw Net plug-in, with
the aim of constructing tutorial pages to help 1st year chemistry
students convert systematic names into stick diagrams.

I had the idea that I could use the SMILES string available from the
Java applet suplied by CambridgeSoft along with a little bit of
JavaScript to test if the structure drawn by the student corresponds
to the name supplied. However, after a few tests I realised the major
flaw in my idea... any particular structure does not have a unique
SMILES string (I would like to add in my defence that I knew this but
had forgotten about it in my excitement about the possibility of
creating the tutorials).

I am aware that methods of creating "unique" strings have been 
discussed but I have not investigated this yet. However, with the CS 
plug-in (or the Office Pro suite) it is possible to create different 
SMILES strings depending on how the structure is draw so the 
availability of these methods is somewhat academic.

So, I am wondering if anyone on the List has attempted to do
anything similar and/or if they have been successful... and would 
like to share theire experiences with the List.

Of course, for simple structures it is relatively straightforward (if
a little dull) to work-out all the SMILES strings (and then test all
the possibilities with the JavaScript) but for more complex "simple"
branched structures it would be considerable more time consuming.
This also makes me wonder if it is possible to calculate the total
number of SMILES strings for a structure?

Thanks for any comments...

Anthony Lewis


C. Anthony Lewis
Petroleum & Environmental Geochemistry Group,
Department of Environmental Sciences,
University of Plymouth,
Plymouth, Devon PL4 8AA, U.K.

tel: +44 (0)1752 233000 ext. 2988
FAX: +44 (0)1752 233035
e-mail: calewis at plymouth.ac.uk

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