Talk:Simplified molecular-input line-entry system

Untitled
To be honest, I'm a SMILES novice, though I've known of its existence for years.

An unambiguous depiction of the atomic structure of molecules is crucial to successfully depicting and communicating about chemistry. Images are often indispensible to such depiction. However, there are a number of issues surrounding the generation and inclusion of images in the Wikipedia (transcluded links hosted offsite aren't part of the central encyclopedia corpus, easy software support of image loading isn't available or if available brings concern of abuse, images seem to generate more copyright concern [whether justified or not] than words contributed, etc.)

It seems that SMILES strings can serve as a very compact adjunct for depicting some molecular structures.

I encourage my fellow Wikipedian science authors to consider the use of SMILES strings in their work.

--JoeAnderson


 * Yes, it would certainly be a nice piece of information to add. Less for depiction perhaps, but it would certainly make information more searchable. Search by substructure would certainly be a nice thing to have.

Shyamal 12:56, 30 Jun 2004 (UTC)

Leaving atoms out
I noticed that the SMILES representations for Citric Acid and Calcium citrate do not show the hydrogen atoms consistently. What is the deal? Say you draw a structure without H's, do you show the SMILES for the structure you drew, or for the molecule as it exists in reality? --Slashme 09:45, 27 October 2005 (UTC)
 * I can't find the examples you mention, however, in general, there are multiple ways to represent almost any given structure using almost any desired notation system. For SMILES, it's okay to omit an explicit H when the atom is attached to the "organic subset" and the number of them is obvious (from valence rules). It's also okay to include them explicitly if you want, either in the square brackets or as explicit attached substituents. That's pretty close to the rule for most structural diagrams, too: you can omit hydrogen from carbon (but not the rest of the SMILES organic subset!) if you want, or you can include some or all of them if it makes the structure more clearly illustrate whatever you're trying to illustrate with it. DMacks 04:52, 26 January 2006 (UTC)

Page title
Any reason why SMILES redirects to Simplified molecular input line entry specification instead of the other way around? I assume SMILES is the most common name. National Aeronautics and Space Administration redirects to NASA, American Standard Code for Information Interchange redirects to ASCII, etc. Not a major problem, but it looks inconsistent. 82.92.119.11 19:17, 14 June 2006 (UTC)

SLN Link
The link to SLN leads to a page a boutdurch sign language. Should it not be changed for something of the sort of ‘SLN (Tripos)’? 11:57, 17 September 2006 (UTC)
 * According to be bold! you are encouraged to edit things on your own. Anyway, I have created a SYBYL Line Notation article which is now cross-linked in both directions. Kind regards, JKW 20:29, 17 September 2006 (UTC)

comparisons of molecules
Is there any software that can given the smile data on two different molecules can output a number value which tells how close each compound is to one another (graph distance?)? 71.114.161.229

Inorganic molecules
I'm an inorganic chemist, and after reading the current form of the article I don't feel able to estimate if (or how) this works for transition metal complexes (not necessarily mononuclear... say big polyoxometalates). Inorganic mixed-valence systems would also pose an interesting problem. Probably the article should give an idea of to what extent this works for inorganic systems. -- 147.156.44.37 17:02, 15 February 2007 (UTC)

Better description
The description needs to be improved, so it's less vague / more complete. A diagram, or rather, a few diagrams would also be nice. Shinobu 13:12, 10 June 2007 (UTC)

Canonical SMILES and Isomeric SMILES
I was just passing through and noticed the word isotope here. Pardon my ignorance but shouldn't this be isomer? Pterre 23:32, 4 October 2007 (UTC)
 * Corrected. Shyamal 01:24, 5 October 2007 (UTC)
 * Re-corrected back to original per daylight's website descriptions. DMacks 02:04, 5 October 2007 (UTC)
 * As I said, pardon my ignorance. How about adding some words (perhaps in the Examples section) to make it clear to the casual reader that this really does mean isotope and is not a typo? Pterre 12:15, 6 October 2007 (UTC)
 * No worries, naming is pretty non-intuitive sometimes. I'm not sure what more we could say that would make it clear that we mean what we say (it's just a definition of a term), but would love to hear suggestions. DMacks 19:49, 6 October 2007 (UTC)
 * I have changed the wording as I also found it rather confusing. Please check for correctness. --Slashme (talk) 12:25, 16 January 2008 (UTC)

Where to start
Is there any standard on which atom to start on when describing a molecule? I assume this is specified in Canonical SMILES? --Slashme (talk) 12:25, 16 January 2008 (UTC)
 * I believe there is no unique way to "canonicalize". Think of it as a set of rules like those used for constructing IUPAC names. Shyamal (talk) 12:44, 22 July 2010 (UTC)

Isotopes
The section on isotopes says that C14 benzene is [14c]1ccccc1. Shouldn't that be [14c]1[14c][14c][14c][14c][14c]1? --Slashme (talk) 12:17, 16 January 2008 (UTC)

Diagram
Suggest copying diagram from the French version of the page. 212.137.63.86 (talk) 14:47, 13 August 2008 (UTC)

1) Disambig; 2) History authorship
1) Which is preferred on the Smiles disambiguation page -- SMILES is a "chemistry notation"? or a "chemical notation"?

2) On the historical record of SMILES' authorship. I quoted referenced daylight~dave smiles acknowledgements. The now 2nd paragraph reads as follows: > "The original SMILES specification was initiated by David Weininger in the 1980s. Acknowledged for their parts in the early development were "Gilman Veith and Rose Russo (USEPA) and Albert Leo and Corwin Hansch(Pomona College) for supporting the work, and Arthur Weininger (Pomona; Daylight CIS) and Jeremy Scofield (Cedar River Software, Renton, WA) for assistance in programming the system."[1] The Environmental Protection Agency funded the initial project to develop SMILES. [2] "<

Only Dave & Corwin have current wiki pages at moment. Yohananw (talk) 00:24, 25 June 2013 (UTC)

Inappropriately included URLs
Under examples, several references to 'see depiction' pointing to stale external addresses, e.g.

http://www.daylight.com/daycgi/depict?4e5b434040485d28432943283d4f294f — Preceding unsigned comment added by 72.249.191.206 (talk) 19:25, 1 June 2015 (UTC)


 * Yes, they are available with archive.org, but someone should substitute all of them with commons formula images. --Itu (talk) 12:31, 25 February 2016 (UTC)

External links modified
Hello fellow Wikipedians,

I have just added archive links to 1 one external link on Simplified molecular-input line-entry system. Please take a moment to review my edit. If necessary, add after the link to keep me from modifying it. Alternatively, you can add to keep me off the page altogether. I made the following changes:
 * Added archive http://web.archive.org/web/20070914100359/http://www.chembiogrid.org:80/cheminfo/smi23d/ to http://www.chembiogrid.org/cheminfo/smi23d/

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P-carborane in SMILES
I was trying to figure out how to make p-carborane (and more generally an icosahedral molecule), and I came across the barrier that when you use a % for a ring number, like %10, you can't use other ring numbers on that one atom (eg. C1%10 isn't allowed). Does anyone know any work arounds to making a figure this way? Thottenjäger (talk) 21:00, 19 December 2017 (UTC)

Molecule codes
I have discovered that, at least for JMOL, SMILES has short codes that can stand for molecules. These do not appear to combine (i.e. cannot be used as functional groups) (e.g. CCCyn and CynCC don't work for Propionitrile), and I think that they should be mentioned in the article. I have begun to compile a table of them:

Certain features not working
Not sure if this is correct forum to post this. When I try to use some features, such as quadruple bond ($) and square planar (@SP) when editing the SMILES model in chembox of a compound on Wikipedia, it ends up either crashing or not rendering correctly. Anyone knows why this may be the case? AnDeargMor (talk) 12:00, 12 June 2024 (UTC)