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==History==
The original SMILES specification was initiated by David Weininger at the USEPA Mid-Continent Ecology Division Laboratory in [[Duluth, Minnesota|Duluth]] in the 1980s.<ref name="Weininger-1988">{{cite journal| last1=Weininger| first1=David| title=SMILES, a chemical language and information system. 1. Introduction to methodology and encoding rules| journal=Journal of Chemical Information and Computer Sciences| volume=28| issue= 1|pages=31–6|date=February 1988|doi=10.1021/ci00057a005 }}</ref><ref name="Weininger-1989">{{cite journal| last1=Weininger| first1=David| last2=Weininger| first2=Arthur| last3=Weininger| first3=Joseph L.| title=SMILES. 2. Algorithm for generation of unique SMILES notation| journal=Journal of Chemical Information and Modeling| volume=29| issue=2| pages=97–101|date=May 1989|doi=10.1021/ci00062a008 }}</ref><ref name="Weininger-1990">{{cite journal| last1=Weininger| first1=David| title=SMILES. 3. DEPICT. Graphical depiction of chemical structures| journal=Journal of Chemical Information and Modeling| volume=30| issue= 3|pages=237–43|date=August 1990|doi=10.1021/ci00067a005 }}</ref><ref name="Swanson-2004">{{cite book |author1=Swanson, Richard Pommier |editor1-last=Rayward |editor1-first=W. [Warden] Boyd |editor2-last=Bowden |editor2-first=Mary Ellen |title=The History and Heritage of Scientific and Technological Information Systems: Proceedings of the 2002 Conference of the American Society of Information Science and Technology and the Chemical Heritage Foundation |date=2004 |publisher=[[Information Today]] |___location=Medford, NJ |isbn=9781573872294 |page=205 |url=https://books.google.com/books?id=76OOQannpBgC
It has since been modified and extended by others, most notably by [[Daylight Chemical Information Systems]]. In 2007, an [[open standard]] called "OpenSMILES" was developed by the [[Blue Obelisk]] open-source chemistry community. Other 'linear' notations include the [[Wiswesser Line Notation]] (WLN), [[ROSDAL]] and [[SYBYL Line Notation|SLN]] (Tripos Inc).
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|(2''S'',5''R'')-[[Chalcogran]]: a [[pheromone]] of the [[Scolytinae|bark beetle]] ''[[Pityogenes chalcographus]]''<ref>{{cite journal|last1=Byers|first1=JA|last2=Birgersson|first2=G|last3=Löfqvist|first3=J
|last4=Appelgren|first4=M|last5=Bergström|first5=G| title = Isolation of pheromone synergists of bark beetle, ''Pityogenes chalcographus'', from complex insect-plant odors by fractionation and subtractive-combination bioassay | journal = Journal of Chemical Ecology | volume = 16 | issue = 3 | pages = 861–76 | date = Mar 1990 | pmid = 24263601 | doi = 10.1007/BF01016496 |s2cid=226090| url = http://www.chemical-ecology.net/pdf/Byersetal1990a.pdf}}</ref>
|[[Image:2S,5R-chalcogran-skeletal.svg|130px|(2''S'',5''R'')-2-ethyl-1,6-dioxaspiro[4.4]nonane]]
|<code>CC[C@H](O1)CC[C@@]12CCCO2</code>
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== Conversion ==
SMILES can be converted back to two-dimensional representations using structure diagram generation (SDG) algorithms.<ref name="Helson-1999">{{cite book |last=Helson |first=H. E. |year=1999 |chapter=Structure Diagram Generation |title= Rev. Comput. Chem. |series=Reviews in Computational Chemistry |editor1-last=Lipkowitz |editor1-first=K. B. |editor2-last=Boyd |editor2-first=D. B. |___location=New York |pages=313–398 |publisher=Wiley-VCH |doi=10.1002/9780470125908.ch6 |volume=13 |isbn=9780470125908 }}</ref> This conversion is not always unambiguous. Conversion to three-dimensional representation is achieved by energy-minimization approaches. There are many downloadable and web-based conversion utilities.
== See also ==
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