SMILES
Tampilan
Ekstensi berkas |
|
---|---|
Jenis MIME | chemical/x-daylight-smiles |
Jenis format | chemical file format |
SMILES,merupakan singkatanbahasa Inggrisdarisimplified molecular-input line-entry system( "sistem entri-baris input-molekuler yang disederhanakan), yaitu suatu spesifikasi dalam bentuknotasi barisuntuk menggambarkan strukturspesies kimiamenggunakanstringASCIIpendek. String dari SMILES dapat diimpor oleh kebanyakanpenyunting molekuluntuk dikonversi kembali menjadi lukisan modeldua dimensiatautiga dimensidari suatu molekul.
Applikasi pada sejumlah molekul
[sunting|sunting sumber]Molekul | Struktur | Rumus SMILES |
---|---|---|
Dinitrogen | N≡N | N#N |
Methyl isocyanate(MIC) | CH3–N=C=O | CN=C=O |
Tembaga(II) sulfat | Cu2+SO42- | [Cu+2].[O-]S(=O)(=O)[O-] |
Oenanthotoxin(C17H22O2) | CCC[C@@H](O)CC\C=C\C=C\C#CC#C\C=C\CO | |
PyrethrinII (C22H28O5) | COC(=O)C(\C)=C\C1C(C)(C)[C@H]1C(=O)O[C@@H]2C(C)=C(C(=O)C2)CC=CC=C | |
AflatoksinB1 (C17H12O6) | O1C=C[C@H]([C@H]1O2)c3c2cc(OC)c4c3OC(=O)C5=C4CCC(=O)5 | |
Glukosa(glucopyranose) (C6H12O6) | OC[C@@H](O1)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)1 | |
Bergenin(cuscutin) (aresin) (C14H16O9) | OC[C@@H](O1)[C@@H](O)[C@H](O)[C@@H]2[C@@H]1c3c(O)c(OC)c(O)cc3C(=O)O2 | |
Suatupheromonedariscale insectasalCalifornia | CC(=O)OCCC(/C)=C\C[C@H](C(C)=C)CCC=C | |
2S,5R-Chalcogran:suatupheromonedaribark beetlePityogenes chalcographus[1] | CC[C@H](O1)CC[C@@]12CCCO2 | |
Vanilin | O=Cc1ccc(O)c(OC)c1 | |
Melatonin(C13H16N2O2) | CC(=O)NCCC1=CNc2c1cc(OC)cc2 | |
Flavopereirin(C17H15N2) | CCc(c1)ccc2[n+]1ccc3c2Nc4c3cccc4 | |
Nikotina(C10H14N2) | CN1CCC[C@H]1c2cccnc2 | |
Alpha-thujone(C10H16O) | CC(C)[C@@]12C[C@@H]1[C@@H](C)C(=O)C2 | |
Tiamina(C12H17N4OS+) (vitamin B1) |
OCCc1c(C)[n+](=cs1)Cc2cnc(C)nc(N)2 |
Konversi
[sunting|sunting sumber]SMILES dapat dikonversi kembali ke representasi 2 dimensi menggunakan algoritme Structure Diagram Generation (Helson, 1999). Konversi ini kadang rancu. Konversi ke representasi 3 dimensi diperoleh dengan pendekatan minimalisasi energi. Ada banyak peranti konversi yang dapat didownload atau berbasis web.
Lihat pula
[sunting|sunting sumber]- SMILES arbitrary target specificationSMARTS language for specification of substructural queries.
- SYBYL Line Notation(another line notation)
- Molecular Query Language–query languageallowing also numerical properties, e.g. physicochemical values or distances
- Chemistry Development Kit(2D layout and conversion)
- International Chemical Identifier(InChI), the free and open alternative to SMILES by theIUPAC.
- OpenBabel,JOELib,OELib(conversion)
Referensi
[sunting|sunting sumber]- ^Byers, J. A.; Birgersson, G.; Löfqvist, J.; Appelgren, M.; Bergström, G. (1990)."Isolation of pheromone synergists of bark beetle, Pityogenes chalcographus, from complex insect-plant odors by fractionation and subtractive-combination bioassay"(PDF).Journal of Chemical Ecology.16(3): 861–76.doi:10.1007/BF01016496.PMID24263601.Diakses tanggalMay 12,2012.
Pustaka
[sunting|sunting sumber]- Anderson, E.; Veith, G. D.; Weininger, D. (1987).SMILES: A line notation and computerized interpreter for chemical structures.Duluth, MN: U.S. EPA, Environmental Research Laboratory-Duluth. Report No. EPA/600/M-87/021.
- Helson, H. E. (1999). "Structure Diagram Generation". Dalam Lipkowitz, K. B.; Boyd, D. B.Rev. Comput. Chem.13.New York: Wiley-VCH. hlm. 313–398.doi:10.1002/9780470125908.ch6.
- Weininger, David (February 1988). "SMILES, a chemical language and information system. 1. Introduction to methodology and encoding rules".Journal of Chemical Information and Modeling.28(1): 31–6.doi:10.1021/ci00057a005.
- Weininger, David; Weininger, Arthur; Weininger, Joseph L. (May 1989). "SMILES. 2. Algorithm for generation of unique SMILES notation".Journal of Chemical Information and Modeling.29(2): 97–101.doi:10.1021/ci00062a008.
- Weininger, David (August 1990). "SMILES. 3. DEPICT. Graphical depiction of chemical structures".Journal of Chemical Information and Modeling.30(3): 237–43.doi:10.1021/ci00067a005.
Pranala luar
[sunting|sunting sumber]Spesifikasi
[sunting|sunting sumber]- "SMILES–A Simplified Chemical Language"
- The OpenSMILES home page
- "SMARTS–SMILES Extension"
- Daylight SMILES tutorial
- Parsing SMILES
Perangkat software terkait SMILES
[sunting|sunting sumber]- NCI/CADD Chemical Identifier Resolver–resolves or generates SMILES from chemical names, CAS Registry Numbers, InChI/InChIKey and many other chemical structure file formats
- NCI/CADD Online SMILES Translator and Structure File GeneratorDiarsipkan2001-05-01 diWayback Machine.–Java online molecule editor
- PubChem server side structure editor–online molecule editor
- smi23dDiarsipkan2007-09-14 diWayback Machine.–3D Coordinate Generation
- Daylight DepictDiarsipkan2001-12-02 diWayback Machine.–Translate a SMILES formula into graphics
- GIF/PNG-Creator for 2D Plots of Chemical StructuresDiarsipkan2004-10-15 diWayback Machine.
- JME molecule editorDiarsipkan2001-04-28 diWayback Machine.- Chemical editor/viewer and SMILES/SMARTS generator in Java
- JSME molecule editorDiarsipkan2015-01-06 diWayback Machine.- Free chemical editor/viewer and SMILES/SMARTS generator in JavaScript
- ACD/ChemSketchDiarsipkan2006-10-18 diWayback Machine.
- MarvinDiarsipkan2007-11-07 diWayback Machine.byChemAxon–online chemical editor/viewer and SMILES generator/converter
- Instant JChemDiarsipkan2007-11-12 diWayback Machine.byChemAxon–desktop application for storing/generating/converting/visualizing/searching SMILES structures, particularly batch processing; personal edition free
- JChem for ExcelDiarsipkan2010-02-03 diWayback Machine.byChemAxon–MS Excel add-in for storing/generating/converting/visualizing/searching SMILES structures
- Smormo-Ed–a molecule editor for Linux which can read and write SMILES
- InChI.info–an unofficial InChI website featuring on-line converter from InChI and SMILES to molecular drawings
- Balloon–A free program for 3D coordinate generation and conformational analysis.
- IndigoDiarsipkan2015-02-11 diWayback Machine.–an open-source cross-platform cheminformatics library with a plugin for IUPAC-compliant molecule and reaction 2D structural formula rendering.
- Open Babel–an open-source chemical toolbox allowing anyone to search, convert, analyze, or store biochemical data.
- Bioclipse–a free and open source workbench for the life sciences
- MolEngineDiarsipkan2019-09-15 diWayback Machine.–A.NET cheminformatics toolkit to read/write SMILES, generate 2D coordinate from SMILES, and convert SMILES from/into otherChemical file formats.
- JSDrawDiarsipkan2011-07-17 diWayback Machine.–A cross-platform javascript chemical structure editor to generate SMILES and SMARTS.