SMILES
SMILES, merupakan singkatan bahasa Inggris dari simplified molecular-input line-entry system ("sistem entri-baris input-molekuler yang disederhanakan), yaitu suatu spesifikasi dalam bentuk notasi baris untuk menggambarkan struktur spesies kimia menggunakan string ASCII pendek. String dari SMILES dapat diimpor oleh kebanyakan penyunting molekul untuk dikonversi kembali menjadi lukisan model dua dimensi atau tiga dimensi dari suatu molekul.
| Ekstensi berkas | |
|---|---|
| Jenis MIME | chemical/x-daylight-smiles |
| Jenis format | chemical file format |
Pembuatan SMILES: Putuskan siklus, kemudian tulis sebagai cabang-cabang dari kerangka utama. (Ciprofloxacin)
Applikasi pada sejumlah molekul
| 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 |
| Pyrethrin II (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 |
| Aflatoksin B1 (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) (a resin) (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 |
| Suatu pheromone dari scale insect asal California |  |
CC(=O)OCCC(/C)=C\C[C@H](C(C)=C)CCC=C |
| 2S,5R-Chalcogran: suatu pheromone dari bark beetle Pityogenes 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
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
- SMILES arbitrary target specification SMARTS language for specification of substructural queries.
- SYBYL Line Notation (another line notation)
- Molecular Query Language – query language allowing 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 the IUPAC.
- OpenBabel, JOELib, OELib (conversion)
Referensi
- 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. PMID 24263601. Diakses tanggal May 12, 2012.
Pustaka
- 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
Spesifikasi
Perangkat software terkait SMILES
- 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 Generator Diarsipkan 2001-05-01 di Wayback Machine. – Java online molecule editor
- PubChem server side structure editor – online molecule editor
- smi23d Diarsipkan 2007-09-14 di Wayback Machine. – 3D Coordinate Generation
- Daylight Depict Diarsipkan 2001-12-02 di Wayback Machine. – Translate a SMILES formula into graphics
- GIF/PNG-Creator for 2D Plots of Chemical Structures Diarsipkan 2004-10-15 di Wayback Machine.
- JME molecule editor Diarsipkan 2001-04-28 di Wayback Machine. - Chemical editor/viewer and SMILES/SMARTS generator in Java
- JSME molecule editor Diarsipkan 2015-01-06 di Wayback Machine. - Free chemical editor/viewer and SMILES/SMARTS generator in JavaScript
- ACD/ChemSketch Diarsipkan 2006-10-18 di Wayback Machine.
- Marvin Diarsipkan 2007-11-07 di Wayback Machine. by ChemAxon – online chemical editor/viewer and SMILES generator/converter
- Instant JChem Diarsipkan 2007-11-12 di Wayback Machine. by ChemAxon – desktop application for storing/generating/converting/visualizing/searching SMILES structures, particularly batch processing; personal edition free
- JChem for Excel Diarsipkan 2010-02-03 di Wayback Machine. by ChemAxon – 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.
- Indigo Diarsipkan 2015-02-11 di Wayback 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
- MolEngine Diarsipkan 2019-09-15 di Wayback Machine. – A .NET cheminformatics toolkit to read/write SMILES, generate 2D coordinate from SMILES, and convert SMILES from/into other Chemical file formats.
- JSDraw Diarsipkan 2011-07-17 di Wayback Machine. – A cross-platform javascript chemical structure editor to generate SMILES and SMARTS.
Pengawasan otoritas  |
|---|
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.