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.
Aplikasi 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 algoritma 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)
Pustaka
Pranala luar
Spesifikasi
- "SMILES–A Simplified Chemical Language"
- The OpenSMILES home page
- "SMARTS–SMILES Extension"
- Daylight SMILES tutorial
- Parsing SMILES
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 –Java online molecule editor
- PubChem server side structure editor–online molecule editor
- smi23d –3D Coordinate Generation
- Daylight Depict –Translate a SMILES formula into graphics
- GIF/PNG-Creator for 2D Plots of Chemical Structures
- JME molecule editor - Chemical editor/viewer and SMILES/SMARTS generator in Java
- JSME molecule editor - Free chemical editor/viewer and SMILES/SMARTS generator in JavaScript
- ACD/ChemSketch
- Marvin by ChemAxon–online chemical editor/viewer and SMILES generator/converter
- Instant JChem by ChemAxon–desktop application for storing/generating/converting/visualizing/searching SMILES structures, particularly batch processing; personal edition free
- JChem for Excel 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 –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 –A .NET cheminformatics toolkit to read/write SMILES, generate 2D coordinate from SMILES, and convert SMILES from/into other Chemical file formats.
- JSDraw –A cross-platform javascript chemical structure editor to generate SMILES and SMARTS.
Referensi
- ↑ J. A. Byers. Isolation of pheromone synergists of bark beetle, Pityogenes chalcographus, from complex insect-plant odors by fractionation and subtractive-combination bioassay. Journal of Chemical Ecology. 1990. Vol. 16 (3). hlm. 861–76. doi:10.1007/BF01016496.
Sumber dan atribusi
Konten artikel ini diadaptasi dari Wikipedia bahasa Indonesia, revisi 28956485 (2026-02-13T08:28:01Z), yang tersedia berdasarkan lisensi Creative Commons Atribusi-BerbagiSerupa (CC BY-SA). Gambar pada artikel ini bersumber dari Wikimedia Commons dan mengikuti ketentuan lisensi masing-masing berkas. Mohon gunakan konten dan media secara bijak serta sesuai dengan ketentuan lisensi yang berlaku.