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id="toc-Description" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Description"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Description</span> </div> </a> <button aria-controls="toc-Description-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Description subsection</span> </button> <ul id="toc-Description-sublist" class="vector-toc-list"> <li id="toc-Atoms" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Atoms"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Atoms</span> </div> </a> <ul id="toc-Atoms-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bonds" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Bonds"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Bonds</span> </div> </a> <ul id="toc-Bonds-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Rings" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Rings"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Rings</span> </div> </a> <ul id="toc-Rings-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Aromaticity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Aromaticity"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Aromaticity</span> </div> </a> <ul id="toc-Aromaticity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Branching" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Branching"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>Branching</span> </div> </a> <ul id="toc-Branching-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Stereochemistry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Stereochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.6</span> <span>Stereochemistry</span> </div> </a> <ul id="toc-Stereochemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Isotopes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Isotopes"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.7</span> <span>Isotopes</span> </div> </a> <ul id="toc-Isotopes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Examples" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Examples"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.8</span> <span>Examples</span> </div> </a> <ul id="toc-Examples-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_examples_of_SMILES" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_examples_of_SMILES"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.9</span> <span>Other examples of SMILES</span> </div> </a> <ul id="toc-Other_examples_of_SMILES-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Extensions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Extensions"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Extensions</span> </div> </a> <ul id="toc-Extensions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Conversion" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Conversion"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Conversion</span> </div> </a> <ul id="toc-Conversion-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Simplified Molecular Input Line Entry System</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 42 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-42" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">42 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%85%D8%AD%D8%AF%D8%AF%D8%A7%D8%AA_%D8%A7%D9%84%D8%A5%D8%AF%D8%AE%D8%A7%D9%84_%D8%A7%D9%84%D8%AE%D8%B7%D9%8A_%D8%A7%D9%84%D9%86%D8%B5%D9%8A_%D8%A7%D9%84%D8%AC%D8%B2%D9%8A%D8%A6%D9%8A_%D8%A7%D9%84%D9%85%D8%A8%D8%B3%D8%B7" title="محددات الإدخال الخطي النصي الجزيئي المبسط – Arabic" lang="ar" hreflang="ar" data-title="محددات الإدخال الخطي النصي الجزيئي المبسط" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/SMILES" title="SMILES – Azerbaijani" lang="az" hreflang="az" data-title="SMILES" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/SMILES" title="SMILES – Bulgarian" lang="bg" hreflang="bg" data-title="SMILES" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/SMILES" title="SMILES – Bosnian" lang="bs" hreflang="bs" data-title="SMILES" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/SMILES" title="SMILES – Catalan" lang="ca" hreflang="ca" data-title="SMILES" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/SMILES" title="SMILES – Czech" lang="cs" hreflang="cs" data-title="SMILES" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/SMILES" title="SMILES – Danish" lang="da" hreflang="da" data-title="SMILES" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Simplified_Molecular_Input_Line_Entry_System" title="Simplified Molecular Input Line Entry System – German" lang="de" hreflang="de" data-title="Simplified Molecular Input Line Entry System" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/SMILES" title="SMILES – Greek" lang="el" hreflang="el" data-title="SMILES" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/SMILES" title="SMILES – Spanish" lang="es" hreflang="es" data-title="SMILES" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Simplified_molecular-input_line-entry_system" title="Simplified molecular-input line-entry system – Esperanto" lang="eo" hreflang="eo" data-title="Simplified molecular-input line-entry system" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%D9%85%D8%A7%DB%8C%D9%84%D8%B2" title="اسمایلز – Persian" lang="fa" hreflang="fa" data-title="اسمایلز" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Simplified_Molecular_Input_Line_Entry_System" title="Simplified Molecular Input Line Entry System – French" lang="fr" hreflang="fr" data-title="Simplified Molecular Input Line Entry System" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/SMILES" title="SMILES – Galician" lang="gl" hreflang="gl" data-title="SMILES" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%8B%A8%EC%88%9C%ED%99%94%EB%90%9C_%EB%B6%84%EC%9E%90%EC%9E%85%EB%A0%A5_%EB%9D%BC%EC%9D%B8%EC%9E%85%EB%A0%A5_%EC%8B%9C%EC%8A%A4%ED%85%9C" title="단순화된 분자입력 라인입력 시스템 – Korean" lang="ko" hreflang="ko" data-title="단순화된 분자입력 라인입력 시스템" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/SMILES" title="SMILES – Indonesian" lang="id" hreflang="id" data-title="SMILES" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/SMILES" title="SMILES – Italian" lang="it" hreflang="it" data-title="SMILES" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A1%D7%9E%D7%99%D7%99%D7%9C%D7%A1" title="סמיילס – Hebrew" lang="he" hreflang="he" data-title="סמיילס" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/SMILES" title="SMILES – Lithuanian" lang="lt" hreflang="lt" data-title="SMILES" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/SMILES" title="SMILES – Hungarian" lang="hu" hreflang="hu" data-title="SMILES" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A3%D0%BF%D1%80%D0%BE%D1%81%D1%82%D0%B5%D0%BD_%D1%81%D0%B8%D1%81%D1%82%D0%B5%D0%BC_%D0%B7%D0%B0_%D0%B7%D0%B0%D0%B2%D0%B5%D0%B4%D1%83%D0%B2%D0%B0%D1%9A%D0%B5_%D0%B2%D0%BE_%D1%80%D0%B5%D0%B4%D0%BE%D0%B2%D0%B8_%D1%81%D0%BE_%D0%BC%D0%BE%D0%BB%D0%B5%D0%BA%D1%83%D0%BB%D0%B0%D1%80%D0%B5%D0%BD_%D0%B2%D0%BD%D0%BE%D1%81" title="Упростен систем за заведување во редови со молекуларен внос – Macedonian" lang="mk" hreflang="mk" data-title="Упростен систем за заведување во редови со молекуларен внос" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%B8%E0%B4%BF%E0%B4%AE%E0%B5%8D%E0%B4%AA%E0%B5%8D%E0%B4%B2%E0%B4%BF%E0%B4%AB%E0%B5%88%E0%B4%A1%E0%B5%8D_%E0%B4%AE%E0%B5%8B%E0%B4%B3%E0%B4%BF%E0%B4%95%E0%B5%8D%E0%B4%AF%E0%B5%82%E0%B4%B2%E0%B4%BE%E0%B5%BC-%E0%B4%87%E0%B5%BB%E0%B4%AA%E0%B5%81%E0%B4%9F%E0%B5%8D_%E0%B4%B2%E0%B5%88%E0%B5%BB%E2%80%8C-%E0%B4%8E%E0%B5%BB%E0%B4%9F%E0%B5%8D%E0%B4%B0%E0%B4%BF_%E0%B4%B8%E0%B4%BF%E0%B4%B8%E0%B5%8D%E0%B4%B1%E0%B5%8D%E0%B4%B1%E0%B4%82" title="സിമ്പ്ലിഫൈഡ് മോളിക്യൂലാർ-ഇൻപുട് ലൈൻ‌-എൻട്രി സിസ്റ്റം – Malayalam" lang="ml" hreflang="ml" data-title="സിമ്പ്ലിഫൈഡ് മോളിക്യൂലാർ-ഇൻപുട് ലൈൻ‌-എൻട്രി സിസ്റ്റം" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/SMILES" title="SMILES – Malay" lang="ms" hreflang="ms" data-title="SMILES" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/SMILES" title="SMILES – Dutch" lang="nl" hreflang="nl" data-title="SMILES" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/SMILES%E8%A8%98%E6%B3%95" title="SMILES記法 – Japanese" lang="ja" hreflang="ja" data-title="SMILES記法" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/SMILES" title="SMILES – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="SMILES" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/SMILES" title="SMILES – Polish" lang="pl" hreflang="pl" data-title="SMILES" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/SMILES" title="SMILES – Portuguese" lang="pt" hreflang="pt" data-title="SMILES" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Simplified_molecular-input_line-entry_system" title="Simplified molecular-input line-entry system – Romanian" lang="ro" hreflang="ro" data-title="Simplified molecular-input line-entry system" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/SMILES" title="SMILES – Russian" lang="ru" hreflang="ru" data-title="SMILES" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification" title="Simplified molecular input line entry specification – Simple English" lang="en-simple" hreflang="en-simple" data-title="Simplified molecular input line entry specification" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sd mw-list-item"><a href="https://sd.wikipedia.org/wiki/%D8%A7%D8%B3%D9%85%D8%A7%D8%A6%D9%84%D8%B3" title="اسمائلس – Sindhi" lang="sd" hreflang="sd" data-title="اسمائلس" data-language-autonym="سنڌي" data-language-local-name="Sindhi" class="interlanguage-link-target"><span>سنڌي</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/SMILES" title="SMILES – Slovenian" lang="sl" hreflang="sl" data-title="SMILES" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/SMILES" title="SMILES – Serbian" lang="sr" hreflang="sr" data-title="SMILES" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/SMILES" title="SMILES – Serbo-Croatian" lang="sh" hreflang="sh" data-title="SMILES" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/SMILES" title="SMILES – Finnish" lang="fi" hreflang="fi" data-title="SMILES" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Simplified_Molecular_Input_Line_Entry_Specification" title="Simplified Molecular Input Line Entry Specification – Swedish" lang="sv" hreflang="sv" data-title="Simplified Molecular Input Line Entry Specification" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%8E%E0%AE%B3%E0%AE%BF%E0%AE%AE%E0%AF%88%E0%AE%AA%E0%AF%8D%E0%AE%AA%E0%AE%9F%E0%AF%81%E0%AE%A4%E0%AF%8D%E0%AE%A4%E0%AE%AA%E0%AF%8D%E0%AE%AA%E0%AE%9F%E0%AF%8D%E0%AE%9F_%E0%AE%AE%E0%AF%82%E0%AE%B2%E0%AE%95%E0%AF%8D%E0%AE%95%E0%AF%82%E0%AE%B1%E0%AF%81-%E0%AE%89%E0%AE%B3%E0%AF%8D%E0%AE%B3%E0%AF%80%E0%AE%9F%E0%AF%81_%E0%AE%B5%E0%AE%B0%E0%AE%BF-%E0%AE%A8%E0%AF%81%E0%AE%B4%E0%AF%88%E0%AE%B5%E0%AF%81_%E0%AE%85%E0%AE%AE%E0%AF%88%E0%AE%AA%E0%AF%8D%E0%AE%AA%E0%AF%81" title="எளிமைப்படுத்தப்பட்ட மூலக்கூறு-உள்ளீடு வரி-நுழைவு அமைப்பு – Tamil" lang="ta" hreflang="ta" data-title="எளிமைப்படுத்தப்பட்ட மூலக்கூறு-உள்ளீடு வரி-நுழைவு அமைப்பு" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a 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href="/w/index.php?title=Simplified_molecular-input_line-entry_system&redirect=no" class="mw-redirect" title="Simplified molecular-input line-entry system">Simplified molecular-input line-entry system</a>)</span></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical species structure notation</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">"SMILES" redirects here. For other uses, see <a href="/wiki/Smiles_(disambiguation)" class="mw-disambig" title="Smiles (disambiguation)">Smiles (disambiguation)</a>.</div> <p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox"><caption class="infobox-title" style="padding-bottom:0.15em;">SMILES</caption><tbody><tr><th scope="row" class="infobox-label" style="line-height:1.2em; padding-right:0.65em;"><a href="/wiki/Filename_extension" title="Filename extension">Filename extension</a></th><td class="infobox-data" style="line-height:1.35em;"><style data-mw-deduplicate="TemplateStyles:r886049734">.mw-parser-output .monospaced{font-family:monospace,monospace}</style><div class="monospaced"> .smi</div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em; padding-right:0.65em;"><a href="/wiki/Media_type" title="Media type">Internet media type</a></th><td class="infobox-data" style="line-height:1.35em;"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886049734"><div class="monospaced"> chemical/x-daylight-smiles</div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em; padding-right:0.65em;">Type of format</th><td class="infobox-data" style="line-height:1.35em;"><a href="/wiki/Chemical_file_format" title="Chemical file format">chemical file format</a></td></tr></tbody></table> <figure typeof="mw:File/Thumb"><a href="/wiki/File:SMILES.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/SMILES.png/300px-SMILES.png" decoding="async" width="300" height="431" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/SMILES.png/450px-SMILES.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/SMILES.png/600px-SMILES.png 2x" data-file-width="625" data-file-height="898" /></a><figcaption>SMILES generation algorithm for <a href="/wiki/Ciprofloxacin" title="Ciprofloxacin">ciprofloxacin</a>: break cycles, then write as branches off a main backbone</figcaption></figure> <p>The <b>Simplified Molecular Input Line Entry System</b> (<b>SMILES</b>) is a specification in the form of a <a href="/wiki/Line_notation" title="Line notation">line notation</a> for describing the structure of <a href="/wiki/Chemical_species" title="Chemical species">chemical species</a> using short <a href="/wiki/ASCII" title="ASCII">ASCII</a> <a href="/wiki/String_(computer_science)" title="String (computer science)">strings</a>. SMILES strings can be imported by most <a href="/wiki/Molecule_editor" title="Molecule editor">molecule editors</a> for conversion back into <a href="/wiki/Two-dimensional" class="mw-redirect" title="Two-dimensional">two-dimensional</a> drawings or <a href="/wiki/Dimension" title="Dimension">three-dimensional</a> models of the molecules. </p><p>The original SMILES specification was initiated in the 1980s. It has since been modified and extended. In 2007, an <a href="/wiki/Open_standard" title="Open standard">open standard</a> called OpenSMILES was developed in the <a href="/wiki/Open_source" title="Open source">open source</a> chemistry community. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The original SMILES specification was initiated by <a href="/wiki/David_Weininger" title="David Weininger">David Weininger</a> at the USEPA Mid-Continent Ecology Division Laboratory in <a href="/wiki/Duluth,_Minnesota" title="Duluth, Minnesota">Duluth</a> in the 1980s.<sup id="cite_ref-Weininger-1988_1-0" class="reference"><a href="#cite_note-Weininger-1988-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Weininger-1989_2-0" class="reference"><a href="#cite_note-Weininger-1989-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Weininger-1990_3-0" class="reference"><a href="#cite_note-Weininger-1990-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Swanson-2004_4-0" class="reference"><a href="#cite_note-Swanson-2004-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Acknowledged for their parts in the early development were "Gilman Veith and Rose Russo (USEPA) and Albert Leo and <a href="/wiki/Corwin_Hansch" title="Corwin Hansch">Corwin Hansch</a> (<a href="/wiki/Pomona_College" title="Pomona College">Pomona College</a>) for supporting the work, and Arthur Weininger (Pomona; Daylight CIS) and Jeremy Scofield (Cedar River Software, Renton, WA) for assistance in programming the system."<sup id="cite_ref-Weininger-1998_5-0" class="reference"><a href="#cite_note-Weininger-1998-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Environmental_Protection_Agency" class="mw-redirect" title="Environmental Protection Agency">Environmental Protection Agency</a> funded the initial project to develop SMILES.<sup id="cite_ref-Anderson-1987_6-0" class="reference"><a href="#cite_note-Anderson-1987-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SMILES_Tutorial:_What_is_SMILES?_7-0" class="reference"><a href="#cite_note-SMILES_Tutorial:_What_is_SMILES?-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>It has since been modified and extended by others, most notably by <a href="/w/index.php?title=Daylight_Chemical_Information_Systems&action=edit&redlink=1" class="new" title="Daylight Chemical Information Systems (page does not exist)">Daylight Chemical Information Systems</a>. In 2007, an <a href="/wiki/Open_standard" title="Open standard">open standard</a> called "OpenSMILES" was developed by the <a href="/wiki/Blue_Obelisk" title="Blue Obelisk">Blue Obelisk</a> open-source chemistry community. Other 'linear' notations include the <a href="/wiki/Wiswesser_Line_Notation" class="mw-redirect" title="Wiswesser Line Notation">Wiswesser Line Notation</a> (WLN), <a href="/w/index.php?title=ROSDAL&action=edit&redlink=1" class="new" title="ROSDAL (page does not exist)">ROSDAL</a> and <a href="/wiki/SYBYL_Line_Notation" class="mw-redirect" title="SYBYL Line Notation">SLN</a> (Tripos Inc). </p><p>In July 2006, the <a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a> introduced the <a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a> as a standard for formula representation. SMILES is generally considered to have the advantage of being more human-readable than InChI; it also has a wide base of software support with extensive theoretical backing (such as <a href="/wiki/Graph_theory" title="Graph theory">graph theory</a>). </p> <div class="mw-heading mw-heading2"><h2 id="Terminology">Terminology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=2" title="Edit section: Terminology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The term SMILES refers to a line notation for encoding molecular structures and specific instances should strictly be called SMILES strings. However, the term SMILES is also commonly used to refer to both a single SMILES string and a number of SMILES strings; the exact meaning is usually apparent from the context. The terms "canonical" and "isomeric" can lead to some confusion when applied to SMILES. The terms describe different attributes of SMILES strings and are not mutually exclusive. </p><p>Typically, a number of equally valid SMILES strings can be written for a molecule. For example, <code>CCO</code>, <code>OCC</code> and <code>C(O)C</code> all specify the structure of <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>. Algorithms have been developed to generate the same SMILES string for a given molecule; of the many possible strings, these algorithms choose only one of them. This SMILES is unique for each structure, although dependent on the <a href="/wiki/Canonicalization" title="Canonicalization">canonicalization</a> algorithm used to generate it, and is termed the canonical SMILES. These algorithms first convert the SMILES to an internal representation of the molecular structure; an algorithm then examines that structure and produces a unique SMILES string. Various algorithms for generating canonical SMILES have been developed and include those by Daylight Chemical Information Systems, <a href="/wiki/OpenEye_Scientific_Software" title="OpenEye Scientific Software">OpenEye Scientific Software</a>, <a href="/w/index.php?title=MEDIT&action=edit&redlink=1" class="new" title="MEDIT (page does not exist)">MEDIT</a>, <a href="/wiki/Chemical_Computing_Group" title="Chemical Computing Group">Chemical Computing Group</a>, <a href="/w/index.php?title=MolSoft&action=edit&redlink=1" class="new" title="MolSoft (page does not exist)">MolSoft</a> LLC, and the <a href="/wiki/Chemistry_Development_Kit" title="Chemistry Development Kit">Chemistry Development Kit</a>. A common application of canonical SMILES is indexing and ensuring uniqueness of molecules in a <a href="/wiki/Chemical_database" title="Chemical database">database</a>. </p><p>The original paper that described the CANGEN<sup id="cite_ref-Weininger-1989_2-1" class="reference"><a href="#cite_note-Weininger-1989-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> algorithm claimed to generate unique SMILES strings for graphs representing molecules, but the algorithm fails for a number of simple cases (e.g. <a href="/wiki/Cuneane" title="Cuneane">cuneane</a>, 1,2-dicyclopropylethane) and cannot be considered a correct method for representing a graph canonically.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> There is currently no systematic comparison across commercial software to test if such flaws exist in those packages. </p><p>SMILES notation allows the specification of <a href="/wiki/Molecular_configuration" title="Molecular configuration">configuration at tetrahedral centers</a>, and double bond geometry. These are structural features that cannot be specified by connectivity alone, and therefore SMILES which encode this information are termed isomeric SMILES. A notable feature of these rules is that they allow rigorous partial specification of chirality. The term isomeric SMILES is also applied to SMILES in which <a href="/wiki/Isomer" title="Isomer">isomers</a> are specified. </p> <div class="mw-heading mw-heading2"><h2 id="Graph-based_definition">Graph-based definition</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=3" title="Edit section: Graph-based definition"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In terms of a graph-based computational procedure, SMILES is a string obtained by printing the symbol nodes encountered in a <a href="/wiki/Depth-first_search" title="Depth-first search">depth-first</a> <a href="/wiki/Tree_traversal" title="Tree traversal">tree traversal</a> of a <a href="/wiki/Chemical_graph" class="mw-redirect" title="Chemical graph">chemical graph</a>. The chemical graph is first trimmed to remove hydrogen atoms and cycles are broken to turn it into a <a href="/wiki/Spanning_tree_(mathematics)" class="mw-redirect" title="Spanning tree (mathematics)">spanning tree</a>. Where cycles have been broken, numeric suffix labels are included to indicate the connected nodes. Parentheses are used to indicate points of branching on the tree. </p><p>The resultant SMILES form depends on the choices: </p> <ul><li>of the bonds chosen to break cycles,</li> <li>of the starting atom used for the depth-first traversal, and</li> <li>of the order in which branches are listed when encountered.</li></ul> <div class="mw-heading mw-heading2"><h2 id="SMILES_definition_as_strings_of_a_context-free_language">SMILES definition as strings of a context-free language</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=4" title="Edit section: SMILES definition as strings of a context-free language"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>From the view point of a formal language theory, SMILES is a word. A SMILES is parsable with a context-free parser. The use of this representation has been in the prediction of biochemical properties (incl. toxicity and <a href="/wiki/Biodegradability" class="mw-redirect" title="Biodegradability">biodegradability</a>) based on the main principle of chemoinformatics that similar molecules have similar properties. The predictive models implemented a syntactic pattern recognition approach (which involved defining a molecular distance)<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> as well as a more robust scheme based on statistical pattern recognition.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Description">Description</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=5" title="Edit section: Description"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Atoms">Atoms</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=6" title="Edit section: Atoms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Atom" title="Atom">Atoms</a> are represented by the standard abbreviation of the <a href="/wiki/Chemical_element" title="Chemical element">chemical elements</a>, in square brackets, such as <code>[Au]</code> for <a href="/wiki/Gold" title="Gold">gold</a>. Brackets may be omitted in the common case of atoms which: </p> <ol><li>are in the "<a href="/wiki/CHON" class="mw-redirect" title="CHON">organic subset</a>" of <a href="/wiki/Boron" title="Boron">B</a>, <a href="/wiki/Carbon" title="Carbon">C</a>, <a href="/wiki/Nitrogen" title="Nitrogen">N</a>, <a href="/wiki/Oxygen" title="Oxygen">O</a>, <a href="/wiki/Phosphorus" title="Phosphorus">P</a>, <a href="/wiki/Sulfur" title="Sulfur">S</a>, <a href="/wiki/Fluorine" title="Fluorine">F</a>, <a href="/wiki/Chlorine" title="Chlorine">Cl</a>, <a href="/wiki/Bromine" title="Bromine">Br</a>, or <a href="/wiki/Iodine" title="Iodine">I</a>, and</li> <li>have no <a href="/wiki/Formal_charge" title="Formal charge">formal charge</a>, and</li> <li>have the number of hydrogens attached implied by the SMILES valence model (typically their normal valence, but for N and P it is 3 or 5, and for S it is 2, 4 or 6), and</li> <li>are the normal <a href="/wiki/Isotope" title="Isotope">isotopes</a>, and</li> <li>are not <a href="/wiki/Stereocenter" title="Stereocenter">chiral centers</a>.</li></ol> <p>All other elements must be enclosed in brackets, and have charges and hydrogens shown explicitly. For instance, the SMILES for <a href="/wiki/Water_(molecule)" class="mw-redirect" title="Water (molecule)">water</a> may be written as either <code>O</code> or <code>[OH2]</code>. Hydrogen may also be written as a separate atom; water may also be written as <code>[H]O[H]</code>. </p><p>When brackets are used, the symbol <code>H</code> is added if the atom in brackets is bonded to one or more hydrogen, followed by the number of hydrogen atoms if greater than 1, then by the sign <code>+</code> for a positive charge or by <code>-</code> for a negative charge. For example, <code>[NH4+]</code> for <a href="/wiki/Ammonium" title="Ammonium">ammonium</a> (<span class="chemf nowrap">NH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span></span>). If there is more than one charge, it is normally written as digit; however, it is also possible to repeat the sign as many times as the ion has charges: one may write either <code>[Ti+4]</code> or <code>[Ti++++]</code> for <a href="/wiki/Titanium" title="Titanium">titanium</a>(IV) Ti<sup>4+</sup>. Thus, the <a href="/wiki/Hydroxide" title="Hydroxide">hydroxide</a> <a href="/wiki/Anion" class="mw-redirect" title="Anion">anion</a> (<span class="Unicode"> </span><a href="/wiki/Hydroxide" title="Hydroxide">OH<sup>−</sup></a>) is represented by <code>[OH-]</code>, the <a href="/wiki/Hydronium" title="Hydronium">hydronium</a> cation (<style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>O<sup class="template-chem2-sup">+</sup></span>) is <code>[OH3+]</code> and the <a href="/wiki/Cobalt" title="Cobalt">cobalt</a>(III) <a href="/wiki/Cation" class="mw-redirect" title="Cation">cation</a> (Co<sup>3+</sup>) is either <code>[Co+3]</code> or <code>[Co+++]</code>. </p> <div class="mw-heading mw-heading3"><h3 id="Bonds">Bonds</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=7" title="Edit section: Bonds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A bond is represented using one of the symbols <code>. - = # $ : / \</code>. </p><p>Bonds between <a href="/wiki/Aliphatic_compound" title="Aliphatic compound">aliphatic</a> atoms are assumed to be single unless specified otherwise and are implied by adjacency in the SMILES string. Although single bonds may be written as <code>-</code>, this is usually omitted. For example, the SMILES for <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> may be written as <code>C-C-O</code>, <code>CC-O</code> or <code>C-CO</code>, but is usually written <code>CCO</code>. </p><p>Double, triple, and quadruple <a href="/wiki/Chemical_bond" title="Chemical bond">bonds</a> are represented by the symbols <code>=</code>, <code>#</code>, and <code>$</code> respectively as illustrated by the SMILES <code>O=C=O</code> (<a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> CO<sub style="font-size: 80%;vertical-align: -0.35em">2</sub>), <code>C#N</code> (<a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a> HCN) and <code>[Ga+]$[As-]</code> (<a href="/wiki/Gallium_arsenide" title="Gallium arsenide">gallium arsenide</a>). </p><p>An additional type of bond is a "non-bond", indicated with <code>.</code>, to indicate that two parts are not bonded together. For example, aqueous <a href="/wiki/Sodium_chloride" title="Sodium chloride">sodium chloride</a> may be written as <code>[Na+].[Cl-]</code> to show the dissociation. </p><p>An aromatic "one and a half" bond may be indicated with <code>:</code>; see <a href="#Aromaticity">§ Aromaticity</a> below. </p><p>Single bonds adjacent to double bonds may be represented using <code>/</code> or <code>\</code> to indicate stereochemical configuration; see <a href="#Stereochemistry">§ Stereochemistry</a> below. </p> <div class="mw-heading mw-heading3"><h3 id="Rings">Rings</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=8" title="Edit section: Rings"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ring structures are written by breaking each ring at an arbitrary point (although some choices will lead to a more legible SMILES than others) to make an <a href="/wiki/Open-chain_compound" title="Open-chain compound">acyclic</a> structure and adding numerical ring closure labels to show connectivity between non-adjacent atoms. </p><p>For example, <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a> and <a href="/wiki/Dioxane" class="mw-redirect" title="Dioxane">dioxane</a> may be written as <code>C1CCCCC1</code> and <code>O1CCOCC1</code> respectively. For a second ring, the label will be 2. For example, <a href="/wiki/Decalin" title="Decalin">decalin</a> (decahydronaphthalene) may be written as <code>C1CCCC2C1CCCC2</code>. </p><p>SMILES does not require that ring numbers be used in any particular order, and permits ring number zero, although this is rarely used. Also, it is permitted to reuse ring numbers after the first ring has closed, although this usually makes formulae harder to read. For example, <a href="/wiki/Bicyclohexyl" title="Bicyclohexyl">bicyclohexyl</a> is usually written as <code>C1CCCCC1C2CCCCC2</code>, but it may also be written as <code>C0CCCCC0C0CCCCC0</code>. </p><p>Multiple digits after a single atom indicate multiple ring-closing bonds. For example, an alternative SMILES notation for decalin is <code>C1CCCC2CCCCC12</code>, where the final carbon participates in both ring-closing bonds 1 and 2. If two-digit ring numbers are required, the label is preceded by <code>%</code>, so <code>C%12</code> is a single ring-closing bond of ring 12. </p><p>Either or both of the digits may be preceded by a bond type to indicate the type of the ring-closing bond. For example, <a href="/wiki/Cyclopropene" title="Cyclopropene">cyclopropene</a> is usually written <code>C1=CC1</code>, but if the double bond is chosen as the ring-closing bond, it may be written as <code>C=1CC1</code>, <code>C1CC=1</code>, or <code>C=1CC=1</code>. (The first form is preferred.) <code>C=1CC-1</code> is illegal, as it explicitly specifies conflicting types for the ring-closing bond. </p><p>Ring-closing bonds may not be used to denote multiple bonds. For example, <code>C1C1</code> is not a valid alternative to <code>C=C</code> for <a href="/wiki/Ethylene" title="Ethylene">ethylene</a>. However, they may be used with non-bonds; <code>C1.C2.C12</code> is a peculiar but legal alternative way to write <a href="/wiki/Propane" title="Propane">propane</a>, more commonly written <code>CCC</code>. </p><p>Choosing a ring-break point adjacent to attached groups can lead to a simpler SMILES form by avoiding branches. For example, <a href="/wiki/Cyclohexane-1,2-diol" title="Cyclohexane-1,2-diol">cyclohexane-1,2-diol</a> is most simply written as <code>OC1CCCCC1O</code>; choosing a different ring-break location produces a branched structure that requires parentheses to write. </p> <div class="mw-heading mw-heading3"><h3 id="Aromaticity">Aromaticity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=9" title="Edit section: Aromaticity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Aromaticity" title="Aromaticity">Aromatic</a> rings such as <a href="/wiki/Benzene" title="Benzene">benzene</a> may be written in one of three forms: </p> <ol><li>In <a href="/wiki/August_Kekul%C3%A9" title="August Kekulé">Kekulé</a> form with alternating single and double bonds, e.g. <code>C1=CC=CC=C1</code>,</li> <li>Using the aromatic bond symbol <code>:</code>, e.g. <code>C:1:C:C:C:C:C1</code>, or</li> <li>Most commonly, by writing the constituent B, C, N, O, P and S atoms in lower-case forms <code>b</code>, <code>c</code>, <code>n</code>, <code>o</code>, <code>p</code> and <code>s</code>, respectively.</li></ol> <p>In the latter case, bonds between two aromatic atoms are assumed (if not explicitly shown) to be aromatic bonds. Thus, <a href="/wiki/Benzene" title="Benzene">benzene</a>, <a href="/wiki/Pyridine" title="Pyridine">pyridine</a> and <a href="/wiki/Furan" title="Furan">furan</a> can be represented respectively by the SMILES <code>c1ccccc1</code>, <code>n1ccccc1</code> and <code>o1cccc1</code>. </p><p>Aromatic nitrogen bonded to hydrogen, as found in <a href="/wiki/Pyrrole" title="Pyrrole">pyrrole</a> must be represented as <code>[nH]</code>; thus <a href="/wiki/Imidazole" title="Imidazole">imidazole</a> is written in SMILES notation as <code>n1c[nH]cc1</code>. </p><p>When aromatic atoms are singly bonded to each other, such as in <a href="/wiki/Biphenyl" title="Biphenyl">biphenyl</a>, a single bond must be shown explicitly: <code>c1ccccc1-c2ccccc2</code>. This is one of the few cases where the single bond symbol <code>-</code> is required. (In fact, most SMILES software can correctly infer that the bond between the two rings cannot be aromatic and so will accept the nonstandard form <code>c1ccccc1c2ccccc2</code>.) </p><p>The Daylight and OpenEye algorithms for generating canonical SMILES differ in their treatment of aromaticity. </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:3-cyanoanisole_SMILES.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/3-cyanoanisole_SMILES.svg/350px-3-cyanoanisole_SMILES.svg.png" decoding="async" width="350" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/3-cyanoanisole_SMILES.svg/525px-3-cyanoanisole_SMILES.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/31/3-cyanoanisole_SMILES.svg/700px-3-cyanoanisole_SMILES.svg.png 2x" data-file-width="625" data-file-height="171" /></a><figcaption>Visualization of 3-cyanoanisole as <code>COc(c1)cccc1C#N</code>.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Branching">Branching</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=10" title="Edit section: Branching"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Branches are described with parentheses, as in <code>CCC(=O)O</code> for <a href="/wiki/Propionic_acid" title="Propionic acid">propionic acid</a> and <code>FC(F)F</code> for <a href="/wiki/Fluoroform" title="Fluoroform">fluoroform</a>. The first atom within the parentheses, and the first atom after the parenthesized group, are both bonded to the same branch point atom. The bond symbol must appear inside the parentheses; outside (E.g.: <code>CCC=(O)O</code>) is invalid. </p><p>Substituted rings can be written with the branching point in the ring as illustrated by the SMILES <code>COc(c1)cccc1C#N</code> (<a rel="nofollow" class="external text" href="https://web.archive.org/web/20130522091354/http://www.daylight.com/daycgi/depict?434f6328633129636363633143234e">see depiction</a>) and <code>COc(cc1)ccc1C#N</code> (<a rel="nofollow" class="external text" href="https://web.archive.org/web/20130522074308/http://www.daylight.com/daycgi/depict?434f6328636331296363633143234e">see depiction</a>) which encode the 3 and 4-cyanoanisole isomers. Writing SMILES for substituted rings in this way can make them more human-readable. </p><p>Branches may be written in any order. For example, <a href="/wiki/Bromochlorodifluoromethane" title="Bromochlorodifluoromethane">bromochlorodifluoromethane</a> may be written as <code>FC(Br)(Cl)F</code>, <code>BrC(F)(F)Cl</code>, <code>C(F)(Cl)(F)Br</code>, or the like. Generally, a SMILES form is easiest to read if the simpler branch comes first, with the final, unparenthesized portion being the most complex. The only caveats to such rearrangements are: </p> <ul><li>If ring numbers are reused, they are paired according to their order of appearance in the SMILES string. Some adjustments may be required to preserve the correct pairing.</li> <li>If stereochemistry is specified, adjustments must be made; see <a href="#Stereochemistry">§ Stereochemistry</a> below.</li></ul> <p>The one form of branch which does <i>not</i> require parentheses are ring-closing bonds: the SMILES fragment <code>C1N</code> is equivalent to <code>C(1)N</code>, both denoting a bond between the <code>C</code> and the <code>N</code>. Choosing ring-closing bonds adjacent to branch points can reduce the number of parentheses required. For example, <a href="/wiki/Toluene" title="Toluene">toluene</a> is normally written as <code>Cc1ccccc1</code> or <code>c1ccccc1C</code>, avoiding the parentheses required if written as <code>c1cc(C)ccc1</code> or <code>c1cc(ccc1)C</code>. </p> <div class="mw-heading mw-heading3"><h3 id="Stereochemistry">Stereochemistry</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=11" title="Edit section: Stereochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a></div><figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Trans-1,2-difluoroethylene.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Trans-1%2C2-difluoroethylene.svg/110px-Trans-1%2C2-difluoroethylene.svg.png" decoding="async" width="110" height="110" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Trans-1%2C2-difluoroethylene.svg/165px-Trans-1%2C2-difluoroethylene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Trans-1%2C2-difluoroethylene.svg/220px-Trans-1%2C2-difluoroethylene.svg.png 2x" data-file-width="180" data-file-height="180" /></a><figcaption><i>trans</i>-1,2-difluoroethylene</figcaption></figure> <p>SMILES permits, but does not require, specification of <a href="/wiki/Stereoisomer" class="mw-redirect" title="Stereoisomer">stereoisomers</a>. </p><p>Configuration around double bonds is specified using the characters <code>/</code> and <code>\</code> to show directional single bonds adjacent to a double bond. For example, <code>F/C=C/F</code> (<a rel="nofollow" class="external text" href="https://web.archive.org/web/20130522072357/http://www.daylight.com/daycgi/depict?462f433d432f46">see depiction</a>) is one representation of <i><a href="/wiki/Trans_isomer" class="mw-redirect" title="Trans isomer">trans</a></i>-<a href="/wiki/1,2-difluoroethylene" class="mw-redirect" title="1,2-difluoroethylene">1,2-difluoroethylene</a>, in which the fluorine atoms are on opposite sides of the double bond (as shown in the figure), whereas <code>F/C=C\F</code> (<a rel="nofollow" class="external text" href="https://web.archive.org/web/20130522074206/http://www.daylight.com/daycgi/depict?462f433d435c46">see depiction</a>) is one possible representation of <i><a href="/wiki/Cis-trans_isomerism" class="mw-redirect" title="Cis-trans isomerism">cis</a></i>-1,2-difluoroethylene, in which the fluorines are on the same side of the double bond. </p><p>Bond direction symbols always come in groups of at least two, of which the first is arbitrary. That is, <code>F\C=C\F</code> is the same as <code>F/C=C/F</code>. When alternating single-double bonds are present, the groups are larger than two, with the middle directional symbols being adjacent to two double bonds. For example, the common form of (2,4)-hexadiene is written <code>C/C=C/C=C/C</code>. </p> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Beta-Carotene_conjugation.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Beta-Carotene_conjugation.svg/190px-Beta-Carotene_conjugation.svg.png" decoding="async" width="190" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Beta-Carotene_conjugation.svg/285px-Beta-Carotene_conjugation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/83/Beta-Carotene_conjugation.svg/380px-Beta-Carotene_conjugation.svg.png 2x" data-file-width="443" data-file-height="91" /></a><figcaption><a href="/wiki/Beta-carotene" class="mw-redirect" title="Beta-carotene">Beta-carotene</a>, with the eleven double bonds highlighted.</figcaption></figure> <p>As a more complex example, <a href="/wiki/Beta-carotene" class="mw-redirect" title="Beta-carotene">beta-carotene</a> has a very long backbone of alternating single and double bonds, which may be written <code>CC1CCC/C(C)=C1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)/CCCC2(C)C</code>. </p><p>Configuration at <a href="/wiki/Stereocenter" title="Stereocenter">tetrahedral carbon</a> is specified by <code>@</code> or <code>@@</code>. Consider the four bonds in the order in which they appear, left to right, in the SMILES form. Looking toward the central carbon from the perspective of the first bond, the other three are either clockwise or counter-clockwise. These cases are indicated with <code>@@</code> and <code>@</code>, respectively (because the <code>@</code> symbol itself is a counter-clockwise spiral). </p> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:L-Alanin_-_L-Alanine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/L-Alanin_-_L-Alanine.svg/110px-L-Alanin_-_L-Alanine.svg.png" decoding="async" width="110" height="82" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/L-Alanin_-_L-Alanine.svg/165px-L-Alanin_-_L-Alanine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/90/L-Alanin_-_L-Alanine.svg/220px-L-Alanin_-_L-Alanine.svg.png 2x" data-file-width="163" data-file-height="121" /></a><figcaption><small>L</small>-Alanine</figcaption></figure> <p>For example, consider the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> <a href="/wiki/Alanine" title="Alanine">alanine</a>. One of its SMILES forms is <code>NC(C)C(=O)O</code>, more fully written as <code>N[CH](C)C(=O)O</code>. <a href="/wiki/L-alanine" class="mw-redirect" title="L-alanine"><small>L</small>-Alanine</a>, the more common <a href="/wiki/Enantiomer" title="Enantiomer">enantiomer</a>, is written as <code>N[C@@H](C)C(=O)O</code> (<a rel="nofollow" class="external text" href="https://web.archive.org/web/20130704043108/http://www.daylight.com/daycgi/depict?4e5b434040485d28432943283d4f294f">see depiction</a>). Looking from the nitrogen–carbon bond, the hydrogen (<code>H</code>), methyl (<code>C</code>), and carboxylate (<code>C(=O)O</code>) groups appear clockwise. <small>D</small>-Alanine can be written as <code>N[C@H](C)C(=O)O</code> (<a rel="nofollow" class="external text" href="https://web.archive.org/web/20130522072012/http://www.daylight.com/daycgi/depict?4e5b4340485d28432943283d4f294f">see depiction</a>). </p><p>While the order in which branches are specified in SMILES is normally unimportant, in this case it matters; swapping any two groups requires reversing the chirality indicator. If the branches are reversed so alanine is written as <code>NC(C(=O)O)C</code>, then the configuration also reverses; <small>L</small>-alanine is written as <code>N[C@H](C(=O)O)C</code> (<a rel="nofollow" class="external text" href="https://web.archive.org/web/20130522073747/http://www.daylight.com/daycgi/depict?4e5b434040485d2843283d4f294f2943">see depiction</a>). Other ways of writing it include <code>C[C@H](N)C(=O)O</code>, <code>OC(=O)[C@@H](N)C</code> and <code>OC(=O)[C@H](C)N</code>. </p><p>Normally, the first of the four bonds appears to the left of the carbon atom, but if the SMILES is written beginning with the chiral carbon, such as <code>C(C)(N)C(=O)O</code>, then all four are to the right, but the first to appear (the <code>[CH]</code> bond in this case) is used as the reference to order the following three: <small>L</small>-alanine may also be written <code>[C@@H](C)(N)C(=O)O</code>. </p><p>The SMILES specification includes elaborations on the <code>@</code> symbol to indicate stereochemistry around more complex chiral centers, such as <a href="/wiki/Trigonal_bipyramidal_molecular_geometry" title="Trigonal bipyramidal molecular geometry">trigonal bipyramidal molecular geometry</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Isotopes">Isotopes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=12" title="Edit section: Isotopes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Isotopes" class="mw-redirect" title="Isotopes">Isotopes</a> are specified with a number equal to the integer isotopic mass preceding the atomic symbol. <a href="/wiki/Benzene" title="Benzene">Benzene</a> in which one atom is <a href="/wiki/Carbon-14" title="Carbon-14">carbon-14</a> is written as <code>[14c]1ccccc1</code> and <a href="/wiki/Deuterochloroform" class="mw-redirect" title="Deuterochloroform">deuterochloroform</a> is <code>[2H]C(Cl)(Cl)Cl</code>. </p> <div class="mw-heading mw-heading3"><h3 id="Examples">Examples</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=13" title="Edit section: Examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable"> <tbody><tr> <th>Molecule</th> <th>Structure</th> <th>SMILES formula </th></tr> <tr> <td><a href="/wiki/Dinitrogen" class="mw-redirect" title="Dinitrogen">Dinitrogen</a> </td> <td>N≡N </td> <td><code>N#N</code> </td></tr> <tr> <td><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a> (MIC) </td> <td>CH<sub>3</sub>−N=C=O </td> <td><code>CN=C=O</code> </td></tr> <tr> <td><a href="/wiki/Copper(II)_sulfate" title="Copper(II) sulfate">Copper(II) sulfate</a> </td> <td>Cu<sup>2+</sup><span class="chemf nowrap">SO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span></span> </td> <td><code>[Cu+2].[O-]S(=O)(=O)[O-]</code> </td></tr> <tr> <td><a href="/wiki/Vanillin" title="Vanillin">Vanillin</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Vanillin.svg" class="mw-file-description" title="Molecular structure of vanillin"><img alt="Molecular structure of vanillin" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/Vanillin.svg/70px-Vanillin.svg.png" decoding="async" width="70" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/Vanillin.svg/105px-Vanillin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/29/Vanillin.svg/140px-Vanillin.svg.png 2x" data-file-width="855" data-file-height="768" /></a></span> </td> <td><code>O=Cc1ccc(O)c(OC)c1</code><br /><code>COc1cc(C=O)ccc1O</code> </td></tr> <tr> <td><a href="/wiki/Melatonin" title="Melatonin">Melatonin</a> (C<sub>13</sub>H<sub>16</sub>N<sub>2</sub>O<sub>2</sub>) </td> <td><span typeof="mw:File"><a href="/wiki/File:Melatonin2.svg" class="mw-file-description" title="Molecular structure of melatonin"><img alt="Molecular structure of melatonin" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/Melatonin2.svg/160px-Melatonin2.svg.png" decoding="async" width="160" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/Melatonin2.svg/240px-Melatonin2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/14/Melatonin2.svg/320px-Melatonin2.svg.png 2x" data-file-width="346" data-file-height="225" /></a></span> </td> <td><code>CC(=O)NCCC1=CNc2c1cc(OC)cc2</code><br /><code>CC(=O)NCCc1c[nH]c2ccc(OC)cc12</code> </td></tr> <tr> <td><a href="/w/index.php?title=Flavopereirin&action=edit&redlink=1" class="new" title="Flavopereirin (page does not exist)">Flavopereirin</a> (C<sub>17</sub>H<sub>15</sub>N<sub>2</sub>) </td> <td><span typeof="mw:File"><a href="/wiki/File:Flavopereirine.svg" class="mw-file-description" title="Molecular structure of flavopereirin"><img alt="Molecular structure of flavopereirin" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Flavopereirine.svg/160px-Flavopereirine.svg.png" decoding="async" width="160" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Flavopereirine.svg/240px-Flavopereirine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Flavopereirine.svg/320px-Flavopereirine.svg.png 2x" data-file-width="200" data-file-height="100" /></a></span> </td> <td><code>CCc(c1)ccc2[n+]1ccc3c2[nH]c4c3cccc4</code><br /><code>CCc1c[n+]2ccc3c4ccccc4[nH]c3c2cc1</code> </td></tr> <tr> <td><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a> (C<sub>10</sub>H<sub>14</sub>N<sub>2</sub>) </td> <td><span typeof="mw:File"><a href="/wiki/File:Nicotine.svg" class="mw-file-description" title="Molecular structure of nicotine"><img alt="Molecular structure of nicotine" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Nicotine.svg/80px-Nicotine.svg.png" decoding="async" width="80" height="67" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Nicotine.svg/120px-Nicotine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Nicotine.svg/160px-Nicotine.svg.png 2x" data-file-width="161" data-file-height="135" /></a></span> </td> <td><code>CN1CCC[C@H]1c2cccnc2</code> </td></tr> <tr> <td><a href="/wiki/Oenanthotoxin" title="Oenanthotoxin">Oenanthotoxin</a> (C<sub>17</sub>H<sub>22</sub>O<sub>2</sub>) </td> <td><span typeof="mw:File"><a href="/wiki/File:Oenanthotoxin-structure.png" class="mw-file-description" title="Molecular structure of oenanthotoxin"><img alt="Molecular structure of oenanthotoxin" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Oenanthotoxin-structure.png/180px-Oenanthotoxin-structure.png" decoding="async" width="180" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Oenanthotoxin-structure.png/270px-Oenanthotoxin-structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/09/Oenanthotoxin-structure.png/360px-Oenanthotoxin-structure.png 2x" data-file-width="1342" data-file-height="449" /></a></span> </td> <td><code>CCC[C@@H](O)CC\C=C\C=C\C#CC#C\C=C\CO</code><br /><code>CCC[C@@H](O)CC/C=C/C=C/C#CC#C/C=C/CO</code> </td></tr> <tr> <td><a href="/wiki/Pyrethrin" title="Pyrethrin">Pyrethrin</a> II (C<sub>22</sub>H<sub>28</sub>O<sub>5</sub>) </td> <td><span typeof="mw:File"><a href="/wiki/File:Pyrethrin-II-2D-skeletal.svg" class="mw-file-description" title="Molecular structure of pyrethrin II"><img alt="Molecular structure of pyrethrin II" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Pyrethrin-II-2D-skeletal.svg/180px-Pyrethrin-II-2D-skeletal.svg.png" decoding="async" width="180" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Pyrethrin-II-2D-skeletal.svg/270px-Pyrethrin-II-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Pyrethrin-II-2D-skeletal.svg/360px-Pyrethrin-II-2D-skeletal.svg.png 2x" data-file-width="597" data-file-height="208" /></a></span> </td> <td><code>CC1=C(C(=O)C[C@@H]1OC(=O)[C@@H]2[C@H](C2(C)C)/C=C(\C)/C(=O)OC)C/C=C\C=C</code> </td></tr> <tr> <td><a href="/wiki/Aflatoxin" title="Aflatoxin">Aflatoxin</a> B<sub>1</sub> (C<sub>17</sub>H<sub>12</sub>O<sub>6</sub>) </td> <td><span typeof="mw:File"><a href="/wiki/File:Aflatoxin_B1.svg" class="mw-file-description" title="Molecular structure of aflatoxin B1"><img alt="Molecular structure of aflatoxin B1" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7f/Aflatoxin_B1.svg/130px-Aflatoxin_B1.svg.png" decoding="async" width="130" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7f/Aflatoxin_B1.svg/195px-Aflatoxin_B1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7f/Aflatoxin_B1.svg/260px-Aflatoxin_B1.svg.png 2x" data-file-width="379" data-file-height="281" /></a></span> </td> <td><code>O1C=C[C@H]([C@H]1O2)c3c2cc(OC)c4c3OC(=O)C5=C4CCC(=O)5</code> </td></tr> <tr> <td><a href="/wiki/Glucose" title="Glucose">Glucose</a> (β-<small>D</small>-glucopyranose) (C<sub>6</sub>H<sub>12</sub>O<sub>6</sub>) </td> <td><span typeof="mw:File"><a href="/wiki/File:Beta-D-Glucose.svg" class="mw-file-description" title="Molecular structure of glucopyranose"><img alt="Molecular structure of glucopyranose" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Beta-D-Glucose.svg/140px-Beta-D-Glucose.svg.png" decoding="async" width="140" height="72" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Beta-D-Glucose.svg/210px-Beta-D-Glucose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Beta-D-Glucose.svg/280px-Beta-D-Glucose.svg.png 2x" data-file-width="620" data-file-height="318" /></a></span> </td> <td><code>OC[C@@H](O1)[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)1</code> </td></tr> <tr> <td><a href="/wiki/Bergenin" title="Bergenin">Bergenin</a> (cuscutin, a <a href="/wiki/Resin" title="Resin">resin</a>) (C<sub>14</sub>H<sub>16</sub>O<sub>9</sub>) </td> <td><span typeof="mw:File"><a href="/wiki/File:Cuscutine.svg" class="mw-file-description" title="Molecular structure of cuscutine (bergenin)"><img alt="Molecular structure of cuscutine (bergenin)" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Cuscutine.svg/130px-Cuscutine.svg.png" decoding="async" width="130" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Cuscutine.svg/195px-Cuscutine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/12/Cuscutine.svg/260px-Cuscutine.svg.png 2x" data-file-width="200" data-file-height="170" /></a></span> </td> <td><code>OC[C@@H](O1)[C@@H](O)[C@H](O)[C@@H]2[C@@H]1c3c(O)c(OC)c(O)cc3C(=O)O2</code> </td></tr> <tr> <td>A <a href="/wiki/Pheromone" title="Pheromone">pheromone</a> of the Californian <a href="/wiki/Scale_insect" title="Scale insect">scale insect</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Pheromone_cochenille_californienne.svg" class="mw-file-description" title="(3Z,6R)-3-methyl-6-(prop-1-en-2-yl)deca-3,9-dien-1-yl acetate"><img alt="(3Z,6R)-3-methyl-6-(prop-1-en-2-yl)deca-3,9-dien-1-yl acetate" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Pheromone_cochenille_californienne.svg/180px-Pheromone_cochenille_californienne.svg.png" decoding="async" width="180" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Pheromone_cochenille_californienne.svg/270px-Pheromone_cochenille_californienne.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Pheromone_cochenille_californienne.svg/360px-Pheromone_cochenille_californienne.svg.png 2x" data-file-width="510" data-file-height="210" /></a></span> </td> <td><code>CC(=O)OCCC(/C)=C\C[C@H](C(C)=C)CCC=C</code> </td></tr> <tr> <td>(2<i>S</i>,5<i>R</i>)-<a href="/w/index.php?title=Chalcogran&action=edit&redlink=1" class="new" title="Chalcogran (page does not exist)">Chalcogran</a>: a <a href="/wiki/Pheromone" title="Pheromone">pheromone</a> of the <a href="/wiki/Scolytinae" class="mw-redirect" title="Scolytinae">bark beetle</a> <i><a href="/w/index.php?title=Pityogenes_chalcographus&action=edit&redlink=1" class="new" title="Pityogenes chalcographus (page does not exist)">Pityogenes chalcographus</a></i><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </td> <td><span typeof="mw:File"><a href="/wiki/File:2S,5R-chalcogran-skeletal.svg" class="mw-file-description" title="(2S,5R)-2-ethyl-1,6-dioxaspiro[4.4]nonane"><img alt="(2S,5R)-2-ethyl-1,6-dioxaspiro[4.4]nonane" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/2S%2C5R-chalcogran-skeletal.svg/130px-2S%2C5R-chalcogran-skeletal.svg.png" decoding="async" width="130" height="65" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/2S%2C5R-chalcogran-skeletal.svg/195px-2S%2C5R-chalcogran-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8e/2S%2C5R-chalcogran-skeletal.svg/260px-2S%2C5R-chalcogran-skeletal.svg.png 2x" data-file-width="120" data-file-height="60" /></a></span> </td> <td><code>CC[C@H](O1)CC[C@@]12CCCO2</code> </td></tr> <tr> <td><a href="/wiki/Thujone" title="Thujone">α-Thujone</a> (C<sub>10</sub>H<sub>16</sub>O) </td> <td><span typeof="mw:File"><a href="/wiki/File:Alpha-thujone.svg" class="mw-file-description" title="Molecular structure of thujone"><img alt="Molecular structure of thujone" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Alpha-thujone.svg/100px-Alpha-thujone.svg.png" decoding="async" width="100" height="57" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Alpha-thujone.svg/150px-Alpha-thujone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Alpha-thujone.svg/200px-Alpha-thujone.svg.png 2x" data-file-width="112" data-file-height="64" /></a></span> </td> <td><code>CC(C)[C@@]12C[C@@H]1[C@@H](C)C(=O)C2</code> </td></tr> <tr> <td><a href="/wiki/Thiamine" title="Thiamine">Thiamine</a> (vitamin B<sub>1</sub>, C<sub>12</sub>H<sub>17</sub>N<sub>4</sub>OS<sup>+</sup>) </td> <td><span typeof="mw:File"><a href="/wiki/File:Thiamin.svg" class="mw-file-description" title="Molecular structure of thiamin"><img alt="Molecular structure of thiamin" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Thiamin.svg/150px-Thiamin.svg.png" decoding="async" width="150" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Thiamin.svg/225px-Thiamin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Thiamin.svg/300px-Thiamin.svg.png 2x" data-file-width="346" data-file-height="201" /></a></span> </td> <td><code>OCCc1c(C)[n+](cs1)Cc2cnc(C)nc2N</code> </td></tr></tbody></table> <div style="clear:both;" class=""></div> <p>To illustrate a molecule with more than 9 rings, consider <a href="/w/index.php?title=Cephalostatin&action=edit&redlink=1" class="new" title="Cephalostatin (page does not exist)">cephalostatin</a>-1,<sup id="cite_ref-PubChem-183413_12-0" class="reference"><a href="#cite_note-PubChem-183413-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> a steroidic 13-ringed <a href="/wiki/Pyrazine" title="Pyrazine">pyrazine</a> with the <a href="/wiki/Empirical_formula" title="Empirical formula">empirical formula</a> C<sub>54</sub>H<sub>74</sub>N<sub>2</sub>O<sub>10</sub> isolated from the <a href="/wiki/Indian_Ocean" title="Indian Ocean">Indian Ocean</a> <a href="/wiki/Hemichordate" title="Hemichordate">hemichordate</a> <i><a href="/wiki/Cephalodiscus_gilchristi" title="Cephalodiscus gilchristi">Cephalodiscus gilchristi</a></i>: </p> <div style="clear:both;" class=""></div> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Cephalostatine-1.svg" class="mw-file-description" title="Molecular structure of cephalostatin-1"><img alt="Molecular structure of cephalostatin-1" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b8/Cephalostatine-1.svg/360px-Cephalostatine-1.svg.png" decoding="async" width="360" height="103" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b8/Cephalostatine-1.svg/540px-Cephalostatine-1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b8/Cephalostatine-1.svg/720px-Cephalostatine-1.svg.png 2x" data-file-width="560" data-file-height="160" /></a></span></dd></dl> <p>Starting with the left-most methyl group in the figure: </p> <dl><dd><code>CC(C)(O1)C[C@@H](O)[C@@]1(O2)[C@@H](C)[C@@H]3CC=C4[C@]3(C2)C(=O)C[C@H]5[C@H]4CC[C@@H](C6)[C@]5(C)Cc(n7)c6nc(C[C@@]89(C))c7C[C@@H]8CC[C@@H]%10[C@@H]9C[C@@H](O)[C@@]%11(C)C%10=C[C@H](O%12)[C@]%11(O)[C@H](C)[C@]%12(O%13)[C@H](O)C[C@@]%13(C)CO</code></dd></dl> <p><code>%</code> appears in front of the index of ring closure labels above 9; see <a href="#Rings">§ Rings</a> above. </p> <div class="mw-heading mw-heading3"><h3 id="Other_examples_of_SMILES">Other examples of SMILES</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=14" title="Edit section: Other examples of SMILES"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The SMILES notation is described extensively in the SMILES theory manual provided by Daylight Chemical Information Systems and a number of illustrative examples are presented. Daylight's depict utility provides users with the means to check their own examples of SMILES and is a valuable educational tool. </p> <div class="mw-heading mw-heading2"><h2 id="Extensions">Extensions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=15" title="Edit section: Extensions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Smiles_arbitrary_target_specification" class="mw-redirect" title="Smiles arbitrary target specification">SMARTS</a> is a line notation for specification of substructural patterns in molecules. While it uses many of the same symbols as SMILES, it also allows specification of <a href="/wiki/Wildcard_character" title="Wildcard character">wildcard</a> atoms and bonds, which can be used to define substructural queries for <a href="/wiki/Chemical_database" title="Chemical database">chemical database</a> searching. One common misconception is that SMARTS-based substructural searching involves matching of SMILES and SMARTS strings. In fact, both SMILES and SMARTS strings are first converted to internal graph representations which are searched for <a href="/wiki/Glossary_of_graph_theory#Subgraphs" title="Glossary of graph theory">subgraph</a> <a href="/wiki/Isomorphism" title="Isomorphism">isomorphism</a>. </p><p><span class="anchor" id="SMIRKS"></span>SMIRKS, a superset of "reaction SMILES" and a subset of "reaction SMARTS", is a line notation for specifying reaction transforms. The general syntax for the reaction extensions is <code>REACTANT>AGENT>PRODUCT</code> (without spaces), where any of the fields can either be left blank or filled with multiple molecules delineated with a dot (<code>.</code>), and other descriptions dependent on the base language. Atoms can additionally be identified with a number (e.g. <code>[C:1]</code>) for mapping,<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> for example in .<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>SMILES corresponds to discrete molecular structures. However many materials are macromolecules, which are too large (and often stochastic) to conveniently generate SMILES for. BigSMILES is an extension of SMILES that aims to provide an efficient representation system for macromolecules.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Conversion">Conversion</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=16" title="Edit section: Conversion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>SMILES can be converted back to two-dimensional representations using structure diagram generation (SDG) algorithms.<sup id="cite_ref-Helson-1999_16-0" class="reference"><a href="#cite_note-Helson-1999-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> This conversion is sometimes ambiguous. Conversion to three-dimensional representation is achieved by energy-minimization approaches. There are many downloadable and web-based conversion utilities. </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=17" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Smiles_arbitrary_target_specification" class="mw-redirect" title="Smiles arbitrary target specification">SMILES arbitrary target specification</a> (SMARTS), an extension of SMILES for specification of substructural queries</li> <li><a href="/wiki/SYBYL_Line_Notation" class="mw-redirect" title="SYBYL Line Notation">SYBYL Line Notation</a>, another line notation</li> <li><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">International Chemical Identifier</a> (InChI), the <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a>'s alternative to SMILES</li> <li><a href="/wiki/Molecular_Query_Language" title="Molecular Query Language">Molecular Query Language</a>, a <a href="/wiki/Query_language" title="Query language">query language</a> allowing also numerical properties, e.g. physicochemical values or distances</li> <li><a href="/wiki/Chemistry_Development_Kit" title="Chemistry Development Kit">Chemistry Development Kit</a>, 2D layout and conversion software</li> <li><a href="/wiki/OpenBabel" class="mw-redirect" title="OpenBabel">OpenBabel</a>, <a href="/wiki/JOELib" title="JOELib">JOELib</a>, <a href="/wiki/OELib" title="OELib">OELib</a> (conversion)</li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Simplified_Molecular_Input_Line_Entry_System&action=edit&section=18" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist 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"Structure Diagram Generation". In Lipkowitz KB, Boyd DB (eds.). <i>Reviews in Computational Chemistry</i>. Vol. 13. New York: Wiley-VCH. pp. 313–398. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9780470125908.ch6">10.1002/9780470125908.ch6</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-12590-8" title="Special:BookSources/978-0-470-12590-8"><bdi>978-0-470-12590-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Structure+Diagram+Generation&rft.btitle=Reviews+in+Computational+Chemistry&rft.place=New+York&rft.pages=313-398&rft.pub=Wiley-VCH&rft.date=1999&rft_id=info%3Adoi%2F10.1002%2F9780470125908.ch6&rft.isbn=978-0-470-12590-8&rft.aulast=Helson&rft.aufirst=HE&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASimplified+Molecular+Input+Line+Entry+System" class="Z3988"></span></span> </li> </ol></div> <div class="navbox-styles"><style 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style="width:1%"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formulas</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Non-structural formulas</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Empirical_formula" title="Empirical formula">Empirical formula</a></li> <li><a href="/wiki/Molecular_formula" class="mw-redirect" title="Molecular formula">Molecular formula</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Structural_formula" title="Structural formula">Structural formulas</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div 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ways</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Molecular_graph" title="Molecular graph">Molecular graph</a></li> <li><a href="/wiki/SMILES" class="mw-redirect" title="SMILES">SMILES</a></li> <li><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChl</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Computational_chemistry_software" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Chemistry_software" title="Template:Chemistry software"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chemistry_software" title="Template talk:Chemistry software"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chemistry_software" title="Special:EditPage/Template:Chemistry software"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Computational_chemistry_software" style="font-size:114%;margin:0 4em"><a href="/wiki/Computational_chemistry" title="Computational chemistry">Computational chemistry</a> software</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cheminformatics" title="Cheminformatics">Cheminformatics</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Free_software" title="Free software">Free software</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Avalon Cheminformatics Toolkit</li> <li><a href="/wiki/Bioclipse" title="Bioclipse">Bioclipse</a></li> <li><a href="/wiki/Blue_Obelisk" title="Blue Obelisk">Blue Obelisk</a></li> <li><a href="/wiki/Chemistry_Development_Kit" title="Chemistry Development Kit">Chemistry Development Kit</a></li> <li><a href="/wiki/Extensible_Computational_Chemistry_Environment" title="Extensible Computational Chemistry Environment">ECCE</a></li> <li><a href="/wiki/JOELib" title="JOELib">JOELib</a></li> <li><a href="/wiki/OELib" title="OELib">OELib</a></li> <li><a href="/wiki/Open_Babel" title="Open Babel">Open Babel</a></li> <li><a href="/wiki/RDKit" title="RDKit">RDKit</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Proprietary_software" title="Proprietary software">Proprietary</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Schr%C3%B6dinger_(company)" class="mw-redirect" title="Schrödinger (company)">Canvas</a></li> <li><a href="/wiki/Chemicalize" title="Chemicalize">Chemicalize</a></li> <li><a href="/wiki/Discovery_Studio" title="Discovery Studio">Discovery Studio</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chemical_kinetics" title="Chemical kinetics">Chemical kinetics</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Free software</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/APBS_(software)" title="APBS (software)">APBS</a></li> <li><a href="/wiki/Cantera_(software)" title="Cantera (software)">Cantera</a></li> <li><a href="/wiki/Kinetic_PreProcessor" title="Kinetic PreProcessor">KPP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Proprietary</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Autochem" title="Autochem">Autochem</a></li> <li><a href="/wiki/Chemical_WorkBench" title="Chemical WorkBench">Chemical WorkBench</a></li> <li><a href="/wiki/CHEMKIN" title="CHEMKIN">CHEMKIN</a></li> <li><a href="/wiki/COSILAB" title="COSILAB">COSILAB</a></li> <li><a href="/wiki/DelPhi_(software)" class="mw-redirect" title="DelPhi (software)">DelPhi</a></li> <li><a href="/wiki/Khimera" title="Khimera">Khimera</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Molecular_modelling" title="Molecular modelling">Molecular modelling</a> <br /> and <br /> <a href="/wiki/Visualization_(graphics)" title="Visualization (graphics)">visualization</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/List_of_molecular_graphics_systems" title="List of molecular graphics systems">List of molecular graphics systems</a> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Free software</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ascalaph_Designer" title="Ascalaph Designer">Ascalaph Designer</a></li> <li><a href="/wiki/Avogadro_(software)" title="Avogadro (software)">Avogadro</a></li> <li><a href="/wiki/BALL" title="BALL">BALL</a></li> <li><a href="/wiki/Biskit" title="Biskit">Biskit</a></li> <li><a href="/wiki/Gabedit" title="Gabedit">Gabedit</a></li> <li><a href="/wiki/Ghemical" title="Ghemical">Ghemical</a></li> <li><a href="/wiki/Jmol" title="Jmol">Jmol</a></li> <li><a href="/wiki/Molekel" title="Molekel">Molekel</a></li> <li><a href="/wiki/PyMOL" title="PyMOL">PyMOL</a></li> <li><a href="/wiki/QuteMol" title="QuteMol">QuteMol</a></li> <li><a href="/wiki/RasMol" title="RasMol">RasMol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Proprietary</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abalone_(molecular_mechanics)" title="Abalone (molecular mechanics)">Abalone</a></li> <li><a href="/wiki/ACD/ChemSketch" title="ACD/ChemSketch">ACD/ChemSketch</a></li> <li><a href="/wiki/Atomistix_ToolKit" title="Atomistix ToolKit">Atomistix ToolKit</a></li> <li><a href="/wiki/ChemDraw" title="ChemDraw">ChemDraw</a></li> <li><a href="/wiki/ChemWindow" title="ChemWindow">ChemWindow</a></li> <li><a href="/wiki/EzMol" title="EzMol">EzMol</a></li> <li><a href="/wiki/Gaussian_(software)" title="Gaussian (software)">Gaussian</a></li> <li><a href="/wiki/Schr%C3%B6dinger_(company)" class="mw-redirect" title="Schrödinger (company)">Maestro</a></li> <li><a href="/wiki/MarvinSketch" class="mw-redirect" title="MarvinSketch">MarvinSketch</a></li> <li><a href="/wiki/MarvinView" class="mw-redirect" title="MarvinView">MarvinView</a></li> <li><a href="/wiki/MODELLER" title="MODELLER">MODELLER</a></li> <li><a href="/wiki/Molecular_Operating_Environment" title="Molecular Operating Environment">Molecular Operating Environment</a></li> <li><a href="/wiki/SAMSON" title="SAMSON">SAMSON</a></li> <li><a href="/wiki/Spartan_(chemistry_software)" title="Spartan (chemistry software)">Spartan</a></li> <li><a href="/wiki/UCSF_Chimera" title="UCSF Chimera">UCSF Chimera</a></li> <li><a href="/wiki/Visual_Molecular_Dynamics" title="Visual Molecular Dynamics">VMD</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Docking_(molecular)" title="Docking (molecular)">Molecular docking</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/List_of_protein-ligand_docking_software" title="List of protein-ligand docking software">List of protein-ligand docking software</a> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Free_software" title="Free software">Free software</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/AutoDock" title="AutoDock">AutoDock</a></li> <li><a href="/wiki/AutoDock_Vina" class="mw-redirect" title="AutoDock Vina">AutoDock Vina</a></li> <li><a href="/wiki/FlexAID" title="FlexAID">FlexAID</a></li> <li><a href="/wiki/RDock" title="RDock">rDock</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Proprietary_software" title="Proprietary software">Proprietary</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glide_(docking)" title="Glide (docking)">Glide</a></li> <li><a href="/wiki/LeDock" title="LeDock">LeDock</a></li> <li><a href="/wiki/Molecular_Operating_Environment" title="Molecular Operating Environment">Molecular Operating Environment</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Molecular_dynamics" title="Molecular dynamics">Molecular dynamics</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Free_software" title="Free software">Free software</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CP2K" title="CP2K">CP2K</a></li> <li><a href="/wiki/GROMACS" title="GROMACS">GROMACS</a></li> <li><a href="/wiki/LAMMPS" title="LAMMPS">LAMMPS</a></li> <li><a href="/wiki/OpenMM" title="OpenMM">OpenMM</a></li> <li><a href="/wiki/PLUMED" title="PLUMED">PLUMED</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Proprietary_software" title="Proprietary software">Proprietary</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abalone_(molecular_mechanics)" title="Abalone (molecular mechanics)">Abalone</a></li> <li><a href="/wiki/AMBER" title="AMBER">AMBER</a></li> <li><a href="/wiki/CHARMM" title="CHARMM">CHARMM</a></li> <li><a href="/wiki/Car%E2%80%93Parrinello_molecular_dynamics" title="Car–Parrinello molecular dynamics">CPMD</a></li> <li><a href="/wiki/Desmond_(software)" title="Desmond (software)">Desmond</a></li> <li><a href="/wiki/GROMOS" title="GROMOS">GROMOS</a></li> <li><a href="/wiki/NAMD" title="NAMD">NAMD</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quantum_chemistry" title="Quantum chemistry">Quantum chemistry</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/List_of_quantum_chemistry_and_solid-state_physics_software" title="List of quantum chemistry and solid-state physics software">List of quantum chemistry and solid-state physics software</a> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Free software</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/ABINIT" title="ABINIT">ABINIT</a></li> <li><a href="/wiki/ACES_(computational_chemistry)" title="ACES (computational chemistry)">ACES</a> (CFOUR)</li> <li><a href="/wiki/AIMAll" title="AIMAll">AIMAll</a></li> <li><a href="/wiki/BigDFT" title="BigDFT">BigDFT</a></li> <li><a href="/wiki/COLUMBUS" title="COLUMBUS">COLUMBUS</a></li> <li><a href="/wiki/CONQUEST" title="CONQUEST">CONQUEST</a></li> <li><a href="/wiki/CP2K" title="CP2K">CP2K</a></li> <li><a href="/wiki/Dalton_(program)" title="Dalton (program)">Dalton</a></li> <li><a href="/wiki/Dirac_(software)" title="Dirac (software)">DIRAC</a></li> <li><a href="/wiki/DP_code" title="DP code">DP code</a></li> <li><a href="/wiki/FLEUR" title="FLEUR">FLEUR</a></li> <li><a href="/wiki/FreeON" title="FreeON">FreeON</a></li> <li><a href="/wiki/MADNESS" title="MADNESS">MADNESS</a></li> <li><a href="/wiki/MOPAC" title="MOPAC">MOPAC</a></li> <li><a href="/wiki/MPQC" class="mw-redirect" title="MPQC">MPQC</a></li> <li><a href="/wiki/NWChem" title="NWChem">NWChem</a></li> <li><a href="/wiki/Octopus_(software)" title="Octopus (software)">Octopus</a></li> <li><a href="/wiki/MOLCAS" title="MOLCAS">OpenMolcas</a></li> <li><a href="/wiki/PARSEC" title="PARSEC">PARSEC</a></li> <li><a href="/wiki/PSI_(computational_chemistry)" title="PSI (computational chemistry)">PSI</a></li> <li><a href="/wiki/PyQuante" title="PyQuante">PyQuante</a></li> <li><a href="/wiki/PySCF" title="PySCF">PySCF</a></li> <li><a href="/wiki/Quantum_ESPRESSO" title="Quantum ESPRESSO">Quantum ESPRESSO</a> (PWscf)</li> <li><a href="/wiki/RMG_(program)" title="RMG (program)">RMG</a></li> <li><a href="/wiki/SIESTA_(computer_program)" title="SIESTA (computer program)">SIESTA</a></li> <li><a href="/wiki/Valence_bond_programs" title="Valence bond programs">VB2000</a></li> <li><a href="/wiki/YAMBO_code" title="YAMBO code">YAMBO code</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Proprietary</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amsterdam_Density_Functional" title="Amsterdam Density Functional">ADF</a></li> <li><a href="/wiki/AMPAC" title="AMPAC">AMPAC</a></li> <li><a href="/wiki/DMol3" title="DMol3">DMol3</a></li> <li><a href="/wiki/CADPAC" title="CADPAC">CADPAC</a></li> <li><a href="/wiki/CASINO" title="CASINO">CASINO</a></li> <li><a href="/wiki/CASTEP" title="CASTEP">CASTEP</a></li> <li><a href="/wiki/Car%E2%80%93Parrinello_molecular_dynamics" title="Car–Parrinello molecular dynamics">CPMD</a></li> <li><a href="/wiki/Valence_bond_programs" title="Valence bond programs">CRUNCH</a></li> <li><a href="/wiki/CRYSTAL_(software)" title="CRYSTAL (software)">CRYSTAL</a></li> <li><a href="/wiki/Firefly_(computer_program)" title="Firefly (computer program)">Firefly</a></li> <li><a href="/wiki/GAMESS_(UK)" title="GAMESS (UK)">GAMESS (UK)</a></li> <li><a href="/wiki/GAMESS_(US)" title="GAMESS (US)">GAMESS (US)</a></li> <li><a href="/wiki/Gaussian_(software)" title="Gaussian (software)">Gaussian</a></li> <li><a href="/wiki/Jaguar_(software)" title="Jaguar (software)">Jaguar</a></li> <li><a href="/wiki/MOLCAS" title="MOLCAS">MOLCAS</a></li> <li><a href="/wiki/MOLPRO" title="MOLPRO">MOLPRO</a></li> <li><a href="/wiki/ONETEP" title="ONETEP">ONETEP</a></li> <li><a href="/wiki/OpenAtom" title="OpenAtom">OpenAtom</a></li> <li><a href="/wiki/ORCA_(quantum_chemistry_program)" title="ORCA (quantum chemistry program)">ORCA</a></li> <li><a href="/wiki/PLATO_(computational_chemistry)" title="PLATO (computational chemistry)">PLATO</a></li> <li><a href="/wiki/PQS_(software)" title="PQS (software)">PQS</a></li> <li><a href="/wiki/Q-Chem" title="Q-Chem">Q-Chem</a></li> <li><a href="/wiki/Quantemol" title="Quantemol">Quantemol</a></li> <li><a href="/wiki/Scigress" title="Scigress">Scigress</a></li> <li><a href="/wiki/Spartan_(chemistry_software)" title="Spartan (chemistry software)">Spartan</a></li> <li><a href="/wiki/TeraChem" title="TeraChem">TeraChem</a></li> <li><a href="/wiki/TURBOMOLE" title="TURBOMOLE">TURBOMOLE</a></li> <li><a href="/wiki/Vienna_Ab_initio_Simulation_Package" title="Vienna Ab initio Simulation Package">VASP</a></li> <li><a href="/wiki/WIEN2k" title="WIEN2k">WIEN2k</a></li> <li><a href="/wiki/Valence_bond_programs" title="Valence bond programs">XMVB</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Skeletal_structure" class="mw-redirect" title="Skeletal structure">Skeletal structure</a> drawing</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Free software</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/JChemPaint" title="JChemPaint">JChemPaint</a></li> <li><a href="/wiki/Molsketch" title="Molsketch">Molsketch</a></li> <li><a href="/wiki/XDrawChem" title="XDrawChem">XDrawChem</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Proprietary</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/ACD/ChemSketch" title="ACD/ChemSketch">ACD/ChemSketch</a></li> <li><a href="/wiki/ISIS/Draw" title="ISIS/Draw">BIOVIA Draw</a></li> <li>ChemDoodle</li> <li><a href="/wiki/ChemDraw" title="ChemDraw">ChemDraw</a></li> <li><a href="/wiki/ChemWindow" title="ChemWindow">ChemWindow</a></li> <li><a href="/wiki/JME_Molecule_Editor" title="JME Molecule Editor">JME Molecule Editor</a></li> <li><a href="/wiki/MarvinSketch" class="mw-redirect" title="MarvinSketch">MarvinSketch</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aqion" title="Aqion">Aqion</a></li> <li><a href="/wiki/Eulim" title="Eulim">Eulim</a></li> <li><a href="/wiki/EXC_code" title="EXC code">EXC code</a></li> <li>GenX</li> <li>GSim</li> <li><a href="/wiki/Mercury_(crystallography)" title="Mercury (crystallography)">Mercury</a></li> <li><a href="/wiki/CrystalExplorer" title="CrystalExplorer">CrystalExplorer</a></li> <li><a href="/wiki/Internal_Coordinate_Mechanics" title="Internal Coordinate Mechanics">ICM</a> (ICM-Browser)</li> <li><a href="/wiki/Materials_Studio" title="Materials Studio">Materials Studio</a></li> <li><a href="/wiki/Molden" title="Molden">Molden</a></li> <li><a href="/wiki/OpenChrom" title="OpenChrom">OpenChrom</a></li> <li>SASHIMI</li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" 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