CINXE.COM

<!DOCTYPE html> <html class="client-nojs vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-sticky-header-enabled vector-toc-available" lang="en" dir="ltr"> <head> <meta charset="UTF-8"> <title>Small molecule - Wikipedia</title> <script>(function(){var className="client-js vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-sticky-header-enabled vector-toc-available";var cookie=document.cookie.match(/(?:^|; )enwikimwclientpreferences=([^;]+)/);if(cookie){cookie[1].split('%2C').forEach(function(pref){className=className.replace(new RegExp('(^| )'+pref.replace(/-clientpref-\w+$|[^\w-]+/g,'')+'-clientpref-\\w+( |$)'),'$1'+pref+'$2');});}document.documentElement.className=className;}());RLCONF={"wgBreakFrames":false,"wgSeparatorTransformTable":["",""],"wgDigitTransformTable":["",""],"wgDefaultDateFormat":"dmy", "wgMonthNames":["","January","February","March","April","May","June","July","August","September","October","November","December"],"wgRequestId":"93edcbfc-5ddb-44dc-9d79-71ecd618d509","wgCanonicalNamespace":"","wgCanonicalSpecialPageName":false,"wgNamespaceNumber":0,"wgPageName":"Small_molecule","wgTitle":"Small molecule","wgCurRevisionId":1262709559,"wgRevisionId":1262709559,"wgArticleId":477588,"wgIsArticle":true,"wgIsRedirect":false,"wgAction":"view","wgUserName":null,"wgUserGroups":["*"],"wgCategories":["Articles with short description","Short description is different from Wikidata","All articles with unsourced statements","Articles with unsourced statements from June 2021","Plant physiology","Drug discovery","Induced stem cells"],"wgPageViewLanguage":"en","wgPageContentLanguage":"en","wgPageContentModel":"wikitext","wgRelevantPageName":"Small_molecule","wgRelevantArticleId":477588,"wgIsProbablyEditable":true,"wgRelevantPageIsProbablyEditable":true,"wgRestrictionEdit":[], "wgRestrictionMove":[],"wgNoticeProject":"wikipedia","wgCiteReferencePreviewsActive":false,"wgFlaggedRevsParams":{"tags":{"status":{"levels":1}}},"wgMediaViewerOnClick":true,"wgMediaViewerEnabledByDefault":true,"wgPopupsFlags":0,"wgVisualEditor":{"pageLanguageCode":"en","pageLanguageDir":"ltr","pageVariantFallbacks":"en"},"wgMFDisplayWikibaseDescriptions":{"search":true,"watchlist":true,"tagline":false,"nearby":true},"wgWMESchemaEditAttemptStepOversample":false,"wgWMEPageLength":10000,"wgEditSubmitButtonLabelPublish":true,"wgULSPosition":"interlanguage","wgULSisCompactLinksEnabled":false,"wgVector2022LanguageInHeader":true,"wgULSisLanguageSelectorEmpty":false,"wgWikibaseItemId":"Q1988322","wgCheckUserClientHintsHeadersJsApi":["brands","architecture","bitness","fullVersionList","mobile","model","platform","platformVersion"],"GEHomepageSuggestedEditsEnableTopics":true,"wgGETopicsMatchModeEnabled":false,"wgGEStructuredTaskRejectionReasonTextInputEnabled":false, "wgGELevelingUpEnabledForUser":false};RLSTATE={"ext.globalCssJs.user.styles":"ready","site.styles":"ready","user.styles":"ready","ext.globalCssJs.user":"ready","user":"ready","user.options":"loading","ext.cite.styles":"ready","skins.vector.search.codex.styles":"ready","skins.vector.styles":"ready","skins.vector.icons":"ready","ext.wikimediamessages.styles":"ready","ext.visualEditor.desktopArticleTarget.noscript":"ready","ext.uls.interlanguage":"ready","wikibase.client.init":"ready"};RLPAGEMODULES=["ext.cite.ux-enhancements","mediawiki.page.media","site","mediawiki.page.ready","mediawiki.toc","skins.vector.js","ext.centralNotice.geoIP","ext.centralNotice.startUp","ext.gadget.ReferenceTooltips","ext.gadget.switcher","ext.urlShortener.toolbar","ext.centralauth.centralautologin","mmv.bootstrap","ext.popups","ext.visualEditor.desktopArticleTarget.init","ext.visualEditor.targetLoader","ext.echo.centralauth","ext.eventLogging","ext.wikimediaEvents","ext.navigationTiming","ext.uls.interface", "ext.cx.eventlogging.campaigns","ext.cx.uls.quick.actions","wikibase.client.vector-2022","ext.checkUser.clientHints","ext.growthExperiments.SuggestedEditSession"];</script> <script>(RLQ=window.RLQ||[]).push(function(){mw.loader.impl(function(){return["user.options@12s5i",function($,jQuery,require,module){mw.user.tokens.set({"patrolToken":"+\\","watchToken":"+\\","csrfToken":"+\\"}); }];});});</script> <link rel="stylesheet" href="/w/load.php?lang=en&modules=ext.cite.styles%7Cext.uls.interlanguage%7Cext.visualEditor.desktopArticleTarget.noscript%7Cext.wikimediamessages.styles%7Cskins.vector.icons%2Cstyles%7Cskins.vector.search.codex.styles%7Cwikibase.client.init&only=styles&skin=vector-2022"> <script async="" src="/w/load.php?lang=en&modules=startup&only=scripts&raw=1&skin=vector-2022"></script> <meta name="ResourceLoaderDynamicStyles" content=""> <link rel="stylesheet" href="/w/load.php?lang=en&modules=site.styles&only=styles&skin=vector-2022"> <meta name="generator" content="MediaWiki 1.44.0-wmf.18"> <meta name="referrer" content="origin"> <meta name="referrer" content="origin-when-cross-origin"> <meta name="robots" content="max-image-preview:standard"> <meta name="format-detection" content="telephone=no"> <meta name="viewport" content="width=1120"> <meta property="og:title" content="Small molecule - Wikipedia"> <meta property="og:type" content="website"> <link rel="preconnect" href="//upload.wikimedia.org"> <link rel="alternate" media="only screen and (max-width: 640px)" href="//en.m.wikipedia.org/wiki/Small_molecule"> <link rel="alternate" type="application/x-wiki" title="Edit this page" href="/w/index.php?title=Small_molecule&action=edit"> <link rel="apple-touch-icon" href="/static/apple-touch/wikipedia.png"> <link rel="icon" href="/static/favicon/wikipedia.ico"> <link rel="search" type="application/opensearchdescription+xml" href="/w/rest.php/v1/search" title="Wikipedia (en)"> <link rel="EditURI" type="application/rsd+xml" href="//en.wikipedia.org/w/api.php?action=rsd"> <link rel="canonical" href="https://en.wikipedia.org/wiki/Small_molecule"> <link rel="license" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en"> <link rel="alternate" type="application/atom+xml" title="Wikipedia Atom feed" href="/w/index.php?title=Special:RecentChanges&feed=atom"> <link rel="dns-prefetch" href="//meta.wikimedia.org" /> <link rel="dns-prefetch" href="login.wikimedia.org"> </head> <body class="skin--responsive skin-vector skin-vector-search-vue mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject mw-editable page-Small_molecule rootpage-Small_molecule skin-vector-2022 action-view"><a class="mw-jump-link" href="#bodyContent">Jump to content</a> <div class="vector-header-container"> <header class="vector-header mw-header"> <div class="vector-header-start"> <nav class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-dropdown" class="vector-dropdown vector-main-menu-dropdown vector-button-flush-left vector-button-flush-right" title="Main menu" > <input type="checkbox" id="vector-main-menu-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-main-menu-dropdown" class="vector-dropdown-checkbox " aria-label="Main menu" > <label id="vector-main-menu-dropdown-label" for="vector-main-menu-dropdown-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-menu mw-ui-icon-wikimedia-menu"></span> <span class="vector-dropdown-label-text">Main menu</span> </label> <div class="vector-dropdown-content"> <div id="vector-main-menu-unpinned-container" class="vector-unpinned-container"> <div id="vector-main-menu" class="vector-main-menu vector-pinnable-element"> <div class="vector-pinnable-header vector-main-menu-pinnable-header vector-pinnable-header-unpinned" data-feature-name="main-menu-pinned" data-pinnable-element-id="vector-main-menu" data-pinned-container-id="vector-main-menu-pinned-container" data-unpinned-container-id="vector-main-menu-unpinned-container" > <div class="vector-pinnable-header-label">Main menu</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-main-menu.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-main-menu.unpin">hide</button> </div> <div id="p-navigation" class="vector-menu mw-portlet mw-portlet-navigation" > <div class="vector-menu-heading"> Navigation </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-mainpage-description" class="mw-list-item"><a href="/wiki/Main_Page" title="Visit the main page [z]" accesskey="z"><span>Main page</span></a></li><li id="n-contents" class="mw-list-item"><a href="/wiki/Wikipedia:Contents" title="Guides to browsing Wikipedia"><span>Contents</span></a></li><li id="n-currentevents" class="mw-list-item"><a href="/wiki/Portal:Current_events" title="Articles related to current events"><span>Current events</span></a></li><li id="n-randompage" class="mw-list-item"><a href="/wiki/Special:Random" title="Visit a randomly selected article [x]" accesskey="x"><span>Random article</span></a></li><li id="n-aboutsite" class="mw-list-item"><a href="/wiki/Wikipedia:About" title="Learn about Wikipedia and how it works"><span>About Wikipedia</span></a></li><li id="n-contactpage" class="mw-list-item"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us" title="How to contact Wikipedia"><span>Contact us</span></a></li> </ul> </div> </div> <div id="p-interaction" class="vector-menu mw-portlet mw-portlet-interaction" > <div class="vector-menu-heading"> Contribute </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-help" class="mw-list-item"><a href="/wiki/Help:Contents" title="Guidance on how to use and edit Wikipedia"><span>Help</span></a></li><li id="n-introduction" class="mw-list-item"><a href="/wiki/Help:Introduction" title="Learn how to edit Wikipedia"><span>Learn to edit</span></a></li><li id="n-portal" class="mw-list-item"><a href="/wiki/Wikipedia:Community_portal" title="The hub for editors"><span>Community portal</span></a></li><li id="n-recentchanges" class="mw-list-item"><a href="/wiki/Special:RecentChanges" title="A list of recent changes to Wikipedia [r]" accesskey="r"><span>Recent changes</span></a></li><li id="n-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_upload_wizard" title="Add images or other media for use on Wikipedia"><span>Upload file</span></a></li><li id="n-specialpages" class="mw-list-item"><a href="/wiki/Special:SpecialPages"><span>Special pages</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> <a href="/wiki/Main_Page" class="mw-logo"> <img class="mw-logo-icon" src="/static/images/icons/wikipedia.png" alt="" aria-hidden="true" height="50" width="50"> <span class="mw-logo-container skin-invert"> <img class="mw-logo-wordmark" alt="Wikipedia" src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" style="width: 7.5em; height: 1.125em;"> <img class="mw-logo-tagline" alt="The Free Encyclopedia" src="/static/images/mobile/copyright/wikipedia-tagline-en.svg" width="117" height="13" style="width: 7.3125em; height: 0.8125em;"> </span> </a> </div> <div class="vector-header-end"> <div id="p-search" role="search" class="vector-search-box-vue vector-search-box-collapses vector-search-box-show-thumbnail vector-search-box-auto-expand-width vector-search-box"> <a href="/wiki/Special:Search" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only search-toggle" title="Search Wikipedia [f]" accesskey="f"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Search</span> </a> <div class="vector-typeahead-search-container"> <div class="cdx-typeahead-search cdx-typeahead-search--show-thumbnail cdx-typeahead-search--auto-expand-width"> <form action="/w/index.php" id="searchform" class="cdx-search-input cdx-search-input--has-end-button"> <div id="simpleSearch" class="cdx-search-input__input-wrapper" data-search-loc="header-moved"> <div class="cdx-text-input cdx-text-input--has-start-icon"> <input class="cdx-text-input__input" type="search" name="search" placeholder="Search Wikipedia" aria-label="Search Wikipedia" autocapitalize="sentences" title="Search Wikipedia [f]" accesskey="f" id="searchInput" > <span class="cdx-text-input__icon cdx-text-input__start-icon"></span> </div> <input type="hidden" name="title" value="Special:Search"> </div> <button class="cdx-button cdx-search-input__end-button">Search</button> </form> </div> </div> </div> <nav class="vector-user-links vector-user-links-wide" aria-label="Personal tools"> <div class="vector-user-links-main"> <div id="p-vector-user-menu-preferences" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-userpage" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-dropdown" class="vector-dropdown " title="Change the appearance of the page's font size, width, and color" > <input type="checkbox" id="vector-appearance-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-appearance-dropdown" class="vector-dropdown-checkbox " aria-label="Appearance" > <label id="vector-appearance-dropdown-label" for="vector-appearance-dropdown-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-appearance mw-ui-icon-wikimedia-appearance"></span> <span class="vector-dropdown-label-text">Appearance</span> </label> <div class="vector-dropdown-content"> <div id="vector-appearance-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div id="p-vector-user-menu-notifications" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-overflow" class="vector-menu mw-portlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="https://donate.wikimedia.org/?wmf_source=donate&wmf_medium=sidebar&wmf_campaign=en.wikipedia.org&uselang=en" class=""><span>Donate</span></a> </li> <li id="pt-createaccount-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:CreateAccount&returnto=Small+molecule" title="You are encouraged to create an account and log in; however, it is not mandatory" class=""><span>Create account</span></a> </li> <li id="pt-login-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:UserLogin&returnto=Small+molecule" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o" class=""><span>Log in</span></a> </li> </ul> </div> </div> </div> <div id="vector-user-links-dropdown" class="vector-dropdown vector-user-menu vector-button-flush-right vector-user-menu-logged-out" title="Log in and more options" > <input type="checkbox" id="vector-user-links-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-user-links-dropdown" class="vector-dropdown-checkbox " aria-label="Personal tools" > <label id="vector-user-links-dropdown-label" for="vector-user-links-dropdown-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-ellipsis mw-ui-icon-wikimedia-ellipsis"></span> <span class="vector-dropdown-label-text">Personal tools</span> </label> <div class="vector-dropdown-content"> <div id="p-personal" class="vector-menu mw-portlet mw-portlet-personal user-links-collapsible-item" title="User menu" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport" class="user-links-collapsible-item mw-list-item"><a href="https://donate.wikimedia.org/?wmf_source=donate&wmf_medium=sidebar&wmf_campaign=en.wikipedia.org&uselang=en"><span>Donate</span></a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:CreateAccount&returnto=Small+molecule" title="You are encouraged to create an account and log in; however, it is not mandatory"><span class="vector-icon mw-ui-icon-userAdd mw-ui-icon-wikimedia-userAdd"></span> <span>Create account</span></a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:UserLogin&returnto=Small+molecule" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>Log in</span></a></li> </ul> </div> </div> <div id="p-user-menu-anon-editor" class="vector-menu mw-portlet mw-portlet-user-menu-anon-editor" > <div class="vector-menu-heading"> Pages for logged out editors <a href="/wiki/Help:Introduction" aria-label="Learn more about editing"><span>learn more</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Special:MyContributions" title="A list of edits made from this IP address [y]" accesskey="y"><span>Contributions</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Special:MyTalk" title="Discussion about edits from this IP address [n]" accesskey="n"><span>Talk</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="Contents" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">Contents</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-Molecular_weight_cutoff" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Molecular_weight_cutoff"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Molecular weight cutoff</span> </div> </a> <ul id="toc-Molecular_weight_cutoff-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Drugs" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Drugs"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Drugs</span> </div> </a> <ul id="toc-Drugs-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Secondary_metabolites" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Secondary_metabolites"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Secondary metabolites</span> </div> </a> <ul id="toc-Secondary_metabolites-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Research_tools" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Research_tools"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Research tools</span> </div> </a> <ul id="toc-Research_tools-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Anti-genomic_therapeutics" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Anti-genomic_therapeutics"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Anti-genomic therapeutics</span> </div> </a> <ul id="toc-Anti-genomic_therapeutics-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">6</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">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>External links</span> </div> </a> <ul id="toc-External_links-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" title="Table of Contents" > <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">Small molecule</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 19 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-19" 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">19 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/%D8%AC%D8%B2%D9%8A%D8%A1_%D8%B5%D8%BA%D9%8A%D8%B1" title="جزيء صغير – Arabic" lang="ar" hreflang="ar" data-title="جزيء صغير" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Mol%C3%A8cula_petita" title="Molècula petita – Catalan" lang="ca" hreflang="ca" data-title="Molècula petita" 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/Mal%C3%A1_molekula" title="Malá molekula – Czech" lang="cs" hreflang="cs" data-title="Malá molekula" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Niedermolekulare_Verbindung" title="Niedermolekulare Verbindung – German" lang="de" hreflang="de" data-title="Niedermolekulare Verbindung" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Mol%C3%A9cula_peque%C3%B1a" title="Molécula pequeña – Spanish" lang="es" hreflang="es" data-title="Molécula pequeña" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%85%D9%88%D9%84%DA%A9%D9%88%D9%84_%DA%A9%D9%88%DA%86%DA%A9" title="مولکول کوچک – Persian" lang="fa" hreflang="fa" data-title="مولکول کوچک" 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/Petite_mol%C3%A9cule" title="Petite molécule – French" lang="fr" hreflang="fr" data-title="Petite molécule" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%A0%80%EB%B6%84%EC%9E%90" title="저분자 – Korean" lang="ko" hreflang="ko" data-title="저분자" 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/Molekul_kecil" title="Molekul kecil – Indonesian" lang="id" hreflang="id" data-title="Molekul kecil" 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-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Molekul_kecil" title="Molekul kecil – Malay" lang="ms" hreflang="ms" data-title="Molekul kecil" 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-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E5%B0%8F%E5%88%86%E5%AD%90" title="小分子 – Japanese" lang="ja" hreflang="ja" data-title="小分子" 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-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Micromol%C3%A9cula" title="Micromolécula – Portuguese" lang="pt" hreflang="pt" data-title="Micromolécula" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9C%D0%B0%D0%BB%D1%8B%D0%B5_%D0%BC%D0%BE%D0%BB%D0%B5%D0%BA%D1%83%D0%BB%D1%8B" title="Малые молекулы – Russian" lang="ru" hreflang="ru" data-title="Малые молекулы" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Mala_molekula" title="Mala molekula – Slovenian" lang="sl" hreflang="sl" data-title="Mala molekula" 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/Mali_molekul" title="Mali molekul – Serbian" lang="sr" hreflang="sr" data-title="Mali molekul" 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/Mali_molekul" title="Mali molekul – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Mali molekul" 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-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%82%E0%B8%A1%E0%B9%80%E0%B8%A5%E0%B8%81%E0%B8%B8%E0%B8%A5%E0%B9%80%E0%B8%A5%E0%B9%87%E0%B8%81" title="โมเลกุลเล็ก – Thai" lang="th" hreflang="th" data-title="โมเลกุลเล็ก" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Ti%E1%BB%83u_ph%C3%A2n_t%E1%BB%AD" title="Tiểu phân tử – Vietnamese" lang="vi" hreflang="vi" data-title="Tiểu phân tử" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%B0%8F%E5%88%86%E5%AD%90" title="小分子 – Chinese" lang="zh" hreflang="zh" data-title="小分子" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q1988322#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Small_molecule" title="View the content page [c]" accesskey="c"><span>Article</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Small_molecule" rel="discussion" title="Discuss improvements to the content page [t]" accesskey="t"><span>Talk</span></a></li> </ul> </div> </div> <div id="vector-variants-dropdown" class="vector-dropdown emptyPortlet" > <input type="checkbox" id="vector-variants-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-variants-dropdown" class="vector-dropdown-checkbox " aria-label="Change language variant" > <label id="vector-variants-dropdown-label" for="vector-variants-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">English</span> </label> <div class="vector-dropdown-content"> <div id="p-variants" class="vector-menu mw-portlet mw-portlet-variants emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> </div> </div> </nav> </div> <div id="right-navigation" class="vector-collapsible"> <nav aria-label="Views"> <div id="p-views" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-views" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-view" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Small_molecule"><span>Read</span></a></li><li id="ca-edit" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Small_molecule&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-history" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Small_molecule&action=history" title="Past revisions of this page [h]" accesskey="h"><span>View history</span></a></li> </ul> </div> </div> </nav> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-dropdown" class="vector-dropdown vector-page-tools-dropdown" > <input type="checkbox" id="vector-page-tools-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-tools-dropdown" class="vector-dropdown-checkbox " aria-label="Tools" > <label id="vector-page-tools-dropdown-label" for="vector-page-tools-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">Tools</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-tools-unpinned-container" class="vector-unpinned-container"> <div id="vector-page-tools" class="vector-page-tools vector-pinnable-element"> <div class="vector-pinnable-header vector-page-tools-pinnable-header vector-pinnable-header-unpinned" data-feature-name="page-tools-pinned" data-pinnable-element-id="vector-page-tools" data-pinned-container-id="vector-page-tools-pinned-container" data-unpinned-container-id="vector-page-tools-unpinned-container" > <div class="vector-pinnable-header-label">Tools</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-page-tools.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-page-tools.unpin">hide</button> </div> <div id="p-cactions" class="vector-menu mw-portlet mw-portlet-cactions emptyPortlet vector-has-collapsible-items" title="More options" > <div class="vector-menu-heading"> Actions </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-more-view" class="selected vector-more-collapsible-item mw-list-item"><a href="/wiki/Small_molecule"><span>Read</span></a></li><li id="ca-more-edit" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Small_molecule&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-more-history" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Small_molecule&action=history"><span>View history</span></a></li> </ul> </div> </div> <div id="p-tb" class="vector-menu mw-portlet mw-portlet-tb" > <div class="vector-menu-heading"> General </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="t-whatlinkshere" class="mw-list-item"><a href="/wiki/Special:WhatLinksHere/Small_molecule" title="List of all English Wikipedia pages containing links to this page [j]" accesskey="j"><span>What links here</span></a></li><li id="t-recentchangeslinked" class="mw-list-item"><a href="/wiki/Special:RecentChangesLinked/Small_molecule" rel="nofollow" title="Recent changes in pages linked from this page [k]" accesskey="k"><span>Related changes</span></a></li><li id="t-upload" class="mw-list-item"><a href="//en.wikipedia.org/wiki/Wikipedia:File_Upload_Wizard" title="Upload files [u]" accesskey="u"><span>Upload file</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Small_molecule&oldid=1262709559" title="Permanent link to this revision of this page"><span>Permanent link</span></a></li><li id="t-info" class="mw-list-item"><a href="/w/index.php?title=Small_molecule&action=info" title="More information about this page"><span>Page information</span></a></li><li id="t-cite" class="mw-list-item"><a href="/w/index.php?title=Special:CiteThisPage&page=Small_molecule&id=1262709559&wpFormIdentifier=titleform" title="Information on how to cite this page"><span>Cite this page</span></a></li><li id="t-urlshortener" class="mw-list-item"><a href="/w/index.php?title=Special:UrlShortener&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FSmall_molecule"><span>Get shortened URL</span></a></li><li id="t-urlshortener-qrcode" class="mw-list-item"><a href="/w/index.php?title=Special:QrCode&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FSmall_molecule"><span>Download QR code</span></a></li> </ul> </div> </div> <div id="p-coll-print_export" class="vector-menu mw-portlet mw-portlet-coll-print_export" > <div class="vector-menu-heading"> Print/export </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="coll-download-as-rl" class="mw-list-item"><a href="/w/index.php?title=Special:DownloadAsPdf&page=Small_molecule&action=show-download-screen" title="Download this page as a PDF file"><span>Download as PDF</span></a></li><li id="t-print" class="mw-list-item"><a href="/w/index.php?title=Small_molecule&printable=yes" title="Printable version of this page [p]" accesskey="p"><span>Printable version</span></a></li> </ul> </div> </div> <div id="p-wikibase-otherprojects" class="vector-menu mw-portlet mw-portlet-wikibase-otherprojects" > <div class="vector-menu-heading"> In other projects </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="t-wikibase" class="wb-otherproject-link wb-otherproject-wikibase-dataitem mw-list-item"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q1988322" title="Structured data on this page hosted by Wikidata [g]" accesskey="g"><span>Wikidata item</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></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">Organic molecule weighing under 1000 daltons</div> <p>In <a href="/wiki/Molecular_biology" title="Molecular biology">molecular biology</a> and <a href="/wiki/Pharmacology" title="Pharmacology">pharmacology</a>, a <b>small molecule</b> or <b>micromolecule</b> is a low molecular weight (≤ 1000 <a href="/wiki/Atomic_mass_unit" class="mw-redirect" title="Atomic mass unit">daltons</a><sup id="cite_ref-Dougherty_Pucci_2012_1-0" class="reference"><a href="#cite_note-Dougherty_Pucci_2012-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>) <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> that may regulate a biological process, with a size on the order of 1 nm<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2021)">citation needed</span></a></i>]</sup>. Many <a href="/wiki/Pharmaceuticals" class="mw-redirect" title="Pharmaceuticals">drugs</a> are small molecules; the terms are equivalent in the literature. <a href="/wiki/Macromolecule" title="Macromolecule">Larger structures</a> such as <a href="/wiki/Nucleic_acid" title="Nucleic acid">nucleic acids</a> and <a href="/wiki/Protein" title="Protein">proteins</a>, and many <a href="/wiki/Polysaccharides" class="mw-redirect" title="Polysaccharides">polysaccharides</a> are not small molecules, although their constituent monomers (ribo- or deoxyribonucleotides, <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a>, and monosaccharides, respectively) are often considered small molecules. Small molecules may be used as research tools to probe <a href="/wiki/Function_(biology)" title="Function (biology)">biological function</a> as well as <a href="/wiki/Lead_compound" title="Lead compound">leads</a> in the development of new <a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">therapeutic agents</a>. Some can inhibit a specific function of a protein or disrupt <a href="/wiki/Protein%E2%80%93protein_interaction" title="Protein–protein interaction">protein–protein interactions</a>.<sup id="cite_ref-pmid15060526_2-0" class="reference"><a href="#cite_note-pmid15060526-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Pharmacology" title="Pharmacology">Pharmacology</a> usually restricts the term "small molecule" to molecules that bind specific biological <a href="/wiki/Macromolecules" class="mw-redirect" title="Macromolecules">macromolecules</a> and act as an <a href="/wiki/Effector_(biology)" title="Effector (biology)">effector</a>, altering the activity or function of the <a href="/wiki/Biological_target" title="Biological target">target</a>. Small molecules can have a variety of biological functions or applications, serving as <a href="/wiki/Cell_signaling" title="Cell signaling">cell signaling</a> molecules, <a href="/wiki/Drug" title="Drug">drugs</a> in <a href="/wiki/Medicine" title="Medicine">medicine</a>, <a href="/wiki/Pesticide" title="Pesticide">pesticides</a> in farming, and in many other roles. These compounds can be natural (such as <a href="/wiki/Secondary_metabolites" class="mw-redirect" title="Secondary metabolites">secondary metabolites</a>) or artificial (such as <a href="/wiki/Antiviral_drug" title="Antiviral drug">antiviral drugs</a>); they may have a beneficial effect against a disease (such as <a href="/wiki/Pharmaceuticals" class="mw-redirect" title="Pharmaceuticals">drugs</a>) or may be detrimental (such as <a href="/wiki/Teratogen" class="mw-redirect" title="Teratogen">teratogens</a> and <a href="/wiki/Carcinogen" title="Carcinogen">carcinogens</a>). </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Molecular_weight_cutoff">Molecular weight cutoff</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Small_molecule&action=edit&section=1" title="Edit section: Molecular weight cutoff"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The upper <a href="/wiki/Molecular_mass" title="Molecular mass">molecular-weight</a> limit for a small molecule is approximately 900 daltons, which allows for the possibility to rapidly diffuse across cell membranes so that it can reach <a href="/wiki/Intracellular" class="mw-redirect" title="Intracellular">intracellular</a> sites of action.<sup id="cite_ref-Dougherty_Pucci_2012_1-1" class="reference"><a href="#cite_note-Dougherty_Pucci_2012-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid12036371_3-0" class="reference"><a href="#cite_note-pmid12036371-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> This molecular weight cutoff is also a necessary but insufficient condition for oral <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> as it allows for <a href="/wiki/Transcellular_transport" title="Transcellular transport">transcellular transport</a> through intestinal <a href="/wiki/Epithelial" class="mw-redirect" title="Epithelial">epithelial</a> cells. In addition to intestinal permeability, the molecule must also possess a reasonably rapid <a href="/wiki/Dissolution_(chemistry)#Rate_of_dissolution" class="mw-redirect" title="Dissolution (chemistry)">rate of dissolution</a> into water and adequate water <a href="/wiki/Solubility" title="Solubility">solubility</a> and moderate to low <a href="/wiki/First_pass_metabolism" class="mw-redirect" title="First pass metabolism">first pass metabolism</a>. A somewhat lower molecular weight cutoff of 500 daltons (as part of the "<a href="/wiki/Rule_of_five" class="mw-redirect" title="Rule of five">rule of five</a>") has been recommended for oral small molecule drug candidates based on the observation that clinical attrition rates are significantly reduced if the molecular weight is kept below this limit.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid17971784_5-0" class="reference"><a href="#cite_note-pmid17971784-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Drugs">Drugs</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Small_molecule&action=edit&section=2" title="Edit section: Drugs"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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">Further information: <a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">Pharmaceutical drug</a> and <a href="/wiki/Targeted_therapy" title="Targeted therapy">Targeted therapy</a></div> <p>Most pharmaceuticals are small molecules, although some drugs can be proteins (e.g., <a href="/wiki/Insulin" title="Insulin">insulin</a> and other <a href="/wiki/Biologic_medical_product" class="mw-redirect" title="Biologic medical product">biologic medical products</a>). With the exception of <a href="/wiki/Monoclonal_antibody_therapy" title="Monoclonal antibody therapy">therapeutic antibodies</a>, many proteins are degraded if administered orally and most often cannot cross <a href="/wiki/Cell_membrane" title="Cell membrane">cell membranes</a>. Small molecules are more likely to be absorbed, although some of them are only absorbed after oral administration if given as <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a>. One advantage that <b>small molecule drugs</b> (SMDs) have over "large molecule" <a href="/wiki/Biologic_medical_product" class="mw-redirect" title="Biologic medical product">biologics</a> is that many small molecules can be taken orally whereas biologics generally require injection or another <a href="/wiki/Parenteral" class="mw-redirect" title="Parenteral">parenteral</a> administration.<sup id="cite_ref-Ganellin_2013_6-0" class="reference"><a href="#cite_note-Ganellin_2013-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Small molecule drugs are also typically simpler to manufacture and cheaper for the purchaser. A downside is that not all targets are amenable to modification with small-molecule drugs; bacteria and <a href="/wiki/Cancers" class="mw-redirect" title="Cancers">cancers</a> are often resistant to their effects.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Secondary_metabolites">Secondary metabolites</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Small_molecule&action=edit&section=3" title="Edit section: Secondary metabolites"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A variety of organisms including bacteria, fungi, and plants, produce small molecule <a href="/wiki/Secondary_metabolite" title="Secondary metabolite">secondary metabolites</a> also known as <a href="/wiki/Natural_product" title="Natural product">natural products</a>, which play a role in cell signaling, pigmentation and in defense against predation. Secondary metabolites are a rich source of biologically active compounds and hence are often used as research tools and leads for drug discovery.<sup id="cite_ref-isbn978-0-444-53836-9_8-0" class="reference"><a href="#cite_note-isbn978-0-444-53836-9-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Examples of secondary metabolites include: </p> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col" style="column-width: 25em;"> <ul><li><a href="/wiki/Alkaloids" class="mw-redirect" title="Alkaloids">Alkaloids</a></li> <li><a href="/wiki/Glycosides" class="mw-redirect" title="Glycosides">Glycosides</a></li> <li><a href="/wiki/Lipids" class="mw-redirect" title="Lipids">Lipids</a></li> <li><a href="/wiki/Nonribosomal_peptide" title="Nonribosomal peptide">Nonribosomal peptides</a>, such as <a href="/wiki/Actinomycin-D" class="mw-redirect" title="Actinomycin-D">actinomycin-D</a></li> <li><a href="/wiki/Phenazines" class="mw-redirect" title="Phenazines">Phenazines</a></li> <li><a href="/wiki/Natural_phenol" class="mw-redirect" title="Natural phenol">Natural phenols</a> (including <a href="/wiki/Flavonoid" title="Flavonoid">flavonoids</a>)</li> <li><a href="/wiki/Polyketide" title="Polyketide">Polyketide</a></li> <li><a href="/wiki/Terpenes" class="mw-redirect" title="Terpenes">Terpenes</a> and <a href="/wiki/Terpenoids" class="mw-redirect" title="Terpenoids">terpenoids</a>, including <a href="/wiki/Steroid" title="Steroid">steroids</a></li> <li><a href="/wiki/Tetrapyrroles" class="mw-redirect" title="Tetrapyrroles">Tetrapyrroles</a>.</li></ul> </div> <div class="mw-heading mw-heading2"><h2 id="Research_tools">Research tools</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Small_molecule&action=edit&section=4" title="Edit section: Research tools"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Regen2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Regen2.svg/200px-Regen2.svg.png" decoding="async" width="200" height="216" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Regen2.svg/300px-Regen2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Regen2.svg/400px-Regen2.svg.png 2x" data-file-width="231" data-file-height="250" /></a><figcaption>Cell culture example of a small molecule as a tool instead of a protein. In <a href="/wiki/Cell_culture" title="Cell culture">cell culture</a> to obtain a <a href="/wiki/Islets_of_Langerhans" class="mw-redirect" title="Islets of Langerhans">pancreatic lineage</a> from <a href="/wiki/Mesoderm" title="Mesoderm">mesodermal</a> <a href="/wiki/Stem_cells" class="mw-redirect" title="Stem cells">stem cells</a>, the <a href="/wiki/Retinoic_acid" title="Retinoic acid">retinoic acid</a> signaling pathway must be activated while the <a href="/wiki/Sonic_hedgehog" class="mw-redirect" title="Sonic hedgehog">sonic hedgehog</a> pathway inhibited, which can be done by adding to the <a href="/wiki/Growth_medium" title="Growth medium">media</a> anti-shh <a href="/wiki/Antibodies" class="mw-redirect" title="Antibodies">antibodies</a>, <a href="/wiki/HHIP" title="HHIP">Hedgehog interacting protein</a>, or <a href="/wiki/Cyclopamine" title="Cyclopamine">cyclopamine</a>, where the first two molecules are proteins and the last a small molecule.<sup id="cite_ref-pmid17272496_9-0" class="reference"><a href="#cite_note-pmid17272496-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></figcaption></figure><p> Enzymes and receptors are often activated or inhibited by <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">endogenous protein</a>, but can be also inhibited by endogenous or exogenous <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">small molecule inhibitors</a> or <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">activators</a>, which can bind to the <a href="/wiki/Active_site" title="Active site">active site</a> or on the <a href="/wiki/Allosteric_regulation" title="Allosteric regulation">allosteric site</a>. </p><p>An example is the teratogen and carcinogen <a href="/wiki/Phorbol_12-myristate_13-acetate" class="mw-redirect" title="Phorbol 12-myristate 13-acetate">phorbol 12-myristate 13-acetate</a>, which is a plant terpene that activates <a href="/wiki/Protein_kinase_C" title="Protein kinase C">protein kinase C</a>, which promotes cancer, making it a useful investigative tool.<sup id="cite_ref-isbn0-471-58651-X_10-0" class="reference"><a href="#cite_note-isbn0-471-58651-X-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> There is also interest in creating small molecule <a href="/wiki/Artificial_transcription_factors" class="mw-redirect" title="Artificial transcription factors">artificial transcription factors</a> to regulate <a href="/wiki/Gene_expression" title="Gene expression">gene expression</a>, examples include wrenchnolol (a wrench shaped molecule).<sup id="cite_ref-pmid17894442_11-0" class="reference"><a href="#cite_note-pmid17894442-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Binding of <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligand</a> can be characterised using a variety of analytical techniques such as <a href="/wiki/Surface_plasmon_resonance" title="Surface plasmon resonance">surface plasmon resonance</a>, <a href="/wiki/Microscale_thermophoresis" title="Microscale thermophoresis">microscale thermophoresis</a><sup id="cite_ref-pmid20981028_12-0" class="reference"><a href="#cite_note-pmid20981028-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> or <a href="/wiki/Dual_polarisation_interferometry" class="mw-redirect" title="Dual polarisation interferometry">dual polarisation interferometry</a> to quantify the reaction affinities and kinetic properties and also any induced <a href="/wiki/Conformational_change" title="Conformational change">conformational changes</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Anti-genomic_therapeutics">Anti-genomic therapeutics</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Small_molecule&action=edit&section=5" title="Edit section: Anti-genomic therapeutics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><b>Small-molecule <a href="/wiki/Antigenome" title="Antigenome">anti-genomic</a> therapeutics</b>, or SMAT, refers to a <a href="/wiki/Biodefense" title="Biodefense">biodefense</a> technology that targets <a href="/wiki/DNA" title="DNA">DNA</a> signatures found in many <a href="/wiki/Biological_warfare" title="Biological warfare">biological warfare</a> agents. SMATs are new, broad-spectrum drugs that unify antibacterial, antiviral and anti-malarial activities into a single therapeutic that offers substantial cost benefits and logistic advantages for physicians and the military.<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> </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=Small_molecule&action=edit&section=6" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Pharmacology" title="Pharmacology">Pharmacology</a></li> <li><a href="/wiki/Druglikeness" title="Druglikeness">Druglikeness</a></li> <li><a href="/wiki/Lipinski%27s_rule_of_five" title="Lipinski's rule of five">Lipinski's rule of five</a></li> <li><a href="/wiki/Metabolite" title="Metabolite">Metabolite</a></li> <li><a href="/wiki/Chemogenomics" title="Chemogenomics">Chemogenomics</a></li> <li><a href="/wiki/Neurotransmitter" title="Neurotransmitter">Neurotransmitter</a></li> <li><a href="/wiki/Peptidomimetic" title="Peptidomimetic">Peptidomimetic</a></li> <li><a href="/wiki/Macromolecule" title="Macromolecule">Macromolecule</a></li></ul> <div style="clear:both;" class=""></div> <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=Small_molecule&action=edit&section=7" 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 reflist-columns references-column-width" style="column-width: 35em;"> <ol class="references"> <li id="cite_note-Dougherty_Pucci_2012-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Dougherty_Pucci_2012_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Dougherty_Pucci_2012_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFMacielag_MJ2012" class="citation book cs1">Macielag MJ (2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=av5SHPiHVcsC&q=oral%20drug%20molecular%20weight%20distribution%20antibiotics&pg=PA800">"Chemical properties of antibacterials and their uniqueness"</a>. In Dougherty TJ, Pucci MJ (eds.). <i>Antibiotic Discovery and Development</i>. Springer. pp. <span class="nowrap">801–</span>2. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4614-1400-1" title="Special:BookSources/978-1-4614-1400-1"><bdi>978-1-4614-1400-1</bdi></a>. <q>The majority of [oral] drugs from the general reference set have molecular weights below 550. In contrast the molecular-weight distribution of oral antibacterial agents is bimodal: 340–450 Da but with another group in the 700–900 molecular weight range.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chemical+properties+of+antibacterials+and+their+uniqueness&rft.btitle=Antibiotic+Discovery+and+Development&rft.pages=%3Cspan+class%3D%22nowrap%22%3E801-%3C%2Fspan%3E2&rft.pub=Springer&rft.date=2012&rft.isbn=978-1-4614-1400-1&rft.au=Macielag+MJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dav5SHPiHVcsC%26q%3Doral%2520drug%2520molecular%2520weight%2520distribution%2520antibiotics%26pg%3DPA800&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASmall+molecule" class="Z3988"></span></span> </li> <li id="cite_note-pmid15060526-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid15060526_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFArkinWells2004" class="citation journal cs1">Arkin MR, Wells JA (April 2004). "Small-molecule inhibitors of protein-protein interactions: progressing towards the dream". <i>Nature Reviews Drug Discovery</i>. <b>3</b> (4): <span class="nowrap">301–</span>17. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnrd1343">10.1038/nrd1343</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15060526">15060526</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:13879559">13879559</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature+Reviews+Drug+Discovery&rft.atitle=Small-molecule+inhibitors+of+protein-protein+interactions%3A+progressing+towards+the+dream&rft.volume=3&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E301-%3C%2Fspan%3E17&rft.date=2004-04&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A13879559%23id-name%3DS2CID&rft_id=info%3Apmid%2F15060526&rft_id=info%3Adoi%2F10.1038%2Fnrd1343&rft.aulast=Arkin&rft.aufirst=MR&rft.au=Wells%2C+JA&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASmall+molecule" class="Z3988"></span></span> </li> <li id="cite_note-pmid12036371-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid12036371_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFVeberJohnsonChengSmith2002" class="citation journal cs1">Veber DF, Johnson SR, Cheng HY, Smith BR, Ward KW, Kopple KD (June 2002). "Molecular properties that influence the oral bioavailability of drug candidates". <i>J. Med. Chem</i>. <b>45</b> (12): <span class="nowrap">2615–</span>23. <a href="/wiki/CiteSeerX_(identifier)" class="mw-redirect" title="CiteSeerX (identifier)">CiteSeerX</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.606.5270">10.1.1.606.5270</a></span>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjm020017n">10.1021/jm020017n</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12036371">12036371</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Med.+Chem.&rft.atitle=Molecular+properties+that+influence+the+oral+bioavailability+of+drug+candidates&rft.volume=45&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2615-%3C%2Fspan%3E23&rft.date=2002-06&rft_id=https%3A%2F%2Fciteseerx.ist.psu.edu%2Fviewdoc%2Fsummary%3Fdoi%3D10.1.1.606.5270%23id-name%3DCiteSeerX&rft_id=info%3Apmid%2F12036371&rft_id=info%3Adoi%2F10.1021%2Fjm020017n&rft.aulast=Veber&rft.aufirst=DF&rft.au=Johnson%2C+SR&rft.au=Cheng%2C+HY&rft.au=Smith%2C+BR&rft.au=Ward%2C+KW&rft.au=Kopple%2C+KD&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASmall+molecule" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLipinski_CA2004" class="citation journal cs1">Lipinski CA (December 2004). "Lead-and drug-like compounds: the rule-of-five revolution". <i>Drug Discovery Today: Technologies</i>. <b>1</b> (4): <span class="nowrap">337–</span>341. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.ddtec.2004.11.007">10.1016/j.ddtec.2004.11.007</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24981612">24981612</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drug+Discovery+Today%3A+Technologies&rft.atitle=Lead-and+drug-like+compounds%3A+the+rule-of-five+revolution&rft.volume=1&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E337-%3C%2Fspan%3E341&rft.date=2004-12&rft_id=info%3Adoi%2F10.1016%2Fj.ddtec.2004.11.007&rft_id=info%3Apmid%2F24981612&rft.au=Lipinski+CA&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASmall+molecule" class="Z3988"></span></span> </li> <li id="cite_note-pmid17971784-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid17971784_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLeesonSpringthorpe2007" class="citation journal cs1">Leeson PD, Springthorpe B (November 2007). "The influence of drug-like concepts on decision-making in medicinal chemistry". <i>Nature Reviews Drug Discovery</i>. <b>6</b> (11): <span class="nowrap">881–</span>90. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnrd2445">10.1038/nrd2445</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17971784">17971784</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:205476574">205476574</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature+Reviews+Drug+Discovery&rft.atitle=The+influence+of+drug-like+concepts+on+decision-making+in+medicinal+chemistry&rft.volume=6&rft.issue=11&rft.pages=%3Cspan+class%3D%22nowrap%22%3E881-%3C%2Fspan%3E90&rft.date=2007-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A205476574%23id-name%3DS2CID&rft_id=info%3Apmid%2F17971784&rft_id=info%3Adoi%2F10.1038%2Fnrd2445&rft.aulast=Leeson&rft.aufirst=PD&rft.au=Springthorpe%2C+B&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASmall+molecule" class="Z3988"></span></span> </li> <li id="cite_note-Ganellin_2013-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ganellin_2013_6-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSamanen_J2013" class="citation book cs1">Samanen J (2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=342JY314Fl4C&q=small+molecule+vs+biologics+oral&pg=PA187">"Chapter 5.2 How do SMDs differ from biomolecular drugs?"</a>. In Ganellin CR, Jefferis R, Roberts SM (eds.). <i>Introduction to Biological and Small Molecule Drug Research and Development: theory and case studies</i> (Kindle ed.). New York: Academic Press. pp. <span class="nowrap">161–</span>203. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FB978-0-12-397176-0.00005-4">10.1016/B978-0-12-397176-0.00005-4</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-397176-0" title="Special:BookSources/978-0-12-397176-0"><bdi>978-0-12-397176-0</bdi></a>. <q>Table 5.13: Route of Administration: Small Molecules: oral administration usually possible; Biomolecules: Usually administered parenterally</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chapter+5.2+How+do+SMDs+differ+from+biomolecular+drugs%3F&rft.btitle=Introduction+to+Biological+and+Small+Molecule+Drug+Research+and+Development%3A+theory+and+case+studies&rft.place=New+York&rft.pages=%3Cspan+class%3D%22nowrap%22%3E161-%3C%2Fspan%3E203&rft.edition=Kindle&rft.pub=Academic+Press&rft.date=2013&rft_id=info%3Adoi%2F10.1016%2FB978-0-12-397176-0.00005-4&rft.isbn=978-0-12-397176-0&rft.au=Samanen+J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D342JY314Fl4C%26q%3Dsmall%2Bmolecule%2Bvs%2Bbiologics%2Boral%26pg%3DPA187&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASmall+molecule" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNgoGarneau-Tsodikova2018" class="citation journal cs1">Ngo, Huy X.; Garneau-Tsodikova, Sylvie (23 April 2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6072476">"What are the drugs of the future?"</a>. <i>MedChemComm</i>. <b>9</b> (5): <span class="nowrap">757–</span>758. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fc8md90019a">10.1039/c8md90019a</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2040-2503">2040-2503</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6072476">6072476</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/30108965">30108965</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=MedChemComm&rft.atitle=What+are+the+drugs+of+the+future%3F&rft.volume=9&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E757-%3C%2Fspan%3E758&rft.date=2018-04-23&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6072476%23id-name%3DPMC&rft.issn=2040-2503&rft_id=info%3Apmid%2F30108965&rft_id=info%3Adoi%2F10.1039%2Fc8md90019a&rft.aulast=Ngo&rft.aufirst=Huy+X.&rft.au=Garneau-Tsodikova%2C+Sylvie&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6072476&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASmall+molecule" class="Z3988"></span></span> </li> <li id="cite_note-isbn978-0-444-53836-9-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-isbn978-0-444-53836-9_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAtta-ur-Rahman2012" class="citation book cs1">Atta-ur-Rahman, ed. (2012). <i>Studies in Natural Products Chemistry</i>. Vol. 36. Amsterdam: Elsevier. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-444-53836-9" title="Special:BookSources/978-0-444-53836-9"><bdi>978-0-444-53836-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Studies+in+Natural+Products+Chemistry&rft.place=Amsterdam&rft.pub=Elsevier&rft.date=2012&rft.isbn=978-0-444-53836-9&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASmall+molecule" class="Z3988"></span></span> </li> <li id="cite_note-pmid17272496-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid17272496_9-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMfopouDe_GrooteXuHeimberg2007" class="citation journal cs1">Mfopou JK, De Groote V, Xu X, Heimberg H, Bouwens L (May 2007). <a rel="nofollow" class="external text" href="https://doi.org/10.1634%2Fstemcells.2006-0720">"Sonic hedgehog and other soluble factors from differentiating embryoid bodies inhibit pancreas development"</a>. <i>Stem Cells</i>. <b>25</b> (5): <span class="nowrap">1156–</span>65. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1634%2Fstemcells.2006-0720">10.1634/stemcells.2006-0720</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17272496">17272496</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:32726998">32726998</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Stem+Cells&rft.atitle=Sonic+hedgehog+and+other+soluble+factors+from+differentiating+embryoid+bodies+inhibit+pancreas+development&rft.volume=25&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1156-%3C%2Fspan%3E65&rft.date=2007-05&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A32726998%23id-name%3DS2CID&rft_id=info%3Apmid%2F17272496&rft_id=info%3Adoi%2F10.1634%2Fstemcells.2006-0720&rft.aulast=Mfopou&rft.aufirst=JK&rft.au=De+Groote%2C+V&rft.au=Xu%2C+X&rft.au=Heimberg%2C+H&rft.au=Bouwens%2C+L&rft_id=https%3A%2F%2Fdoi.org%2F10.1634%252Fstemcells.2006-0720&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASmall+molecule" class="Z3988"></span></span> </li> <li id="cite_note-isbn0-471-58651-X-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-isbn0-471-58651-X_10-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFVoetVoet1995" class="citation book cs1">Voet JG, Voet D (1995). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/biochemistry00voet_0"><i>Biochemistry</i></a></span>. New York: J. Wiley & Sons. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-58651-7" title="Special:BookSources/978-0-471-58651-7"><bdi>978-0-471-58651-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Biochemistry&rft.place=New+York&rft.pub=J.+Wiley+%26+Sons&rft.date=1995&rft.isbn=978-0-471-58651-7&rft.aulast=Voet&rft.aufirst=JG&rft.au=Voet%2C+D&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fbiochemistry00voet_0&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASmall+molecule" class="Z3988"></span></span> </li> <li id="cite_note-pmid17894442-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid17894442_11-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKohZheng2007" class="citation journal cs1">Koh JT, Zheng J (September 2007). <a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcb700183s">"The new biomimetic chemistry: artificial transcription factors"</a>. <i>ACS Chem. Biol</i>. <b>2</b> (9): <span class="nowrap">599–</span>601. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcb700183s">10.1021/cb700183s</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17894442">17894442</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=ACS+Chem.+Biol.&rft.atitle=The+new+biomimetic+chemistry%3A+artificial+transcription+factors&rft.volume=2&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E599-%3C%2Fspan%3E601&rft.date=2007-09&rft_id=info%3Adoi%2F10.1021%2Fcb700183s&rft_id=info%3Apmid%2F17894442&rft.aulast=Koh&rft.aufirst=JT&rft.au=Zheng%2C+J&rft_id=https%3A%2F%2Fdoi.org%2F10.1021%252Fcb700183s&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASmall+molecule" class="Z3988"></span></span> </li> <li id="cite_note-pmid20981028-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid20981028_12-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWienkenBaaskeRothbauerBraun2010" class="citation journal cs1">Wienken CJ, Baaske P, Rothbauer U, Braun D, Duhr S (2010). <a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fncomms1093">"Protein-binding assays in biological liquids using microscale thermophoresis"</a>. <i>Nat Commun</i>. <b>1</b> (7): 100. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2010NatCo...1..100W">2010NatCo...1..100W</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fncomms1093">10.1038/ncomms1093</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20981028">20981028</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nat+Commun&rft.atitle=Protein-binding+assays+in+biological+liquids+using+microscale+thermophoresis&rft.volume=1&rft.issue=7&rft.pages=100&rft.date=2010&rft_id=info%3Apmid%2F20981028&rft_id=info%3Adoi%2F10.1038%2Fncomms1093&rft_id=info%3Abibcode%2F2010NatCo...1..100W&rft.aulast=Wienken&rft.aufirst=CJ&rft.au=Baaske%2C+P&rft.au=Rothbauer%2C+U&rft.au=Braun%2C+D&rft.au=Duhr%2C+S&rft_id=https%3A%2F%2Fdoi.org%2F10.1038%252Fncomms1093&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASmall+molecule" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLevine_DS2003" class="citation web cs1">Levine DS (2003). <a rel="nofollow" class="external text" href="http://www.bizjournals.com/sanfrancisco/stories/2003/04/28/story6.html">"Bio-defense company re-ups"</a>. San Francisco Business Times<span class="reference-accessdate">. Retrieved <span class="nowrap">September 6,</span> 2006</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Bio-defense+company+re-ups&rft.pub=San+Francisco+Business+Times&rft.date=2003&rft.au=Levine+DS&rft_id=http%3A%2F%2Fwww.bizjournals.com%2Fsanfrancisco%2Fstories%2F2003%2F04%2F28%2Fstory6.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASmall+molecule" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Small_molecule&action=edit&section=8" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://meshb.nlm.nih.gov/record/ui?name=Small+Molecule+Libraries">Small+Molecule+Libraries</a> at the U.S. National Library of Medicine <a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">Medical Subject Headings</a> (MeSH)</li></ul>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Small_molecule&oldid=1262709559">https://en.wikipedia.org/w/index.php?title=Small_molecule&oldid=1262709559</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Plant_physiology" title="Category:Plant physiology">Plant physiology</a></li><li><a href="/wiki/Category:Drug_discovery" title="Category:Drug discovery">Drug discovery</a></li><li><a href="/wiki/Category:Induced_stem_cells" title="Category:Induced stem cells">Induced stem cells</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_is_different_from_Wikidata" title="Category:Short description is different from Wikidata">Short description is different from Wikidata</a></li><li><a href="/wiki/Category:All_articles_with_unsourced_statements" title="Category:All articles with unsourced statements">All articles with unsourced statements</a></li><li><a href="/wiki/Category:Articles_with_unsourced_statements_from_June_2021" title="Category:Articles with unsourced statements from June 2021">Articles with unsourced statements from June 2021</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 12 December 2024, at 19:57<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. By using this site, you agree to the <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Terms_of_Use" class="extiw" title="foundation:Special:MyLanguage/Policy:Terms of Use">Terms of Use</a> and <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy" class="extiw" title="foundation:Special:MyLanguage/Policy:Privacy policy">Privacy Policy</a>. Wikipedia® is a registered trademark of the <a rel="nofollow" class="external text" href="https://wikimediafoundation.org/">Wikimedia Foundation, Inc.</a>, a non-profit organization.</li> </ul> <ul id="footer-places"> <li id="footer-places-privacy"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy">Privacy policy</a></li> <li id="footer-places-about"><a href="/wiki/Wikipedia:About">About Wikipedia</a></li> <li id="footer-places-disclaimers"><a href="/wiki/Wikipedia:General_disclaimer">Disclaimers</a></li> <li id="footer-places-contact"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us">Contact Wikipedia</a></li> <li id="footer-places-wm-codeofconduct"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Universal_Code_of_Conduct">Code of Conduct</a></li> <li id="footer-places-developers"><a href="https://developer.wikimedia.org">Developers</a></li> <li id="footer-places-statslink"><a href="https://stats.wikimedia.org/#/en.wikipedia.org">Statistics</a></li> <li id="footer-places-cookiestatement"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Cookie_statement">Cookie statement</a></li> <li id="footer-places-mobileview"><a href="//en.m.wikipedia.org/w/index.php?title=Small_molecule&mobileaction=toggle_view_mobile" class="noprint stopMobileRedirectToggle">Mobile view</a></li> </ul> <ul id="footer-icons" class="noprint"> <li id="footer-copyrightico"><a href="https://wikimediafoundation.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><picture><source media="(min-width: 500px)" srcset="/static/images/footer/wikimedia-button.svg" width="84" height="29"><img src="/static/images/footer/wikimedia.svg" width="25" height="25" alt="Wikimedia Foundation" lang="en" loading="lazy"></picture></a></li> <li id="footer-poweredbyico"><a href="https://www.mediawiki.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><picture><source media="(min-width: 500px)" srcset="/w/resources/assets/poweredby_mediawiki.svg" width="88" height="31"><img src="/w/resources/assets/mediawiki_compact.svg" alt="Powered by MediaWiki" lang="en" width="25" height="25" loading="lazy"></picture></a></li> </ul> </footer> </div> </div> </div> <div class="vector-header-container vector-sticky-header-container"> <div id="vector-sticky-header" class="vector-sticky-header"> <div class="vector-sticky-header-start"> <div class="vector-sticky-header-icon-start vector-button-flush-left vector-button-flush-right" aria-hidden="true"> <button class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-sticky-header-search-toggle" tabindex="-1" data-event-name="ui.vector-sticky-search-form.icon"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Search</span> </button> </div> <div role="search" class="vector-search-box-vue vector-search-box-show-thumbnail vector-search-box"> <div class="vector-typeahead-search-container"> <div class="cdx-typeahead-search cdx-typeahead-search--show-thumbnail"> <form action="/w/index.php" id="vector-sticky-search-form" class="cdx-search-input cdx-search-input--has-end-button"> <div class="cdx-search-input__input-wrapper" data-search-loc="header-moved"> <div class="cdx-text-input cdx-text-input--has-start-icon"> <input class="cdx-text-input__input" type="search" name="search" placeholder="Search Wikipedia"> <span class="cdx-text-input__icon cdx-text-input__start-icon"></span> </div> <input type="hidden" name="title" value="Special:Search"> </div> <button class="cdx-button cdx-search-input__end-button">Search</button> </form> </div> </div> </div> <div class="vector-sticky-header-context-bar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-sticky-header-toc" class="vector-dropdown mw-portlet mw-portlet-sticky-header-toc vector-sticky-header-toc vector-button-flush-left" > <input type="checkbox" id="vector-sticky-header-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-sticky-header-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-sticky-header-toc-label" for="vector-sticky-header-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-sticky-header-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div class="vector-sticky-header-context-bar-primary" aria-hidden="true" ><span class="mw-page-title-main">Small molecule</span></div> </div> </div> <div class="vector-sticky-header-end" aria-hidden="true"> <div class="vector-sticky-header-icons"> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-talk-sticky-header" tabindex="-1" data-event-name="talk-sticky-header"><span class="vector-icon mw-ui-icon-speechBubbles mw-ui-icon-wikimedia-speechBubbles"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-subject-sticky-header" tabindex="-1" data-event-name="subject-sticky-header"><span class="vector-icon mw-ui-icon-article mw-ui-icon-wikimedia-article"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-history-sticky-header" tabindex="-1" data-event-name="history-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-history mw-ui-icon-wikimedia-wikimedia-history"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only mw-watchlink" id="ca-watchstar-sticky-header" tabindex="-1" data-event-name="watch-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-star mw-ui-icon-wikimedia-wikimedia-star"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-edit-sticky-header" tabindex="-1" data-event-name="wikitext-edit-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-wikiText mw-ui-icon-wikimedia-wikimedia-wikiText"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-ve-edit-sticky-header" tabindex="-1" data-event-name="ve-edit-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-edit mw-ui-icon-wikimedia-wikimedia-edit"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-viewsource-sticky-header" tabindex="-1" data-event-name="ve-edit-protected-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-editLock mw-ui-icon-wikimedia-wikimedia-editLock"></span> <span></span> </a> </div> <div class="vector-sticky-header-buttons"> <button class="cdx-button cdx-button--weight-quiet mw-interlanguage-selector" id="p-lang-btn-sticky-header" tabindex="-1" data-event-name="ui.dropdown-p-lang-btn-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-language mw-ui-icon-wikimedia-wikimedia-language"></span> <span>19 languages</span> </button> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive" id="ca-addsection-sticky-header" tabindex="-1" data-event-name="addsection-sticky-header"><span class="vector-icon mw-ui-icon-speechBubbleAdd-progressive mw-ui-icon-wikimedia-speechBubbleAdd-progressive"></span> <span>Add topic</span> </a> </div> <div class="vector-sticky-header-icon-end"> <div class="vector-user-links"> </div> </div> </div> </div> </div> <div class="mw-portlet mw-portlet-dock-bottom emptyPortlet" id="p-dock-bottom"> <ul> </ul> </div> <script>(RLQ=window.RLQ||[]).push(function(){mw.config.set({"wgHostname":"mw-web.codfw.main-64b5bb4b79-ffg58","wgBackendResponseTime":155,"wgPageParseReport":{"limitreport":{"cputime":"0.230","walltime":"0.292","ppvisitednodes":{"value":1244,"limit":1000000},"postexpandincludesize":{"value":35473,"limit":2097152},"templateargumentsize":{"value":1338,"limit":2097152},"expansiondepth":{"value":12,"limit":100},"expensivefunctioncount":{"value":4,"limit":500},"unstrip-depth":{"value":1,"limit":20},"unstrip-size":{"value":52886,"limit":5000000},"entityaccesscount":{"value":0,"limit":400},"timingprofile":["100.00% 251.904 1 -total"," 51.90% 130.749 1 Template:Reflist"," 29.36% 73.956 4 Template:Cite_book"," 22.75% 57.303 1 Template:Short_description"," 13.42% 33.818 8 Template:Cite_journal"," 12.75% 32.111 2 Template:Pagetype"," 11.05% 27.834 1 Template:Citation_needed"," 9.52% 23.975 1 Template:Fix"," 7.55% 19.016 1 Template:Further"," 6.66% 16.771 5 Template:Main_other"]},"scribunto":{"limitreport-timeusage":{"value":"0.133","limit":"10.000"},"limitreport-memusage":{"value":5488697,"limit":52428800}},"cachereport":{"origin":"mw-web.codfw.main-84b999ff94-w5lrj","timestamp":"20250204091815","ttl":2592000,"transientcontent":false}}});});</script> <script type="application/ld+json">{"@context":"https:\/\/schema.org","@type":"Article","name":"Small molecule","url":"https:\/\/en.wikipedia.org\/wiki\/Small_molecule","sameAs":"http:\/\/www.wikidata.org\/entity\/Q1988322","mainEntity":"http:\/\/www.wikidata.org\/entity\/Q1988322","author":{"@type":"Organization","name":"Contributors to Wikimedia projects"},"publisher":{"@type":"Organization","name":"Wikimedia Foundation, Inc.","logo":{"@type":"ImageObject","url":"https:\/\/www.wikimedia.org\/static\/images\/wmf-hor-googpub.png"}},"datePublished":"2004-02-20T01:49:25Z","dateModified":"2024-12-12T19:57:58Z"}</script> </body> </html>