cinnamic acid | Ligand page | IUPHAR/BPS Guide to PHARMACOLOGY

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<div style="clear: both;"></div> <div class="contentboxfullhelp"> <table class="fullwidth" style="position:relative; margin-bottom: 10px;"> <tr> <td style="width:453px;min-width:453px;text-align:left;vertical-align:top;"> <div class="textright_ligsum"> <a style="color:white; padding-right:8px;" title="Ligand has a PDB structure"><img src="images/protein_structure_icon.png" height="22px" alt="PDB Ligand"/></a> </div> <div class="textright_ligsum"><b>Compound class:</b> <a href="LigandListForward?type=Synthetic-organic" > Synthetic organic </a></div> <div class="textright_ligsum"> </div> <div class="imageleft" style="margin-top:10px;"><a class="popup-trigger" rel="nofollow" title="Ligand activity charts help"><img style="vertical-align:baseline; height:20px;" src="images/gtopblue_transparent_help_icon.png" alt="Click here for help" onmouseover="this.src='images/gtopblue_transparent_help_icon_hover.png';" onmouseout="this.src='images/gtopblue_transparent_help_icon.png';")"/></a> <div class="popup" style="text-align:left;"> <h3>Ligand Activity Visualisation Charts</h3> <p>These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.</p> <span class="popup-btn-close">✖</span>  </div> </div> <div class="textright_ligactchr" style="margin-top:18px;"><p style="font-weight: bold;"> <a href="LigandActivityRangeVisForward?ligandId=3203" target="_blank">  <i class="fa fa-bar-chart fa-2x" style="color: #1e3363;"></i> View interactive charts of activity data across species</a></p> </div>  </td> <td style="min-width:10px;width:10px;"></td> <td style="width:453px;min-width:453px;text-align:left;vertical-align:top;"> <table id="structure_and_props" class="tablesorter inner_receptor_data_tables" style="width:453px;margin:0px;"> <tbody> <tr class="info"> <td class="ligand_header_category" colspan="2"><div class="imageleft">2D Structure </div><div><a class="popup-trigger" rel="nofollow" title="2D structure help"><img style="vertical-align:middle; height:19px;margin-left:5px;" src="images/gtopblue_transparent_help_icon.png" alt="Click here for help" onmouseover="this.src='images/gtopblue_transparent_help_icon_hover.png';" onmouseout="this.src='images/gtopblue_transparent_help_icon.png';")"/></a> <div class="popup" style="text-align:left;"> <h3>2D Structure</h3> <p>An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.</p> <span class="popup-btn-close">✖</span>  </div> </div></td> </tr> <tr class="info"> <td style="vertical-align:middle;text-align:center;height:250px;" colspan="2"> <a style="color:white;" href="RefineChemicalStructureSearchForward?ligandId=3203" title="Click here for structure editor"> <img id="ligand_structure_display" src="https://www.guidetopharmacology.org/CHEMSTRUCT/iuphar/3203.gif" onerror="this.src='https://www.simolecule.com/cdkdepict/depict/cot/svg?smi=OC%28%3DO%29%2FC%3DC%2Fc1ccccc1&abbr=on&hdisp=bridgehead&showtitle=false&annotate=none'" alt="Click here for structure editor"/> </a> </td> </tr> <tr class="info"> <td class="ligand_header_category"><div class="imageleft">Physico-chemical Properties </div><div><a class="popup-trigger" rel="nofollow" title="Physico-chemical properties help"><img style="vertical-align:middle; height:19px;margin-left:5px;" src="images/gtopblue_transparent_help_icon.png" alt="Click here for help" onmouseover="this.src='images/gtopblue_transparent_help_icon_hover.png';" onmouseout="this.src='images/gtopblue_transparent_help_icon.png';")"/></a> <div class="popup" style="text-align:left;"> <h3>Physico-chemical Properties</h3> <p>Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the <a href="JavaScript:callRef('helpPagePopup.jsp#ligProperties', 800, 400)">help pages</a>.</p> <span class="popup-btn-close">✖</span>  </div> </div></td> <td title="toggle" style="min-width:30px;width:30px;background-color:#CCCCCC" valign="middle"> <a name="chemprops" title="view physico-chemical properties" class="toggle"><div class="arrow"></div></a> </td> </tr> <tr class="tablesorter-childRow info"> <td colspan="2"> <table style="width: 100%; border: none; border-collapse: collapse;" class="info"> <tr class="info"> <td> Hydrogen bond acceptors </td> <td style="text-align:center"> 2 </td> </tr> <tr class="info"> <td> Hydrogen bond donors </td> <td style="text-align:center"> 1 </td> </tr> <tr class="info"> <td> Rotatable bonds </td> <td style="text-align:center"> 2 </td> </tr> <tr class="info"> <td> Topological polar surface area </td> <td style="text-align:center"> 37.3 </td> </tr> <tr class="info"> <td> Molecular weight </td> <td style="text-align:center"> 148.05 </td> </tr> <tr class="info"> <td> XLogP </td> <td style="text-align:center"> 1.91 </td> </tr> <tr class="info"> <td> No. Lipinski's rules broken </td> <td style="text-align:center"> 0 </td> </tr> </table> </td> </tr> <tr class="info"> <td class="ligand_header_category"><div class="imageleft">SMILES / InChI / InChIKey </div><div><a class="popup-trigger" rel="nofollow" title="SMILES and InChI help"><img style="vertical-align:middle; height:19px;margin-left:5px;" src="images/gtopblue_transparent_help_icon.png" alt="Click here for help" onmouseover="this.src='images/gtopblue_transparent_help_icon_hover.png';" onmouseout="this.src='images/gtopblue_transparent_help_icon.png';")"/></a> <div class="popup" style="text-align:left;"> <h3>SMILES / InChI / InChIKey</h3> <p><b>SMILES</b> (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.<br><br> <b>Standard InChI</b> (IUPAC International Chemical Identifier) and <b>InChIKey</b> InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.</p> <span class="popup-btn-close">✖</span>  </div> </div></td> <td title="toggle" style="min-width:30px;width:30px;background-color:#CCCCCC" valign="middle"> <a name="smilesinchi" title="view SMILES, InchI and InChI Key" class="toggle"><div class="arrow"></div></a> </td> </tr> <tr class="tablesorter-childRow info"> <td colspan="2"> <table style="width: 100%; border: none; border-collapse: collapse; word-break:break-word;" class="info"> <tr class="info"> <td style="text-align:left; min-width:60px;"> Canonical SMILES </td> <td style="text-align:left;" > OC(=O)C=Cc1ccccc1 </td> </tr> <tr class="info"> <td style="text-align:left; min-width:60px;"> Isomeric SMILES </td> <td style="text-align:left;" > OC(=O)/C=C/c1ccccc1 </td> </tr> <tr class="info"> <td style="text-align:left; min-width:60px;"> InChI </td> <td style="text-align:left; min-width:60px;" > InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ </td> </tr> <tr class="info"> <td style="text-align:left;"> InChI Key </td> <td style="text-align:left;" > WBYWAXJHAXSJNI-VOTSOKGWSA-N </td> </tr> </table> </td> </tr> </tbody> </table> <script type="text/javascript"> $(function(){ $("#structure_and_props").tablesorter(); }); </script> </td> </tr> </table> </div> </div>  <div class="grid_16 alpha"> <div class="contentboxfullhelp"> <div id='cssmenu'> <ul > <li class='active'><a href="LigandDisplayForward?tab=summary&ligandId=3203">Summary</a></li> <li ><a href="LigandDisplayForward?tab=biology&ligandId=3203">Biological activity</a></li> <li ><a href="LigandDisplayForward?tab=refs&ligandId=3203">References</a></li> <li ><a href="LigandDisplayForward?tab=structure&ligandId=3203">Structure</a></li> <li ><a href="LigandDisplayForward?tab=similarity&ligandId=3203">Similar ligands</a></li> </ul> </div> <div class="clear"></div> <div class="data_tables_container" style="padding-top:10px; padding-bottom: 10px;"> <table class="receptor_data_tables" style="width:100%;"> <tr> <td class="category" colspan="2">Classification <a style="color:#CCCCCC;" href="JavaScript:callRef('helpPagePopup.jsp#ligClass', 800, 400)" title="Click here for help"><img style="vertical-align:baseline;" src="images/help_blue_small_transparent_bkground.png" alt="Click here for help"/></a></td> </tr> <tr> <td class="info" align="left" style="min-width:250px;max-width:250px;width:250px;">Compound class</td> <td class="info"> <a href="LigandListForward?type=Synthetic-organic" > Synthetic organic </a> </td> </tr> </table> <table class="receptor_data_tables" style="width:100%;"> <tr> <td class="category">IUPAC Name <a style="color:#CCCCCC;" href="JavaScript:callRef('helpPagePopup.jsp#ligIUPAC', 800, 400)" title="Click here for help"><img style="vertical-align:baseline;" src="images/help_blue_small_transparent_bkground.png" alt="Click here for help"/></a></td> </tr> <tr class="info"> <td>3-phenylprop-2-enoic acid</td> </tr> </table> <a name="DatabaseLinks"></a> <table class="receptor_data_tables" style="width:100%;"> <tr> <td class="category" colspan="2">Database Links <a style="color:#CCCCCC;" href="JavaScript:callRef('helpPagePopup.jsp#ligDBLinks', 800, 400)" title="Click here for help"><img style="vertical-align:baseline;" src="images/help_blue_small_transparent_bkground.png" alt="Click here for help"/></a></td> </tr> <tr> <td class="info" colspan="2" style="font-style: italic; font-weight: bold;"> Specialist databases </td> </tr> <tr> <td class="info" style="min-width:250px;max-width:250px;width:250px;"> GPCRdb Ligand </td> <td class="info"> <a href="https://gpcrdb.org/ligand/3203/gtp_info" target="_blank" title="Tools for visualising and analysing data on sequence and structure of GPCRs." onClick="recordEvent(this, 'Ligand database links', 'https://gpcrdb.org/ligand/3203/gtp_info', 'GPCRdb Ligand');return false;">cinnamic acid</a> </td> </tr> <tr> <td class="info" colspan="2" style="font-style: italic; font-weight: bold;"> Other databases </td> </tr> <tr> <td class="info" style="min-width:250px;max-width:250px;width:250px;"> CAS Registry No. </td> <td class="info"> 621-82-9 (source: Scifinder) </td> </tr> <tr> <td class="info" style="min-width:250px;max-width:250px;width:250px;"> ChEBI </td> <td class="info"> <a href="http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:27386" target="_blank" title="Chemical Entities of Biological Interest: dictionary of molecular entities focused on 'small' chemical compounds" onClick="recordEvent(this, 'Ligand database links', 'http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:27386', 'ChEBI');return false;">CHEBI:27386</a> </td> </tr> <tr> <td class="info" style="min-width:250px;max-width:250px;width:250px;"> ChEMBL Ligand </td> <td class="info"> <a href="https://www.ebi.ac.uk/chembldb/compound/inspect/CHEMBL27246" target="_blank" title="Database of bioactive drug-like small molecules and targets" onClick="recordEvent(this, 'Ligand database links', 'https://www.ebi.ac.uk/chembldb/compound/inspect/CHEMBL27246', 'ChEMBL Ligand');return false;">CHEMBL27246</a> </td> </tr> <tr> <td class="info" style="min-width:250px;max-width:250px;width:250px;"> GtoPdb PubChem SID </td> <td class="info"> <a href="http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=135650101" target="_blank" title="Database of chemical structures and information on their biological activities. This link is to the GtoPdb-deposited PubChem Substance entry." onClick="recordEvent(this, 'Ligand database links', 'http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=135650101', 'GtoPdb PubChem SID');return false;">135650101</a> </td> </tr> <tr> <td class="info" style="min-width:250px;max-width:250px;width:250px;"> PubChem CID </td> <td class="info"> <a href="http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=444539" target="_blank" title="Database of chemical structures and information on their biological activities. The PubChem Compound Database contains validated chemical depiction information." onClick="recordEvent(this, 'Ligand database links', 'http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=444539', 'PubChem CID');return false;">444539</a> </td> </tr> <tr> <td class="info" style="min-width:250px;max-width:250px;width:250px;"> RCSB PDB Ligand </td> <td class="info"> <a href="http://www.rcsb.org/ligand/TCA" target="_blank" title="RCSB Protein Data Bank ligand" onClick="recordEvent(this, 'Ligand database links', 'http://www.rcsb.org/ligand/TCA', 'RCSB PDB Ligand');return false;">TCA</a> </td> </tr> <tr> <td class="info" style="min-width:250px;max-width:250px;width:250px;"> Search Google for chemical match using the InChIKey </td> <td class="info"> <a href="https://www.google.com/search?q=WBYWAXJHAXSJNI-VOTSOKGWSA-N" target="_blank" title="Search Google for exact chemical matches using the InChI key" onClick="recordEvent(this, 'Ligand database links', 'https://www.google.com/search?q=WBYWAXJHAXSJNI-VOTSOKGWSA-N', 'Google InChIKey exact match search');return false;">WBYWAXJHAXSJNI-VOTSOKGWSA-N</a> </td> </tr> <tr> <td class="info" style="min-width:250px;max-width:250px;width:250px;"> Search Google for chemicals with the same backbone </td> <td class="info"> <a href="https://www.google.com/search?q=WBYWAXJHAXSJNI" target="_blank" title="Search Google for chemicals with the same backbone structure using the InChI key outer layer" onClick="recordEvent(this, 'Ligand database links', 'https://www.google.com/search?q=WBYWAXJHAXSJNI', 'Google InChIKey backbone search');return false;">WBYWAXJHAXSJNI</a> </td> </tr> <tr> <td class="info" style="min-width:250px;max-width:250px;width:250px;"> UniChem Compound Search for chemical match using the InChIKey </td> <td class="info"> <a href="https://www.ebi.ac.uk/unichem/compoundsources?type=inchikey&compound=WBYWAXJHAXSJNI-VOTSOKGWSA-N" target="_blank" title="UniChem Compound Search finds source for a given compound via InChIkey" onClick="recordEvent(this, 'Ligand database links', 'https://www.ebi.ac.uk/unichem/compoundsources?type=inchikey&compound=WBYWAXJHAXSJNI-VOTSOKGWSA-N', 'UniChem InChIKey Compound Search');return false;">WBYWAXJHAXSJNI-VOTSOKGWSA-N</a> </td> </tr> <tr> <td class="info" style="min-width:250px;max-width:250px;width:250px;"> UniChem Connectivity Search for chemical match using the InChIKey </td> <td class="info"> <a href="https://www.ebi.ac.uk/unichem/search/connectivity?type=inchikey&compound=WBYWAXJHAXSJNI-VOTSOKGWSA-N" target="_blank" title="UniChem Connectivity Search fetches multiple source data sets for a given compound with common connectivity to a given InChIkey" onClick="recordEvent(this, 'Ligand database links', 'https://www.ebi.ac.uk/unichem/search/connectivity?type=inchikey&compound=WBYWAXJHAXSJNI-VOTSOKGWSA-N', 'UniChem InChIKey Connectivity Search');return false;">WBYWAXJHAXSJNI-VOTSOKGWSA-N</a> </td> </tr> <tr> <td class="info" style="min-width:250px;max-width:250px;width:250px;"> Wikipedia </td> <td class="info"> <a href="http://en.wikipedia.org/wiki/Cinnamic_acid" target="_blank" title="The Free Encyclopedia" onClick="recordEvent(this, 'Ligand database links', 'http://en.wikipedia.org/wiki/Cinnamic_acid', 'Wikipedia');return false;">Cinnamic_acid</a> </td> </tr> </table> </div> </div> </div>  </div>  <script type="application/ld+json"> { "@context": "http://schema.org", "@id": "https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=3203", "@type": "DataRecord", "dct:conformsTo": "https://bioschemas.org/profiles/MolecularEntity/0.5-RELEASE", "includedInDataset" : { "@type": "Dataset", "@id": "https://www.guidetopharmacology.org/index.jsp#dataset" }, "mainEntity": { "@id": "https://identifiers.org/iuphar.ligand:3203", "@type": "MolecularEntity", "name": "cinnamic acid", "alternateName": [], "description": "", "identifier": "3203", "inChI": "InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+", "inChIKey": "WBYWAXJHAXSJNI-VOTSOKGWSA-N", "iupacName": "3-phenylprop-2-enoic acid", "molecularWeight": 148.05, "smiles": "OC(=O)C=Cc1ccccc1", "url": "https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=3203" } } </script> <script> // Popup Window var scrollTop = ''; 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