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    <!-- http://purl.obolibrary.org/obo/CHEBI_166895 -->

    <Class rdf:about="http://purl.obolibrary.org/obo/CHEBI_166895">
        <rdfs:label>procyanidin</rdfs:label>
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    <!-- http://purl.obolibrary.org/obo/CHEBI_75632 -->

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        <rdfs:label>procyanidin B2</rdfs:label>
        <rdfs:subClassOf rdf:resource="http://purl.obolibrary.org/obo/CHEBI_166895"/>
        <ns4:charge rdf:datatype="http://www.w3.org/2001/XMLSchema#integer">0</ns4:charge>
        <ns4:monoisotopic_mass rdf:datatype="http://www.w3.org/2001/XMLSchema#decimal">578.14243</ns4:monoisotopic_mass>
        <ns4:mass rdf:datatype="http://www.w3.org/2001/XMLSchema#decimal">578.526</ns4:mass>
        <ns4:inchi_key_string>XFZJEEAOWLFHDH-NFJBMHMQSA-N</ns4:inchi_key_string>
        <oboInOwl:hasDbXref>pubmed:23250807</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>pubmed:23474305</oboInOwl:hasDbXref>
        <oboInOwl:hasRelatedSynonym>EC-(4b,8)-EC</oboInOwl:hasRelatedSynonym>
        <oboInOwl:hasDbXref>reaxys:1279736</oboInOwl:hasDbXref>
        <ns4:smiles_string>Oc1cc(O)c2c(c1)O[C@H](c1ccc(O)c(O)c1)[C@H](O)[C@H]2c1c(O)cc(O)c2c1O[C@H](c1ccc(O)c(O)c1)[C@H](O)C2</ns4:smiles_string>
        <oboInOwl:hasDbXref>hmdb:HMDB0033973</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>pubmed:23811048</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>pubmed:24136906</oboInOwl:hasDbXref>
        <ns4:generalized_empirical_formula>C30H26O12</ns4:generalized_empirical_formula>
        <oboInOwl:hasDbXref>pubmed:23460126</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>cas:29106-49-8</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>pubmed:23922881</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>pubmed:23472464</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>pubmed:23360097</oboInOwl:hasDbXref>
        <oboInOwl:hasRelatedSynonym>(2R,2&#39;R,3R,3&#39;R,4R)-2,2&#39;-bis(3,4-dihydroxyphenyl)-3,3&#39;,4,4&#39;-tetrahydro-2H,2&#39;H-4,8&#39;-bichromene-3,3&#39;,5,5&#39;,7,7&#39;-hexol</oboInOwl:hasRelatedSynonym>
        <oboInOwl:hasOBONamespace>chebi_ontology</oboInOwl:hasOBONamespace>
        <oboInOwl:hasExactSynonym>(2R,2&#39;R,3R,3&#39;R,4R)-2,2&#39;-bis(3,4-dihydroxyphenyl)-3,3&#39;,4,4&#39;-tetrahydro-2H,2&#39;H-4,8&#39;-bichromene-3,3&#39;,5,5&#39;,7,7&#39;-hexol</oboInOwl:hasExactSynonym>
        <oboInOwl:hasDbXref>pubmed:23985492</oboInOwl:hasDbXref>
        <oboInOwl:id>CHEBI:75632</oboInOwl:id>
        <oboInOwl:hasRelatedSynonym>Proanthocyanidin B2</oboInOwl:hasRelatedSynonym>
        <oboInOwl:hasDbXref>wikipedia.en:Procyanidin_B2</oboInOwl:hasDbXref>
        <ns4:inchi_string>InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28-,29-/m1/s1</ns4:inchi_string>
        <oboInOwl:hasDbXref>pubmed:23285083</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>kegg.compound:C17639</oboInOwl:hasDbXref>
        <oboInOwl:hasRelatedSynonym>Epicathechin-(4beta-&gt;8)-epicathechin</oboInOwl:hasRelatedSynonym>
        <oboInOwl:hasRelatedSynonym>Procyanidol B2</oboInOwl:hasRelatedSynonym>
        <ns3:IAO_0000115>A proanthocyanidin consisting of two molecules of (−)-epicatechin joined by a bond between positions 4 and 8&#39; in a β-configuration. Procyanidin B2 can be found in &lt;em&gt;Cinchona pubescens&lt;/em&gt; (Chinchona, in the rind, bark and cortex), in &lt;em&gt;Cinnamomum verum&lt;/em&gt; (Ceylon cinnamon, in the rind, bark and cortex), in &lt;em&gt;Crataegus monogyna&lt;/em&gt; (Common hawthorn, in the flower and blossom), in &lt;em&gt;Uncaria guianensis&lt;/em&gt; (Cat&#39;s claw, in the root), in &lt;em&gt;Vitis vinifera&lt;/em&gt; (Common grape vine, in the leaf), in &lt;em&gt;Litchi chinensis&lt;/em&gt; (litchi, in the pericarp), in the apple, in &lt;em&gt;Ecdysanthera utilis&lt;/em&gt; and in red wine.</ns3:IAO_0000115>
        <oboInOwl:hasDbXref>lipidmaps:LMPK12030002</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>pubmed:22042007</oboInOwl:hasDbXref>
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