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    <!-- http://purl.obolibrary.org/obo/CHEBI_16990 -->

    <Class rdf:about="http://purl.obolibrary.org/obo/CHEBI_16990">
        <rdfs:label>bilirubin IXalpha</rdfs:label>
        <rdfs:subClassOf rdf:resource="http://purl.obolibrary.org/obo/CHEBI_24532"/>
        <rdfs:subClassOf rdf:resource="http://purl.obolibrary.org/obo/CHEBI_33575"/>
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        <ns4:monoisotopic_mass rdf:datatype="http://www.w3.org/2001/XMLSchema#decimal">584.26348</ns4:monoisotopic_mass>
        <ns4:mass rdf:datatype="http://www.w3.org/2001/XMLSchema#decimal">584.673</ns4:mass>
        <ns4:inchi_key_string>BPYKTIZUTYGOLE-IFADSCNNSA-N</ns4:inchi_key_string>
        <oboInOwl:hasDbXref>Beilstein:74376</oboInOwl:hasDbXref>
        <oboInOwl:hasExactSynonym>3,18-diethenyl-2,7,13,17-tetramethyl-1,19-dioxo-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acid</oboInOwl:hasExactSynonym>
        <oboInOwl:hasAlternativeId>CHEBI:13898</oboInOwl:hasAlternativeId>
        <oboInOwl:hasExactSynonym>Bilirubin</oboInOwl:hasExactSynonym>
        <oboInOwl:hasDbXref>NCIt:C305</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>knapsack:C00029828</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>pdb-ccd:BLR</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>cas:635-65-4</oboInOwl:hasDbXref>
        <ns4:smiles_string>C=CC1=C(C)/C(=C/c2nc(Cc3nc(/C=C4NC(=O)C(C)=C4C=C)c(C)c3CCC(=O)O)c(CCC(=O)O)c2C)NC1=O</ns4:smiles_string>
        <ns4:generalized_empirical_formula>C33H36N4O6</ns4:generalized_empirical_formula>
        <oboInOwl:hasDbXref>pubmed:30224965</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>pubmed:23763371</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>metacyc.compound:BILIRUBIN</oboInOwl:hasDbXref>
        <oboInOwl:hasRelatedSynonym>2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid</oboInOwl:hasRelatedSynonym>
        <oboInOwl:hasDbXref>ChemIDplus:635-65-4</oboInOwl:hasDbXref>
        <ns3:IAO_0000115>A member of the class of  biladienes that is a linear tetrapyrrole with the dipyrrole units being of both exovinyl and endovinyl type. A product of heme degradation, it is produced in the reticuloendothelial system by the reduction of biliverdin and transported to the liver as a complex with serum albumin.</ns3:IAO_0000115>
        <oboInOwl:hasDbXref>gmelin:411033</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>pubmed:18442622</oboInOwl:hasDbXref>
        <ns4:inchi_string>InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-</ns4:inchi_string>
        <oboInOwl:hasAlternativeId>CHEBI:3099</oboInOwl:hasAlternativeId>
        <oboInOwl:hasRelatedSynonym>8,12-bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbiladiene-ac-1,19(21H,24H)-dione</oboInOwl:hasRelatedSynonym>
        <oboInOwl:hasRelatedSynonym>1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionic acid</oboInOwl:hasRelatedSynonym>
        <oboInOwl:hasDbXref>kegg.compound:C00486</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>KEGG COMPOUND:635-65-4</oboInOwl:hasDbXref>
        <oboInOwl:hasRelatedSynonym>2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acid</oboInOwl:hasRelatedSynonym>
        <oboInOwl:hasRelatedSynonym>bilirubin-IXalpha</oboInOwl:hasRelatedSynonym>
        <oboInOwl:hasRelatedSynonym>3,18-diethenyl-2,7,13,17-tetramethyl-1,19-dioxo-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acid</oboInOwl:hasRelatedSynonym>
        <oboInOwl:hasRelatedSynonym>bilirubin</oboInOwl:hasRelatedSynonym>
        <oboInOwl:hasDbXref>pubmed:9587403</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>hmdb:HMDB0000054</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>wikipedia.en:Bilirubin</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>pubmed:23768684</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>KEGG COMPOUND:C00486</oboInOwl:hasDbXref>
        <oboInOwl:hasRelatedSynonym>Bilirubin</oboInOwl:hasRelatedSynonym>
        <oboInOwl:hasDbXref>pubmed:12799017</oboInOwl:hasDbXref>
        <oboInOwl:hasOBONamespace>chebi_ontology</oboInOwl:hasOBONamespace>
        <oboInOwl:hasExactSynonym>bilirubin</oboInOwl:hasExactSynonym>
        <oboInOwl:hasAlternativeId>CHEBI:22870</oboInOwl:hasAlternativeId>
        <oboInOwl:hasDbXref>Gmelin:411033</oboInOwl:hasDbXref>
        <oboInOwl:hasRelatedSynonym>bilirubin(Z,Z)</oboInOwl:hasRelatedSynonym>
        <oboInOwl:hasDbXref>reaxys:74376</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>MESH:D001663</oboInOwl:hasDbXref>
        <oboInOwl:id>CHEBI:16990</oboInOwl:id>
        <oboInOwl:hasDbXref>SNOMEDCT:79706000</oboInOwl:hasDbXref>
        <oboInOwl:hasDbXref>pubmed:8605219</oboInOwl:hasDbXref>
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    <!-- http://purl.obolibrary.org/obo/CHEBI_24532 -->

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        <rdfs:label>organic heterocyclic compound</rdfs:label>
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    <!-- http://purl.obolibrary.org/obo/CHEBI_33575 -->

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        <rdfs:label>carboxylic acid</rdfs:label>
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