CHEBI:78591 - pederin

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ChEBI Name pederin ChEBI ID CHEBI:78591 Definition A polyketide and carboxamide produced by a (Pseudomonas) bacterial endosymbiont of certain rove beetles (genus Paederus). Pederin is the agent responsible for the vesicant effects (linear or Paederus dermatitis) when the beetle is crushed against the skin. It is a powerful inhibitor of protein biosynthesis and mitosis and a potent antitumour agent. Stars This entity has been manually annotated by the ChEBI Team. Supplier Information Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Wikipedia License Read full article at Wikipedia Formula C25H45NO9 Net Charge 0 Average Mass 503.62610 Monoisotopic Mass 503.30943 InChI InChI=1S/C25H45NO9/c1-14-12-25(33-9,35-16(3)15(14)2)21(28)22(29)26-23(32-8)18-11-19(27)24(4,5)20(34-18)10-17(31-7)13-30-6/h15-21,23,27-28H,1,10-13H2,2-9H3,(H,26,29)/t15-,16-,17+,18+,19-,20-,21-,23+,25-/m1/s1 InChIKey ZNEZZONMADKYTB-VRCUBXEUSA-N SMILES COC[C@H](C[C@H]1O[C@@H](C[C@@H](O)C1(C)C)[C@@H](NC(=O)[C@@H](O)[C@]1(CC(=C)[C@@H](C)[C@@H](C)O1)OC)OC)OC Roles Classification Biological Role(s): bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. vesicant Any compound that causes severe skin, eye and mucosal pain and irritation. antimitotic Any compound that inhibits cell division (mitosis). Application(s): antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. View more via ChEBI Ontology ChEBI Ontology Outgoing pederin (CHEBI:78591) has role antimitotic (CHEBI:64911) pederin (CHEBI:78591) has role antineoplastic agent (CHEBI:35610) pederin (CHEBI:78591) has role bacterial metabolite (CHEBI:76969) pederin (CHEBI:78591) has role vesicant (CHEBI:78592) pederin (CHEBI:78591) is a cyclic ketal (CHEBI:59779) pederin (CHEBI:78591) is a diol (CHEBI:23824) pederin (CHEBI:78591) is a oxanes (CHEBI:46942) pederin (CHEBI:78591) is a polyketide (CHEBI:26188) pederin (CHEBI:78591) is a secondary alcohol (CHEBI:35681) pederin (CHEBI:78591) is a secondary carboxamide (CHEBI:140325) IUPAC Name (2S)-N-[(S)-{(2S,4R,6R)-6-[(2S)-2,3-dimethoxypropyl]-4-hydroxy-5,5-dimethyltetrahydro-2H-pyran-2-yl}(methoxy)methyl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2H-pyran-2-yl]acetamide Synonyms Sources (+)-pederin ChEBI (+)-pederine ChEBI paederine ChEBI pederine ChemIDplus Manual Xrefs Databases C15760 KEGG COMPOUND Pederin Wikipedia US7771972 Patent View more database links Registry Numbers Types Sources 27973-72-4 CAS Registry Number KEGG COMPOUND 27973-72-4 CAS Registry Number ChemIDplus 3598743 Reaxys Registry Number Reaxys Citations Types Sources 11077605 PubMed citation Europe PMC 11166312 PubMed citation Europe PMC 11886773 PubMed citation Europe PMC 12057588 PubMed citation Europe PMC 12381784 PubMed citation Europe PMC 14695518 PubMed citation Europe PMC 17645272 PubMed citation Europe PMC 19206228 PubMed citation Europe PMC 21268211 PubMed citation Europe PMC 21426381 PubMed citation Europe PMC 21902245 PubMed citation Europe PMC 22444588 PubMed citation Europe PMC 22772477 PubMed citation Europe PMC 23581998 PubMed citation Europe PMC 23898213 PubMed citation Europe PMC 3295241 PubMed citation Europe PMC 5959934 PubMed citation Europe PMC Last Modified 07 March 2018