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.
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Formula C25H45NO9
Net Charge 0
Average Mass 503.62610
Monoisotopic Mass 503.309
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.
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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 Waiting for Citations Types Sources
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Last Modified
07 March 2018