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CHEBI:78591 - pederin

ChEBI IDCHEBI:78591
ChEBI Namepederin
Stars
DefinitionA 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.
Last Modified7 March 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC25H45NO9
Net Charge0
Average Mass503.633
Monoisotopic Mass503.30943
SMILESC=C1C[C@](OC)([C@H](O)C(=O)N[C@@H](OC)[C@@H]2C[C@@H](O)C(C)(C)[C@@H](C[C@@H](COC)OC)O2)O[C@H](C)[C@@H]1C
InChIInChI=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
InChIKeyZNEZZONMADKYTB-VRCUBXEUSA-N
Wikipedia
Roles Classification
Biological Roles:
antimitotic  Any compound that inhibits cell division (mitosis).
vesicant  Any compound that causes severe skin, eye and mucosal pain and irritation.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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  Source
(+)-pederineChEBI
(+)-pederinChEBI
pederineChemIDplus
paederineChEBI
Manual XrefsDatabases
PederinWikipedia
C15760KEGG COMPOUND
US7771972Patent
Registry NumbersSources
Reaxys:3598743Reaxys
CAS:27973-72-4ChemIDplus
CAS:27973-72-4KEGG COMPOUND
Citations