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CHEBI:67556 - zeaenol

ChEBI IDCHEBI:67556
ChEBI Namezeaenol
Stars
DefinitionA macrolide that is a 14-memebered macrocycle fused to a 3-methoxyphenol ring. Isolated from Fungi and Cochliobolus lunatus, it exhibits antibacterial and inhibitory activity against NF-κB.
Last Modified19 July 2013
DownloadsMolfile
FormulaC19H24O7
Net Charge0
Average Mass364.394
Monoisotopic Mass364.15220
SMILESCOc1cc(O)c2c(c1)/C=C/C[C@H](O)[C@H](O)[C@@H](O)/C=C/C[C@H](C)OC2=O
InChIInChI=1S/C19H24O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3-4,6-7,9-11,14-15,18,20-23H,5,8H2,1-2H3/b6-4+,7-3+/t11-,14-,15-,18+/m0/s1
InChIKeyBPOLRDGTYHVUAY-YMFWJEOZSA-N
Species of MetaboliteComponentSourceComments
Cochliobolus lunatus (ncbitaxon:5503) - PubMed (21348465) EtOAc extract, fungus isolated from gorgonian coral Dichotella gemmacea
Fungi- PubMed (21513293) MeOH-CHCl3(1:1) extract of Mycosynthetix fungus isolated from leaflitter Strain: MSX 63935
Roles Classification
Biological Roles:
NF-kappaB inhibitor  An inhibitor of NF-κB (nuclear factor κ-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
zeaenol (CHEBI:67556) has role antibacterial agent (CHEBI:33282)
zeaenol (CHEBI:67556) has role metabolite (CHEBI:25212)
zeaenol (CHEBI:67556) has role NF-κB inhibitor (CHEBI:73240)
zeaenol (CHEBI:67556) is a aromatic ether (CHEBI:35618)
zeaenol (CHEBI:67556) is a macrolide (CHEBI:25106)
zeaenol (CHEBI:67556) is a phenols (CHEBI:33853)
zeaenol (CHEBI:67556) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(3S,5E,7S,8S,9S,11E)-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-1H-2-benzoxacyclotetradecin-1-one
Synonym  Source
(2E,5S,6S,7S,8E,11S)-5,6,7,15-tetrahydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaen-13-oneChEBI
Registry NumbersSources
Reaxys:5484017Reaxys
Citations