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CHEBI:67558 - 5E-7-oxozeaenol

Default Structure
ChEBI IDCHEBI:67558
ChEBI Name5E-7-oxozeaenol
Stars
ASCII Name5E-7-oxozeaenol
DefinitionA macrolide that is the 7-oxo derivative of zeaenol (the 5E stereoisomer). Isolated from Fungi, it exhibits cytotoxic, antibacterial and inhibitory activity against NF-κB.
Last Modified6 February 2018
DownloadsMolfile
FormulaC19H22O7
Net Charge0
Average Mass362.378
Monoisotopic Mass362.13655
SMILESCOc1cc(O)c2c(c1)/C=C/C[C@H](O)[C@H](O)C(=O)/C=C/C[C@H](C)OC2=O
InChIInChI=1S/C19H22O7/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/h3-4,6-7,9-11,15,18,21-23H,5,8H2,1-2H3/b6-4+,7-3+/t11-,15-,18+/m0/s1
InChIKeyNEQZWEXWOFPKOT-ULSULSEOSA-N
Species of MetaboliteComponentSourceComments
Fungi- PubMed (21513293) MeOH-CHCl3(1:1) extract of Mycosynthetix fungus isolated from leaflitter Strain: MSX 63935
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
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.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
5E-7-oxozeaenol (CHEBI:67558) has role antibacterial agent (CHEBI:33282)
5E-7-oxozeaenol (CHEBI:67558) has role antineoplastic agent (CHEBI:35610)
5E-7-oxozeaenol (CHEBI:67558) has role metabolite (CHEBI:25212)
5E-7-oxozeaenol (CHEBI:67558) has role NF-κB inhibitor (CHEBI:73240)
5E-7-oxozeaenol (CHEBI:67558) is a aromatic ether (CHEBI:35618)
5E-7-oxozeaenol (CHEBI:67558) is a macrolide (CHEBI:25106)
5E-7-oxozeaenol (CHEBI:67558) is a phenols (CHEBI:33853)
5E-7-oxozeaenol (CHEBI:67558) is a secondary alcohol (CHEBI:35681)
5E-7-oxozeaenol (CHEBI:67558) is a secondary α-hydroxy ketone (CHEBI:2468)
IUPAC Name 
(3S,5E,8S,9S,11E)-8,9,16-trihydroxy-14-methoxy-3-methyl-3,4,9,10-tetrahydro-1H-2-benzoxacyclotetradecine-1,7(8H)-dione
Synonyms  Source
(2E,5S,6S,8E,11S)-5,6,15-trihydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(18),2,8,14,16-pentaene-7,13-dioneChEBI
LL-Z1640-1ChEBI
Registry NumbersSources
Reaxys:5452473Reaxys
Citations