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CHEBI:67558 - 5E-7-oxozeaenol

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:
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.
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