CHEBI:67558 - 5E-7-oxozeaenol

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ChEBI Name 5E-7-oxozeaenol
ChEBI ID CHEBI:67558
ChEBI ASCII Name 5E-7-oxozeaenol
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C19H22O7
Net Charge 0
Average Mass 362.37380
Monoisotopic Mass 362.13655
InChI InChI=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
InChIKey NEQZWEXWOFPKOT-ULSULSEOSA-N
SMILES COc1cc(O)c2C(=O)O[C@@H](C)C\C=C\C(=O)[C@@H](O)[C@@H](O)C\C=C\c2c1
Metabolite of Species Details
Fungi MeOH-CHCl3(1:1) extract of Mycosynthetix fungus isolated from leaflitter of strain MSX 63935 See: PubMed
Roles Classification
Biological Role(s): 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-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 α-hydroxy ketone (CHEBI:2468)
5E-7-oxozeaenol (CHEBI:67558) is a secondary alcohol (CHEBI:35681)
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 Sources
(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-dione ChEBI
LL-Z1640-1 ChEBI
Registry Number Type Source
5452473 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21513293 PubMed citation Europe PMC
Last Modified
06 February 2018