CHEBI:67556 - zeaenol

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ChEBI Name zeaenol
ChEBI ID CHEBI:67556
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C19H24O7
Net Charge 0
Average Mass 364.38970
Monoisotopic Mass 364.15220
InChI InChI=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
InChIKey BPOLRDGTYHVUAY-YMFWJEOZSA-N
SMILES COc1cc(O)c2C(=O)O[C@@H](C)C\C=C\[C@H](O)[C@@H](O)[C@@H](O)C\C=C\c2c1
Metabolite of Species Details
Cochliobolus lunatus (NCBI:txid5503) EtOAc extract, fungus isolated from gorgonian coral Dichotella gemmacea See: PubMed
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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-one ChEBI
Registry Number Type Source
5484017 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
20429578 PubMed citation Europe PMC
21348465 PubMed citation Europe PMC
21513293 PubMed citation Europe PMC
Last Modified
19 July 2013