CHEBI:70649 - liriodenine

ChEBI IDCHEBI:70649
ChEBI Nameliriodenine
Stars
DefinitionAn oxoaporphine alkaloid that is 4,5,6,6a-tetradehydronoraporphin-7-one substituted by a methylenedioxy group across positions 1 and 2. It is isolated from Annona glabra and has been shown to exhibit antimicrobial and cytotoxic activities.
Secondary ChEBI IDCHEBI:6502
Last Modified12 August 2016
DownloadsMolfile
FormulaC17H9NO3
Net Charge0
Average Mass275.263
Monoisotopic Mass275.05824
SMILESO=C1c2ccccc2-c2c3c(cc4ccnc1c24)OCO3
InChIInChI=1S/C17H9NO3/c19-16-11-4-2-1-3-10(11)14-13-9(5-6-18-15(13)16)7-12-17(14)21-8-20-12/h1-7H,8H2
InChIKeyMUMCCPUVOAUBAN-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Annona glabra (ncbitaxon:301703) stem wood (BTO:0001469) DOI (10.1021/np100247r) Ethanolic extract of stemwood
Roles Classification
Biological Roles:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
EC 3.1.1.7 (acetylcholinesterase) inhibitor  An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
EC 3.2.1.20 (alpha-glucosidase) inhibitor  An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of α-glucosidase (EC 3.2.1.20).
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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)
liriodenine (CHEBI:70649) has functional parent aporphine (CHEBI:35643)
liriodenine (CHEBI:70649) has role antifungal agent (CHEBI:35718)
liriodenine (CHEBI:70649) has role antimicrobial agent (CHEBI:33281)
liriodenine (CHEBI:70649) has role antineoplastic agent (CHEBI:35610)
liriodenine (CHEBI:70649) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
liriodenine (CHEBI:70649) has role EC 3.2.1.20 (α-glucosidase) inhibitor (CHEBI:67239)
liriodenine (CHEBI:70649) has role metabolite (CHEBI:25212)
liriodenine (CHEBI:70649) is a alkaloid antibiotic (CHEBI:86322)
liriodenine (CHEBI:70649) is a cyclic ketone (CHEBI:3992)
liriodenine (CHEBI:70649) is a organic heteropentacyclic compound (CHEBI:38164)
liriodenine (CHEBI:70649) is a oxacycle (CHEBI:38104)
liriodenine (CHEBI:70649) is a oxoaporphine alkaloid (CHEBI:132998)
IUPAC Name 
8H-[1,3]benzodioxolo[6,5,4-de]benzo[g]quinolin-8-one
Synonyms  Source
LiriodenineKEGG COMPOUND
OxoushinsunineChemIDplus
Noraporphin-7-one, 4,5,6,6a-tetradehydro-1,2-(methylenedioxy)-ChemIDplus
SpermatheridineChemIDplus
Micheline BChemIDplus
OxoushinsunineKEGG COMPOUND
Manual XrefsDatabases
C09567KEGG COMPOUND
C00001878KNApSAcK
Registry NumbersSources
Reaxys:273167Reaxys
CAS:475-75-2KEGG COMPOUND
CAS:475-75-2ChemIDplus
Citations