CHEBI:70649 - liriodenine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name liriodenine
ChEBI ID CHEBI:70649
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:6502
Supplier Information ChemicalBook:CB8855316, eMolecules:508553, ZINC000006845904
Download Molfile XML SDF
Formula C17H9NO3
Net Charge 0
Average Mass 275.25830
Monoisotopic Mass 275.05824
InChI InChI=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
InChIKey MUMCCPUVOAUBAN-UHFFFAOYSA-N
SMILES O=C1c2ccccc2-c2c3OCOc3cc3ccnc1c23
Metabolite of Species Details
Annona glabra (NCBI:txid301703) Found in stem wood (BTO:0001469). Ethanolic extract of stemwood See: DOI
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.
(via alkaloid )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via alkaloid antibiotic )
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.
EC 3.2.1.20 (alpha-glucosidase) inhibitor
An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-glucosidase (EC 3.2.1.20).
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
Liriodenine KEGG COMPOUND
Micheline B ChemIDplus
Noraporphin-7-one, 4,5,6,6a-tetradehydro-1,2-(methylenedioxy)- ChemIDplus
Oxoushinsunine KEGG COMPOUND
Oxoushinsunine ChemIDplus
Spermatheridine ChemIDplus
Manual Xrefs Databases
C00001878 KNApSAcK
C09567 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
273167 Reaxys Registry Number Reaxys
475-75-2 CAS Registry Number KEGG COMPOUND
475-75-2 CAS Registry Number ChemIDplus
Citations Types Sources
19764006 PubMed citation Europe PMC
21790492 PubMed citation Europe PMC
21950162 PubMed citation Europe PMC
21960256 PubMed citation Europe PMC
22119096 PubMed citation Europe PMC
7420287 PubMed citation Europe PMC
Last Modified
12 August 2016