CHEBI:6601 - lycorine

ChEBI IDCHEBI:6601
ChEBI Namelycorine
Stars
DefinitionAn indolizidine alkaloid that is 3,12-didehydrogalanthan substituted by hydroxy groups at positions and 2 and a methylenedioxy group across positions 9 and 10. Isolated from Crinum asiaticum, it has been shown to exhibit antimalarial activity.
Last Modified23 April 2020
DownloadsMolfile
FormulaC16H17NO4
Net Charge0
Average Mass287.315
Monoisotopic Mass287.11576
SMILES[H][C@@]12C3=C[C@H](O)[C@@H](O)[C@@]1([H])c1cc4c(cc1CN2CC3)OCO4
InChIInChI=1S/C16H17NO4/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19/h3-5,11,14-16,18-19H,1-2,6-7H2/t11-,14-,15+,16+/m0/s1
InChIKeyXGVJWXAYKUHDOO-DANNLKNASA-N
Species of MetaboliteComponentSourceComments
Crinum asiaticum var. sinicum (ncbitaxon:223245)
leaf (BTO:0000713) PubMed (21314165) 95% ethanolic extract of dried, powdered leaves
bulb (BTO:0000159) PubMed (21314165) 95% ethanolic extract of dried, powdered leaves
Roles Classification
Biological Roles:
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
protein synthesis inhibitor  A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
anticoronaviral agent  Any antiviral agent which inhibits the activity of coronaviruses.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
ChEBI Ontology
Outgoing Relation(s)
lycorine (CHEBI:6601) has parent hydride galanthan (CHEBI:35646)
lycorine (CHEBI:6601) has role anticoronaviral agent (CHEBI:149553)
lycorine (CHEBI:6601) has role antimalarial (CHEBI:38068)
lycorine (CHEBI:6601) has role plant metabolite (CHEBI:76924)
lycorine (CHEBI:6601) has role protein synthesis inhibitor (CHEBI:48001)
lycorine (CHEBI:6601) is a indolizidine alkaloid (CHEBI:38511)
IUPAC Name 
9,10-(methylenedioxy)-3,12-didehydrogalanthan-1α,2β-diol
Synonyms  Source
AmaryllineChemIDplus
GalanthidineChemIDplus
LicorineChemIDplus
(−)-lycorineChEBI
LycorineKEGG COMPOUND
NarcissineChemIDplus
Manual XrefsDatabases
3KDPDBeChem
C00001576KNApSAcK
C08532KEGG COMPOUND
Registry NumbersSources
Reaxys:93605Reaxys
CAS:476-28-8ChemIDplus
CAS:476-28-8KEGG COMPOUND
Citations