lycorine (CHEBI:6601)

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ChEBI Name	lycorine

ChEBI ID	CHEBI:6601

Definition	An 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C16H17NO4

Net Charge

Average Mass

287.31050

Monoisotopic Mass

287.11576

InChI

InChI=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

InChIKey

XGVJWXAYKUHDOO-DANNLKNASA-N

SMILES

[H][C@]12[C@H](O)[C@@H](O)C=C3CCN(Cc4cc5OCOc5cc14)[C@@]23[H]

Metabolite of Species	Details
Crinum asiaticum var. sinicum (NCBI:txid223245)	Found in leaf (BTO:0000713). 95% ethanolic extract of dried, powdered leaves See: PubMed
Crinum asiaticum var. sinicum (NCBI:txid223245)	Found in bulb (BTO:0000159). 95% ethanolic extract of dried, powdered leaves See: PubMed

Roles Classification
Biological Role(s):	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. 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. protein synthesis inhibitor A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid )

Application(s):	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	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

Last Modified

23 April 2020