cassiarin B (CHEBI:65597)

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ChEBI Name	cassiarin B

ChEBI ID	CHEBI:65597

Definition	An isoquinoline alkaloid that is pyrano[2,3,4-ij]isoquinolin-8(4H)-one substituted by methyl groups at positions 2 and 5 and a 4-methoxy-4-oxobutyl group at position 4. It is isolated from the leaves of Cassia siamea and exhibits antiplasmodial activity against Plasmodium falciparum.

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

Supplier Information

Download	Molfile XML SDF

Formula

C18H19NO4

Net Charge

Average Mass

313.34780

Monoisotopic Mass

313.13141

InChI

InChI=1S/C18H19NO4/c1-11-7-13-9-14(20)10-16-18(13)15(8-12(2)23-16)19(11)6-4-5-17(21)22-3/h7-10H,4-6H2,1-3H3

InChIKey

OTLORQJLOJHVHW-UHFFFAOYSA-N

SMILES

COC(=O)CCCn1c(C)cc2cc(=O)cc3oc(C)cc1c23

Metabolite of Species	Details
Senna siamea (NCBI:txid346999)	Found in leaf (BTO:0000713). 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. 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	cassiarin B (CHEBI:65597) has role antimalarial (CHEBI:38068) cassiarin B (CHEBI:65597) has role plant metabolite (CHEBI:76924) cassiarin B (CHEBI:65597) is a enone (CHEBI:51689) cassiarin B (CHEBI:65597) is a isoquinoline alkaloid (CHEBI:24921) cassiarin B (CHEBI:65597) is a isoquinolines (CHEBI:24922) cassiarin B (CHEBI:65597) is a methyl ester (CHEBI:25248) cassiarin B (CHEBI:65597) is a organic heterotricyclic compound (CHEBI:26979)

IUPAC Name

methyl 4-(2,5-dimethyl-8-oxopyrano[2,3,4-ij]isoquinolin-4(8H)-yl)butanoate

Registry Number	Type	Source
11166746	Reaxys Registry Number	Reaxys

Last Modified

11 March 2015