CHEBI:31505 - dioncophylline C

ChEBI IDCHEBI:31505
ChEBI Namedioncophylline C
Stars
DefinitionAn isoquinoline alkaloid that is the biaryl resulting from substitution of the hydrogen at the 5-position of (1R,3R)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol by a 5-hydroxy-4-methoxy-2-methylnaphthalen-1-yl group. It is a naphthylisoquinoline alkaloid isolated from the roots and stem barks of Triphyophyllum peltatum and exhibits antimalarial activity.
Secondary ChEBI IDCHEBI:66274
Last Modified23 November 2012
DownloadsMolfile
FormulaC23H25NO3
Net Charge0
Average Mass363.457
Monoisotopic Mass363.18344
SMILESCOc1cc(C)c(-c2ccc(O)c3c2C[C@@H](C)N[C@@H]3C)c2cccc(O)c12
InChIInChI=1S/C23H25NO3/c1-12-10-20(27-4)23-16(6-5-7-18(23)25)21(12)15-8-9-19(26)22-14(3)24-13(2)11-17(15)22/h5-10,13-14,24-26H,11H2,1-4H3/t13-,14-/m1/s1
InChIKeyNALOMJPIDNQZKW-ZIAGYGMSSA-N
Species of MetaboliteComponentSourceComments
Triphyophyllum peltatum (ncbitaxon:63090)
stem (BTO:0001300) PubMed (9371362) Previous component: stem bark;
root (BTO:0001188) PubMed (9371362)
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.
antiplasmodial drug  An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
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.
Applications:
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.
antiplasmodial drug  An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
ChEBI Ontology
Outgoing Relation(s)
dioncophylline C (CHEBI:31505) has role antimalarial (CHEBI:38068)
dioncophylline C (CHEBI:31505) has role antiplasmodial drug (CHEBI:64915)
dioncophylline C (CHEBI:31505) has role metabolite (CHEBI:25212)
dioncophylline C (CHEBI:31505) is a aromatic ether (CHEBI:35618)
dioncophylline C (CHEBI:31505) is a biaryl (CHEBI:64459)
dioncophylline C (CHEBI:31505) is a isoquinoline alkaloid (CHEBI:24921)
dioncophylline C (CHEBI:31505) is a isoquinolines (CHEBI:24922)
dioncophylline C (CHEBI:31505) is a methoxynaphthalene (CHEBI:48851)
dioncophylline C (CHEBI:31505) is a methylnaphthalenes (CHEBI:25324)
dioncophylline C (CHEBI:31505) is a naphthols (CHEBI:25392)
IUPAC Name 
(1R,3R)-5-(5-hydroxy-4-methoxy-2-methylnaphthalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol
Synonym  Source
Dioncophylline CKEGG COMPOUND
Manual XrefsDatabases
C12337KEGG COMPOUND
Registry NumbersSources
Reaxys:5883382Reaxys
Citations