CHEBI:31505 - dioncophylline C

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ChEBI Name dioncophylline C
ChEBI ID CHEBI:31505
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:66274
Supplier Information
Download Molfile XML SDF
Formula C23H25NO3
Net Charge 0
Average Mass 363.44950
Monoisotopic Mass 363.18344
InChI InChI=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
InChIKey NALOMJPIDNQZKW-ZIAGYGMSSA-N
SMILES COc1cc(C)c(-c2ccc(O)c3[C@@H](C)N[C@H](C)Cc23)c2cccc(O)c12
Metabolite of Species Details
Triphyophyllum peltatum (NCBI:txid63090) Found in root (BTO:0001188). See: PubMed
Triphyophyllum peltatum (NCBI:txid63090) Found in stem (BTO:0001300). Previous component: stem bark; 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.
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.
(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.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 C KEGG COMPOUND
Manual Xref Database
C12337 KEGG COMPOUND
View more database links
Registry Number Type Source
5883382 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17263326 PubMed citation Europe PMC
17315144 PubMed citation Europe PMC
22459968 PubMed citation Europe PMC
8762401 PubMed citation Europe PMC
9272557 PubMed citation Europe PMC
Last Modified
23 November 2012