CHEBI:31504 - dioncophylline A

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ChEBI Name dioncophylline A
ChEBI ID CHEBI:31504
Definition An isoquinoline alkaloid that is the biaryl resulting from substitution of the hydrogen at the 7-position of (1R,3R)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol by a 4,5-dimethoxy-2-methylnaphthalen-1-yl group. It is a naphthylisoquinoline alkaloid isolated from the roots and stem barks of Triphyophyllum peltatum and exhibits antifungal, antimalarial, antineoplastic and molluscicidal activites.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:66271
Supplier Information
Download Molfile XML SDF
Formula C24H27NO3
Net Charge 0
Average Mass 377.47610
Monoisotopic Mass 377.19909
InChI InChI=1S/C24H27NO3/c1-13-11-20(28-5)23-17(7-6-8-19(23)27-4)21(13)18-10-9-16-12-14(2)25-15(3)22(16)24(18)26/h6-11,14-15,25-26H,12H2,1-5H3/t14-,15-/m1/s1
InChIKey MXIZZLBQRBAZEX-HUUCEWRRSA-N
SMILES COc1cccc2c(c(C)cc(OC)c12)-c1ccc2C[C@@H](C)N[C@H](C)c2c1O
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.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
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.
molluscicide
A substance used to destroy pests of the phylum Mollusca.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing dioncophylline A (CHEBI:31504) has role antifungal agent (CHEBI:35718)
dioncophylline A (CHEBI:31504) has role antimalarial (CHEBI:38068)
dioncophylline A (CHEBI:31504) has role metabolite (CHEBI:25212)
dioncophylline A (CHEBI:31504) has role molluscicide (CHEBI:33904)
dioncophylline A (CHEBI:31504) is a biaryl (CHEBI:64459)
dioncophylline A (CHEBI:31504) is a isoquinoline alkaloid (CHEBI:24921)
dioncophylline A (CHEBI:31504) is a isoquinolines (CHEBI:24922)
dioncophylline A (CHEBI:31504) is a methoxynaphthalene (CHEBI:48851)
dioncophylline A (CHEBI:31504) is a methylnaphthalenes (CHEBI:25324)
IUPAC Name
(1R,3R)-7-(4,5-dimethoxy-2-methylnaphthalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol
Synonym Source
Dioncophylline A KEGG COMPOUND
Manual Xrefs Databases
C00025302 KNApSAcK
C12336 KEGG COMPOUND
US5260315 Patent
View more database links
Registry Numbers Types Sources
5830236 Reaxys Registry Number Reaxys
60142-17-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16971341 PubMed citation Europe PMC
17252498 PubMed citation Europe PMC
17263326 PubMed citation Europe PMC
8953426 PubMed citation Europe PMC
9134743 PubMed citation Europe PMC
9371362 PubMed citation Europe PMC
Last Modified
28 July 2014