AntibioticMech

dioncophylline C

CHEBI:31505 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

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. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:24921 CHEBI:24921
• CHEBI:24922 CHEBI:24922
• CHEBI:25324 CHEBI:25324
• CHEBI:25392 CHEBI:25392
• CHEBI:35618 CHEBI:35618
• CHEBI:48851 CHEBI:48851
• CHEBI:64459 CHEBI:64459

Chemical structure

Computed structure properties

Molecular formula	C23H25NO3
Charge	0
Average mass	363.457 Da
Monoisotopic mass	363.18344 Da
Source	ChEBI
InChIKey	NALOMJPIDNQZKW-ZIAGYGMSSA-N

SMILES

COc1cc(C)c(-c2ccc(O)c3c2C[C@@H](C)N[C@@H]3C)c2cccc(O)c12

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

Also called

• (1R,3R)-5-(5-hydroxy-4-methoxy-2-methylnaphthalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol (EXACT_SYNONYM)— chebi
• Dioncophylline C (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• kegg.compound:C12337
• reaxys:5883382

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

• CHEBI:38068 CHEBI:38068
• CHEBI:64915 CHEBI:64915

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record

Source	Native ID	Label	Minted CURIE	Version
CHEBI	CHEBI:31505	dioncophylline C	antibioticmech:chebi-8da3c3871d	2026-08-30

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.