berberine

CHEBI:16118 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:22754 CHEBI:22754
CHEBI:38164 CHEBI:38164
CHEBI:86322 CHEBI:86322
CHEBI:86494 CHEBI:86494

Chemical structure

Computed structure properties
Molecular formula	C20H18NO4
Charge	1
Average mass	336.367 Da
Monoisotopic mass	336.12303 Da
Source	ChEBI
InChIKey	YBHILYKTIRIUTE-UHFFFAOYSA-N

SMILES

COc1ccc2cc3[n+](cc2c1OC)CCc1cc2c(cc1-3)OCO2

InChI

InChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1

Also called

9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium (EXACT_SYNONYM)— chebi
5,6-dihydro-9,10-dimethoxy-1,3-benzodioxolo[5,6-a]benzo[g]quinolizinium (EXACT_SYNONYM)— chebi
7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbinium (EXACT_SYNONYM)— chebi
9,10-dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetradehydroberbinium (EXACT_SYNONYM)— chebi
BERBERINE (EXACT_SYNONYM)— chebi
Berberin (EXACT_SYNONYM)— chebi
Berberine (EXACT_SYNONYM)— chebi
Umbellatine (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

beilstein:3570374
cas:2086-83-1
chemspider:2263
drugbank:DB04115
foodb.food:FDB023165
hmdb:HMDB0003409
kegg.compound:C00757
knapsack:C00001819
lincs.smallmolecule:LSM-6553
metacyc.compound:BERBERINE
pdb-ccd:BER
pesticides:berberine
wikipedia.en:Berberine

Activity roles

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

CHEBI:33281 CHEBI:33281
CHEBI:35718 CHEBI:35718

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:16118`	berberine	`antibioticmech:chebi-f4288792c2`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
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.