AntibioticMech

(−)-cubebin

CHEBI:65684 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

A lignan that consists of tetrahydrofuran-2-ol substituted by two 1,3-benzodioxol-5-ylmethyl groups at positions 3 and 4 respectively (the 2S,3R,4R stereoisomer). It is isolated from the leaves of Piper nigrum and exhibits analgesic, anti-inflammatory, antimicrobial and trypanocidal activities. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:25036 CHEBI:25036
• CHEBI:35681 CHEBI:35681
• CHEBI:38131 CHEBI:38131
• CHEBI:38298 CHEBI:38298
• CHEBI:59770 CHEBI:59770

Chemical structure

Computed structure properties

Molecular formula	C20H20O6
Charge	0
Average mass	356.374 Da
Monoisotopic mass	356.12599 Da
Source	ChEBI
InChIKey	DIYWRNLYKJKHAM-MDOVXXIYSA-N

SMILES

[H][C@]1(Cc2ccc3c(c2)OCO3)CO[C@H](O)[C@]1([H])Cc1ccc2c(c1)OCO2

InChI

InChI=1S/C20H20O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15,20-21H,5-6,9-11H2/t14-,15+,20-/m0/s1

Also called

• (2S,3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)tetrahydrofuran-2-ol (EXACT_SYNONYM)— chebi
• (8R,8'R,9S)-cubebin (EXACT_SYNONYM)— chebi
• 3,4-bis(2H-1,3-benzodioxol-5-ylmethyl)oxolan-2-ol (EXACT_SYNONYM)— chebi
• 9-Hydroxy-3,4:3',4'-bis(methylenedioxy)-9,9'-epoxylignan (EXACT_SYNONYM)— chebi
• β-cubebin (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• cas:18423-69-3
• hmdb:HMDB0030682
• kegg.compound:C10549
• knapsack:C00002591
• patent:EP2517705
• patent:JP2011098968
• reaxys:6489121

Activity roles

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

• CHEBI:33281 CHEBI:33281
• CHEBI:36335 CHEBI:36335

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:65684	(−)-cubebin	antibioticmech:chebi-60d0e03199	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.