5-hydroxy-7-prop-2-en-(E)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one

CHEBI:65800 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

An organic heterobicyclic compound that is 7,7a-dihydrocyclopenta[b]pyran-6(2H)-one substituted by a hydroxy group at position 5 and a prop-2-en-1-ylidene group at position 7 (the E isomer). Isolated from the sponge Ulosa and ascidian Diplosoma virens, it exhibits antimicrobial activity and toxicity against HCT116 cells (human colorectal cancer cells) by triggering apoptotic cell death. — ChEBI

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:27171 CHEBI:27171
CHEBI:33823 CHEBI:33823
CHEBI:37407 CHEBI:37407
CHEBI:51689 CHEBI:51689

Chemical structure

Computed structure properties
Molecular formula	C11H10O3
Charge	0
Average mass	190.198 Da
Monoisotopic mass	190.06299 Da
Source	ChEBI
InChIKey	CCVQPAZRNPBPPA-DAXSKMNVSA-N

SMILES

C=C/C=C1/C(=O)C(O)=C2C=CCOC21

InChI

InChI=1S/C11H10O3/c1-2-4-7-9(12)10(13)8-5-3-6-14-11(7)8/h2-5,11,13H,1,6H2/b7-4-

Also called

(7E)-5-hydroxy-7-(prop-2-en-1-ylidene)-7,7a-dihydrocyclopenta[b]pyran-6(2H)-one (EXACT_SYNONYM)— chebi
Diplosoma ylidene 1 (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:15800346

Activity roles

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

CHEBI:33281 CHEBI:33281

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:65800`	5-hydroxy-7-prop-2-en-(E)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one	`antibioticmech:chebi-b5d615353b`	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.