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

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

ChEBI ID	CHEBI:65800

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

Definition	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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C11H10O3

Net Charge

Average Mass

190.19530

Monoisotopic Mass

190.06299

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-

InChIKey

CCVQPAZRNPBPPA-DAXSKMNVSA-N

SMILES

OC1=C2C=CCOC2\C(=C/C=C)C1=O

Roles Classification
Biological Role(s):	antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	5-hydroxy-7-prop-2-en-(E)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one (CHEBI:65800) has role antimicrobial agent (CHEBI:33281) 5-hydroxy-7-prop-2-en-(E)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one (CHEBI:65800) has role antineoplastic agent (CHEBI:35610) 5-hydroxy-7-prop-2-en-(E)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one (CHEBI:65800) has role metabolite (CHEBI:25212) 5-hydroxy-7-prop-2-en-(E)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one (CHEBI:65800) is a cyclic ether (CHEBI:37407) 5-hydroxy-7-prop-2-en-(E)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one (CHEBI:65800) is a enol (CHEBI:33823) 5-hydroxy-7-prop-2-en-(E)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one (CHEBI:65800) is a enone (CHEBI:51689) 5-hydroxy-7-prop-2-en-(E)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one (CHEBI:65800) is a organic heterobicyclic compound (CHEBI:27171)

IUPAC Name

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

Synonym	Source
Diplosoma ylidene 1	ChEBI

Registry Number	Type	Source
15800346	Reaxys Registry Number	Reaxys

Citation	Type	Source
18463568	PubMed citation	Europe PMC

Last Modified

14 January 2013