5-hydroxy-7-prop-2-en-(Z)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one (CHEBI:65801)

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CHEBI:65801 - 5-hydroxy-7-prop-2-en-(Z)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one

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ChEBI ID	CHEBI:65801
ChEBI Name	5-hydroxy-7-prop-2-en-(Z)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one
Stars
ASCII Name	5-hydroxy-7-prop-2-en-(Z)-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 Z 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.
Last Modified	14 January 2013
Downloads	Molfile

Formula	C11H10O3
Net Charge	0
Average Mass	190.198
Monoisotopic Mass	190.06299
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+
InChIKey	CCVQPAZRNPBPPA-QPJJXVBHSA-N

Species of Metabolite	Component	Source	Comments
Ulosa (ncbitaxon:85796)	-	DOI (10.1016/S0040-4039(01)85425-3)
Diplosoma virens (ncbitaxon:322858)	-	PubMed (18463568)

Roles Classification

Biological Roles:	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:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	5-hydroxy-7-prop-2-en-(Z)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one (CHEBI:65801) has role antimicrobial agent (CHEBI:33281)
	5-hydroxy-7-prop-2-en-(Z)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one (CHEBI:65801) has role antineoplastic agent (CHEBI:35610)
	5-hydroxy-7-prop-2-en-(Z)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one (CHEBI:65801) has role metabolite (CHEBI:25212)
	5-hydroxy-7-prop-2-en-(Z)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one (CHEBI:65801) is a cyclic ether (CHEBI:37407)
	5-hydroxy-7-prop-2-en-(Z)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one (CHEBI:65801) is a enol (CHEBI:33823)
	5-hydroxy-7-prop-2-en-(Z)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one (CHEBI:65801) is a enone (CHEBI:51689)
	5-hydroxy-7-prop-2-en-(Z)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one (CHEBI:65801) is a organic heterobicyclic compound (CHEBI:27171)

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

Synonym	Source
Diplosoma ylidene 2	ChEBI

Registry Numbers	Sources
Reaxys:15800347	Reaxys

Citations