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CHEBI:65773 - 3,5-dihydroxy-2-(1'-oxo-3'-hexadecenyl)-2-cyclohexene-1-one

ChEBI IDCHEBI:65773
ChEBI Name3,5-dihydroxy-2-(1'-oxo-3'-hexadecenyl)-2-cyclohexene-1-one
Stars
DefinitionA polyketide that consists of cyclohex-2-en-1-one substituted by hydroxy groups at positions 3 and 5 and a hexadec-3-enoyl group at position 2 (the 3E stereoisomer). It is isolated form the leaves of Virola sebifera an exhibits cytotoxic activity against human tumour cells.
Last Modified3 April 2013
DownloadsMolfile
FormulaC22H36O4
Net Charge0
Average Mass364.526
Monoisotopic Mass364.26136
SMILESCCCCCCCCCCCC/C=C/CC(=O)C1=C(O)CC(O)CC1=O
InChIInChI=1S/C22H36O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(24)22-20(25)16-18(23)17-21(22)26/h13-14,18,23,25H,2-12,15-17H2,1H3/b14-13+
InChIKeyYEFDDSMURKQPEL-BUHFOSPRSA-N
Species of MetaboliteComponentSourceComments
Virola sebifera (ncbitaxon:224866) leaf (BTO:0000713) PubMed (17685388)
Roles Classification
Biological Role:
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)
3,5-dihydroxy-2-(1'-oxo-3'-hexadecenyl)-2-cyclohexene-1-one (CHEBI:65773) has role antineoplastic agent (CHEBI:35610)
3,5-dihydroxy-2-(1'-oxo-3'-hexadecenyl)-2-cyclohexene-1-one (CHEBI:65773) has role metabolite (CHEBI:25212)
3,5-dihydroxy-2-(1'-oxo-3'-hexadecenyl)-2-cyclohexene-1-one (CHEBI:65773) is a enol (CHEBI:33823)
3,5-dihydroxy-2-(1'-oxo-3'-hexadecenyl)-2-cyclohexene-1-one (CHEBI:65773) is a enone (CHEBI:51689)
3,5-dihydroxy-2-(1'-oxo-3'-hexadecenyl)-2-cyclohexene-1-one (CHEBI:65773) is a polyketide (CHEBI:26188)
IUPAC Name 
2-[(3E)-hexadec-3-enoyl]-3,5-dihydroxycyclohex-2-en-1-one
Citations