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CHEBI:65522 - brevipolide A

ChEBI IDCHEBI:65522
ChEBI Namebrevipolide A
Stars
DefinitionA pyranone that is a carboxylic ester of trans-4-coumaric acid. It is isolated from the whole plant of Hyptis brevipes and has been found to exhibit cytotoxicity against HT-29 cancer cells.
Last Modified11 May 2016
DownloadsMolfile
FormulaC23H24O8
Net Charge0
Average Mass428.437
Monoisotopic Mass428.14712
SMILES[H][C@]1([C@@H](OC(C)=O)[C@@]2([H])C[C@]2([H])C(=O)C(C)OC(=O)/C=C/c2ccc(O)cc2)CC=CC(=O)O1
InChIInChI=1S/C23H24O8/c1-13(29-21(27)11-8-15-6-9-16(25)10-7-15)22(28)17-12-18(17)23(30-14(2)24)19-4-3-5-20(26)31-19/h3,5-11,13,17-19,23,25H,4,12H2,1-2H3/b11-8+/t13?,17-,18-,19+,23-/m0/s1
InChIKeyHEYOPWSFHOXZQH-ZEEHAMELSA-N
Species of MetaboliteComponentSourceComments
Hyptis brevipes (ncbitaxon:204123) whole plant (BTO:0001461) PubMed (19422206)
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)
brevipolide A (CHEBI:65522) has functional parent trans-4-coumaric acid (CHEBI:32374)
brevipolide A (CHEBI:65522) has role antineoplastic agent (CHEBI:35610)
brevipolide A (CHEBI:65522) has role metabolite (CHEBI:25212)
brevipolide A (CHEBI:65522) is a 2-pyranones (CHEBI:75885)
brevipolide A (CHEBI:65522) is a acetate ester (CHEBI:47622)
brevipolide A (CHEBI:65522) is a cinnamate ester (CHEBI:36087)
brevipolide A (CHEBI:65522) is a cyclopropanes (CHEBI:51454)
brevipolide A (CHEBI:65522) is a phenols (CHEBI:33853)
IUPAC Name 
1-[(1S,2S)-2-{(S)-(acetyloxy)[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]methyl}cyclopropyl]-1-oxopropan-2-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
Registry NumbersSources
Reaxys:21155677Reaxys
Citations