CHEBI:65522 - brevipolide A

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name brevipolide A
ChEBI ID CHEBI:65522
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C23H24O8
Net Charge 0
Average Mass 428.43190
Monoisotopic Mass 428.14712
InChI InChI=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
InChIKey HEYOPWSFHOXZQH-ZEEHAMELSA-N
SMILES [H][C@@]1(CC=CC(=O)O1)[C@@H](OC(C)=O)[C@@]1([H])C[C@]1([H])C(=O)C(C)OC(=O)\C=C\c1ccc(O)cc1
Metabolite of Species Details
Hyptis brevipes (NCBI:txid204123) Found in whole plant (BTO:0001461). See: PubMed
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
21155677 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
19422206 PubMed citation Europe PMC
Last Modified
11 May 2016