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CHEBI:66270 - trilobacin

ChEBI IDCHEBI:66270
ChEBI Nametrilobacin
Stars
DefinitionA polyketide isolated from the bark of Asimina triloba. It has been shown to exhibit cytotoxicity in the NCI human tumor cell line screen.
Last Modified27 November 2014
DownloadsMolfile
FormulaC37H66O7
Net Charge0
Average Mass622.928
Monoisotopic Mass622.48085
SMILES[H][C@]1([C@H](O)CCCCCCCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)CC[C@]([H])([C@]2([H])CC[C@]([H])([C@H](O)CCCCCCCCCC)O2)O1
InChIInChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30(38)27-29-26-28(2)42-37(29)41/h26,28,30-36,38-40H,3-25,27H2,1-2H3/t28-,30+,31+,32+,33+,34+,35-,36+/m0/s1
InChIKeyMBABCNBNDNGODA-YVKOSWGISA-N
Species of MetaboliteComponentSourceComments
Asimina triloba (ncbitaxon:12953) bark (BTO:0001301) PubMed (1593281)
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
trilobacin (CHEBI:66270) has role antineoplastic agent (CHEBI:35610)
trilobacin (CHEBI:66270) has role plant metabolite (CHEBI:76924)
trilobacin (CHEBI:66270) is a butenolide (CHEBI:50523)
trilobacin (CHEBI:66270) is a polyketide (CHEBI:26188)
trilobacin (CHEBI:66270) is a triol (CHEBI:27136)
IUPAC Name 
(5S)-3-[(2R,13R)-2,13-dihydroxy-13-{(2R,2'S,5R,5'R)-5'-[(1R)-1-hydroxyundecyl]octahydro-2,2'-bifuran-5-yl}tridecyl]-5-methylfuran-2(5H)-one
Manual XrefsDatabases
HMDB0031369HMDB
Registry NumbersSources
Reaxys:7344197Reaxys
CAS:140224-67-5ChemIDplus
Citations