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CHEBI:65368 - aculeatol E

ChEBI IDCHEBI:65368
ChEBI Nameaculeatol E
Stars
DefinitionAn oxaspiro compound that is 1,7-dioxadispiro[5.1.5.2]pentadec-9-en-11-one substituted by hydroxy groups at positions 4 and 13 and a tridecyl group at position 2 (the (2R,4R,6S,8R,13S stereoisomer). It is isolated from the leaves of Amomum aculeatum and exhibits toxicity against some cancer cell lines like human lung carcinoma, hormone-dependent lung carcinoma and human breast carcinoma.
Last Modified26 February 2013
DownloadsMolfile
FormulaC26H44O5
Net Charge0
Average Mass436.633
Monoisotopic Mass436.31887
SMILESCCCCCCCCCCCCC[C@@H]1C[C@@H](O)C[C@@]2(CC[C@]3(C=CC(=O)C[C@@H]3O)O2)O1
InChIInChI=1S/C26H44O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-23-18-22(28)20-26(30-23)17-16-25(31-26)15-14-21(27)19-24(25)29/h14-15,22-24,28-29H,2-13,16-20H2,1H3/t22-,23-,24+,25+,26+/m1/s1
InChIKeyUBFNRKJKPNNCHD-JMTTVTNBSA-N
Species of MetaboliteComponentSourceComments
Amomum aculeatum (ncbitaxon:1076729) leaf (BTO:0000713) PubMed (18260638)
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)
aculeatol E (CHEBI:65368) has role antineoplastic agent (CHEBI:35610)
aculeatol E (CHEBI:65368) has role metabolite (CHEBI:25212)
aculeatol E (CHEBI:65368) is a enone (CHEBI:51689)
aculeatol E (CHEBI:65368) is a organic heterotricyclic compound (CHEBI:26979)
aculeatol E (CHEBI:65368) is a oxaspiro compound (CHEBI:37948)
aculeatol E (CHEBI:65368) is a spiroketal (CHEBI:72600)
IUPAC Name 
(2R,4R,6S,8R,13S)-4,13-dihydroxy-2-tridecyl-1,7-dioxadispiro[5.1.5.2]pentadec-9-en-11-one
Synonym  Source
(2R,4R,6S,8R,9S)-4,9-dihydroxy-2-tridecyl-1,7-dioxadispiro[5.1.5.2]pentadec-12-en-11-oneChEBI
Registry NumbersSources
Reaxys:18832053Reaxys
Citations