CHEBI:65368 - aculeatol E

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ChEBI Name aculeatol E
ChEBI ID CHEBI:65368
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C26H44O5
Net Charge 0
Average Mass 436.62460
Monoisotopic Mass 436.31887
InChI InChI=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
InChIKey UBFNRKJKPNNCHD-JMTTVTNBSA-N
SMILES CCCCCCCCCCCCC[C@@H]1C[C@@H](O)C[C@@]2(CC[C@@]3(O2)C=CC(=O)C[C@@H]3O)O1
Metabolite of Species Details
Amomum aculeatum (NCBI:txid1076729) Found in leaf (BTO:0000713). 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 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-one ChEBI
Registry Number Type Source
18832053 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
18260638 PubMed citation Europe PMC
Last Modified
26 February 2013