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CHEBI:68006 - lehualide F

ChEBI IDCHEBI:68006
ChEBI Namelehualide F
Stars
DefinitionA member of the class of 2-pyranones that is 2H-pyran-2-one substituted by a methoxy group at position 3, a hydroxy group at position 4, a methyl group at position 5 and a (2E)-3-methyl-9-phenylnon-2-en-1-yl group at position 6. Isolated from the marine sponge of the genus Plakortis, it exhibits cytotoxicity against human promyeloid leukemic HL-60 cells.
Last Modified17 March 2014
DownloadsMolfile
FormulaC23H30O4
Net Charge0
Average Mass370.489
Monoisotopic Mass370.21441
SMILESCOc1c(O)c(C)c(C/C=C(\C)CCCCCCc2ccccc2)oc1=O
InChIInChI=1S/C23H30O4/c1-17(11-7-4-5-8-12-19-13-9-6-10-14-19)15-16-20-18(2)21(24)22(26-3)23(25)27-20/h6,9-10,13-15,24H,4-5,7-8,11-12,16H2,1-3H3/b17-15+
InChIKeyRLHYLTRNTUTEBU-BMRADRMJSA-N
Species of MetaboliteComponentSourceComments
Plakortis (ncbitaxon:86044) - PubMed (21351759) Methanolic extract of frozen sample
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)
lehualide F (CHEBI:68006) has role antineoplastic agent (CHEBI:35610)
lehualide F (CHEBI:68006) has role metabolite (CHEBI:25212)
lehualide F (CHEBI:68006) is a 2-pyranones (CHEBI:75885)
lehualide F (CHEBI:68006) is a ether (CHEBI:25698)
lehualide F (CHEBI:68006) is a polyketide (CHEBI:26188)
IUPAC Name 
4-hydroxy-3-methoxy-5-methyl-6-[(2E)-3-methyl-9-phenylnon-2-en-1-yl]-2H-pyran-2-one
Registry NumbersSources
Reaxys:21452356Reaxys
Citations