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CHEBI:66433 - schizolaenone A

ChEBI IDCHEBI:66433
ChEBI Nameschizolaenone A
Stars
DefinitionA trihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5, 7 and 4', a geranyl group at position 3' and a prenyl group at position 6. Isolated from Schizolaena hystrix, it exhibits cytotoxicity against ovarian cancer cell line.
Last Modified5 April 2018
DownloadsMolfile
FormulaC30H36O5
Net Charge0
Average Mass476.613
Monoisotopic Mass476.25627
SMILESCC(C)=CCC/C(C)=C/Cc1cc([C@@H]2CC(=O)c3c(cc(O)c(CC=C(C)C)c3O)O2)ccc1O
InChIInChI=1S/C30H36O5/c1-18(2)7-6-8-20(5)10-11-21-15-22(12-14-24(21)31)27-17-26(33)29-28(35-27)16-25(32)23(30(29)34)13-9-19(3)4/h7,9-10,12,14-16,27,31-32,34H,6,8,11,13,17H2,1-5H3/b20-10+/t27-/m0/s1
InChIKeyNALIGSFHPZUJQO-KIAIXJHNSA-N
Species of MetaboliteComponentSourceComments
Schizolaena hystrix (IPNI:790101-1) fruit (BTO:0000486) PubMed (15787448)
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)
schizolaenone A (CHEBI:66433) has role antineoplastic agent (CHEBI:35610)
schizolaenone A (CHEBI:66433) has role metabolite (CHEBI:25212)
schizolaenone A (CHEBI:66433) is a 4'-hydroxyflavanones (CHEBI:140331)
schizolaenone A (CHEBI:66433) is a trihydroxyflavanone (CHEBI:38739)
IUPAC Name 
(2S)-2-{3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-4-hydroxyphenyl}-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen-4-one
Synonym  Source
(2S)-5,7,4'-trihydroxy-6-(3-methyl-but-2-enyl)-3'-(geranyl)flavanoneChEBI
Registry NumbersSources
Reaxys:11068913Reaxys
Citations