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CHEBI:66434 - schizolaenone B

Default Structure
ChEBI IDCHEBI:66434
ChEBI Nameschizolaenone B
Stars
DefinitionA tetrahydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5, 7, 4' and 5', 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 Modified6 April 2018
DownloadsMolfile
FormulaC30H36O6
Net Charge0
Average Mass492.612
Monoisotopic Mass492.25119
SMILESCC(C)=CCC/C(C)=C/Cc1cc([C@@H]2CC(=O)c3c(cc(O)c(CC=C(C)C)c3O)O2)cc(O)c1O
InChIInChI=1S/C30H36O6/c1-17(2)7-6-8-19(5)10-11-20-13-21(14-25(33)29(20)34)26-16-24(32)28-27(36-26)15-23(31)22(30(28)35)12-9-18(3)4/h7,9-10,13-15,26,31,33-35H,6,8,11-12,16H2,1-5H3/b19-10+/t26-/m0/s1
InChIKeyLFIGQOMCYZOIQK-XBPZWBIKSA-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 B (CHEBI:66434) has role antineoplastic agent (CHEBI:35610)
schizolaenone B (CHEBI:66434) has role metabolite (CHEBI:25212)
schizolaenone B (CHEBI:66434) is a 4'-hydroxyflavanones (CHEBI:140331)
schizolaenone B (CHEBI:66434) is a tetrahydroxyflavanone (CHEBI:38742)
IUPAC Name 
(2S)-2-{3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-4,5-dihydroxyphenyl}-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen-4-one
Synonym  Source
(2S)-5,7,3',4'-tetrahydroxy-6-(3-methyl-but-2-enyl)-3'-(geranyl)flavanoneChEBI
Registry NumbersSources
Reaxys:11068914Reaxys
Citations