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CHEBI:66483 - sigmoidin B

Default Structure
ChEBI IDCHEBI:66483
ChEBI Namesigmoidin B
Stars
DefinitionA tetrahydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' and a prenyl group at position 5'. Isolated from Erythrina sigmoidea, it exhibits anti-inflammatory and antioxidant activities.
Last Modified6 April 2018
DownloadsMolfile
FormulaC20H20O6
Net Charge0
Average Mass356.374
Monoisotopic Mass356.12599
SMILESCC(C)=CCc1cc([C@@H]2CC(=O)c3c(O)cc(O)cc3O2)cc(O)c1O
InChIInChI=1S/C20H20O6/c1-10(2)3-4-11-5-12(6-16(24)20(11)25)17-9-15(23)19-14(22)7-13(21)8-18(19)26-17/h3,5-8,17,21-22,24-25H,4,9H2,1-2H3/t17-/m0/s1
InChIKeySFQIGPZCFNTPOD-KRWDZBQOSA-N
Species of MetaboliteComponentSourceComments
Erythrina sigmoidea (IPNI:494581-1) bark (BTO:0001301) PubMed (14994185)
Roles Classification
Chemical Role:
radical scavenger  A role played by a substance that can react readily with, and thereby eliminate, radicals.
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
Application:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
sigmoidin B (CHEBI:66483) has functional parent (2S)-flavanone (CHEBI:15606)
sigmoidin B (CHEBI:66483) has role anti-inflammatory agent (CHEBI:67079)
sigmoidin B (CHEBI:66483) has role antibacterial agent (CHEBI:33282)
sigmoidin B (CHEBI:66483) has role metabolite (CHEBI:25212)
sigmoidin B (CHEBI:66483) has role radical scavenger (CHEBI:48578)
sigmoidin B (CHEBI:66483) is a 4'-hydroxyflavanones (CHEBI:140331)
sigmoidin B (CHEBI:66483) is a tetrahydroxyflavanone (CHEBI:38742)
Synonyms  Source
(2S)- 2-(3,4-dihydroxy-5-(3-methyl-2-butenyl)phenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-oneChEBI
(2S)-2-[3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-oneChEBI
5,7,3',4'-tetrahydroxy-5'-prenylflavoneChEBI
Manual XrefsDatabases
LMPK12140397LIPID MAPS
Registry NumbersSources
Reaxys:5137677Reaxys
CAS:87746-47-2ChemIDplus
Citations