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CHEBI:66483 - sigmoidin B

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:
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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