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CHEBI:66482 - sigmoidin A

Default Structure
ChEBI IDCHEBI:66482
ChEBI Namesigmoidin A
Stars
DefinitionA tetrahydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' and prenyl groups at positions 2' and 5'. Isolated from Erythrina sigmoidea, it exhibits anti-inflammatory and antioxidant activities.
Last Modified6 April 2018
DownloadsMolfile
FormulaC25H28O6
Net Charge0
Average Mass424.493
Monoisotopic Mass424.18859
SMILESCC(C)=CCc1cc([C@@H]2CC(=O)c3c(O)cc(O)cc3O2)c(CC=C(C)C)c(O)c1O
InChIInChI=1S/C25H28O6/c1-13(2)5-7-15-9-18(17(8-6-14(3)4)25(30)24(15)29)21-12-20(28)23-19(27)10-16(26)11-22(23)31-21/h5-6,9-11,21,26-27,29-30H,7-8,12H2,1-4H3/t21-/m0/s1
InChIKeyBVHLNRAYBCPKOY-NRFANRHFSA-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.
anti-obesity agent  Any substance which is used to reduce or control weight.
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 A (CHEBI:66482) has functional parent (2S)-flavanone (CHEBI:15606)
sigmoidin A (CHEBI:66482) has role anti-inflammatory agent (CHEBI:67079)
sigmoidin A (CHEBI:66482) has role anti-obesity agent (CHEBI:74518)
sigmoidin A (CHEBI:66482) has role antibacterial agent (CHEBI:33282)
sigmoidin A (CHEBI:66482) has role metabolite (CHEBI:25212)
sigmoidin A (CHEBI:66482) has role radical scavenger (CHEBI:48578)
sigmoidin A (CHEBI:66482) is a 4'-hydroxyflavanones (CHEBI:140331)
sigmoidin A (CHEBI:66482) is a tetrahydroxyflavanone (CHEBI:38742)
IUPAC Name 
(2S)-2-[3,4-dihydroxy-2,5-bis(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
Synonyms  Source
(2S)- 2-(3,4-dihydroxy-2,5-bis(3-methyl-2-butenyl)phenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-oneChEBI
5,7,3',4'-tetrahydroxy-2',5'-diprenylflavoneChEBI
Manual XrefsDatabases
LMPK12140398LIPID MAPS
Registry NumbersSources
Reaxys:5171104Reaxys
CAS:87746-48-3ChemIDplus
Citations