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CHEBI:66482 - sigmoidin A

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:
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
anti-obesity agent  Any substance which is used to reduce or control weight.
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 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