sigmoidin B (CHEBI:66483)

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ChEBI Name	sigmoidin B

ChEBI ID	CHEBI:66483

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C20H20O6

Net Charge

Average Mass

356.36920

Monoisotopic Mass

356.12599

InChI

InChI=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

InChIKey

SFQIGPZCFNTPOD-KRWDZBQOSA-N

SMILES

CC(C)=CCc1cc(cc(O)c1O)[C@@H]1CC(=O)c2c(O)cc(O)cc2O1

Metabolite of Species	Details
Erythrina sigmoidea (IPNI:494581-1)	Found in bark (BTO:0001301). See: PubMed

Roles Classification
Chemical Role(s):	radical scavenger A role played by a substance that can react readily with, and thereby eliminate, radicals.

Biological Role(s):	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(s):	anti-inflammatory agent Any compound that has anti-inflammatory effects.

ChEBI Ontology
Outgoing	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	Sources
(2S)- 2-(3,4-dihydroxy-5-(3-methyl-2-butenyl)phenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one	ChEBI
(2S)-2-[3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one	ChEBI
5,7,3',4'-tetrahydroxy-5'-prenylflavone	ChEBI

Last Modified

06 April 2018