CHEBI:66482 - sigmoidin A

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name sigmoidin A
ChEBI ID CHEBI:66482
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C25H28O6
Net Charge 0
Average Mass 424.48620
Monoisotopic Mass 424.18859
InChI InChI=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
InChIKey BVHLNRAYBCPKOY-NRFANRHFSA-N
SMILES CC(C)=CCc1cc([C@@H]2CC(=O)c3c(O)cc(O)cc3O2)c(CC=C(C)C)c(O)c1O
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): 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(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
(2S)- 2-(3,4-dihydroxy-2,5-bis(3-methyl-2-butenyl)phenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one ChEBI
5,7,3',4'-tetrahydroxy-2',5'-diprenylflavone ChEBI
Manual Xref Database
LMPK12140398 LIPID MAPS
View more database links
Registry Numbers Types Sources
5171104 Reaxys Registry Number Reaxys
87746-48-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
14994185 PubMed citation Europe PMC
19941260 PubMed citation Europe PMC
22978690 PubMed citation Europe PMC
2343463 PubMed citation Europe PMC
Last Modified
06 April 2018