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CHEBI:65891 - exiguaflavanone A

ChEBI IDCHEBI:65891
ChEBI Nameexiguaflavanone A
Stars
DefinitionA tetrahydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5, 7, 2' and 6' and a lavandulyl group at position 8. Isolated from Sophora exigua and Artemisia indica, it exhibits antimalarial activity.
Last Modified31 January 2013
DownloadsMolfile
FormulaC25H28O6
Net Charge0
Average Mass424.493
Monoisotopic Mass424.18859
SMILES[H][C@@]1(c2c(O)cccc2O)CC(=O)c2c(O)cc(O)c(C[C@@H](CC=C(C)C)C(=C)C)c2O1
InChIInChI=1S/C25H28O6/c1-13(2)8-9-15(14(3)4)10-16-19(28)11-20(29)24-21(30)12-22(31-25(16)24)23-17(26)6-5-7-18(23)27/h5-8,11,15,22,26-29H,3,9-10,12H2,1-2,4H3/t15-,22+/m1/s1
InChIKeyFPUREMWTZVLZBZ-QRQCRPRQSA-N
Species of MetaboliteComponentSourceComments
Artemisia indica (ncbitaxon:318067) stem (BTO:0001300) PubMed (9748386)
Sophora exigua (IPNI:518828-1) root (BTO:0001188) DOI (10.1016/0031-9422(92)80056-K)
Roles Classification
Biological Roles:
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
ChEBI Ontology
Outgoing Relation(s)
exiguaflavanone A (CHEBI:65891) has functional parent (2S)-flavanone (CHEBI:15606)
exiguaflavanone A (CHEBI:65891) has role antimalarial (CHEBI:38068)
exiguaflavanone A (CHEBI:65891) has role metabolite (CHEBI:25212)
exiguaflavanone A (CHEBI:65891) is a tetrahydroxyflavanone (CHEBI:38742)
IUPAC Name 
(2S)-2-(2,6-dihydroxyphenyl)-5,7-dihydroxy-8-[(2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-4H-chromen-4-one
Manual XrefsDatabases
LMPK12140111LIPID MAPS
Registry NumbersSources
Reaxys:5362663Reaxys
Citations