EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:66559 - leachianone A

ChEBI IDCHEBI:66559
ChEBI Nameleachianone A
Stars
DefinitionA trihydroxyflavanone that is (2S)-flavanone substituted by a lavandulyl group at position 8, hydroxy groups at positions 5, 7 and 4' and a methoxy group at position 2'. Isolated from the roots of Sophora flavescens and Sophora leachiana, it exhibits antineoplastic and antimalarial activity.
Last Modified5 April 2018
DownloadsMolfile
FormulaC26H30O6
Net Charge0
Average Mass438.520
Monoisotopic Mass438.20424
SMILESC=C(C)[C@H](CC=C(C)C)Cc1c(O)cc(O)c2c1O[C@H](c1ccc(O)cc1OC)CC2=O
InChIInChI=1S/C26H30O6/c1-14(2)6-7-16(15(3)4)10-19-20(28)12-21(29)25-22(30)13-24(32-26(19)25)18-9-8-17(27)11-23(18)31-5/h6,8-9,11-12,16,24,27-29H,3,7,10,13H2,1-2,4-5H3/t16-,24+/m1/s1
InChIKeyYLTPWCZXKJSORQ-GYCJOSAFSA-N
Species of MetaboliteComponentSourceComments
Sophora flavescens (ncbitaxon:49840) root (BTO:0001188) PubMed (10843587)
Sophora leachiana (IPNI:240761-2) root (BTO:0001188) DOI (10.1016/0031-9422(90)85209-X)
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
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)
leachianone A (CHEBI:66559) has functional parent (2S)-flavanone (CHEBI:15606)
leachianone A (CHEBI:66559) has role antimalarial (CHEBI:38068)
leachianone A (CHEBI:66559) has role antineoplastic agent (CHEBI:35610)
leachianone A (CHEBI:66559) has role metabolite (CHEBI:25212)
leachianone A (CHEBI:66559) is a 4'-hydroxyflavanones (CHEBI:140331)
leachianone A (CHEBI:66559) is a monomethoxyflavanone (CHEBI:38738)
leachianone A (CHEBI:66559) is a trihydroxyflavanone (CHEBI:38739)
IUPAC Name 
(2S)-5,7-dihydroxy-2-(4-hydroxy-2-methoxyphenyl)-8-[(2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-4H-chromen-4-one
Synonyms  Source
(2S)-5,7-dihydroxy-2-(4-hydroxy-2-methoxyphenyl)-8-[(2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-3,4-dihydro-2H-1-benzopyran-4-oneChEBI
(2S)-5,7,4'-trihydroxy-8-lavandulyl-2'-methoxyflavanoneChEBI
Manual XrefsDatabases
LMPK12140468LIPID MAPS
KR20010084363Patent
Registry NumbersSources
Reaxys:8594952Reaxys
Citations