CHEBI:66559 - leachianone A

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ChEBI Name leachianone A
ChEBI ID CHEBI:66559
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C26H30O6
Net Charge 0
Average Mass 438.51280
Monoisotopic Mass 438.20424
InChI InChI=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
InChIKey YLTPWCZXKJSORQ-GYCJOSAFSA-N
SMILES COc1cc(O)ccc1[C@@H]1CC(=O)c2c(O)cc(O)c(C[C@@H](CC=C(C)C)C(C)=C)c2O1
Metabolite of Species Details
Sophora leachiana (IPNI:240761-2) Found in root (BTO:0001188). See: DOI
Sophora flavescens (NCBI:txid49840) Found in root (BTO:0001188). See: PubMed
Roles Classification
Biological Role(s): 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(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
(2S)-5,7,4'-trihydroxy-8-lavandulyl-2'-methoxyflavanone ChEBI
(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-one ChEBI
Manual Xrefs Databases
KR20010084363 Patent
LMPK12140468 LIPID MAPS
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Registry Number Type Source
8594952 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
10843587 PubMed citation Europe PMC
Last Modified
05 April 2018