CHEBI:66150 - (2S)-(−)-kurarinone

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ChEBI Name (2S)-(−)-kurarinone
ChEBI ID CHEBI:66150
ChEBI ASCII Name (2S)-(-)-kurarinone
Definition A trihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 7, 2' and 4', a lavandulyl group at position 8 and a methoxy group at position 5. Isolated from the roots of Sophora flavescens, it exhibits cytotoxicity against human myeloid leukemia HL-60 cells.
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)10-19-21(29)12-24(31-5)25-22(30)13-23(32-26(19)25)18-9-8-17(27)11-20(18)28/h6,8-9,11-12,16,23,27-29H,3,7,10,13H2,1-2,4-5H3/t16-,23+/m1/s1
InChIKey LTTQKYMNTNISSZ-MWTRTKDXSA-N
SMILES COc1cc(O)c(C[C@@H](CC=C(C)C)C(C)=C)c2O[C@@H](CC(=O)c12)c1ccc(O)cc1O
Metabolite of Species Details
Sophora flavescens (NCBI:txid49840) Found in root (BTO:0001188). See: PubMed
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (2S)-(−)-kurarinone (CHEBI:66150) has functional parent (2S)-flavanone (CHEBI:15606)
(2S)-(−)-kurarinone (CHEBI:66150) has role antineoplastic agent (CHEBI:35610)
(2S)-(−)-kurarinone (CHEBI:66150) has role metabolite (CHEBI:25212)
(2S)-(−)-kurarinone (CHEBI:66150) is a 4'-hydroxyflavanones (CHEBI:140331)
(2S)-(−)-kurarinone (CHEBI:66150) is a monomethoxyflavanone (CHEBI:38738)
(2S)-(−)-kurarinone (CHEBI:66150) is a trihydroxyflavanone (CHEBI:38739)
Incoming (2S)-2'-methoxykurarinone (CHEBI:66151) has functional parent (2S)-(−)-kurarinone (CHEBI:66150)
IUPAC Name
(2S)-2-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-8-[(2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-4H-chromen-4-one
Synonym Source
7,2',4'-trihydroxy-8-lavandulyl-5-methoxyflavanone ChEBI
Manual Xrefs Databases
C17446 KEGG COMPOUND
CN102018697 Patent
LMPK12140499 LIPID MAPS
WO2005095375 Patent
View more database links
Registry Number Type Source
9739392 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10843587 PubMed citation Europe PMC
21831037 PubMed citation Europe PMC
22932446 PubMed citation Europe PMC
23333426 PubMed citation Europe PMC
Last Modified
06 April 2018