CHEBI:66267 - 5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone

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ChEBI Name 5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone
ChEBI ID CHEBI:66267
ChEBI ASCII Name 5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone
Definition An extended flavonoid that consists of (2S)-flavanone substituted by hydroxy groups at positions 5, 7 and 3', prenyl groups at positions 8 and 2' and a gem-dimethyl pyran ring fused across positions 4' and 5'. Isolated from Dendrolobium lanceolatum, it exhibits antimalarial activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H34O6
Net Charge 0
Average Mass 490.58740
Monoisotopic Mass 490.23554
InChI InChI=1S/C30H34O6/c1-16(2)7-9-19-21(13-18-11-12-30(5,6)36-28(18)27(19)34)25-15-24(33)26-23(32)14-22(31)20(29(26)35-25)10-8-17(3)4/h7-8,11-14,25,31-32,34H,9-10,15H2,1-6H3/t25-/m0/s1
InChIKey WHMJSNMIIPVCHC-VWLOTQADSA-N
SMILES CC(C)=CCc1c(O)c2OC(C)(C)C=Cc2cc1[C@@H]1CC(=O)c2c(O)cc(O)c(CC=C(C)C)c2O1
Metabolite of Species Details
Dendrolobium lanceolatum (NCBI:txid185705) 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): 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 5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone (CHEBI:66267) has functional parent (2S)-flavanone (CHEBI:15606)
5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone (CHEBI:66267) has role antimalarial (CHEBI:38068)
5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone (CHEBI:66267) has role metabolite (CHEBI:25212)
5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone (CHEBI:66267) is a extended flavonoid (CHEBI:71037)
5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone (CHEBI:66267) is a trihydroxyflavanone (CHEBI:38739)
IUPAC Name
(2S)-5,7,8'-trihydroxy-2',2'-dimethyl-7',8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-2'H,4H-2,6'-bichromen-4-one
Synonym Source
(2S)-5,7,8'-trihydroxy-2',2'-dimethyl-7',8-bis(3-methyl-2-butenyl)-[2,6'-bi-2H-1-benzopyran]-4(3H)-one ChEBI
Registry Number Type Source
10044719 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15217275 PubMed citation Europe PMC
Last Modified
29 April 2013