CHEBI:65683 - (2S)-6-(γ,γ-dimethylallyl)-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone

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ChEBI Name (2S)-6-(γ,γ-dimethylallyl)-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone
ChEBI ID CHEBI:65683
ChEBI ASCII Name (2S)-6-(gamma,gamma-dimethylallyl)-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone
Definition An extended flavonoid that consists of (2S)-flavanone substituted methoxy groups at positions 3' and 4', a prenyl group at position 6 and a gem-dimethylpyran ring fused across positions 7 and 8. Isolated from Lonchocarpus utilis and Lonchocarpus urucu, it acts as a NADH:ubiquinone reductase inhibitor.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C27H30O5
Net Charge 0
Average Mass 434.52410
Monoisotopic Mass 434.20932
InChI InChI=1S/C27H30O5/c1-16(2)7-8-18-13-20-21(28)15-23(17-9-10-22(29-5)24(14-17)30-6)31-26(20)19-11-12-27(3,4)32-25(18)19/h7,9-14,23H,8,15H2,1-6H3/t23-/m0/s1
InChIKey KJBZFWLVOZNDBN-QHCPKHFHSA-N
SMILES COc1ccc(cc1OC)[C@@H]1CC(=O)c2cc(CC=C(C)C)c3OC(C)(C)C=Cc3c2O1
Metabolite of Species Details
Lonchocarpus urucu (IPNI:503126-1) Found in root (BTO:0001188). Cube resin, and extract of roots of Lonchocarpus utilis and Lonchocarpus urucu See: PubMed
Lonchocarpus utilis (IPNI:503127-1) Found in root (BTO:0001188). Cube resin, and extract of roots of Lonchocarpus utilis and Lonchocarpus urucu See: PubMed
Roles Classification
Biological Role(s): EC 1.6.5.3 [NADH:ubiquinone reductase (H(+)-translocating)] inhibitor
A respiratory-chain inhibitor that interferes with the action of the the enzyme NADH:ubiquinone reductase (H+-translocating), EC 1.6.5.3.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (2S)-6-(γ,γ-dimethylallyl)-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65683) has role EC 1.6.5.3 [NADH:ubiquinone reductase (H+-translocating)] inhibitor (CHEBI:38503)
(2S)-6-(γ,γ-dimethylallyl)-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65683) has role plant metabolite (CHEBI:76924)
(2S)-6-(γ,γ-dimethylallyl)-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65683) is a 3'-methoxyflavanones (CHEBI:140351)
(2S)-6-(γ,γ-dimethylallyl)-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65683) is a 4'-methoxyflavanones (CHEBI:140332)
(2S)-6-(γ,γ-dimethylallyl)-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65683) is a dimethoxyflavanone (CHEBI:38743)
(2S)-6-(γ,γ-dimethylallyl)-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65683) is a extended flavonoid (CHEBI:71037)
(2S)-6-(γ,γ-dimethylallyl)-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65683) is a pyranochromane (CHEBI:74632)
IUPAC Name
(2S)-2-(3,4-dimethoxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H,8H-pyrano[2,3-f]chromen-4-one
Registry Number Type Source
8288982 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
10075742 PubMed citation Europe PMC
Last Modified
09 April 2018