CHEBI:65680 - (2S)-6-(γ,γ-dimethylallyl)-5-hydroxy-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name (2S)-6-(γ,γ-dimethylallyl)-5-hydroxy-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone
ChEBI ID CHEBI:65680
ChEBI ASCII Name (2S)-6-(gamma,gamma-dimethylallyl)-5-hydroxy-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone
Definition An extended flavonoid that consists of (2S)-flavanone substituted by a hydroxy group at position 5, 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
Download Molfile XML SDF
Formula C27H30O6
Net Charge 0
Average Mass 450.52350
Monoisotopic Mass 450.20424
InChI InChI=1S/C27H30O6/c1-15(2)7-9-17-24(29)23-19(28)14-21(16-8-10-20(30-5)22(13-16)31-6)32-26(23)18-11-12-27(3,4)33-25(17)18/h7-8,10-13,21,29H,9,14H2,1-6H3/t21-/m0/s1
InChIKey FUBFEZXQVKEAMQ-NRFANRHFSA-N
SMILES COc1ccc(cc1OC)[C@@H]1CC(=O)c2c(O)c(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): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via (2S)-6-(gamma,gamma-dimethylallyl)-5-hydroxy-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone )
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.
(via (2S)-6-(gamma,gamma-dimethylallyl)-5-hydroxy-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (2S)-6-(γ,γ-dimethylallyl)-5-hydroxy-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65680) has role EC 1.6.5.3 [NADH:ubiquinone reductase (H+-translocating)] inhibitor (CHEBI:38503)
(2S)-6-(γ,γ-dimethylallyl)-5-hydroxy-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65680) has role plant metabolite (CHEBI:76924)
(2S)-6-(γ,γ-dimethylallyl)-5-hydroxy-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65680) is a 3'-methoxyflavanones (CHEBI:140351)
(2S)-6-(γ,γ-dimethylallyl)-5-hydroxy-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65680) is a 4'-methoxyflavanones (CHEBI:140332)
(2S)-6-(γ,γ-dimethylallyl)-5-hydroxy-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65680) is a dimethoxyflavanone (CHEBI:38743)
(2S)-6-(γ,γ-dimethylallyl)-5-hydroxy-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65680) is a extended flavonoid (CHEBI:71037)
(2S)-6-(γ,γ-dimethylallyl)-5-hydroxy-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65680) is a monohydroxyflavanone (CHEBI:38748)
(2S)-6-(γ,γ-dimethylallyl)-5-hydroxy-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65680) is a pyranochromane (CHEBI:74632)
IUPAC Name
(2S)-2-(3,4-dimethoxyphenyl)-5-hydroxy-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
8292718 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
10075742 PubMed citation Europe PMC
Last Modified
09 April 2018