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

ChEBI IDCHEBI:65680
ChEBI Name(2S)-6-(γ,γ-dimethylallyl)-5-hydroxy-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone
Stars
ASCII Name(2S)-6-(gamma,gamma-dimethylallyl)-5-hydroxy-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone
DefinitionAn 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.
Last Modified9 April 2018
DownloadsMolfile
FormulaC27H30O6
Net Charge0
Average Mass450.531
Monoisotopic Mass450.20424
SMILESCOc1ccc([C@@H]2CC(=O)c3c(O)c(CC=C(C)C)c4c(c3O2)C=CC(C)(C)O4)cc1OC
InChIInChI=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
InChIKeyFUBFEZXQVKEAMQ-NRFANRHFSA-N
Species of MetaboliteComponentSourceComments
Lonchocarpus urucu (IPNI:503126-1) root (BTO:0001188) PubMed (10075742) Cube resin, and extract of roots of Lonchocarpus utilis and Lonchocarpus urucu
Lonchocarpus utilis (IPNI:503127-1) root (BTO:0001188) PubMed (10075742) Cube resin, and extract of roots of Lonchocarpus utilis and Lonchocarpus urucu
Roles Classification
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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.
ChEBI Ontology
Outgoing Relation(s)
(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 NumbersSources
Reaxys:8292718Reaxys
Citations