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CHEBI:65681 - (2S)-6-(γ,γ-dimethylallyl)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone

ChEBI IDCHEBI:65681
ChEBI Name(2S)-6-(γ,γ-dimethylallyl)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone
Stars
ASCII Name(2S)-6-(gamma,gamma-dimethylallyl)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone
DefinitionAn extended flavonoid that consists of (2S)-flavanone substituted by hydroxy groups at positions 5 and 3', a methoxy group at position 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 Modified6 April 2018
DownloadsMolfile
FormulaC26H28O6
Net Charge0
Average Mass436.504
Monoisotopic Mass436.18859
SMILESCOc1ccc([C@@H]2CC(=O)c3c(O)c(CC=C(C)C)c4c(c3O2)C=CC(C)(C)O4)cc1O
InChIInChI=1S/C26H28O6/c1-14(2)6-8-16-23(29)22-19(28)13-21(15-7-9-20(30-5)18(27)12-15)31-25(22)17-10-11-26(3,4)32-24(16)17/h6-7,9-12,21,27,29H,8,13H2,1-5H3/t21-/m0/s1
InChIKeyRGXSRPKLOMKRQU-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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65681) has role EC 1.6.5.3 [NADH:ubiquinone reductase (H+-translocating)] inhibitor (CHEBI:38503)
(2S)-6-(γ,γ-dimethylallyl)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65681) has role metabolite (CHEBI:25212)
(2S)-6-(γ,γ-dimethylallyl)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65681) is a 4'-methoxyflavanones (CHEBI:140332)
(2S)-6-(γ,γ-dimethylallyl)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65681) is a dihydroxyflavanone (CHEBI:38749)
(2S)-6-(γ,γ-dimethylallyl)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65681) is a extended flavonoid (CHEBI:71037)
(2S)-6-(γ,γ-dimethylallyl)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65681) is a monomethoxyflavanone (CHEBI:38738)
(2S)-6-(γ,γ-dimethylallyl)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65681) is a pyranochromane (CHEBI:74632)
IUPAC Name 
(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-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:8292865Reaxys
Citations