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

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

ChEBI ID	CHEBI:65683
ChEBI Name	(2S)-6-(γ,γ-dimethylallyl)-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone
Stars
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.
Last Modified	9 April 2018
Downloads	Molfile

Formula	C27H30O5
Net Charge	0
Average Mass	434.532
Monoisotopic Mass	434.20932
SMILES	COc1ccc([C@@H]2CC(=O)c3cc(CC=C(C)C)c4c(c3O2)C=CC(C)(C)O4)cc1OC
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

Species of Metabolite	Component	Source	Comments
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:

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.

ChEBI Ontology

Outgoing Relation(s)
	(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 Numbers	Sources
Reaxys:8288982	Reaxys

Citations