(2S)-6-(gamma,gamma-dimethylallyl)-5,4'-dihydroxy-3'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65682)

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CHEBI:65682 - (2S)-6-(γ,γ-dimethylallyl)-5,4'-dihydroxy-3'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone

ChEBI ID	CHEBI:65682
ChEBI Name	(2S)-6-(γ,γ-dimethylallyl)-5,4'-dihydroxy-3'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone
Stars
ASCII Name	(2S)-6-(gamma,gamma-dimethylallyl)-5,4'-dihydroxy-3'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone
Definition	An extended flavonoid that consists of (2S)-flavanone substituted by hydroxy groups at positions 5 and 4', a methoxy group at position 3' , 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	C26H28O6
Net Charge	0
Average Mass	436.504
Monoisotopic Mass	436.18859
SMILES	COc1cc([C@@H]2CC(=O)c3c(O)c(CC=C(C)C)c4c(c3O2)C=CC(C)(C)O4)ccc1O
InChI	InChI=1S/C26H28O6/c1-14(2)6-8-16-23(29)22-19(28)13-20(15-7-9-18(27)21(12-15)30-5)31-25(22)17-10-11-26(3,4)32-24(16)17/h6-7,9-12,20,27,29H,8,13H2,1-5H3/t20-/m0/s1
InChIKey	KCZWDIXZSAGPCD-FQEVSTJZSA-N

Species of Metabolite	Component	Source	Comments
Lonchocarpus utilis (IPNI:503127-1)	root (BTO:0001188)	PubMed (10075742)	Cube resin, and extract of roots of Lonchocarpus utilis and Lonchocarpus urucu
Lonchocarpus urucu (IPNI:503126-1)	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)-5,4'-dihydroxy-3'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65682) has role EC 1.6.5.3 [NADH:ubiquinone reductase (H⁺-translocating)] inhibitor (CHEBI:38503)
	(2S)-6-(γ,γ-dimethylallyl)-5,4'-dihydroxy-3'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65682) has role metabolite (CHEBI:25212)
	(2S)-6-(γ,γ-dimethylallyl)-5,4'-dihydroxy-3'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65682) is a 3'-methoxyflavanones (CHEBI:140351)
	(2S)-6-(γ,γ-dimethylallyl)-5,4'-dihydroxy-3'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65682) is a 4'-hydroxyflavanones (CHEBI:140331)
	(2S)-6-(γ,γ-dimethylallyl)-5,4'-dihydroxy-3'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65682) is a dihydroxyflavanone (CHEBI:38749)
	(2S)-6-(γ,γ-dimethylallyl)-5,4'-dihydroxy-3'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65682) is a extended flavonoid (CHEBI:71037)
	(2S)-6-(γ,γ-dimethylallyl)-5,4'-dihydroxy-3'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65682) is a monomethoxyflavanone (CHEBI:38738)
	(2S)-6-(γ,γ-dimethylallyl)-5,4'-dihydroxy-3'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone (CHEBI:65682) is a pyranochromane (CHEBI:74632)

IUPAC Name
(2S)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-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:8293113	Reaxys

Citations