EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:66284 - quercetin 3-O-α-(6'''-caffeoylglucosyl-β-1,2-rhamnoside)

ChEBI IDCHEBI:66284
ChEBI Namequercetin 3-O-α-(6'''-caffeoylglucosyl-β-1,2-rhamnoside)
Stars
ASCII Namequercetin 3-O-alpha-(6'''-caffeoylglucosyl-beta-1,2-rhamnoside)
DefinitionA quercetin O-glycoside that is quercetin substituted by a α-6'''-caffeoylglucosyl-β-1,2-rhamnosyl residue at position 3 via glycosidic linkage. Isolated from Sedum sarmentosum, it exhibits inhibitory activity against angiotensin-converting enzyme.
Last Modified28 October 2019
DownloadsMolfile
FormulaC36H36O19
Net Charge0
Average Mass772.665
Monoisotopic Mass772.18508
SMILESC[C@@H]1O[C@@H](Oc2c(-c3ccc(O)c(O)c3)oc3cc(O)cc(O)c3c2=O)[C@H](O[C@@H]2O[C@H](COC(=O)/C=C/c3ccc(O)c(O)c3)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O
InChIInChI=1S/C36H36O19/c1-13-26(44)30(48)34(55-35-31(49)29(47)27(45)23(53-35)12-50-24(43)7-3-14-2-5-17(38)19(40)8-14)36(51-13)54-33-28(46)25-21(42)10-16(37)11-22(25)52-32(33)15-4-6-18(39)20(41)9-15/h2-11,13,23,26-27,29-31,34-42,44-45,47-49H,12H2,1H3/b7-3+/t13-,23+,26-,27+,29-,30+,31+,34+,35-,36-/m0/s1
InChIKeyYFERBGPVRSLDSL-GVZNLTFMSA-N
Species of MetaboliteComponentSourceComments
Sedum sarmentosum (ncbitaxon:91146) aerial part (BTO:0001658) PubMed (15577228)
Roles Classification
Biological Roles:
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor  An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor  An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).
ChEBI Ontology
Outgoing Relation(s)
quercetin 3-O-α-(6'''-caffeoylglucosyl-β-1,2-rhamnoside) (CHEBI:66284) has functional parent trans-caffeic acid (CHEBI:16433)
quercetin 3-O-α-(6'''-caffeoylglucosyl-β-1,2-rhamnoside) (CHEBI:66284) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
quercetin 3-O-α-(6'''-caffeoylglucosyl-β-1,2-rhamnoside) (CHEBI:66284) has role metabolite (CHEBI:25212)
quercetin 3-O-α-(6'''-caffeoylglucosyl-β-1,2-rhamnoside) (CHEBI:66284) is a cinnamate ester (CHEBI:36087)
quercetin 3-O-α-(6'''-caffeoylglucosyl-β-1,2-rhamnoside) (CHEBI:66284) is a disaccharide derivative (CHEBI:63353)
quercetin 3-O-α-(6'''-caffeoylglucosyl-β-1,2-rhamnoside) (CHEBI:66284) is a quercetin O-glycoside (CHEBI:76424)
IUPAC Name 
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-deoxy-2-O-{6-O-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-β-D-glucopyranosyl}-α-L-mannopyranoside
Registry NumbersSources
Reaxys:10143373Reaxys
Citations