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CHEBI:132850 - trifloroside

ChEBI IDCHEBI:132850
ChEBI Nametrifloroside
Stars
DefinitionA secoiridoid glycoside that is (4aS,5R,6R)-6-hydroxy-5-vinyl-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one in which the hydroxy group has been converted to the corresponding 2,3,6-tri-O-acetyl-β-D-glucoside, the 4-hydroxy group of which has been esterified by formal condensation with the carboxy group of 2,3-dihydroxybenzoic acid 3-β-D-glucoside. It is a component of Gentiana scabra root extract, which is used as an internal remedy in traditional Korean medicine for the treatment of diabetes mellitus.
Last Modified25 August 2016
Submitterliuqingping
DownloadsMolfile
FormulaC35H42O20
Net Charge0
Average Mass782.701
Monoisotopic Mass782.22694
SMILES[H][C@@]12CCOC(=O)C1=CO[C@@H](O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(=O)c3cccc(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c3O)[C@H](OC(C)=O)[C@H]1OC(C)=O)[C@@H]2C=C
InChIInChI=1S/C35H42O20/c1-5-17-18-9-10-46-31(44)20(18)12-48-33(17)55-35-30(50-16(4)39)29(49-15(3)38)28(23(53-35)13-47-14(2)37)54-32(45)19-7-6-8-21(24(19)40)51-34-27(43)26(42)25(41)22(11-36)52-34/h5-8,12,17-18,22-23,25-30,33-36,40-43H,1,9-11,13H2,2-4H3/t17-,18+,22-,23-,25-,26+,27-,28-,29+,30-,33+,34-,35+/m1/s1
InChIKeyRMBMLYUFYBZPCX-XQARLGSBSA-N
Species of MetaboliteComponentSourceComments
Gentiana scabra (ncbitaxon:292393)
root (BTO:0001188) PubMed (26129938)
rhizome (BTO:0001181) PubMed (17404979) From rhizomes and rooots.
Gentiana triflora (ncbitaxon:55190) - PubMed (23599008) In ethanol extract.
Gentiana lutea (ncbitaxon:38851) seed (BTO:0001226) PubMed (12822897) Main glycosidic component
Gentiana gelida (ncbitaxon:553046) aerial part (BTO:0001658) PubMed (17221438)
Gentiana tibetica (ncbitaxon:374099) root (BTO:0001188) PubMed (9611826) Ethanol extract.
Gentiana siphonantha (ncbitaxon:374097) root (BTO:0001188) PubMed (9396170) Methanol extract of rhizomes and roots.
Gentiana macrophylla (ncbitaxon:50765) root (BTO:0001188) PubMed (9397205) Aqueous acetone extract.
ChEBI Ontology
Outgoing Relation(s)
trifloroside (CHEBI:132850) is a acetate ester (CHEBI:47622)
trifloroside (CHEBI:132850) is a phenols (CHEBI:33853)
trifloroside (CHEBI:132850) is a pyranopyranone (CHEBI:131901)
trifloroside (CHEBI:132850) is a secoiridoid glycoside (CHEBI:50274)
trifloroside (CHEBI:132850) is a β-D-glucoside (CHEBI:22798)
trifloroside (CHEBI:132850) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(4aS,5R,6S)-1-oxo-5-vinyl-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl 2,3,6-tri-O-acetyl-4-O-[3-(β-D-glucopyranosyloxy)-2-hydroxybenzoyl]-β-D-glucopyranoside
Manual XrefsDatabases
C00010796KNApSAcK
Registry NumbersSources
Reaxys:7970578Reaxys
CAS:53823-10-2ChemIDplus
CAS:53823-10-2KNApSAcK
Citations