CHEBI:132850 - trifloroside

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ChEBI Name trifloroside
ChEBI ID CHEBI:132850
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter qingping liu
Supplier Information
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Formula C35H42O20
Net Charge 0
Average Mass 782.697
Monoisotopic Mass 782.22694
InChI InChI=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
InChIKey RMBMLYUFYBZPCX-XQARLGSBSA-N
SMILES O1[C@@H](O[C@@H]2OC=C3[C@]([C@H]2C=C)(CCOC3=O)[H])[C@H](OC(=O)C)[C@@H](OC(=O)C)[C@H](OC(=O)C4=C(O)C(O[C@@H]5O[C@@H]([C@@H](O)[C@H](O)[C@H]5O)CO)=CC=C4)[C@H]1COC(=O)C
Metabolite of Species Details
Gentiana scabra (NCBI:txid292393) Found in root (BTO:0001188). See: PubMed
Gentiana scabra (NCBI:txid292393) Found in rhizome (BTO:0001181). From rhizomes and rooots. See: PubMed
Gentiana siphonantha (NCBI:txid374097) Found in root (BTO:0001188). Methanol extract of rhizomes and roots. See: PubMed
Gentiana tibetica (NCBI:txid374099) Found in root (BTO:0001188). Ethanol extract. See: PubMed
Gentiana lutea (NCBI:txid38851) Found in seed (BTO:0001226). Main glycosidic component See: PubMed
Gentiana macrophylla (NCBI:txid50765) Found in root (BTO:0001188). Aqueous acetone extract. See: PubMed
Gentiana triflora (NCBI:txid55190) In ethanol extract. See: PubMed
Gentiana gelida (NCBI:txid553046) Found in aerial part (BTO:0001658). See: PubMed
ChEBI Ontology
Outgoing trifloroside (CHEBI:132850) is a β-D-glucoside (CHEBI:22798)
trifloroside (CHEBI:132850) is a δ-lactone (CHEBI:18946)
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)
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 Xref Database
C00010796 KNApSAcK
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Registry Numbers Types Sources
53823-10-2 CAS Registry Number ChemIDplus
53823-10-2 CAS Registry Number KNApSAcK
7970578 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12822897 PubMed citation Europe PMC
17221438 PubMed citation Europe PMC
17404979 PubMed citation Europe PMC
23599008 PubMed citation Europe PMC
26129938 PubMed citation Europe PMC
9396170 PubMed citation Europe PMC
9397205 PubMed citation Europe PMC
9611826 PubMed citation Europe PMC
PMC4131568 PubMed Central citation Europe PMC
Last Modified
25 August 2016