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CHEBI:66773 - (2S)-poncirin

ChEBI IDCHEBI:66773
ChEBI Name(2S)-poncirin
Stars
ASCII Name(2S)-poncirin
DefinitionA flavanone glycoside that is 4'-methoxy-5,7-dihydroxyflavanone attached to a neohesperidose (α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranose) residue via a glycosidic linkage. It has been isolated from the fruits of Poncirus trifoliata and exhibits inhibitory activity against liopolysaccharide (LPS)-induced prostaglandin E2 and interleukin-6 (IL-6) production.
Secondary ChEBI IDCHEBI:8332
Last Modified6 April 2018
DownloadsMolfile
FormulaC28H34O14
Net Charge0
Average Mass594.566
Monoisotopic Mass594.19486
SMILES[H][C@@]1(O[C@H]2[C@H](Oc3cc(O)c4c(c3)O[C@H](c3ccc(OC)cc3)CC4=O)O[C@H](CO)[C@@H](O)[C@@H]2O)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
InChIInChI=1S/C28H34O14/c1-11-21(32)23(34)25(36)27(38-11)42-26-24(35)22(33)19(10-29)41-28(26)39-14-7-15(30)20-16(31)9-17(40-18(20)8-14)12-3-5-13(37-2)6-4-12/h3-8,11,17,19,21-30,32-36H,9-10H2,1-2H3/t11-,17-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
InChIKeyNLAWPKPYBMEWIR-SKYQDXIQSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Poncirus trifoliata (ncbitaxon:37690) fruit (BTO:0000486) PubMed (17666859)
Roles Classification
Biological Role:
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)-poncirin (CHEBI:66773) has functional parent 4'-methoxy-5,7-dihydroxyflavanone (CHEBI:27552)
(2S)-poncirin (CHEBI:66773) has role plant metabolite (CHEBI:76924)
(2S)-poncirin (CHEBI:66773) is a 4'-methoxyflavanones (CHEBI:140332)
(2S)-poncirin (CHEBI:66773) is a disaccharide derivative (CHEBI:63353)
(2S)-poncirin (CHEBI:66773) is a flavanone glycoside (CHEBI:72730)
(2S)-poncirin (CHEBI:66773) is a monomethoxyflavanone (CHEBI:38738)
(2S)-poncirin (CHEBI:66773) is a neohesperidoside (CHEBI:25495)
IUPAC Name 
(2S)-5-hydroxy-2-(4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside
Synonyms  Source
Isosakuranetin 7-O-neohesperidosideKEGG COMPOUND
CitrifoliosideHMDB
Isosakuranetin-7-O-beta-D-neohesperidosideHMDB
Manual XrefsDatabases
C00000995KNApSAcK
C09830KEGG COMPOUND
PoncirinWikipedia
HMDB0037487HMDB
Registry NumbersSources
Reaxys:74301Reaxys
CAS:14941-08-3ChemIDplus
CAS:14941-08-3KEGG COMPOUND
Citations