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CHEBI:66418 - myrciacitrin II

ChEBI IDCHEBI:66418
ChEBI Namemyrciacitrin II
Stars
DefinitionA flavanone glycoside that is (2S)-flavanone substituted by methyl groups at positions 6 and 8, hydroxy groups at positions 5 and 2', a methoxy group at position 5' and a β-D-glucopyranosyloxy residue at position 7. Isolated from the leaves of Myrcia multiflora, it exhibits inhibitory activity against α-glucosidase and aldose reductase.
Last Modified9 April 2018
DownloadsMolfile
FormulaC24H28O11
Net Charge0
Average Mass492.477
Monoisotopic Mass492.16316
SMILESCOc1ccc(O)c([C@@H]2CC(=O)c3c(O)c(C)c(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c(C)c3O2)c1
InChIInChI=1S/C24H28O11/c1-9-18(28)17-14(27)7-15(12-6-11(32-3)4-5-13(12)26)33-23(17)10(2)22(9)35-24-21(31)20(30)19(29)16(8-25)34-24/h4-6,15-16,19-21,24-26,28-31H,7-8H2,1-3H3/t15-,16+,19+,20-,21+,24-/m0/s1
InChIKeyNKSFQBQBCJYBBO-WUQIJIJDSA-N
Species of MetaboliteComponentSourceComments
Myrcia multiflora (ncbitaxon:375255) leaf (BTO:0000713) PubMed (9468642)
Roles Classification
Biological Roles:
EC 3.2.1.20 (alpha-glucosidase) inhibitor  An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of α-glucosidase (EC 3.2.1.20).
EC 1.1.1.21 (aldehyde reductase) inhibitor  An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).
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)
myrciacitrin II (CHEBI:66418) has role EC 1.1.1.21 (aldehyde reductase) inhibitor (CHEBI:48550)
myrciacitrin II (CHEBI:66418) has role EC 3.2.1.20 (α-glucosidase) inhibitor (CHEBI:67239)
myrciacitrin II (CHEBI:66418) has role plant metabolite (CHEBI:76924)
myrciacitrin II (CHEBI:66418) is a dihydroxyflavanone (CHEBI:38749)
myrciacitrin II (CHEBI:66418) is a flavanone glycoside (CHEBI:72730)
myrciacitrin II (CHEBI:66418) is a monomethoxyflavanone (CHEBI:38738)
myrciacitrin II (CHEBI:66418) is a monosaccharide derivative (CHEBI:63367)
myrciacitrin II (CHEBI:66418) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
(2S)-5-hydroxy-2-(2-hydroxy-5-methoxyphenyl)-6,8-dimethyl-4-oxo-3,4-dihydro-2H-chromen-7-yl β-D-glucopyranoside
Synonym  Source
(2S)-6,8-dimethyl-5,7,2'-trihydroxy-5'-methoxy-flavanone-7-O-β-D-glucopyranosideChEBI
Registry NumbersSources
Reaxys:8024149Reaxys
Citations