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CHEBI:66417 - myrciacitrin I

Default Structure
ChEBI IDCHEBI:66417
ChEBI Namemyrciacitrin I
Stars
DefinitionA flavanone glycoside that is (2S)-flavanone substituted by methyl groups at positions 6 and 8, hydroxy groups at positions 5, 2' and 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 Modified12 April 2013
DownloadsMolfile
FormulaC23H26O11
Net Charge0
Average Mass478.450
Monoisotopic Mass478.14751
SMILESCc1c(O)c2c(c(C)c1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)O[C@H](c1cc(O)ccc1O)CC2=O
InChIInChI=1S/C23H26O11/c1-8-17(28)16-13(27)6-14(11-5-10(25)3-4-12(11)26)32-22(16)9(2)21(8)34-23-20(31)19(30)18(29)15(7-24)33-23/h3-5,14-15,18-20,23-26,28-31H,6-7H2,1-2H3/t14-,15+,18+,19-,20+,23-/m0/s1
InChIKeyXIMHLIFRXMEWEW-HMFSKKNISA-N
Species of MetaboliteComponentSourceComments
Myrcia multiflora (ncbitaxon:375255) leaf (BTO:0000713) PubMed (9468642)
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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).
ChEBI Ontology
Outgoing Relation(s)
myrciacitrin I (CHEBI:66417) has role EC 1.1.1.21 (aldehyde reductase) inhibitor (CHEBI:48550)
myrciacitrin I (CHEBI:66417) has role EC 3.2.1.20 (α-glucosidase) inhibitor (CHEBI:67239)
myrciacitrin I (CHEBI:66417) has role metabolite (CHEBI:25212)
myrciacitrin I (CHEBI:66417) is a flavanone glycoside (CHEBI:72730)
myrciacitrin I (CHEBI:66417) is a monosaccharide derivative (CHEBI:63367)
myrciacitrin I (CHEBI:66417) is a trihydroxyflavanone (CHEBI:38739)
myrciacitrin I (CHEBI:66417) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
(2S)-2-(2,5-dihydroxyphenyl)-5-hydroxy-6,8-dimethyl-4-oxo-3,4-dihydro-2H-chromen-7-yl β-D-glucopyranoside
Synonym  Source
(2S)-6,8-dimethyl-5,7,2',5'-tetrahydroxyflavanone-7-O-β-D-glucopyranosideChEBI
Registry NumbersSources
Reaxys:8023603Reaxys
Citations