EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:66417 - myrciacitrin I

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:
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).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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