EMBL-EBI | Chemical Biology | ChEBI

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

CHEBI:66419 - myrciacitrin III

ChEBI IDCHEBI:66419
ChEBI Namemyrciacitrin III
Stars
DefinitionA flavanone glycoside that is (2S)-flavanone substituted by hydroxy groups at positions 5, 7 and 5', methyl group at positions 6 and 8 and a β-D-glucopyranosyloxy residue at position 2'. Isolated from the leaves of Myrcia multiflora, it exhibits inhibitory activity against aldose reductase.
Last Modified12 April 2013
DownloadsMolfile
FormulaC23H26O11
Net Charge0
Average Mass478.450
Monoisotopic Mass478.14751
SMILESCc1c(O)c(C)c2c(c1O)C(=O)C[C@@H](c1cc(O)ccc1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)O2
InChIInChI=1S/C23H26O11/c1-8-17(27)9(2)22-16(18(8)28)12(26)6-14(32-22)11-5-10(25)3-4-13(11)33-23-21(31)20(30)19(29)15(7-24)34-23/h3-5,14-15,19-21,23-25,27-31H,6-7H2,1-2H3/t14-,15+,19+,20-,21+,23+/m0/s1
InChIKeyVOYSOOOEBGYFAP-UZLUQKTDSA-N
Species of MetaboliteComponentSourceComments
Myrcia multiflora (ncbitaxon:375255) leaf (BTO:0000713) PubMed (11911215)
Roles Classification
Biological Roles:
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 III (CHEBI:66419) has role EC 1.1.1.21 (aldehyde reductase) inhibitor (CHEBI:48550)
myrciacitrin III (CHEBI:66419) has role metabolite (CHEBI:25212)
myrciacitrin III (CHEBI:66419) is a flavanone glycoside (CHEBI:72730)
myrciacitrin III (CHEBI:66419) is a monosaccharide derivative (CHEBI:63367)
myrciacitrin III (CHEBI:66419) is a trihydroxyflavanone (CHEBI:38739)
myrciacitrin III (CHEBI:66419) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
2-[(2S)-5,7-dihydroxy-6,8-dimethyl-4-oxo-3,4-dihydro-2H-chromen-2-yl]-4-hydroxyphenyl β-D-glucopyranoside
Synonym  Source
(2S)-6,8-dimethyl-5,7,2',5'-tetrahydroxyflavanone-2'-O-β-D-glucopyranosideChEBI
Registry NumbersSources
Reaxys:9173871Reaxys
Citations