CHEBI:66419 - myrciacitrin III

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ChEBI Name myrciacitrin III
ChEBI ID CHEBI:66419
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C23H26O11
Net Charge 0
Average Mass 478.44590
Monoisotopic Mass 478.14751
InChI InChI=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
InChIKey VOYSOOOEBGYFAP-UZLUQKTDSA-N
SMILES Cc1c(O)c(C)c2O[C@@H](CC(=O)c2c1O)c1cc(O)ccc1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Metabolite of Species Details
Myrcia multiflora (NCBI:txid375255) Found in leaf (BTO:0000713). See: PubMed
Roles Classification
Biological Role(s): 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.
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ChEBI Ontology
Outgoing 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 β-D-glucoside (CHEBI:22798)
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)
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-glucopyranoside ChEBI
Registry Number Type Source
9173871 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
11911215 PubMed citation Europe PMC
Last Modified
12 April 2013