CHEBI:66417 - myrciacitrin I

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ChEBI Name myrciacitrin I
ChEBI ID CHEBI:66417
Definition A 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.
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(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
InChIKey XIMHLIFRXMEWEW-HMFSKKNISA-N
SMILES Cc1c(O)c2C(=O)C[C@H](Oc2c(C)c1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1cc(O)ccc1O
Metabolite of Species Details
Myrcia multiflora (NCBI:txid375255) Found in leaf (BTO:0000713). See: PubMed
Roles Classification
Biological Role(s): EC 3.2.1.20 (alpha-glucosidase) inhibitor
An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 β-D-glucoside (CHEBI:22798)
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)
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-glucopyranoside ChEBI
Registry Number Type Source
8023603 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
9468642 PubMed citation Europe PMC
Last Modified
12 April 2013