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CHEBI:66420 - myrciacitrin IV

Default Structure
ChEBI IDCHEBI:66420
ChEBI Namemyrciacitrin IV
Stars
DefinitionA flavanone glycoside that is (2S)-flavanone substituted by hydroxy groups at positions 5, 2' and 5', methyl groups at positions 6 and 8 and a (6''-O-p-coumaroyl)-β-D-glucopyranosyloxy residue at position 7. Isolated from the leaves of Myrcia multiflora, it exhibits inhibitory activity against aldose reductase.
Last Modified12 April 2013
DownloadsMolfile
FormulaC32H32O13
Net Charge0
Average Mass624.595
Monoisotopic Mass624.18429
SMILESCc1c(O)c2c(c(C)c1O[C@@H]1O[C@H](COC(=O)/C=C/c3ccc(O)cc3)[C@@H](O)[C@H](O)[C@H]1O)O[C@H](c1cc(O)ccc1O)CC2=O
InChIInChI=1S/C32H32O13/c1-14-26(38)25-21(36)12-22(19-11-18(34)8-9-20(19)35)43-31(25)15(2)30(14)45-32-29(41)28(40)27(39)23(44-32)13-42-24(37)10-5-16-3-6-17(33)7-4-16/h3-11,22-23,27-29,32-35,38-41H,12-13H2,1-2H3/b10-5+/t22-,23+,27+,28-,29+,32-/m0/s1
InChIKeyVPHZQTMMIZNNMH-DHVWHUDASA-N
Species of MetaboliteComponentSourceComments
Myrcia multiflora (ncbitaxon:375255) leaf (BTO:0000713) PubMed (11911215)
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 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 IV (CHEBI:66420) has functional parent trans-4-coumaric acid (CHEBI:32374)
myrciacitrin IV (CHEBI:66420) has role EC 1.1.1.21 (aldehyde reductase) inhibitor (CHEBI:48550)
myrciacitrin IV (CHEBI:66420) has role metabolite (CHEBI:25212)
myrciacitrin IV (CHEBI:66420) is a cinnamate ester (CHEBI:36087)
myrciacitrin IV (CHEBI:66420) is a flavanone glycoside (CHEBI:72730)
myrciacitrin IV (CHEBI:66420) is a monosaccharide derivative (CHEBI:63367)
myrciacitrin IV (CHEBI:66420) is a trihydroxyflavanone (CHEBI:38739)
myrciacitrin IV (CHEBI:66420) 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 6-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-β-D-glucopyranoside
Synonym  Source
(2S)-6,8-dimethyl-5,7,2',5'-tetrahydroxyflavanone7-O-(6''-O-p-coumaroyl)-β-D-glucopyranosideChEBI
Registry NumbersSources
Reaxys:9178916Reaxys
Citations