CHEBI:66420 - myrciacitrin IV

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name myrciacitrin IV
ChEBI ID CHEBI:66420
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C32H32O13
Net Charge 0
Average Mass 624.58870
Monoisotopic Mass 624.18429
InChI InChI=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
InChIKey VPHZQTMMIZNNMH-DHVWHUDASA-N
SMILES Cc1c(O)c2C(=O)C[C@H](Oc2c(C)c1O[C@@H]1O[C@H](COC(=O)\C=C\c2ccc(O)cc2)[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 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 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 β-D-glucoside (CHEBI:22798)
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)
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-glucopyranoside ChEBI
Registry Number Type Source
9178916 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
11911215 PubMed citation Europe PMC
Last Modified
12 April 2013