myrciacitrin II
Basic information
- CAS
203734-34-3- Standard SMILES
COc1ccc(O)c([C@@H]2CC(=O)c3c(O)c(C)c(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c(C)c3O2)c1- InChIKey
NKSFQBQBCJYBBO-WUQIJIJDSA-N- Molecular formula
- C24H28O11
- Average molar mass
- 492.5 g/mol
- Monoisotopic mass
- 492.16316171
Overview
Myrciacitrin II is a flavanone glycoside that is (2S)-flavanone substituted by methyl groups at positions 6 and 8, hydroxy groups at positions 5 and 2', a methoxy group at position 5' and a beta-D-glucopyranosyloxy residue at position 7. Isolated from the leaves of Myrcia multiflora, it exhibits inhibitory activity against alpha-glucosidase and aldose reductase. It has a role as an EC 1.1.1.21 (aldehyde reductase) inhibitor, an EC 3.2.1.20 (alpha-glucosidase) inhibitor and a plant metabolite. It is a beta-D-glucoside, a monomethoxyflavanone, a dihydroxyflavanone, a monosaccharide derivative and a flavanone glycoside.
Names & identifiers
- Preferred name
- myrciacitrin II
- IUPAC
- (2S)-5-hydroxy-2-(2-hydroxy-5-methoxyphenyl)-6,8-dimethyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
Names & synonyms
Myrciacitrin II203734-34-3(2S)-5-hydroxy-2-(2-hydroxy-5-methoxyphenyl)-6,8-dimethyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-oneCHEBI:66418(2S)-6,8-dimethyl-5,7,2'-trihydroxy-5'-methoxy-flavanone-7-O-beta-D-glucopyranoside(2S)-5-hydroxy-2-(2-hydroxy-5-methoxyphenyl)-6,8-dimethyl-4-oxo-3,4-dihydro-2H-chromen-7-yl beta-D-glucopyranoside(2S)-5-hydroxy-2-(2-hydroxy-5-methoxyphenyl)-6,8-dimethyl-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-2,3-dihydrochromen-4-oneRefChem:160363(2S)-6,8-Dimethyl-5,7,2'-trihydroxy-5'-methoxy-flavanone-7-O-b-D-glucopyranoside(2S)-6,8-Dimethyl-5,7,2'-trihydroxy-5'-methoxy-flavanone-7-O-I2-D-glucopyranosideSCHEMBL29711399DTXSID60942533
Show more names
Q27134975(2S)-5-Hydroxy-2-(2-hydroxy-5-methoxyphenyl)-6,8-dimethyl-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl beta-D-glucopyranoside5-Hydroxy-2-(2-hydroxy-5-methoxyphenyl)-6,8-dimethyl-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl hexopyranoside
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 175 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 5
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 736
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