Myrciacitrin I
Basic information
- CAS
203734-33-2- Standard SMILES
Cc1c(O)c2c(c(C)c1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)O[C@H](c1cc(O)ccc1O)CC2=O- InChIKey
XIMHLIFRXMEWEW-HMFSKKNISA-N- Molecular formula
- C23H26O11
- Average molar mass
- 478.4 g/mol
- Monoisotopic mass
- 478.14751164
Overview
Myrciacitrin I is 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 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 a metabolite, an EC 1.1.1.21 (aldehyde reductase) inhibitor and an EC 3.2.1.20 (alpha-glucosidase) inhibitor. It is a beta-D-glucoside, a trihydroxyflavanone, a monosaccharide derivative and a flavanone glycoside.
Names & identifiers
- Preferred name
- Myrciacitrin I
- IUPAC
- (2S)-2-(2,5-dihydroxyphenyl)-5-hydroxy-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 I203734-33-2(2S)-2-(2,5-dihydroxyphenyl)-5-hydroxy-6,8-dimethyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-oneCHEBI:664174H-1-Benzopyran-4-one, 2-(2,5-dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-2,3-dihydro-5-hydroxy-6,8-dimethyl-, (2S)-(2S)-6,8-dimethyl-5,7,2',5'-tetrahydroxyflavanone-7-O-beta-D-glucopyranoside(2S)-2-(2,5-dihydroxyphenyl)-5-hydroxy-6,8-dimethyl-4-oxo-3,4-dihydro-2H-chromen-7-yl beta-D-glucopyranoside(2S)-2-(2,5-dihydroxyphenyl)-5-hydroxy-6,8-dimethyl-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-2,3-dihydrochromen-4-oneRefChem:160362(2S)-6,8-Dimethyl-5,7,2',5'-tetrahydroxyflavanone-7-O-b-D-glucopyranoside(2S)-6,8-Dimethyl-5,7,2',5'-tetrahydroxyflavanone-7-O-I2-D-glucopyranosideSCHEMBL29711602
Show more names
DTXSID00942532Q27134974(2S)-2-(2,5-Dihydroxyphenyl)-5-hydroxy-6,8-dimethyl-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl beta-D-glucopyranoside2-(2,5-Dihydroxyphenyl)-5-hydroxy-6,8-dimethyl-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl hexopyranoside
Properties
Computed structural properties
- XLogP
- 1
- Topological polar surface area
- 186 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 4
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 721
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