Limonin17-beta-D-glucopyranoside
Basic information
- CAS
123564-61-4- Standard SMILES
CC1(C)OC2CC(=O)OCC23C1CC(=O)C1(C)C3CCC(C)(C(OC2OC(CO)C(O)C(O)C2O)c2ccoc2)C12OC2C(=O)O- InChIKey
FYIKIBQJAJRKQM-UHFFFAOYSA-N- Molecular formula
- C32H42O14
- Average molar mass
- 650.7 g/mol
- Monoisotopic mass
- 650.25745601
Names & identifiers
- Preferred name
- Limonin17-beta-D-glucopyranoside
- IUPAC
- 5-[furan-3-yl-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-5,7,11,11-tetramethyl-8,15-dioxospiro[12,16-dioxatetracyclo[8.7.0.01,13.02,7]heptadecane-6,3'-oxirane]-2'-carboxylic acid
- English name
- LiMoNiN17-beta-D-glucopyranoside
- Molecular formula
- C32H42O14
- Molecular weight
- 650.67
Names & synonyms
Limonin17-beta-D-glucopyranosideLimonin 17-?-D-GlucopyranosideDTXSID80924538YEA56461C32H42O14MFCD0384056910-[(Furan-3-yl)(hexopyranosyloxy)methyl]-6,6,8a,10-tetramethyl-3,8-dioxodecahydro-1H,3H,6H-spiro[naphtho[1',2':3,4]furo[3,2-c]pyran-9,2'-oxirane]-3'-carboxylic acid5-[3-furyl-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-methyl]-5,7,11,11-tetramethyl-8,15-dioxo-spiro[12,16-dioxatetracyclo[8.7.0.01,13.02,7]heptadecane-6,3'-oxirane]-2'-carboxylic acid5-[furan-3-yl-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-5,7,11,11-tetramethyl-8,15-dioxospiro[12,16-dioxatetracyclo[8.7.0.01,13.02,7]heptadecane-6,3'-oxirane]-2'-carboxylic acidCcris 6986LIMONIN GLUCOSIDE(RG)limonin 17-beta-D-glucoside
Show more names
Spiro[9H,11H-naphtho[1',2':3,4]furo[3,2-c]pyran-5(2H),2'-oxirane]-3'-carboxylic acid, 6-[(S)-3-furanyl(β-D-glucopyranosyloxy)methyl]decahydro-2,2,4a,6-tetramethyl-4,11-dioxo-, (2aR,3'S,4aS,5R,6S,8aR,8bR,12aS)-
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 215 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 6
- Heavy atoms
- 46
- Formal charge
- 0
- Complexity
- 1,290
Physicochemical properties
- Boiling point
- 866.8 · 866.8±65.0 °C(Predicted)
- Density
- 1.51 · 1.51±0.1 g/cm3(Predicted)
- solubility
- Methanol: SolubleWater: Soluble
- pka
- 3.31 · 3.31±0.70(Predicted)
- FDA UNII
- 9553 Q8Z7PF · 9553Q8Z7PF
Chemistry & industry
Applications
UsesLimonin glucoside can be isolated from seeds of Citrus reticulata. Limonin glucoside induces activation of caspase-3. Limonin glucoside inhibits the proliferation of human colon adenocarcinoma (SW480) cells (IC50: 37.39 μM)[1].
Additional notes
DefinitionChEBI: Limonin 17-beta-D-glucoside is a beta-D-glucoside. It is functionally related to a limonin. It is a conjugate acid of a limonin 17-beta-D-glucoside(1-).
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