Lonicerin
Basic information
- CAS
25694-72-8- Standard SMILES
C[C@@H]1O[C@@H](O[C@H]2[C@H](Oc3cc(O)c4c(=O)cc(-c5ccc(O)c(O)c5)oc4c3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O- InChIKey
SHPPXMGVUDNKLV-KMFFXDMSSA-N- Molecular formula
- C27H30O15
- Average molar mass
- 594.5 g/mol
- Monoisotopic mass
- 594.15847025
Overview
Luteolin 7-O-neohesperidoside is a disaccharide derivative that is luteolin substituted by a 2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as a metabolite and an antibacterial agent. It is a neohesperidoside, a trihydroxyflavone, a glycosyloxyflavone and a disaccharide derivative. It is functionally related to a luteolin.
Names & identifiers
- Preferred name
- Lonicerin
- IUPAC
- 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxychromen-4-one
- English name
- Lonicerin
- Molecular formula
- C27H30O15
- Molecular weight
- 594.52
Names & synonyms
LonicerinVeronicastroside25694-72-8Luteolin-7-O-rhamnosideLuteoline-7-rhamnoglucosideALJ2FB4ZDM7-((2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5-hydroxy-4H-1-benzopyran-4-oneDTXSID301803897-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxychromen-4-one7-((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)oxy-2-(3,4-dihydroxyphenyl)-5-hydroxychromen-4-oneRefChem:924914DTXCID90102880
Show more names
ScolymosideLUTEOLIN-7-RUTINOSIDELonicerin-RMLonicerin, 10 mM in DMSOLuteolin-7-neohesperidosideLuteolin 7-beta-neohesperidosideLonicerin Luteolin 7-neohesperidosideLonicerin（Luteolin-7-O-neohesperidoside）
Luteolin 7-O-neohesperidosideLUTEOLIN-7-O-NEOHESPERIDOSIDELuteolin 7-neohesperidosideUNII-ALJ2FB4ZDMCHEMBL452979SCHEMBL2146638EX-A67737-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-2-(3,4-dihydroxyphenyl)-5-hydroxy-4H-chromen-4-one
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 245 Ų
- Hydrogen bond donors
- 9
- Hydrogen bond acceptors
- 15
- Rotatable bonds
- 6
- Heavy atoms
- 42
- Formal charge
- 0
- Complexity
- 979
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 957.8 · 957.8±65.0 °C(Predicted)
- Density
- 1.76 · 1.76±0.1 g/cm3(Predicted)
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- 50 mg/ml; · DMF: 50 mg/ml; DMSO: 50 mg/ml
- form
- A crystalline solid
- pka
- 6.08 · 6.08±0.40(Predicted)
- color
- Light yellow to yellow
- InChIKey
- SHPPXMGVUDNKLV-KMFFXDMSSA-N
- SMILES
- O1[C@H]([C@@H]([C@@H]([C@H]([C@@H]1C)O)O)O)O[C@H]2[C@@H](O[C@@H]([C@H]([C@@H]2O)O)CO)Oc3cc4[o]c(c[c](c4c(c3)O)=O)c5cc(c(cc5)O)O
- FDA UNII
- 2 FB4ZDM · ALJ2FB4ZDM
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS02
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H320-H335-H336-H226
- Precautionary statements
- P501-P261-P240-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P303+P361+P353-P304+P340+P312-P403+P233-P403+P235-P405
Chemistry & industry
Applications
UsesLonicerin is an anti-algE (alginate secretion protein) flavonoid with inhibitory activity for P. aeruginosa. Lonicerin prevents inflammation and apoptosis in LPS-induced acute lung injury[1][2].
Additional notes
DefinitionChEBI: A disaccharide derivative that is luteolin substituted by a 2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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