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131189-57-6

131189-57-6 | 2H-Pyran-5-carboxylic acid, 3-ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-[2-[(3,4,5-trihydroxybenzoyl)oxy]ethyl]-, methyl ester, (2S,3R,4S)-

CAS No: 131189-57-6 Catalog No: AG000VNU MDL No:MFCD21606970

Product Description

Catalog Number:
AG000VNU
Chemical Name:
2H-Pyran-5-carboxylic acid, 3-ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-[2-[(3,4,5-trihydroxybenzoyl)oxy]ethyl]-, methyl ester, (2S,3R,4S)-
CAS Number:
131189-57-6
Molecular Formula:
C24H30O14
Molecular Weight:
542.4866
MDL Number:
MFCD21606970
IUPAC Name:
methyl (2S,3R,4S)-3-ethenyl-4-[2-(3,4,5-trihydroxybenzoyl)oxyethyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
InChI:
InChI=1S/C24H30O14/c1-3-11-12(4-5-35-21(32)10-6-14(26)17(28)15(27)7-10)13(22(33)34-2)9-36-23(11)38-24-20(31)19(30)18(29)16(8-25)37-24/h3,6-7,9,11-12,16,18-20,23-31H,1,4-5,8H2,2H3/t11-,12+,16-,18-,19+,20-,23+,24+/m1/s1
InChI Key:
SMTKSCGLXONVGL-UPIRYGIPSA-N
SMILES:
C=C[C@H]1[C@@H](OC=C([C@H]1CCOC(=O)c1cc(O)c(c(c1)O)O)C(=O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O

Properties

Complexity:
851  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Defined Bond Stereocenter Count:
0
Exact Mass:
542.164g/mol
Formal Charge:
0
Heavy Atom Count:
38  
Hydrogen Bond Acceptor Count:
14  
Hydrogen Bond Donor Count:
7  
Isotope Atom Count:
0
Molecular Weight:
542.49g/mol
Monoisotopic Mass:
542.164g/mol
Rotatable Bond Count:
11  
Topological Polar Surface Area:
222A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.2  

Literature

Title Journal
[Optimization of microwave-assisted extraction with RSM and HPLC determination for three iridoid glycosides in Cornus officinalis]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20110701
Protective roles of cornuside in acute myocardial ischemia and reperfusion injury in rats. Phytomedicine : international journal of phytotherapy and phytopharmacology 20110215
Protective effect of cornuside against carbon tetrachloride-induced acute hepatic injury. Bioscience, biotechnology, and biochemistry 20110101
Cornuside suppresses lipopolysaccharide-induced inflammatory mediators by inhibiting nuclear factor-kappa B activation in RAW 264.7 macrophages. Biological & pharmaceutical bulletin 20110101
Effect of cornuside on experimental sepsis. Planta medica 20090501
Cornuside attenuates apoptosis and ameliorates mitochondrial energy metabolism in rat cortical neurons. Pharmacology 20090101
Simultaneous determination of six active components in crude and processed Fructus Corni by high performance liquid chromatography. Journal of pharmaceutical and biomedical analysis 20080910
Endothelial NO/cGMP-dependent vascular relaxation of cornuside isolated from the fruit of Cornus officinalis. Planta medica 20071101
Cornuside suppresses cytokine-induced proinflammatory and adhesion molecules in the human umbilical vein endothelial cells. Biological & pharmaceutical bulletin 20070901

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