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SILENEOSIDE G

Year of first isolation: 1998
Formula:C39H64O17
Molecular weight:804
Occurence in plants:
Silene brahuica [Caryophyllaceae] » Images of Silene brahuica Wikipedia: Silene brahuica [Caryophyllaceae]
Occurence in animals:
 
SILENEOSIDE G

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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C1[C@]2([C@@](C[C@H]([C@H]1O)O[C@H]1C(C([C@H](C(O1)CO)O)O)O)(C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O[C@@H]1C(C([C@H](C(O1)CO)O)O)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,13R,14S,17S)-17-((2R,3R)-2,6-dihydroxy-6-methyl-3-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)heptan-2-yl)-2,14-dihydroxy-10,13-dimethyl-3-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
DFOWOAPXMUUUGC-FGZXGESCSA-N
InChIInChI=1S/C39H64O18/c1-34(2,50)9-8-25(57-33-31(49)29(47)27(45)22(16-41)56-33)37(5,51)23-7-11-38(52)18-12-24(43)39(53)14-20(54-32-30(48)28(46)26(44)21(15-40)55-32)19(42)13-36(39,4)17(18)6-10-35(23,38)3/h12,17,19-23,25-33,40-42,44-53H,6-11,13-16H2,1-5H3/t17-,19-,20+,21?,22?,23-,25+,26-,27-,28?,29?,30?,31?,32+,33+,35+,36+,37+,38+,39+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)588 (M+-162-3H2O) (2.5), 570 (2), 426 (38), 363 (35), 345 (40), 327 (41), 311 (35), 309 (38), 300 (35), 145 (50), 143 (52), 99 (100), 81 (97), 69 (98)
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0139.36
0268.05
0379.72
0431.61
0551.41
06203.01
07121.46
08166.54
0934.22
1038.50
1121.01
1231.97
1348.05
1484.15
1531.72
1621.42
1749.85
1818.05
1924.24
2077.81
2122.28
2290.96
2327.11
2441.75
2569.72
2629.73
2729.73
gal-1'103.68
gal-2'70.93
gal-3'71.75
gal-4'71.15
gal-5'72.44
gal-6'62.59
Galactose (3-O-) 
glu-1"104.04
glu-2"73.44
glu-3"79.10
glu-4"71.19
glu-5"78.30
glu-6"62.74
Glucose (22-O-) 
C5D5N
01-Ha 
01-He 
02-Ha4.10 (m)
03-He4.10 (m)
04-Ha 
04-He 
05-H2.79 (dd, 13.4, 3.6)
07-H6.02 (s)
09-H3.50 (t, 7.9)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.96 (t, 8.5)
18-Me1.24 (s)
19-Me0.97 (s)
21-Me1.67 (s)
22-H3.78 (d, 9)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.40 (s)*
27-Me1.47 (s)*
H-1"5.69 (d, 4.03)
H-1'5.62 (d, 3.9)

PHYSICAL PROPERTIES

M.P.225-227 °C ;
[α]D20+ 121 ? 2 ° (c 0.10; MeOH)
IR (KBr) ν max (cm-1)3372 (OH), 1653 (7-ene-6-one)
UV (EtOH) λ max (log ε)245 (4.01) ;

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSADIKOV, Z.T. et al. (1998) Khim. Prir. Soedin., 663-665 Search more

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© Université Pierre & Marie Curie, Paris 6, France
© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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