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SILENEOSIDE J

Year of first isolation: 2021
Formula:C39H64O17
Molecular weight:804
Occurence in plants:
Silene tatarinowii [Caryophyllaceae] » Images of Silene tatarinowii
Occurence in animals:
 
SILENEOSIDE J

STRUCTURE DESCRIPTORS

Isomeric SMILES
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C[C@@]12[C@@](C(C=C3C2CC[C@@]4(C)[C@@]3(O)CC[C@@H]4[C@](C)([C@H](O)CCC(C)(O)C)O)=O)([H])C[C@@H](O[C@@H]5[C@H](O)[C@@H](O[C@@H]6[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O6)[C@@H](O)[C@@H](CO)O5)[C@@H](O)C1 » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,13R,14S,17S)-3-(((2S,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-2,14-dihydroxy-10,13-dimethyl-17-((2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl)-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 ]
XTTUTXJVCFWKEU-IPYTTYCSSA-N
InChIInChI=1S/C39H64O17/c1-35(2,50)9-8-26(44)38(5,51)25-7-11-39(52)18-12-20(42)19-13-22(21(43)14-36(19,3)17(18)6-10-37(25,39)4)53-34-31(49)32(28(46)24(16-41)55-34)56-33-30(48)29(47)27(45)23(15-40)54-33/h12,17,19,21-34,40-41,43-52H,6-11,13-16H2,1-5H3/t17?,19-,21-,22+,23+,24+,25-,26+,27-,28-,29-,30+,31+,32-,33+,34-,36+,37+,38+,39+/m0/s1

MASS SPECTRUM

HRESIMS (positive ion mode) m/z 827.4034 [M+Na]+, calc. for C39H64O17Na 827.4041

CARBON NMR

PROTON NMR

C5D5N
0139.0
0268.6
0381.5
0432.2
0552.9
06203.4
07122.0
08167.1
0934.7
1039.8
1121.5
1232.4
1348.5
1484.6
1532.4
1622.2
1750.6
1818.4
1924.7
2077.4
2122.0
2278.1
2328.0
2443.2
2570.1
2630.6
2730.5
[Gal] 1'104.2
[Gal] 2'71.3
[Gal] 3'79.9
[Gal] 4'71.8
[Gal] 5'73.1
[Gal] 6'61.3
 [Gal] 1"103.7
 [Gal] 2"71.8
 [Gal] 3"71.6
 [Gal] 4"71.8
 [Gal] 5"73.9
 [Gal] 6"63.1
C5D5N
01-Ha2.13 (m)
01-Hb1.73 (m) [Gal] 1'-H 5.77 (d, 3.6)
02-Ha4.06 (m) [Gal] 2'-H 4.70 (m)
03-He4.72 (m) [Gal] 3'-H 4.06 (m)
04-Ha2.13 (m) [Gal] 4'-H 4.50 (m)
04-Hb1.86 (m) [Gal] 5'-H 4.70 (m)
05-H2.47 (dd, 12.6, 2.4) [Gal] 6'-Ha 4.56 (m)
07-H6.21 (s) [Gal] 6'-Hb 4.28 (m)
09-H3.47 (t, 8.2)
11-Ha1.76 (m)
11-Hb1.66 (m)
12-Ha2.55 (m) [Gal] 2
12-Hb1.98 (m) [Gal] 3
15-Ha2.13 (m) [Gal] 4
15-Hb1.76 (m) [Gal] 5
16-Ha2.44 (m) [Gal] 6
16-Hb2.09 (m) [Gal] 6
17-H2.97 (t, 8.4)
18-Me1.20 (s)
19-Me0.93 (s)
21-Me1.59 (s)
22-H3.86 (m)
23-Ha2.13(m)
23-Hb1.81 (m)
24-Ha2.29 (m)
24-Hb1.81 (m)
26-Me1.36 (s)
27-Me1.36 (s)
[Gal] 1'-H5.77 (d, 3.6)
[Gal] 2'-H4.70 (m)
[Gal] 3'-H4.06 (m)
[Gal] 4'-H4.50 (m)
[Gal] 5'-H4.70 (m)
[Gal] 6'-Ha4.56 (m)
[Gal] 6'-Hb4.28 (m)
 [Gal] 1"-H5.53 (d, 1.6)
 [Gal] 2"-H4.54 (m)
 [Gal] 3"-H4.70 (m)
 [Gal] 4"-H4.54 (m)
 [Gal] 5"-H4.90 (m)
 [Gal] 6"Ha4.44 (m)
 [Gal] 6"Hb4.31 (m)

PHYSICAL PROPERTIES

M.P.— °C
[α]D2547.8 (c 0.2; MeOH)
IR (KBr) ν max3393, 2963, 2940, 1653, 1379, 1057 (cm-1)
UV (MeOH) λ max230, 270 (nm)

CHROMATOGRAPHY

GLC
TLC
HPTLC
HPLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationZHANG, H. et al. (2020) Rec. Nat. Products 15, 1 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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