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SILENEOSIDE H

Year of first isolation: 2000
Formula:C35H56O14
Molecular weight:700
Occurence in plants:
Silene brahuica [Caryophyllaceae] » Images of Silene brahuica Wikipedia: Silene brahuica [Caryophyllaceae]
Occurence in animals:
 
SILENEOSIDE H

STRUCTURE DESCRIPTORS

Canonical SMILESCC(=O)OC(C)(C)CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(C(C(C(C4)O)O)O)C)C)O)O)OC5C(C(C(C(O5)CO)O)O)O
Isomeric SMILES
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[C@@H]1([C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)OC(=O)C)O[C@@H]1C(C([C@@H](C(O1)CO)O)O)O)O)O)C)C)O » JSMol: View in 3D
IUPAC Name[(5R,6R)-6-hydroxy-2-methyl-6-[(1S,2R,3R,5R,9R,10R,13R,14S,17S)-1,2,3,14-tetrahydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl] acetate
CAS-RN 
PubChem CID10699909
InChiKey
[ ChemIDPlus: search ]
NFANXDIFZWNPKW-GFUCUAQMSA-N
InChIInChI=1S/C35H56O14/c1-16(37)49-31(2,3)10-9-24(48-30-28(43)27(42)26(41)22(15-36)47-30)34(6,45)23-8-12-35(46)18-13-20(38)19-14-21(39)25(40)29(44)33(19,5)17(18)7-11-32(23,35)4/h13,17,19,21-30,36,39-46H,7-12,14-15H2,1-6H3/t17-,19-,21+,22+,23-,24+,25+,26-,27-,28+,29+,30+,32+,33+,34+,35+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z700 (M+), 682 (M+ - 18), 644 (M+ - 2x18), 640 (M+ - CH3COOH), 623, 605, 587, 569, 479, 461, 443, 180 (hexose)
EI-MS m/z (relative intensity %)?
HR-MS700.3893 (C35H58O13N) (calc. 700.3907).

CARBON NMR

PROTON NMR

D2O
0175.6
0268.2
0370.0
0432.7
0546.5
06--
07122.1
08--
0935.4
1043.2
1121.3
1231.9
1348.4
1486.0
1531.5
1621.2
1750.1
1818.2
1920.0
2080.6
2121.8
2290.6
2326.4
2438.5
2585.9
2626.5
2726.7
AcO23.1, 174.9
gal-1'102.9
gal-2'70.9*
gal-3'70.1*
gal-4'70.3
gal-5'72.2
gal-6'61.8
D2O
01-He3.93 (br, s)
02-Ha4.05 (br, t, 3.1)
03-He4.15 (br s, w1/2 = 12)
04-Ha1.79
04-He1.82
05-H2.62 (br, dd, 11, 6)
07-H5.99 (br, s, w1/2 = 6)
09-H3.05 (m, w1/2 = 23)
11-Ha1.75
11-He1.80
12-Ha1.95
12-He1.75
15-Ha1.67
15-Hb2.06
16-Ha1.90
16-Hb1.75
17-H2.29 (t, 8.7)
18-Me0.87 (s)
19-Me1.09 (s)
21-Me1.30 (s)
22-H3.42 (d, 9.5)
23-Ha1.47
23-Hb1.59
24-Ha1.95
24-Hb2.06
26-Me1.42 (s)*
27-Me1.47 (s)*
AcO2.04 (s)
H-1'5.10 (d, 3.4)
H-2'3.91 (dd, 10.3, 3.4)
H-3'3.94 '
H-4'4.04 (dd, 3, 1.2)
H-5'4.11 (dt, 6.5, 1.2)
H-6"3.76 (dd, 11.7, 6.7)
H-6'3.74 (dd, 11.7, 5.8)

PHYSICAL PROPERTIES

M.P.210-212 °C ;
[α]D20 
IR (KBr) ν max (cm-1)3398 (OH), 1655 (7-ene-6-one), 1707
UV (EtOH) λ max (log ε)242 ( ) ;

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSADIKOV, Z.T. et al. (2000) J. Nat. Prod. 63, 987-988 Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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