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SILENEOSIDE D

Year of first isolation: 1984
Formula:C33H54O12
Molecular weight:642
Occurence in plants:
Silene brahuica [Caryophyllaceae] » Images of Silene brahuica Wikipedia: Silene brahuica [Caryophyllaceae]
Occurence in animals:
 
SILENEOSIDE D

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)OC5C(C(C(C(O5)CO)O)O)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O
Isomeric SMILES
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C1[C@]2([C@@H](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)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-2,14-dihydroxy-10,13-dimethyl-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN93552-68-2
PubChem CID21768882
InChiKey
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APFXLSITBUTSAO-SDNJJZGQSA-N
InChIInChI=1S/C33H54O12/c1-29(2,41)9-8-24(37)32(5,42)23-7-11-33(43)17-12-19(35)18-13-21(44-28-27(40)26(39)25(38)22(15-34)45-28)20(36)14-30(18,3)16(17)6-10-31(23,33)4/h12,16,18,20-28,34,36-43H,6-11,13-15H2,1-5H3/t16-,18-,20-,21+,22+,23-,24+,25-,26-,27+,28-,30+,31+,32+,33+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)624 (M-18)+ (0.5), 606 (0.8), 588 (5), 570 (1), 514 (0.8), 507 (0.7), 490 (0.9), 473 (0.6), 462 (1), 444 (1), 426 (11), 411 (2), 408 (3), 393 (1), 375 (1), 363 (5), 345 (55), 327 (13), 309 (10), 300 (11), 284 (11), 145 (10), 143 (12), 135 (11), 99 (100), 81 (55), 69 (53).
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
01 
0268.0
0379.0 *
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
1484.2
15 
16 
17 
18 
19 
2076.8
21 
2277.5
23 
24 
2569.6
26 
27 
s1'103.5
s2'70.9
s3'71.6
s4'70.9
s5'73.3
s6'62.5
C5D5N
01-Ha 
01-He 
02-Ha3.96 (m )
03-He3.96 (m )
04-Ha 
04-He 
05-H 
07-H6.10
09-Ha3.37
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.09
19-Me0.86
21-Me1.48
22-H3.75
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.25
27-Me1.25
H-1'5.48 (d, 3.9)
CDCl3 (hepta-OAc)
01-Ha 
01-He 
02-Ha5.13 (m, w1/2=21)
03-He4.09 (m, w1/2=8)
04-Ha 
04-He 
05-H 
07-H6.07
09-Ha3.49
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.01
19-Me0.89
21-Me1.49
22-H5.29 (d br )
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.32
27-Me1.33
H-1'5.63 (d, 3.6)

PHYSICAL PROPERTIES

M.P.240-242 °C
[α]D20+ 91.2 ? 2 ° (c 1.01; MeOH)
IR (KBr) ν max (cm-1)3380-3430 (OH), 1648 (cyclohexenone)
UV (EtOH) λ max (log ε)247 (4.15)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 
LCsilicagel with CHCl3-MeOH (4:1, v/v)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 3.0 x 10-5M

REFERENCES

First isolationSAATOV, Z. et al. (1984) Khim. Prir. Soedin., 741-744 Search more
BioactivitiesDINAN, L. et al. (2005) In: Comprehensive Molecular Insect Science (eds. L. I. Gilbert, C. Iatrou, S. Gill), Elsevier, Oxford, III, 197-242 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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