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ECDYSTEROSIDE

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

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)O)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[C@@H]1C(C([C@H](C(O1)CO)O)O)O)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-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID102316919
InChiKey
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QMUZULHLTKODCA-FNKAHMMCSA-N
InChIInChI=1S/C39H64O17/c1-35(2,50)9-8-26(43)38(5,51)25-7-11-39(52)18-12-20(41)19-13-22(21(42)14-36(19,3)17(18)6-10-37(25,39)4)54-34-32(49)30(47)28(45)24(56-34)16-53-33-31(48)29(46)27(44)23(15-40)55-33/h12,17,19,21-34,40,42-52H,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

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)588 (3), 573 (3), 570 (6), 555 (2.1), 552 (2.4), 534 (2.1), 516 (1.5), 501, 462, 455, 444 (30), 426 (36), 411 (15), 408 (15), 393 (10), 375, 357, 345 (12), 327, 300 (100), 99 (30, 81 (27).
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0138.53
0268.08
0379.15
0431.43
0552.43
06202.97
07121.51
08166.51
0934.25
1039.39
1121.04
1231.68
1348.06
1484.12
1531.68
1621.46
1750.10
1817.84
1924.27
2076.87
2121.67
2277.57
2322.45
2442.60
2569.57
2629.99
2730.06
H-01'103.71
H-02'71.02
H-03'71.78
H-04'71.02
H-05'73.46
H-06'62.62
H-1"101.75
H-2"70.95
H-3"71.66
H-4"70.56
H-5"72.59
H-6"62.62
C5D5N
01-Ha 
01-He 
02-Ha4.04
03-He4.08
04-Ha 
04-He 
05-H 
07-H6.19
09-H3.45 (m)
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.19 (s)
19-Me0.97 (s)
21-Me1.57 (s)
22-H3.84 (dd)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.35 (s)
27-Me1.35 (s)
H-01'5.56 (d, 4)
H-1''5.16 (d, 4)

PHYSICAL PROPERTIES

M.P.228-230 °C ;
[α]D20+ 100.4 ? ° (c 2.59 ; MeOH)
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationBALTAYEV, U.A. et al. (1998) Phytochemistry 47, 1233-1235 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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