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ECDYSONE 25-O-β-D-GLUCOPYRANOSIDE

Year of first isolation: 1987
Formula:C33H54O11
Molecular weight:626
Occurence in plants:
 
Occurence in animals:
Parascaris equorum [Nematoda] » Images of Parascaris equorum Wikipedia: Parascaris equorum [Nematoda]
ECDYSONE 25-O-β-D-GLUCOPYRANOSIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)C(CCC(C)(C)OC5C(C(C(C(O5)CO)O)O)O)O
Isomeric SMILES
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C[C@@H]([C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)C)O)[C@@H](CCC(C)(C)OC5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17R)-2,3,14-trihydroxy-17-[(2S,3R)-3-hydroxy-6-methyl-6-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN112172-82-4
PubChem CID11988271
InChiKey
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YJBCWBWOULRKGL-OKFUDBSCSA-N
InChIInChI=1S/C33H54O11/c1-16(21(35)8-9-30(2,3)44-29-28(41)27(40)26(39)25(15-34)43-29)17-7-11-33(42)19-12-22(36)20-13-23(37)24(38)14-31(20,4)18(19)6-10-32(17,33)5/h12,16-18,20-21,23-29,34-35,37-42H,6-11,13-15H2,1-5H3/t16-,17+,18-,20-,21+,23+,24-,25+,26+,27-,28+,29?,31+,32+,33+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %) 
FAB-MS m/z625 (M-H)-
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
01 
02 
03 
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
14 
15 
16 
17 
18 
19 
20 
21 
22 
23 
24 
25 
26 
27 
D2O
01-Ha 
01-He 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H 
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me 
19-Me 
21-Me 
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me 
27-Me 
H-1'4.65 (d, 7.9)
H-2'3.21 (dd, 7.9, 9.4)
H-3'3.48 (dd, 9.4, 9.0)
H-4'3.34 (dd, 9.0. 9.8)
H-5'3.46 (m )
H-6"3.66 (dd, 6.4, 12.3)
H-6'3.90 (dd, 2.1, 12.3)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC1- Retention time 10.5 min [Radial-Pak C18 100 mm x 8 mm i.d., linear gradient (30 min) of MeOH-H2O from 1:1 to 1:0 v/v , flow-rate 1 ml.min-1] (20E : 9 min; E : 15 min); 2-Retention time 14.5 min [Radial-Pak C18 100 mm x 8 mm i.d., concave gradient (30 min) of MeOH-H2O 9:11 to 1:0, flow-rate 1 ml.min-1] (20E : 12.5 min; E : 25 min); 3-Retention time 13.5 min [Radial-Pak NH2 100 mm x 8 mm i.d., solvent dichloroethane-MeOH 4:1 v/v, flow-rate 1 ml.min-1] (20E and E : 5-6 min).

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationO`HANLON, G.M. et al. (1987) Biochem. J. 248, 305-307 Search more

see Important notice
© 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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