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20-HYDROXYECDYSONE 3-β-D-GLUCOSIDE

Year of first isolation: 1994
Formula:C33H54O12
Molecular weight:642
Occurence in plants:
Silene otites [Caryophyllaceae] » Images of Silene otites Wikipedia: Silene otites [Caryophyllaceae]
Rhaponticum uniflorum [Asteraceae] » Images of Rhaponticum uniflorum Wikipedia: Rhaponticum uniflorum [Asteraceae]
Limnanthes douglasii [Limnanthaceae] » Images of Limnanthes douglasii Wikipedia: Limnanthes douglasii [Limnanthaceae]
Trisetum flavescens [Poaceae] » Images of Trisetum flavescens Wikipedia: Trisetum flavescens [Poaceae]
Diploclisia glaucescens [Menispermaceae] » Images of Diploclisia glaucescens Wikipedia: Diploclisia glaucescens [Menispermaceae]
Occurence in animals:
 
20-HYDROXYECDYSONE 3-β-D-GLUCOSIDE

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-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-[(2R)-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-RN 
PubChem CID66869428
InChiKey
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APFXLSITBUTSAO-PGIMLHNSSA-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 %) 
FAB-MS m/z665 [M+Na]+, 647 [M+Na-H2O]+, 643 [M+H]+, 625 [M+H-H2O]+
HR-FAB-MS[M+H] found 643.3658, calc. 643.3694

CARBON NMR

PROTON NMR

C5D5N
0138.99
0268.34
0377.39
0430.80
0551.41
06203.56
07121.69
08166.75
0934.35
1038.73
1121.15
1232.03
1348.15
1484.30
1531.80
1621.57
1750.20
1817.99
1924.12
2077.03
2121.80
2277.73
2327.56
2442.73
2569.79
2630.12
2730.04
glu-01´103.98
glu-02´75.03
glu-03´78.74
glu-04´71.73
glu-05´78.54
glu-06´62.70
CD3OD
0136.1
0266.0
0376.4
0432.5
0551.9
06206.2
07122.1
08168.1
0935.0
1039.5
1121.5
1232.1
1348.4
1485.3
1531.7
1621.4
1750.5
1818.1
1924.2
2077.9
2121.1
2278.4
2327.4
2442.4
2571.7
2629.0
2729.7
glu-01´102.7
glu-02´75.2
glu-03´77.9
glu-04´71.3
glu-05´78.0
glu-06´62.7
C5D5N
01-Ha 
01-Hb 
02-Ha4.11 (dt, 12.3, 3.0, 3.0)
03-He4.31 (brq, 3.0)
04-Ha 
04-He 
05-H2.93 (dd, 13.3, 3.5)
07-H6.21 (d, 2.3)
09-Ha3.53 (m )
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.98 (t, 9.0)
18-Me1.170 (s )
19-Me0.858 (s )
21-Me1.576 (s )
22-H3.87 (dd, 9.6, 1.0)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.374 (s )
27-Me1.374 (s )
H-1´4.90 (d, 7.8)
H-2´4.03 (dd, 7.8, 9.0)
H-3´4.22 (t, 9.0, 9.0)
H-4´4.18 (t, 9.0, 9.0)
H-5´3.92 (ddd, 9.0, 2.2, 5.8)
H-6a´4.53 (dd, 11.7, 2.2)
H-6b´4.30 (dd, 11.7, 5.8)
CD3OD
01-Ha 
01-Hb 
02-Ha4.02 (dt, 11.5, 5.0)
03-He4.13 (brq, 2.0)
04-Ha 
04-He 
05-H2.38 (m)
07-H5.80 (d, 2.5)
09-Ha3.15 (m)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.38 (m)
18-Me0.88 (s)
19-Me0.96 (s)
21-Me1.18 (s)
22-H3.30 (m)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.19 (s)
27-Me1.19 (s)
H-1´4.48 (d, 8.0)
H-2´3.20 (t, 8.5)
H-3´3.36 (t, 9.0)
H-4´3.33 (t, 9.8)
H-5´3.30 (m)
H-6a´3.69 (dd, 11.8, 5.2)
H-6b´3.87 (d, 10.0)

PHYSICAL PROPERTIES

M.P.297-300 °C
[α]D20 
IR (KBr) ν max (cm-1)3419 (-OH), 1660 (C=O), 1051 (C-O) ;
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

TLC 
GLC 
HPLCRP-HPLC, column Spherisorb 5ODS2 25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1, eluted with 18% ACN-iPrOH (5:2) in 0.1% TFA in H2O, Ret 10.5 min (20E 13.9 min); column Separon SGX-C18 25 cm long, 8 mm i.d., flow-rate 4 ml.min-1, eluted with 40% MeOH in water, Ret 13.5 min. NP-HPLC, column Zorbax-ODS 25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1, eluted with cyclohexane-iPrOH-H2O (80:40:3), Ret 47.0 min (20E 10.1 min). LC on SEPHADEX LH20, solvent CHCl3-MeOH (1:1)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 1.3 x 10-5M

REFERENCES

SynthesisPIS, J. et al. (1994) Tetrahedron 50, 9679-9690 Search more
First isolationPIS, J. et al. (1995) Eur. J. Entomol. 92, 41-50 Search more
BioactivitiesHARMATHA, J. et al. (1997) Arch. Insect Biochem. Physiol. 35, 219-225 Search more
GeneralSARKER, S.D. et al. (1997) Phytochemistry 44, 513-521 Search more
GeneralSARKER, S.D. et al. (1998) Biochem. Syst. Ecol. 26, 135-137 Search more
First isolationBÁTHORI, M. et al. (2000) Biomed. Chromatogr. 14, 464-467 Search more
First isolationLI, X. et al. (2000) Shenyang Yaoke Daxue Xuebao 17, 260-262 Search more
IdentificationJAYASINGHE, U.L.B et al. (2003) Tetrahedron Lett. 44, 8769-8771 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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