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2,14,22-TRIDEOXYECDYSONE 3,25-O-β-D-DIGLUCOSIDE

Year of first isolation: 2019
Formula:C39H64O13
Molecular weight:740
Occurence in plants:
Silene montbretiana [Caryophyllaceae] » Images of Silene montbretiana
Occurence in animals:
 
2,14,22-TRIDEOXYECDYSONE 3,25-O-β-D-DIGLUCOSIDE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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[ ChemSpider: search ]
C1[C@]2([C@@H](C[C@H](C1)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CCCC(C)(C)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(3S,5R,9R,10R,13R,14R,17R)-10,13-dimethyl-17-((2R)-6-methyl-6-(((2S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)heptan-2-yl)-3-(((2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
GLAZBYIKYBWQAO-FOIXINSOSA-N
InChIInChI=1S/C39H64O13/c1-19(7-6-12-37(2,3)52-36-34(48)32(46)30(44)28(18-41)51-36)22-8-9-23-21-16-26(42)25-15-20(10-13-39(25,5)24(21)11-14-38(22,23)4)49-35-33(47)31(45)29(43)27(17-40)50-35/h16,19-20,22-25,27-36,40-41,43-48H,6-15,17-18H2,1-5H3/t19-,20+,22-,23+,24+,25+,27?,28?,29-,30-,31?,32?,33?,34?,35-,36+,38-,39-/m1/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z  
HRESI-MS m/z (positive ion mode) m/z763.4255 [M+Na] + , calc. for C39H64O13Na 763.4245

CARBON NMR

PROTON NMR

CD3OD
0136.0
0229.4
0377.8
0426.6
0553.4
06202.2
07124.2
08166.6
0950.4
1038.6
1121.1
1239.7
1345.1
1456.8
1523.0
1623.4
1757.2
1811.8
1912.6
2036.0
2118.4
2237.1
2327.5
2442.3
2578.2
2626.0
2726.0`
[glu@C03] 1102.6
[glu@C03] 274.8
[glu@C03] 377.7
[glu@C03] 471.4
[glu@C03] 577.4
[glu@C03] 662.5
[glu@C25] 198.7
[glu@C25] 274.7
[glu@C25] 378.1
[glu@C25] 471.7
[glu@C25] 577.1
[glu@C25] 662.1
CD3OD
01-Ha1.94 (m)
01-Hb1.11 (m)
02-Ha1.51 (m)
02-Hb1.96 (m)
03-He3.79 (m)
04-Ha2.31 (m)
04-Hb1.44 (m)
05-H2.40 (dd, 12.7, 4.0)
07-H5.70 (s)
09-H2.35 (dd, 3.4, 12.6)
11-Ha1.49 (m)
11-Hb1.17 (m)
12-Ha2.20 (m)
12-Hb1.51 (m)
14-H2.22 (m)
15-Ha1.80 (m)
15-Hb1.70 (m)
16-Ha1.60 (m)
16-Hb1.58 (m)
17-H1.42 (m)
18-Me0.69 (s)
19-Me0.90 (s)
20-H1.49 (m)
21-Me1.02 (d, 6.5)
22-Ha1.44 (m)
22-Hb1.90 (m)
23-Ha1.44 (m)
23-Hb2.03 (m)
24-Ha1.53 (m)
24-Hb1.58 (m)
25-H-
26-Me1.27 (s)
27-Me1/27 (s)
[glu@C03] 14.48 (d; 7.5)
[glu@C03] 23.19 (dd, 9.0, 7.5)
[glu@C03] 33.41 (dd, 9.0, 9.0)
[glu@C03] 43.34 (dd, 9.0, 9.0)
[glu@C03] 53.27 (m)
[glu@C03] 63.68 (dd, 12.0, 4.5)
[glu@C03] 6'3.88 (dd, 12.0, 2.5)
[glu@C25] 14.46 (d, 7.5)
[glu@C25] 23.17 (dd, 9.0, 7.5)
[glu@C25] 33.40 (dd, 9.0, 9.0)
[glu@C25] 43.30 (dd, 9.0, 9.0)
[glu@C25] 53.31 (m)
[glu@C25] 63.71 (dd, 12.0, 4.5)
[glu@C25] 6'3.86 (dd, 12.0, 2.5)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D25- 6.45° (c 0.3; MeOH)
IR (KBr) ν max (cm-1)3425, 2930, 1660, 1650, 1265, 1050
UV (MeOH) λ max (log ε)nm (-) ;

CHROMATOGRAPHY

HPTLC
GLC
HPLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationKILINC, H. et al. (2019) Nat. Prod. Res. 33 (3), 335-339 Search more

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