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25-ACETOXY-20-HYDROXYECDYSONE 3-O-β-D-GLUCOPYRANOSIDE

Year of first isolation: 2007
Formula:C35H56O13
Molecular weight:684
Occurence in plants:
Sida rhombifolia [Malvaceae] » Images of Sida rhombifolia Wikipedia: Sida rhombifolia [Malvaceae]
Occurence in animals:
 
25-ACETOXY-20-HYDROXYECDYSONE 3-O-β-D-GLUCOPYRANOSIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(=O)OC(C)(C)CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)OC5C(C(C(C(O5)CO)O)O)O)O)C)C)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)OC(=O)C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name[(5R,6R)-6-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,14-dihydroxy-10,13-dimethyl-6-oxo-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-5,6-dihydroxy-2-methylheptan-2-yl] acetate
CAS-RN 
PubChem CID102393301
InChiKey
[ ChemIDPlus: search ]
NJIPVBZFJXLEEQ-ZHOBEPCUSA-N
InChIInChI=1S/C35H56O13/c1-17(37)48-31(2,3)10-9-26(40)34(6,44)25-8-12-35(45)19-13-21(38)20-14-23(46-30-29(43)28(42)27(41)24(16-36)47-30)22(39)15-32(20,4)18(19)7-11-33(25,35)5/h13,18,20,22-30,36,39-45H,7-12,14-16H2,1-6H3/t18-,20-,22-,23+,24+,25-,26+,27+,28-,29+,30+,32+,33+,34+,35+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
HR-ESI-MS707.3683 [M+Na]+ (calc. 707.3619 for [C35H56O13Na]+)
CI-MS (NH3) m/z

CARBON NMR

PROTON NMR

C5D5N
0139.4
0267.9
0378.0
0431.0
0551.8
06203.5
07122.0
08166.8
0934.7
1039.1
1121.5
1232.4
1348.4
1484.5
1532.1
1621.9
1750.6
1818.3
1924.5
2077.2
2122.0
2277.9
2327.3
2439.7
2582.8
2626.6
2726.7
CH3CO22.7, 170.7
[sugar] 1'104.3
[sugar] 2'74.9
[sugar] 3'78.9
[sugar] 4'71.8
[sugar] 5'78.7
[sugar] 6'62.7
C5D5N
01-Ha1.78 (br, s)
01-He2.00-2.06
02-Ha4.08-4.11
03-He4.31 (br, s)
04-Ha1.67-1.75
04-He2.21-2.25
05-H2.91-2.96
07-H6.21 (s)
09-H3.54 (br, s)
11-Ha1.75-2.04
11-He1.83-1.90
12-Ha2.54-2.59
12-He2.00-2.04
15-Ha2.04-2.06
15-Hb2.54-2.59
16-Ha2.00-2.04
16-Hb2.39-2.45
17-H2.96-2.99
18-Me1.20 (s)
19-Me0.90 (s)
21-Me1.61 (s)
22-H3.84 (br, d, 10.4)
23-Ha1.67-1.71
23-Hb1.97-1.90
24-Ha2.21-2.25
24-Hb2.39-2.45
26-Me1.44 (s)
27-Me1.50 (s)
CH3CO1.96 (s)
[sugar] 1'4.93 (d, 7.6)
[sugar] 2'4.03 (t, 7.2)
[sugar] 3'3.93 (br, s)
[sugar] 4'4.21 (m)
[sugar] 5'4.20 (m)
[sugar] 6'4.32 (m)
[sugar] 6''4.52 (d, 11.6)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D20+ 18.1 (c 2.87; pyridine)
UV (MeOH) λ max (ε)244 (1579) ;
IR (NaCl) ν max (cm-1)3386, 1649, 1373, 1272, 1075

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationJADHAV, A.N. et al. (2007) Chemistry & Biodiversity 4, 2225-2230 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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