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POLYPODOSAPONIN

Year of first isolation: 1971
Formula:C39H62O13
Molecular weight:738
Occurence in plants:
Polypodium vulgare [Polypodiaceae] » Images of Polypodium vulgare Wikipedia: Polypodium vulgare [Polypodiaceae]
Occurence in animals:
 
POLYPODOSAPONIN

STRUCTURE DESCRIPTORS

Canonical SMILESCC1CCC(OC1O)C(C)C2CCC3C2(CCC4C3=CC(=O)C5C4(CCC(C5)OC6C(C(C(C(O6)CO)O)O)OC7C(C(C(C(O7)C)O)O)O)C)C
Isomeric SMILES
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C1[C@]2([C@H](C[C@H](C1)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O[C@H]1C(C([C@H](C(O1)C)O)O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H]([C@H]1CC[C@@H]([C@H](O1)O)C)C)C)C » JSMol: View in 3D
IUPAC Name(3S,5S,9R,10R,13R,14R,17R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-17-[(1S)-1-(6-hydroxy-5-methyloxan-2-yl)ethyl]-10,13-dimethyl-1,2,3,4,5,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID101306874
InChiKey
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MLAYKJNHCRIBKC-KUGLUBNCSA-N
InChIInChI=1S/C39H62O13/c1-17-6-9-27(50-35(17)47)18(2)22-7-8-23-21-15-26(41)25-14-20(10-12-39(25,5)24(21)11-13-38(22,23)4)49-37-34(32(45)30(43)28(16-40)51-37)52-36-33(46)31(44)29(42)19(3)48-36/h15,17-20,22-25,27-37,40,42-47H,6-14,16H2,1-5H3/t17?,18-,19-,20-,22+,23-,24-,25+,27?,28+,29-,30+,31+,32-,33+,34+,35?,36-,37+,38+,39+/m0/s1

MASS SPECTRUM

ESI-MS m/z (relative intensity %)658 (2) [M-H+D+Na-C4H8O3]+, 642 (3) [M-H+D+Na-C4H8O4]+, 616 (100), 331 (2) [C12H20O9Na]+
HR-ESI-MS[M+H]+ 739.4236 (calculated for C39H63O13, 739.4263, delta: 3.6 ppm)

CARBON NMR

PROTON NMR

CD3OD
0137.9
0229.9
0377.6
0427.3
0554.4
06202.6
07123.6
08167.2
0951.4
1039.6
1123.0
1240.1
1346.1
1456.5
1523.8
1628.2
1754.3
1812.8
1913.6
2041.6
2114.4
22 
2325.1
2432.5
2538.9
26102.6
2717.3
Glu 1'101.1
Glu 2'79.3
Glu 3' 
Glu 4'72.0
Glu 5'77.9
Glu 6'63.0
Rha 1''  102.4
Rha 2'' 72.4
Rha 3''72.5
Rha 4'' 74.2
Rha 5'' 70.0
Rha 6''18.2
CD3OD
01-Ha; 01-Hb1.42; 1.86
02-Ha; 02-Hb1.46; 1.90
03-He3.80 (tt,11.3, 4.3)
04-Ha; 04-Hb1.39; 2.33
05-H2.35
07-H5.67 (t, 2.1)
09-Ha2.31
11-Ha1.69
11-Hb1.86
12-Ha1.49
12-Hb2.17
14-H2.18
15-Ha1.56
15-Hb1.68
16-Ha1.47
16-Hb1.89
17-H1.43
18-Me0.67 (s)
19-Me0.88 (s)
20-H1.78
21-Me1.01 (d, 6.8)
22-H3.48
23-Ha1.32
23-Hb1.43
24-Ha; 24-Hb1.19; 1.82
25-H1.31
26-H4.24 (d, 8.3)
27-Me0.92 (d, 6.5)
glu H-1'4.55 (d, 7.7)
glu H-2'3.37 (dd, 9.3, 7.8)
glu H-3'3.48 (t, 9.1)
glu H-4'3.26
glu H-5'3.26
glu H-6a';H-6b'3.65; 3.85
rha H-1''5.19 (d, 1.6)
rha H-2''3.94 (dd, 93.1, 1.8)
rha H-3''3.73 (dd, 9.5, 3.3)
rha H-4''3.37
rha H-5''4.13
rha Me-6''1.24 (d, 6.3)

PHYSICAL PROPERTIES

M.P.198-201 °C
[α]D28- 37 ° (c 0.1; MeOH)
IR (Nujol) ν max (cm-1)3450 (OH), 1711 (CO), 1675 (cyclohexenone), 1624
UV (EtOH) λ max (log ε)246 (4.06)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationJIZBA, J. et al. (1971) Chem. Ber. 104, 837-846 Search more
IdentificationSIMON, A. et al. (2011) Steroids 76, 1419-1424 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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