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26-METHOXYPOLYPODOSAPONIN

Year of first isolation: 1971
Formula:C40H64O13
Molecular weight:752
Occurence in plants:
Polypodium vulgare [Polypodiaceae] » Images of Polypodium vulgare Wikipedia: Polypodium vulgare [Polypodiaceae]
Occurence in animals:
 
26-METHOXYPOLYPODOSAPONIN

STRUCTURE DESCRIPTORS

Canonical SMILESCC1CCC(OC1OC)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)C1CCC(C(O1)OC)C)C)C  » JSMol: View in 3D
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)C1CC[C@H]([C@H](O1)OC)C)C)C  » JSMol: View in 3D
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)C1CC[C@H]([C@@H](O1)OC)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-methoxy-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 CID101534443
InChiKey
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WBAQZGCULGWMSH-PSNSKPJSSA-N
InChIInChI=1S/C40H64O13/c1-18-7-10-28(51-36(18)48-6)19(2)23-8-9-24-22-16-27(42)26-15-21(11-13-40(26,5)25(22)12-14-39(23,24)4)50-38-35(33(46)31(44)29(17-41)52-38)53-37-34(47)32(45)30(43)20(3)49-37/h16,18-21,23-26,28-38,41,43-47H,7-15,17H2,1-6H3/t18?,19-,20-,21-,23+,24-,25-,26+,28?,29+,30-,31+,32+,33-,34+,35+,36?,37-,38+,39+,40+/m0/s1

MASS SPECTRUM

HRESI-MS [M+H]+ = 753.4420, calculated for C40H65O13 753.4420
CI-MS (NH3) m/z
ESI-MS m/z (relative intensity %) 671 (2) [M+Na-C4H803]+, 655 (3) [M+Na-C4H804]+, 629 (100), 331 (1) [C12H20O9Na]+

CARBON NMR

PROTON NMR

CD3OD
0137.9
0229.9
0377.6
0427.4
0554.4
06202.6
07123.6
08167.2
0951.4
1039.7
1123.0
1240.1
1346.1
1456.5
1523.8
1628.2
1754.3
1812.8
1913.6
2041.5
2114.4
22 
2325.2
2432.4
2537.3
26109.9
2716.9
2856.7
[sugar] 1"102.4
[sugar] 1'100.1
[sugar] 2"72.4
[sugar] 2'79.4
[sugar] 3"72.5
[sugar] 3' 
[sugar] 4"74.2
[sugar] 4'72.1
[sugar] 5"70.0
[sugar] 5'77.9
[sugar] 6"18.1
[sugar] 6'63.0
CD3OD
01-Ha1.44
01-Hb1.87
02-Ha1.44
02-Hb1.89
03-He3.81 (tt, 11.2, 4.3)
04-Ha1.40
04-Hb2.33
05-H2.35
07-H5.67 (t, 2.2)
09-H2.31
11-Ha1.69
11-Hb1.87
12-Ha1.49
12-Hb2.18
14-H2.18
15-Ha1.59
15-Hb1.69
16-Ha1.49
16-Hb1.89
17-H1.44
18-Me0.68 (s)
19-Me0.88 (s)
20-H1.79
21-Me1.01 (d, 6.7)
22-H3.45
23-Ha1.30 (qd, 12.5, 3.4)
23-Hb1.43 (d, 12.5)
24-Ha1.20 (qd, 12.5, 3.4)
24-Hb1.82 (d, 12.5)
25-H1.35
26-H3.95 (d, 8.5)
27-Me0.89 (d, 6.8)
28-Me4.55 (d, 7.8)
[sugar] H1'4.55 (d, 7.8)
[sugar] H1''5.19 (d, 1.7)
[sugar] H2'3.37
[sugar] H2''3.93 (dd, 3.4, 1.7)
[sugar] H3'3.49
[sugar] H3''3.72 (dd, 9.6, 3.4)
[sugar] H4'3.26
[sugar] H4''3.37
[sugar] H5'3.26
[sugar] H5''4.13
[sugar] H6'3.64
[sugar] Me6''1.24 (d, 6.2)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D28-10 ° (c 0.1 ; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)241 (3.84) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

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

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