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(5α)-POLYPODINE B 3-β-D-GLUCOSIDE

Year of first isolation: 1987
Formula:C33H54O13
Molecular weight:658
Occurence in plants:
Helleborus odorus [Ranunculaceae] » Images of Helleborus odorus Wikipedia: Helleborus odorus [Ranunculaceae]
Helleborus purpurascens [Ranunculaceae] » Images of Helleborus purpurascens Wikipedia: Helleborus purpurascens [Ranunculaceae]
Occurence in animals:
 
(5α)-POLYPODINE B 3-β-D-GLUCOSIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4(C3(CC(C(C4)OC5C(C(C(C(O5)CO)O)O)O)O)C)O)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O
Isomeric SMILES
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C1[C@]2([C@](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@@H](CCC(C)(C)O)O)(C)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,17S)-2,5,14-trihydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID184117
InChiKey
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AYZWKPWGZYTYNN-UHWXVGLPSA-N
InChIInChI=1S/C33H54O13/c1-28(2,41)9-8-22(36)31(5,42)21-7-11-32(43)17-12-23(37)33(44)14-19(45-27-26(40)25(39)24(38)20(15-34)46-27)18(35)13-30(33,4)16(17)6-10-29(21,32)3/h12,16,18-22,24-27,34-36,38-44H,6-11,13-15H2,1-5H3/t16-,18-,19+,20+,21-,22+,24+,25-,26+,27+,29+,30+,31+,32?,33-/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %) 
HR-MS 
PD-MS (plasma desorption 252Cf)705 (M+1+2Na)+, 704 (M+2Na)+, 682 (M+1+Na)+, 681 (M+Na)+, 357 (M+Na - glu - 18)+

CARBON NMR

PROTON NMR

C5D5N
0138.7
0266.8
0375.7
0435.5
0579.6
06200.6
07120.2
08166.5
0938.4
1044.9
1121.9
1232.0
1348.1
1484.1
1531.6
1621.4
1750.0
1817.8
1917.0
2076.9
2121.7
2277.6
2327.5
2442.6
2569.7
2630.0
2730.1
glu-01'102.6
glu-02'75.4
glu-03'78.4
glu-04'71.8
glu-05'78.6
glu-06'62.8
C5D5N
01-Ha 
01-He 
02-Ha 
03-He 
04-Ha 
04-He 
07-H6.27
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
14-OH 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.17
19-Me1.01
21-Me1.55
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.38
27-Me1.38
DMSO-d6
01-Ha 
01-He 
02-Ha 
03-He4.00
04-Ha 
04-He 
07-H5.63 (d, 2)
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
14-OH4.09
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.75
19-Me0.80
21-Me1.05
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.05
27-Me1.07
H-1 & OH-64.34 - 4.41
H-33.13
H-42.96
H-5masked by HDO
H-63.45
OH-2, 3 &44.67 - 4.93
sugar sign 

PHYSICAL PROPERTIES

M.P.162 °C
[α]D20 
IR (KBr) ν max (cm-1)-- (OH), 1650, 1630 (cyclohexenone)
UV (EtOH) λ max (log ε)242 (?)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationKISSMER, B. et al. (1987) Arch. Pharm. (Weinheim) 320, 541-546 Search more

see Important notice
© 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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