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POLYPODOGENIN

Year of first isolation: 1971
Formula:C27H42O4
Molecular weight:430
Occurence in plants:
Polypodium vulgare [Polypodiaceae] » Images of Polypodium vulgare Wikipedia: Polypodium vulgare [Polypodiaceae]
Occurence in animals:
 
POLYPODOGENIN

STRUCTURE DESCRIPTORS

Canonical SMILESCC1CCC(OC1O)C(C)C2CCC3C2(CCC4C3=CC(=O)C5C4(CCC(C5)O)C)C
Isomeric SMILES
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C1[C@]2([C@H](C[C@H](C1)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,5R,9R,10R,13R,14R,17R)-3-hydroxy-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 CID101306873
InChiKey
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FCMDISUJEUTJIU-KBBSIBECSA-N
InChIInChI=1S/C27H42O4/c1-15-5-8-24(31-25(15)30)16(2)19-6-7-20-18-14-23(29)22-13-17(28)9-11-27(22,4)21(18)10-12-26(19,20)3/h14-17,19-22,24-25,28,30H,5-13H2,1-4H3/t15?,16-,17-,19+,20-,21-,22-,24?,25?,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z430 (M)+
ES-MS m/z (relative intensity %)MS of 26-OMe deriv.: 444 (7, M)+, 413 (21, M-OMe), 412 (33, M-MeOH), 384 (21, M-MeOH-CO), 342 (30), 316 (78), 287 (32, M- side chain), 285 (44), 261 (26), 129 (100), 97 (33).

CARBON NMR

PROTON NMR

C5D5N
01 
02 
03 
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
14 
15 
16 
17 
18 
19 
20 
21 
22 
23 
24 
25 
26 
27 
DMSO-d6
 comp.native 26-Ome
01-Ha 
01-Hb 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H 5.7
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.57 (s ) 0.86 (s )
19-Me0.75 (s ) 0.65 (s )
21-Me 0.98 (d, 7)
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-H 
27-Me 0.98 (d, 7)

PHYSICAL PROPERTIES

M.P.162-164 °C ;
[α]D25+ 6.6 ° (c 0.50; MeOH)
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 
LC on silica(elution with CHCl3, then CHCl3-MeOH 50:1)

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationJIZBA, J. et al. (1971) Chem. Ber. 104, 837-846 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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