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PALYTHOALONE A

Year of first isolation: 1999
Formula:C28H46O8
Molecular weight:510
Occurence in plants:
 
Occurence in animals:
Palythoa australiae [Zoanthidae] » Images of Palythoa australiae Wikipedia: Palythoa australiae [Zoanthidae]
PALYTHOALONE A

STRUCTURE DESCRIPTORS

Canonical SMILESCC(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4(C3(CC(C(C4)O)O)C)O)C)O)O)O)C(C)CO
Isomeric SMILES
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C1[C@]2([C@@](C[C@H]([C@H]1O)O)(C(=O)C=C1C2CC[C@]2([C@]1(CC[C@@H]2[C@]([C@@H](CC([C@H](CO)C)C)O)(O)C)O)C)O)C  » JSMol: View in 3D
C1[C@]2([C@@](C[C@H]([C@H]1O)O)(C(=O)C=C1C2CC[C@]2([C@]1(CC[C@@H]2[C@]([C@@H](C[C@H]([C@H](CO)C)C)O)(O)C)O)C)O)C  » JSMol: View in 3D
C1[C@]2([C@@](C[C@H]([C@H]1O)O)(C(=O)C=C1C2CC[C@]2([C@]1(CC[C@@H]2[C@]([C@@H](C[C@@H]([C@H](CO)C)C)O)(O)C)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R,5S,6R)-2,3,7-trihydroxy-5,6-dimethylheptan-2-yl]-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID100956102
InChiKey
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SCHNJHTVEMNUAG-AHAWHJSRSA-N
InChIInChI=1S/C28H46O8/c1-15(16(2)14-29)10-22(32)26(5,34)21-7-9-27(35)18-11-23(33)28(36)13-20(31)19(30)12-25(28,4)17(18)6-8-24(21,27)3/h11,15-17,19-22,29-32,34-36H,6-10,12-14H2,1-5H3/t15-,16-,17-,19-,20+,21-,22+,24+,25+,26+,27+,28+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %) 
HR-FAB-MS511.3263 [M+H]+, - 0.8 mmu

CARBON NMR

PROTON NMR

C5D5N
0135.0 (t)
0268.0 (d)
0369.9 (d)
0436.1 (t)
0580.0 (s)
06200.9 (s)
07119.8 (d)
08166.9 (s)
0938.4 (d)
1044.9 (s)
1121.5 (t)
1231.7 (t)
1348.2 (s)
1484.0 (s)
1532.2 (t)
1622.2 (t)
1749.9 (d)
1818.0 (q)
1917.3 (q)
2076.8 (s)
2121.6 (q)
2274.1 (d)
2337.9 (t)
2431.0 (d)
2537.7 (d)
2666.8 (t)
2710.9 (q)
2815.9 (q)
C5D5N
01-Ha2.21 (s)
01-He2.10 (m)
02-Ha4.25 (br d 11.8)
03-He4.15 (br, s)
04-Ha2.13 (m)
04-He1.99 (dd)
07-H6.28 (d)
09-H3.65 (m)
11-Ha1.91 (m)
11-He1.83 (m)
12-Ha2.18 (m)
12-He1.81 (m)
15-Ha2.60 (dt)
15-Hb2.03 (m)
16-Ha2.44 (m)
16-Hb2.05 (m)
17-H2.93 (t)
18-Me1.22 (s)
19-Me1.16 (s)
21-Me1.58 (s)
22-H3.99 (d)
23-Ha1.88 (d)
23-Hb1.54 (m)
24-H2.54 (m)
25-H2.24 (m)
26-Ha3.79 (dd)
26-Hb3.72 (dd)
27-Me0.92 (d)
28-Me0.91 (d)

PHYSICAL PROPERTIES

M.P. 
[α]D26+ 87 ? ° (c 2.2; MeOH)
IR (film) ν max (cm-1)3435, 1635
UV (MeOH) λ max (log ε)243 (4.0)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSHIGEMORI, H. et al. (1999) J. Nat. Prod. 62, 372-374 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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