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ECDYSONELACTONE A

Year of first isolation: 2018
Formula:C29H44O9
Molecular weight:536
Occurence in plants:
 
Occurence in animals:
Antipathozoanthus hickmani [Parazoanthidae] » Images of Antipathozoanthus hickmani Wikipedia: Antipathozoanthus hickmani [Parazoanthidae]
ECDYSONELACTONE A

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4(C3(CC5(CC(=O)OC5C4)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]3[C@]1(CC(=O)O3)O)(C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(1R,2R,4S,8R,10S,14S,17S,18R)-4,10,14-trihydroxy-2,18-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-7-oxapentacyclo[11.7.0.02,10.04,8.014,18]icos-12-ene-6,11-dione
CAS-RN 
PubChem CID138453996
InChiKey
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KLKWMODQIPKUOL-PYXHJTNMSA-N
InChIInChI=1S/C29H44O9/c1-23(2,33)9-8-19(30)26(5,34)18-7-11-28(36)17-12-20(31)29(37)13-21-27(35,14-22(32)38-21)15-25(29,4)16(17)6-10-24(18,28)3/h12,16,18-19,21,30,33-37H,6-11,13-15H2,1-5H3/t16-,18-,19+,21+,24+,25+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z  
HRESI-MS m/z (positive ion mode) m/z537.3070 [M+H] + , calc. for C29H45O9 537.3058 (∆ +2.2 ppm)

CARBON NMR

PROTON NMR

CD3OD
0138.4
0274.2
0382.5
0431.9
0577.8
06203.9
07120.1
08169.2
0939.2
1042.4
1122.3
1232.5
1348.7
1484.9
1531.9
1621.5
1750.4
1818.1
1916.7
2077.9
2121.0
2278.4
2327.3
2442.4
2571.3
2628.9
2729.7
…01'176.3
…02'47.5
CD3OD
01-Ha1.87 (d, 15.0)
01-Hb1.71 (d, 15.0)
02-H–
03-He4.50 (br, d, 4.5)
04-Ha2.35 (dd, 16.0, 4.5)
04-Hb1.91 (m)
05-H–
07-H5.88 (d, 2.5)
09-H3.91 (m)
11-Ha1.93 (m)
11-Hb1.68 (m)
12-Ha2.14 (td, 13.0, 4.5)
12-Hb1.83 (td, 13.0, 4.5)
15-Ha1.97
15-Hb1.59 (t, 10.0)
16-Ha1.98 (m)
16-Hb1.73 (m)
17-H2.39 (m)
18-Me0.90 (s)
19-Me0.86 (s)
21-Me1.19 (s)
22-H3.32 (m)
23-Ha1.67 (m)
23-Hb1.28 (m)
24-Ha1.80 (m)
24-Hb1.42 (td, 12.5, 4.5)
25-H–
26-Me1.19 (s)
27-Me1.20 (s)
…2'a2.74 (d, 17.0)
…2'b2.56 (d, 17.0)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D20+22 ° (c 0.1; MeOH)
IR (KBr) ν max (cm-1) 
UV (DAD) λ max (log ε)248 (—) ;

CHROMATOGRAPHY


BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationGUILLEN, P.O. et al. (2018) Mar. Drugs 16, article 58  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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