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ECDYSONELACTONE C

Year of first isolation: 2018
Formula:C29H44O8
Molecular weight:520
Occurence in plants:
 
Occurence in animals:
Antipathozoanthus hickmani [Parazoanthidae] » Images of Antipathozoanthus hickmani Wikipedia: Antipathozoanthus hickmani [Parazoanthidae]
ECDYSONELACTONE C

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC5(CC(=O)OC5C4)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O
Isomeric SMILES
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C1[C@]2([C@@H](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)C » JSMol: View in 3D
IUPAC Name(1R,2R,4S,8R,10R,14S,17S,18R)-4,14-dihydroxy-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 CID138453998
InChiKey
[ ChemIDPlus: search ]
KPRLZEATQBILFE-JITQUFICSA-N
InChIInChI=1S/C29H44O8/c1-24(2,33)9-8-21(31)27(5,34)20-7-11-29(36)17-12-19(30)18-13-22-28(35,14-23(32)37-22)15-25(18,3)16(17)6-10-26(20,29)4/h12,16,18,20-22,31,33-36H,6-11,13-15H2,1-5H3/t16-,18-,20-,21+,22+,25+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z  
EI-MS m/z (relative intensity %)
HRESI-MS m/z (positive ion mode) m/z521.3107 [M+H] + , calc. for C29H45O8 521.3109 (∆ -0.38 ppm)

CARBON NMR

PROTON NMR

CD3OD
0141.9
0274.0
0382.0
0425.1
0552.1
06205.3
07121.6
08169.3
0935.7
1037.0
1121.4
1232.5
1348.8
1485.1
1531.9
1621.5
1750.5
1818.1
1924.1
2077.9
2121.0
2278.4
2327.3
2442.4
2571.3
2628.9
2729.7
…01'176.1
…02'47.1
CD3OD
01-Ha2.11 (M)
01-Hb1.09 (d, 15.0)
02-H–
03-He4.50 (br, s)
04-Ha2.13 (m)
04-Hb1.93 (m)
05-H2.10 (m)
07-H5.83 (d, 2.0)
09-H3.80 (ddd, 11.5, 6.5, 2.0)
11-Ha1.93 (m)
11-Hb1.65 (m)
12-Ha2.15 (m)
12-Hb1.84 (m)
15-Ha1.98 (m)
15-Hb1.59 (t, 10.0)
16-Ha1.98 (m)
16-Hb1.73 (m)
17-H2.39 (t, 8.6)
18-Me0.89 (s)
19-Me0.93 (s)
21-Me1.19 (s)
22-H3.33 (m)
23-Ha1.66 (m)
23-Hb1.28 (m)
24-Ha1.80 (td, 12.5, 4.5)
24-Hb1.43 (td, 12.5, 4.5)
25-H–
26-Me1.19 (s)
27-Me1.20 (s)
…2'a2.71 (d, 17.0)
…2'b2.50 (d, 17.0)

PHYSICAL PROPERTIES

M.P.— °C ;
[α]D20+30 ° (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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