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CYCLEASTERONE A

Year of first isolation: 2019
Formula:C27H58O6
Molecular weight:458
Occurence in plants:
Cyclea barbata [Menispermaceae] » Images of Cyclea barbata Wikipedia: Cyclea barbata [Menispermaceae]
Occurence in animals:
 
CYCLEASTERONE A

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@@]1(C)OC(C(=O)C=C1)(C)C)O)C)C » JSMol: View in 3D
IUPAC Name(6S)-2,2,6-trimethyl-6-((2S,3R,5R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2H-pyran-3(6H)-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
BBTAMRYXORPDJR-HLUMLXHKSA-N
InChIInChI=1S/C27H38O6/c1-23(2)22(31)8-10-26(5,33-23)21-7-11-27(32)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-9-25(21,27)4/h8,10,12,15,17,19-21,29-30,32H,6-7,9,11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,24+,25+,26-,27+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z  
HRESIMS (positive ion mode) m/z 481.2551 [M+Na] + , calc. for C27H58O6Na 481.2560

CARBON NMR

PROTON NMR

CD3OD
0137.4
0268.7
0368.5
0432.9
0551.8
06206.4
07122.0
08167.7
0935.0
1039.3
1121.5
1232.2
1348.1
1485.4
1531.6
1623.5
1754.0
1818.1
1924.4
2094.7
2128.8
22137.8
23128.3
24212.4
2597.4
2626.8
2725.4`
CD3OD
01-Ha1.73 (m)
01-Hb1.38 (m)
02-H3.77 (ddd, 12.0, 3.6, 3.6)
03-He3.89 (br d, 2.4)
04-Ha1.67 (m)
04-Hb1.67 (m)
05-H2.32 (dd, 13.2, 4.8)
07-H5.74 (d, 3.0)
09-H3.09 (ddd, 10.8, 7.2, 3.0)
11-Ha1.76 (m)
11-Hb1.64 (m)
12-Ha2.08 (ddd, 13.2, 13.2, 4.8)
12-Hb1.79 (m)
15-Ha1.86 (m)
15-Hb1.51 (ddd, 12.6, 9.6, 2.4)
16-Ha1.66 (m)
16-Hb1.35 (m)
17-H2.38 (dd, 9.0, 9.0)
18-Me0.84 (s)
19-Me0.91 (s)
21-Me1.39 (s)
22-H5.78 (d, 6.0)
23-H5.79 (d, 6.0)
24-Ha2.03 (m)
26-Me1.33 (s)
27-Me2.20 (s)

PHYSICAL PROPERTIES

M.P. 
[α]D20+ 31.81 (c 0.2867 ; MeOH)
IR (KBr) ν max (cm-1)34.67, 2940, 1714, 1645, 1098, 1068, 875
UV (MeOH) λ max (log ε)242 nm (2.81) ;

CHROMATOGRAPHY

TLC
HPTLC
HPLC
GLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationWANG, X.J. et al. (2019) J. Asian Nat. Prod. Res. 21 (3), 217-226 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
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