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SPHENOCENTROSIDE A

Year of first isolation: 2019
Formula:C33H54O11
Molecular weight:626
Occurence in plants:
Sphenocentrum jollyanum [Menispermaceae] » Images of Sphenocentrum jollyanum Wikipedia: Sphenocentrum jollyanum [Menispermaceae]
Occurence in animals:
 
SPHENOCENTROSIDE A

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)[C@H](CC1=C2CC[C@]2(C1=CC[C@@H]2[C@]([C@@H](CCC(C)(C)O)O[C@@H]1C(C([C@@H](C(O1)CO)O)O)O)(O)C)C)O)C » JSMol: View in 3D
IUPAC Name(2R,5S)-2-(((2R,3R)-2,6-dihydroxy-6-methyl-2-((2S,3R,5R,6S,10S,13R,17S)-2,3,6-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)heptan-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
DQKMEUKDFNTCGB-NIBMHSDCSA-N
InChIInChI=1S/C33H54O11/c1-30(2,41)10-9-25(44-29-28(40)27(39)26(38)23(15-34)43-29)33(5,42)24-7-6-17-16-12-20(35)19-13-21(36)22(37)14-32(19,4)18(16)8-11-31(17,24)3/h6,19-29,34-42H,7-15H2,1-5H3/t19-,20-,21+,22-,23?,24-,25+,26+,27?,28?,29+,31-,32+,33+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z  
EI-MS m/z (relative intensity %)
HRESI-MS m/z (positive ion mode) m/z649.3587 [M+Na] + , calc. for C33H54O11Na 649.3565

CARBON NMR

PROTON NMR

CD3OD
0139.46
0270.16
0369.89
0427.70
0542.48
0665.85
0732.57
08124.53
09136.69
1042.68
1123.05
1238.97
1347.46
14151.07
15118.63
1631.51
1758.25
1818.65
1930.22
2076.87
2121.63
2289.94
2327.49
2440.92
2571.38
2629.77
2728.94`
[sugar] 1'105.62
[sugar] 2'75.44
[sugar] 3'71.34
[sugar] 4'77.94
[sugar] 5' 78.08
[sugar] 6' 62.39
CD3OD
01-Ha1.83 (dd, 3.6, 13.2)
01-Hb1.69 (m)
02-H3.27 (m)
03-He3.94 (m)
04-Ha1.91 (m)
04-Hb1.28 (m)
05-H1.92 (m)
06-H4.29 (m)
07-Ha2.30 (dd, 6.8, 16.4)
07-Hb2.15 (m)
09-H-
11-Ha2.23 (m)
11-Hb 
12-Ha2.22 (m)
12-Hb1.45 (m)
15-H5.40 (br t, 2.4)
16-Ha2.66 (dd, 10.7, 15.4)
16-Hb2.12 (m)
17-H1.92 (m)
18-Me1.14 (s)
19-Me1.08 (s)
21-Me1.27 (s)
22-H3.49 (m)
23-Ha1.67 (m)
23-Hb1.55 (m)
24-Ha2.05 (m)
24-Hb1.44 (m)
25-H-
26-Me1.19 (s)
27-Me1.17 (s)
[sugar] 1'4.35 (d, 7.8)
[sugar] 2'3.27 (m)
[sugar] 3'3.35 (m)
[sugar] 4'3.39 (m)
[sugar] 5'3.33 (m)
[sugar] 6'3.86 (m)
[sugar] 6''3.67 (m)

PHYSICAL PROPERTIES

M.P. 
[α]D20+
IR (KBr) ν max (cm-1)
UV (DAD) λ max (log ε)- () ;

CHROMATOGRAPHY

HPLC
GLC
TLC
HPTLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationAJAYI, I.O. et al. (2019) Steroids 150, 108456 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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