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22-EPI-AJUGASTERONE C

Year of first isolation: 2018
Formula:C27H44O7
Molecular weight:480
Occurence in plants:
Serratula cichoracea [Asteraceae] » Images of Serratula cichoracea  Wikipedia: Serratula cichoracea [Asteraceae]
Occurence in animals:
 
22-EPI-AJUGASTERONE C

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)(C1CCC2(C1(CC(C3C2=CC(=O)C4C3(CC(C(C4)O)O)C)O)C)O)O)O
Isomeric SMILES
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[ ChemSpider: search ]
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H](CCC(C)C)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,11R,13R,14S)-17-[(2S,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,11,14-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID44231360
InChiKey
[ ChemIDPlus: search ]
LQGNCUXDDPRDJH-GXSDRAAHSA-N
InChIInChI=1S/C27H44O7/c1-14(2)6-7-22(32)26(5,33)21-8-9-27(34)16-11-17(28)15-10-18(29)19(30)12-24(15,3)23(16)20(31)13-25(21,27)4/h11,14-15,18-23,29-34H,6-10,12-13H2,1-5H3/t15-,18+,19-,20+,21?,22+,23?,24-,25+,26-,27+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z  
HR-ESIMS503.2974 [M+Na]+, calc. for C27H44O7Na 503.2985

CARBON NMR

PROTON NMR

CD3OD
0139.94
0269.76
0369.42
0434.11
0553.62
06207.60
07123.57
08166.62
0943.80
1040.76
1170.36
1244.63
1352.30
1485.74
1532.67
1622.37
1751.13
1819.72
1925.45
2078.82
2121.82
2278.66
2331.32
2438.48
2530?05
2624.24
2723.59
CD3OD
01-Ha1.23 (dd, 12.9; 4.3)
01-He2.48 (dd, 13.9, 4.3)
02-Ha3.92 (dt, 11.2, 4.3)
03-He3.86 (q, 3.0)
04-Ha1.67 (td, 13.5, 2.5)
04-He1.60 (dt, 13.5, 3.5)
05-H2.24 (dd, 12.9, 3.8)
07-H5.70 (dd, 2.8, 0.8)
09-H3.05 (dd, 9.0, 2.9)
11-H4.01 (ddd 10.6, 8.8;, 6.8)
12-Ha2.09 (dd, 12.3, 10.6)
12-He2.03 (dd, 12.3, 6.1)
15-Ha1.86 (m)
15-Hb1.48 (m)
16-Ha1.88 (m)
16-Hb1.61 (m)
17-H2.34 (t, 11.2)
18-Me0.77 (s)
19-Me0.97 (s)
21-Me1.10 (s)
22-H3.23
23-Ha1.17 (m)
23-Hb1.65 (m)
24-Ha1.37 (m)
24-Hb1.15 (m)
25-H1.48
26-Me0.81 (d, 6.6)
27-Me0.83 (d, 6.6)

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

HPLC
GLC
TLC
HPTLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationALIOUCHE, L. et al. (2018) Current Bioactive Compounds 14, 60-66 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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