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AJUGASTERONE 20,22-DIOXOLANE A

Year of first isolation: 2022
Formula:C33H52O8
Molecular weight:576
Occurence in plants:
Ajuga decumbens [Lamiaceae (alt. Labiatae)] » Images of Ajuga decumbens Wikipedia: Ajuga decumbens [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
AJUGASTERONE 20,22-DIOXOLANE A

STRUCTURE DESCRIPTORS

Isomeric SMILES
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C[C@@]12[C@@](C(C=C3C2[C@H](O)C[C@@]4(C)[C@@]3(O)CC[C@@H]4[C@@]5(C)[C@H](OC(CCCO)O5)CC(C(C)O)C(C)=C)=O)([H])C[C@@H](O)[C@@H](O)C1 » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-17-((4S,5R)-5-(2-(1-hydroxyethyl)-3-methylbut-3-en-1-yl)-2-(3-hydroxypropyl)-4-methyl-1,3-dioxolan-4-yl)-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
WRESURRAMOMIKG-NGXGVZSLSA-N
InChIInChI=1S/C33H52O9/c1-17(2)19(18(3)35)12-27-32(6,42-28(41-27)8-7-11-34)26-9-10-33(40)21-14-22(36)20-13-23(37)24(38)15-30(20,4)29(21)25(39)16-31(26,33)5/h14,18-20,23-29,34-35,37-40H,1,7-13,15-16H2,2-6H3/t18?,19?,20-,23+,24-,25+,26-,27+,28?,29?,30-,31+,32-,33+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z  
EI-MS m/z (relative intensity %)
HRESIMS (positive ion mode) m/z 577.3737 [M+H]+, calc. 577.3737

CARBON NMR

PROTON NMR

CD3OD
0135.9
0267.4
0367.2
0430.4
0550.4
06205.4
07120.8
08166.5
0933.8
1037.9
1121.2
1230.8
1349.7
1483.7
1537.8
1621.3
1746.9
1816.3
1923.1
2084.0
2122.3
2280.9
2320.1
2452.8
25145.4
26113.2
2718.6
2869.2
2921.0
30104.0
3131.5
3226.8
3361.6
CD3OD
01-Ha1.42 (m)
01-Hb1.79 (m)
02-Ha3.95 (d, 3.0)
03-He3.84 (td, 8.3, 5.0)
04-Ha2.05 (m)
04-Hb1.70 (m)
05-H2.38 (dd, 12.3, 5.1)
07-H5.81 (d, 2.5)
09-H3.14 (m)
11-Ha1.85 (m)
11-Hb1.77 (m)
12-Ha2.07 (m)
12-Hb1.82 (m)
15-Ha2.02 (m)
15-Hb1.39 (m)
16-Ha1.92 (m)
16-Hb1.89 (m)
17-H2.29 (m)
18-Me0.85 (s)
19-Me0.96 (s)
21-Me1.16 (s)
22-H3.66 (d, 10.0)
23-Ha1.30 (m)
23-Hb 
24-H2.20 (m)
26-Ha4.89 (s)
26-Hb4.79 (s)
27-Me1.66 (s)
28-H3.62 (m)
29-Me1.13 (d, 6.2)
30-H5.04 (s)
31-Ha1.72 (m)
31-Hb1.72 (m)
32-H1.64 (m)
33-H3.57 (m)

PHYSICAL PROPERTIES

M.P.261-264 °C;
[α]D20– (c ; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)nm (-) ; –

CHROMATOGRAPHY

HPTLC
TLC
GLC
HPLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationOLATUNDE, O.Z. et al. (2022) Steroids 186, article 109089 Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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