Welcome to online ecdysteroids database ! . .
Access data · History · Contact

DECUMBESTERONE A

Year of first isolation: 1999
Formula:C29H46O7
Molecular weight:506
Occurence in plants:
Ajuga decumbens [Lamiaceae (alt. Labiatae)] » Images of Ajuga decumbens Wikipedia: Ajuga decumbens [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
DECUMBESTERONE A

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)C(=C)C)O
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
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@](C)([C@@H](C[C@H](C(=C)C)C(O)C)O)O)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1C2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](C[C@H](C(=C)C)C(C)O)O)O)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1C2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](C[C@H](C(=C)C)C(C)O)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R,5R)-2,3-dihydroxy-5-(1-hydroxyethyl)-6-methylhept-6-en-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID100975967
InChiKey
[ ChemIDPlus: search ]
VEIMPAGTQSNXNE-YAUYKCKZSA-N
InChIInChI=1S/C29H46O7/c1-15(2)17(16(3)30)11-25(34)28(6,35)24-8-10-29(36)19-12-21(31)20-13-22(32)23(33)14-26(20,4)18(19)7-9-27(24,29)5/h12,16-18,20,22-25,30,32-36H,1,7-11,13-14H2,2-6H3/t16?,17-,18+,20+,22-,23+,24+,25-,26-,27-,28-,29-/m1/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)488, 470, 452, 434, 363, 345, 327, 300, 282, 187, 169, 151, 143, 125 (base peak), 107
HR-FAB-MS[M+H]+ 507.3295 (calculated 507.3333 for C29H47O7)

CARBON NMR

PROTON NMR

C5D5N
0138.02 (t)
0268.17 (d)
0360.08 (d)
0432.56 (t)
0551.44 (d)
06203.54 (s)
07121.56 (d)
08166.32 (s)
0934.47 (d)
1038.68 (s)
1121.13 (t)
1231.98 (t)
1348.04 (s)
1484.11 s)
1531.72 (t)
1621.38 (t)
1749.95 (d)
1817.86 (q)
1924.51 (q)
2076.73 (s)
2121.65 (q)
2274.27 (d)
2332.80 (t)
2453.91 d)
25147.19 (s)
26113.22 (t)
2719.99 (q)
2869.30 (d)
2923.16 (q)
C5D5N
01-Ha 
01-He 
02-Ha4.20 (m)
03-He4.27 (m)
04-Ha 
04-He 
05-H3.05 (dd, 13.2, 3.6)
07-H6.29 (d, 2.2)
09-H3.62 (br, t, 10.4)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.97 (br, t, 8.8)
18-Me1.18 (s)
19-Me1.09 (s)
21-Me1.58 (s)
22-H3.93 (m)
23-Ha 
23-Hb 
24-H2.87 (br, dt, 9.8, 2.8)
26-H4.91 (d, 2.2) , 4.97 (d, 2.2)
27-Me1.77 (s)
28-H3.96 (m)
29-Me1.40 (d, 5.9)

PHYSICAL PROPERTIES

M.P. 
[α]D20+ 64.8 ° (c 0.77; MeOH)
IR (KBr) ν max (cm-1)4300, 2960, 1640
UV (EtOH) λ max (log ε)244 (4.090)

CHROMATOGRAPHY

TLC 
HPTLC 
HPLC 
GLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationTAKASAKI, M. et al. (1999) J. Nat. Prod. 62, 972-975 Search more

see Important notice
© 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
designed by Cybersales a.s.
Powered by Cybersales
PRINTER READY | MEDIUM | WIDE