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SENDREISTERONE

Year of first isolation: 2009
Formula:C30H48O8
Molecular weight:536
Occurence in plants:
Ajuga reptans var. reptans [Lamiaceae (alt. Labiatae)] » Images of Ajuga reptans var. reptans Wikipedia: Ajuga reptans var. reptans [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
SENDREISTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCCC1(CC(OC(C1C)OC)(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)O)O
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@](C)([C@@H]1O[C@@H]([C@H]([C@](C1)(CC)O)C)OC)O)O)C)C  » JSMol: View in 3D
CC[C@]1(C[C@@](O[C@@H]([C@H]1C)OC)([C@@](C)([C@H]2CC[C@@]3([C@@]2(CC[C@H]4C3=CC(=O)[C@H]5[C@@]4(C[C@@H]([C@@H](C5)O)O)C)C)O)O)O)O » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(1R)-1-[(2R,4R,5S,6S)-4-ethyl-2,4-dihydroxy-6-methoxy-5-methyloxan-2-yl]-1-hydroxyethyl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one (PubChem structure)
CAS-RN 
PubChem CID101477049
InChiKey
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XQNZRCPIFDQCEV-FVMDOQFWSA-N
InChIInChI=1S/C30H48O9/c1-7-28(35)15-30(37,39-24(38-6)16(28)2)27(5,34)23-9-11-29(36)18-12-20(31)19-13-21(32)22(33)14-25(19,3)17(18)8-10-26(23,29)4/h12,16-17,19,21-24,32-37H,7-11,13-15H2,1-6H3/t16-,17+,19+,21-,22+,23+,24+,25-,26-,27-,28-,29-,30-/m1/s1

MASS SPECTRUM

CI-MS (NH3) m/zHR-ESIMS
ESI-MS m/z (relative intensity %)560 [M+Na+H]+ (27), 559 [M+Na]+ (100), 537 [M+H]+ (25.5), 521 [M-CH3]+ (14), 519 [M+H-H2O]+ (26), 505 (19.5), 482 [M-3H2O]+ (18), 445 (20.7), 437 (16.5), 413 (27.9), 391 (7.5), 365 (37.9), 356 (14.8)

CARBON NMR

PROTON NMR

CD3OD
0137.5
0268.9
0368.7
0433.0
0552.0
06206.6
07122.3
08168.1
0935.2
1039.4
1121.65
1232.6
1348.6
1485.4
1531.9
1622.1
1750.7
1818.3
1924.5
2077.4
2121.84
2277.5
2336.8
2474.2
2549.2
26106.4
278.8
2825.3
297.5
3057.2
CD3OD
01-Ha1.43
01-He1.80
02-Ha3.84
03-He3.95
04-Ha1.70
04-He1.75
05-H2.39
07-H5.81
09-H3.16
11-Ha1.70
11-He1.81
12-Ha2.17
12-He1.85
15-Ha1.63
15-Hb2.00
16-Ha1.81
16-Hb2.01
17-H2.50
18-Me0.87
19-Me0.97
21-Me1.27 (s)
22-H3.26 (dd, 12.0, 1.2)
23-Ha1.2 (t, 12.4)
23-He2.02
25-H1.53
26-H4.13 (d, 8.9)
27-Me0.92 (d, 7.0)
28-Ha1.52
28-Hb1.57
29-Me0.933 (t, 7.4)
30-OMe3.50 (s)

PHYSICAL PROPERTIES

M.P.253-255 °C ;
[α]D28+ 22 ° (c 0.1; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)240 (3.62) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationVÁNYOLÓS, A. et al. (2009) J. Nat. Prod. 72, 929-932 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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