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VENUSTONE

Year of first isolation: 1995
Formula:C31H50O9
Molecular weight:566
Occurence in plants:
Penstemon venustus [Scrophulariaceae] » Images of Penstemon venustus Wikipedia: Penstemon venustus [Scrophulariaceae]
Occurence in animals:
 
VENUSTONE

STRUCTURE DESCRIPTORS

Canonical SMILES 
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](CCC(C)(C)O)OC(=O)CC(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2R,3R)-2,6-dihydroxy-6-methyl-2-((2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)heptan-3-yl 3-hydroxybutanoate
CAS-RN 
PubChem CID 
InChiKey
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FCKMDUFNBYPSNI-NCTSFRKGSA-N
InChIInChI=1S/C31H50O9/c1-17(32)13-26(36)40-25(9-10-27(2,3)37)30(6,38)24-8-12-31(39)19-14-21(33)20-15-22(34)23(35)16-28(20,4)18(19)7-11-29(24,31)5/h14,17-18,20,22-25,32,34-35,37-39H,7-13,15-16H2,1-6H3/t17?,18-,20-,22+,23-,24-,25+,28+,29+,30+,31+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
FAB-MS (negative-ion mode) m/z (relative intensity %)565 [M-H]- (7), 479 (12), 183 (100), 103 (20), 91 (43)
EI-MS m/z (relative intensity %)530 [M-2H2O]+ (0.5), 512 (0.9), 494 (1), 468 (2), 444 (2), 426 (11), 387 (6), 363 (32), 345 (100), 327 (40), 285 (18), 269 (16), 215 (16), 173 (19), 99 (51), 81 (28), 69 (40).
HR-MS 

CARBON NMR

PROTON NMR

CD3OD
0137.4
0268.7
0368.5
0432.8
0551.8
06206.4
07122.2
08167.8
0935.1
1039.3
1121.5
1232.6
1348.7
1485.2
1531.8
1621.5
1750.8
1818.1
1924.4
2077.6
2121.9
2280.8
2326.1
2441.5
2571.0
2629.5
2728.9
ac1'173.5
ac2'45.2
ac3'65.6
ac4'23.2
CD3OD
01-Ha1.42
01-He1.79
02-Ha3.83
03-He3.94
04-Ha1.70
04-He1.70
05-H2.38
07-H5.80 (d, 2)
09-Ha3.15
11-Ha1.69
11-He1.81
12-Ha2.15 (ddd, 13.1, 13.1, 4.9)
12-He1.86
15-Ha1.95
15-Hb1.61
16-Ha2.03
16-Hb1.75
17-H2.38
18-Me0.87 (s )
19-Me0.95 (s )
21-Me1.28 (s )
22-H4.92
23-Ha1.14
23-Hb1.47
24-Ha1.77
24-Hb1.42
26-Me1.17 (s )
27-Me1.15 (s )
H-2'a2.43 (dd, 15.1, 8.3)
H-2'b2.57 (dd, 15.1, 4.8)
H-3'4.23
H4'-Me1.23 (d, 6.2)

PHYSICAL PROPERTIES

M.P. 
[α]D20+ 57 ° (c 0.2; MeOH)
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCRP-HPLC : Lichrosorb RP-18 (H2O-MeOH), gradient (0-32 min) : 10-93% MeOH, flow-rate 2 ml.min-1.

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationROTH, U. et al. (1995) Phytochemistry 39, 941-942 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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