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20-DEOXYSHIDASTERONE

Year of first isolation: 2011
Formula:C27H42O5
Molecular weight:446
Occurence in plants:
Polypodium vulgare [Polypodiaceae] » Images of Polypodium vulgare Wikipedia: Polypodium vulgare [Polypodiaceae]
Occurence in animals:
 
20-DEOXYSHIDASTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)C5CCC(O5)(C)C
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@H](C)C1CCC(O1)(C)C)O)C)C  » JSMol: View in 3D
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@H](C)[C@@H]1CCC(O1)(C)C)O)C)C  » JSMol: View in 3D
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@H](C)[C@H]1CCC(O1)(C)C)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17R)-17-[1-(5,5-dimethyloxolan-2-yl)ethyl]-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 CID101534442
InChiKey
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XGNGGFFPHLDOLR-RXLYROFRSA-N
InChIInChI=1S/C27H42O5/c1-15(23-8-9-24(2,3)32-23)16-7-11-27(31)18-12-20(28)19-13-21(29)22(30)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19,21-23,29-31H,6-11,13-14H2,1-5H3/t15?,16-,17+,19+,21-,22+,23?,25-,26-,27-/m1/s1

MASS SPECTRUM

HRESI-MS/MS [M+H]+ = 447.3105, calculated for C27H43O5, 447.3105
ESI-MS/MS m/z (relative intensity %) 447 (0.1), 429 (100) [M+H-H2O]+, 411 (12) [M+H-2H2O]+, 393 (4) [M+H-3H2O]+, 375 (1), [M+H-4H2O]+, 331 (11)

CARBON NMR

PROTON NMR

CD3OD
0137.5
0268.9
0368.7
0433.0
0551.9
06
07122.2
08167.7
0935.6
1039.5
1121.7
1232.2
1348.5
1485.2
1532.3
1627.3
1749.5
1816.3
1924.6
2039.3
2113.1
2282.2
2325.9
2439.8
2581.8
2628.4
2729.0
CD3OD
01-Ha1.43 (dd, 13.3, 12.5)
01-He1.80
02-Ha3.84
03-He3.95 (q, 2.9)
04-Ha1.70*
04-He1.75*
05-H2.39 (dd, 12.8, 4.6)
07-H5.82 (d 2.6)
09-H3.15
11-Ha1.67
11-He1.81
12-Ha2.11 (td, 13.0, 4.9)
12-He1.79
15-Ha1.60
15-Hb1.98
16-Ha1.52
16-Hb1.98
17-H1.94
18-Me0.74 (s)
19-Me0.97 (s)
20-H1.85
21-Me0.935 (d, 6.5)
22-H4.11 (ABX)
23-Ha1.79
23-Hb1.79
24-Ha1.75
24-Hb1.75
26-Me1.246 (s)
27-Me1.246 (s)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D2812 ° (c = 0.1 ; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)242 (3.72) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSIMON, A. et al. (2011) Steroids 76, 1419-1424 Search more

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© Université Pierre & Marie Curie, Paris 6, France
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