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20-HYDROXYECDYSONE 3-ACETATE 2-PHOSPHATE

Year of first isolation: 1984
Formula:C29H47O11P
Molecular weight:602
Occurence in plants:
 
Occurence in animals:
Schistocerca gregaria [Orthoptera] » Images of Schistocerca gregaria Wikipedia: Schistocerca gregaria [Orthoptera]
Locusta migratoria [Orthoptera] » Images of Locusta migratoria Wikipedia: Locusta migratoria [Orthoptera]
Labidura riparia [Dermaptera] » Images of Labidura riparia Wikipedia: Labidura riparia [Dermaptera]
20-HYDROXYECDYSONE 3-ACETATE 2-PHOSPHATE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1OP(=O)([O-])[O-])OC(=O)C)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-3-acetoxy-14-hydroxy-10,13-dimethyl-6-oxo-17-((2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl)-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl phosphate
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
ZOBGNTMEECHANU-FORVDKSSSA-L
InChIInChI=1S/C29H47O11P/c1-16(30)39-21-14-19-20(31)13-18-17(26(19,4)15-22(21)40-41(36,37)38)7-11-27(5)23(8-12-29(18,27)35)28(6,34)24(32)9-10-25(2,3)33/h13,17,19,21-24,32-35H,7-12,14-15H2,1-6H3,(H2,36,37,38)/p-2/t17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %) 
FAB-MS m/z623 (M-H+Na)-, 601 (M-H)-, 585, 583, 569, 541, 483, 467, 439, 396, 371, 319, 215, 183, 181, 149, 123, 97, 79
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
01 
02 
03 
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
14 
15 
16 
17 
18 
19 
20 
21 
22 
23 
24 
25 
26 
27 
28 
29 
CD3OD
01-Ha 
01-He 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H 
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.885 (s )
19-Me0.995 (s )
21-Me1.19 (s )
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me1.19 (s )
27-Me1.20 (s )
O-Ac2.09 (s )

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCRP-HPLC with ion suppression, Retention volume 22 ml (Waters column Resolve 15 cm x 4.6 mm i.d. eluted with MeOH-20 mM sodium citrate pH 6.5, 3:7 v/v, flow-rate 1 ml.min-1).

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationISAAC, R.E. et al. (1984) Biochem. J. 231, 459-464 Search more
First isolationMODDE, J.-F. et al. (1984) Int. J. Invertebr. Reprod. Develop. 7, 161-183 Search more
GeneralDIEHL, P.A. et al. (1985) Methods Enzymol. 111, 377-410 Search more
GeneralHETRU, C. et al. (1985) Methods Enzymol. 111, 411-419 Search more
GeneralSAYAH, F. et al. (1995) Netherl. J. Zool. 45, 89-92 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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