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3-EPI-22-DEOXY-20,26-DIHYDROXYECDYSONE 2-PHOSPHATE

Year of first isolation: 2000
Formula:C27H45O10P
Molecular weight:560
Occurence in plants:
 
Occurence in animals:
Bombyx mori [Bombycidae] » Images of Bombyx mori Wikipedia: <br />
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3-EPI-22-DEOXY-20,26-DIHYDROXYECDYSONE 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-])O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)(CCCC(CO)(C)O)O)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@@H]([C@H]1OP(=O)([O-])[O-])O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)(CCCC(CO)(C)O)O)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@@H]([C@H]1OP(=O)([O-])[O-])O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)(CCCC(CO)(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name 
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
HDFBSOFKEFOGKM-IPIKEVATSA-L
InChIInChI=1S/C27H45O10P/c1-23(31,15-28)8-5-9-26(4,32)22-7-11-27(33)17-12-19(29)18-13-20(30)21(37-38(34,35)36)14-24(18,2)16(17)6-10-25(22,27)3/h12,16,18,20-22,28,30-33H,5-11,13-15H2,1-4H3,(H2,34,35,36)/p-2/t16-,18-,20-,21-,22-,23?,24+,25+,26-,27+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
FAB-MS m/z97 [H2PO4] -, 79 [PO3] -

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
CD3OD
01-Ha 
01-He 
02-Ha4.24 (m, w1/2 = 34)
03-Ha3.55 (m, w1/2 = 22)
04-Ha 
04-He 
05-H2.09 (dd, 14.3, 3.8)
07-H5.81 (d, 2.4)
09-Hoverlap with solvent
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.84 (s)
19-Me0.95 (s)
21-Me1.27 (s)
22-Ha 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-H2/33.35 (s)
27-Me1.13 (s)

PHYSICAL PROPERTIES

M.P.- °C ;
[α]D20? ° (c ; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)243 nm (-) ;

CHROMATOGRAPHY

HPLCRP-HPLC column Wakosil 5C18, 250x10 mm, flow-rate 2 ml/min, solvent linear gradient of MeOH in 20 mM phosphate buffer, pH 5.56, changing from 1:9 to 7:3 in 70 min, Ret 49.8 min.RP-HPLC column Wakosil 5C18, 250x4.6 mm, flow-rate 1 ml/min, solvent 25 % aqueous MeOH, Ret 9.7 min.
GLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationKAMBA, M. et al. (2000) Nat. Prod. Lett. 14, 469-476 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
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