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3-EPI-22-DEOXY-20-HYDROXYECDYSONE 2-PHOSPHATE

Year of first isolation: 1995
Formula:C27H45O9P
Molecular weight:544
Occurence in plants:
 
Occurence in animals:
Bombyx mori [Bombycidae] » Images of Bombyx mori Wikipedia: Bombyx mori [Bombycidae]
3-EPI-22-DEOXY-20-HYDROXYECDYSONE 2-PHOSPHATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)OP(=O)(O)O)C)C1(CCC2C(C)(CCCC(C)(C)O)O)O
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(C)(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name[(2S,3S,5R,9R,10R,13R,14S,17S)-17-[(2S)-2,6-dihydroxy-6-methylheptan-2-yl]-3,14-dihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl] dihydrogen phosphate
CAS-RN 
PubChem CID101915845
InChiKey
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GQXLTWAYLDYLHA-FTUASRNISA-N
InChIInChI=1S/C27H45O9P/c1-23(2,30)9-6-10-26(5,31)22-8-12-27(32)17-13-19(28)18-14-20(29)21(36-37(33,34)35)15-24(18,3)16(17)7-11-25(22,27)4/h13,16,18,20-22,29-32H,6-12,14-15H2,1-5H3,(H2,33,34,35)/t16-,18-,20-,21-,22-,24+,25+,26-,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %) 
FAB-MS m/z565 (M-H+Na)-, 543 (M-H)-, 97 (H2PO4)-, 79 (PO3)-
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 
CD3OD
01-Ha 
01-Hb 
02-Ha4.24 (m )
03-Ha3.56 (m )
04-Ha 
04-He 
05-H 
07-H5.81 (br, s )
09-Ha3.21 (m )
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.85 (s )
19-Me0.95 (s )
21-Me1.27 (s )
22-Ha 
22-Hb 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.19 (s )
27-Me1.19 (s )

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

HPTLC 
TLC 
HPLCRP-HPLC, column Wakosil 5C18, 25 cm long, 10 mm i.d., linear gradient (70 min) of MeOH in 20 mM phosphate buffer (pH 5.56), changing from 1:9 to 7:3, 2 ml.min-1, Ret 58.5 min (numerous other references are run in this system); Anion-exchange chromatography column Chemcosorb 7 SAX, 25 cm long, 4.6 mm i.d, isocratic 0.1 M ammonium acetate, 2 ml.min-1, Ret 10 min.

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationMAMIYA, Y. et al. (1995) Experientia 51, 363-367 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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