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3-EPI-2-DEOXYECDYSONE 3-PHOSPHATE

Year of first isolation: 1982
Formula:C27H45O8P
Molecular weight:528
Occurence in plants:
 
Occurence in animals:
Locusta migratoria [Orthoptera] » Images of Locusta migratoria Wikipedia: <br />
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Schistocerca gregaria [Orthoptera] » Images of Schistocerca gregaria Wikipedia: <br />
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3-EPI-2-DEOXYECDYSONE 3-PHOSPHATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CCC(C4)OP(=O)(O)O)C)C)O)C(CCC(C)(C)O)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@@H](C1)OP(=O)([O-])[O-])C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(C)(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name[(3R,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-14-hydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] dihydrogen phosphate
CAS-RN 
PubChem CID21724362
InChiKey
[ ChemIDPlus: search ]
GIUAFYXKULGOEW-DUIYOXMUSA-N
InChIInChI=1S/C27H45O8P/c1-16(22(28)9-10-24(2,3)30)18-8-13-27(31)20-15-23(29)21-14-17(35-36(32,33)34)6-11-25(21,4)19(20)7-12-26(18,27)5/h15-19,21-22,28,30-31H,6-14H2,1-5H3,(H2,32,33,34)/t16-,17+,18+,19-,21-,22+,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %) 
FAB-MS m/z549 (M-H+Na)-, 527 (M-H)-, 97, 79
HR-MS 

CARBON NMR

PROTON NMR

D2O
0134.00 (t )
0229.70 (t )
0374.60 (d )
0433.60 (t )
0559.60 (d )
06207.80 (s )
07121.70 (d )
08169.60 (s )
0934.60 (d )
1037.20 (t )
1121.00 (t )
1231.70 (t )
1348.00 (s )
1485.90 (s )
1532.20 (t )
1625.20 (t )
1748.50 (d )
1816.40 (q )
1923.80 (q )
2042.70 (d )
2113.50 (q )
2275.50 (d )
2326.60 (t )
2441.50 (t )
2572.70 (s )
2629.10 (q )
2728.80 (q )
CD3OD
01-Ha 
01-He 
02-Ha 
03-He4.08 (m, w1/2=20)
04-Ha 
04-He 
05-H 
07-H5.80
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.73 (s )
19-Me0.91 (s )
21-Me0.95 (d, 6)
22-H3.60 (m, w1/2=19)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.19 (s )
27-Me1.20 (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 26 ml (column Partisil-ODS3, 25 cm x 4.6 mm i.d. eluted with a gradient of MeOH in 20 mM sodium citrate pH 6.5, 2:3 v/v to 4:1 v/v over 25 min, flow-rate 2 ml.min-1)

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationTSOUPRAS, G. et al. (1982) Tetrahedron Lett., 2045-2048 Search more
GeneralISAAC, R.E. et al. (1984) Biochem. J. 221, 459-464 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

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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