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26-HYDROXYECDYSONE 2-PHOSPHATE

Year of first isolation: 1973
Formula:C27H45O10P
Molecular weight:560
Occurence in plants:
 
Occurence in animals:
Manduca sexta [Lepidoptera] » Images of Manduca sexta Wikipedia: Manduca sexta [Lepidoptera]
26-HYDROXYECDYSONE 2-PHOSPHATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)OP(=O)(O)O)C)C)O)C(CCC(C)(CO)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@H](C)[C@@H](CCC(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@H](C)[C@@H](CCC(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@H](C)[C@@H](CCC(CO)(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name[(2S,3R,5R,9R,10R,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-6-oxo-17-[(2S)-3,6,7-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl] dihydrogen phosphate
CAS-RN 
PubChem CID66869499
InChiKey
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KAAIKLQKKVDABE-YHEWSBQBSA-N
InChIInChI=1S/C27H45O10P/c1-15(20(29)7-8-24(2,32)14-28)16-6-10-27(33)18-11-21(30)19-12-22(31)23(37-38(34,35)36)13-25(19,3)17(18)5-9-26(16,27)4/h11,15-17,19-20,22-23,28-29,31-33H,5-10,12-14H2,1-4H3,(H2,34,35,36)/t15-,16+,17-,19-,20?,22+,23-,24?,25+,26+,27+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %) 
FAB-MS m/z559 (M-H)-, 543 (M-OH)-, 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 
D2O
01-Ha 
01-He 
02-Ha4.300 (m br )
03-He4.235
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-Me0.748 (s )
19-Me1.005 (s )
21-Me0.948 (d, )
22-H3.702 (d, )
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-CH2-OH3.468 (s , 2H)
27-Me1.183 (s )

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε)240 (?) ;

CHROMATOGRAPHY

HPTLCNP-HPTLC : Rf 0.15 (precoated plates for nanoTLC, Silicagel 60F254, Merck, solvent CHCl3-MeOHl-10NNH4OH 15:35:3.5)
TLC 
GLC 
HPLCRP-HPLC, Retention time 10.5 min (column IBM C8, 15 cm long, 4.6 mm i.d., eluted isocratically with EtOH-30mM aqueous NaH2PO4, pH 5, 26:74 v/v, flow-rate 1 ml.min-1).

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationTHOMPSON, J.A. et al. (1987) Arch. Insect Biochem. Physiol. 4, 183-190 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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