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26-HYDROXYECDYSONE 26-PHOSPHATE

Year of first isolation: 1985
Formula:C27H45O10P
Molecular weight:560
Occurence in plants:
 
Occurence in animals:
Manduca sexta [Lepidoptera] » Images of Manduca sexta Wikipedia: Manduca sexta [Lepidoptera]
26-HYDROXYECDYSONE 26-PHOSPHATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)C(CCC(C)(COP(=O)(O)O)O)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(COP(=O)([O-])[O-])(C)O)O)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(COP(=O)([O-])[O-])(C)O)O)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(COP(=O)([O-])[O-])(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name[(6S)-2,5-dihydroxy-2-methyl-6-[(2S,3R,5R,9R,10R,13R,14S,17R)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptyl] dihydrogen phosphate
CAS-RN 
PubChem CID66869246
InChiKey
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UAVLECYANOCBPS-YHEWSBQBSA-N
InChIInChI=1S/C27H45O10P/c1-15(20(28)7-8-24(2,32)14-37-38(34,35)36)16-6-10-27(33)18-11-21(29)19-12-22(30)23(31)13-25(19,3)17(18)5-9-26(16,27)4/h11,15-17,19-20,22-23,28,30-33H,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 (negative mode) 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-Ha4.00
03-He4.085
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-Me0.745 (s )
19-Me1.005 (s )
21-Me0.945 (d, 6.4)
22-H3.66
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H--
26-CH2-O-3.704 (d, 4.8)
27-Me1.214 (s )

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCRP-HPLC, Retention time 10.63 min (column ?Bondapak C18, 30 cm long, 4 mm i.d., solvent isocratic MeOH-aqueous 25 mM NaH2PO4, pH 5, 30:70 v/v, flow-rate 1 ml.min-1)

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationTHOMPSON, M.J. et al. (1985) Arch. Insect Biochem. Physiol. 2, 227-236 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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