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(20R)-1α,20-DIHYDROXYECDYSONE

Year of first isolation: 1998
Formula:C27H44O8
Molecular weight:496
Occurence in plants:
Axyris amaranthoides [Chenopodiaceae] » Images of Axyris amaranthoides Wikipedia: <br />
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Occurence in animals:
 
(20R)-1α,20-DIHYDROXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(C(C(C(C4)O)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O
Isomeric SMILES
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C[C@]12CC[C@H]3C(=CC(=O)[C@H]4[C@@]3([C@H]([C@@H]([C@@H](C4)O)O)O)C)[C@@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O » JSMol: View in 3D
IUPAC Name(1R,2R,3R,5R,9R,10R,13R,14S,17S)-1,2,3,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID10625088
InChiKey
[ ChemIDPlus: search ]
VJRBXZFHKYDEQV-HACZXUJGSA-N
InChIInChI=1S/C27H44O8/c1-23(2,33)9-8-20(30)26(5,34)19-7-11-27(35)15-12-17(28)16-13-18(29)21(31)22(32)25(16,4)14(15)6-10-24(19,27)3/h12,14,16,18-22,29-35H,6-11,13H2,1-5H3/t14-,16-,18+,19-,20+,21+,22-,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %) 
LSI-MS495 [M-H] -

CARBON NMR

PROTON NMR

C5D5N
0176.2
0268.1
0370.5
0433.0
0546.4
06--
07121.6
08--
0935.0
1042.0
1121.4
1232.0
1347.0
1484.2
1531.5
1621.5
1750.1
1817.8
1920.3
2076.8
2121.6
2277.5
2327.5
2442.6
2569.5
2630.0
2730.1
CD3OD
01-Ha4.31 (bs)
02-Ha4.29 (m)
03-He4.30 (m)
04-Ha1.85
04-He2.10
05-H3.30
07-H6.30 (d: 2.5)
09-H3.60 (m)
11-Ha1.76
11-He1.89
12-Ha2.60 (dd: 13, 5)
12-He2.00
15-Ha2.20
15-Hb1.90
16-Ha2.46
16-Hb2.10
17-H3.01 (t: 8)
18-Me1.25 (s)
19-Me1.44 (s)
21-Me1.59 (s)
22-H3.87 (m)
23-Ha1.84
23-Hb2.14
24-Ha2.30
24-Hb1.85
26-Me1.38 (s)
27-Me1.38 (s)
C5D5N
01-Ha3.82 (bs, w1/2 6.8)
02-Ha3.87 (bt)
03-He4.03 (m)
04-Ha1.70
04-He1.80
05-H2.60 (dd: 13, 4)
07-H5.82 (d: 2.3)
09-H3.07 (m)
11-Ha1.70
11-He1.80
12-Ha2.14 (dd: 13, 5)
12-He1.82
15-Ha2.01
15-Hb1.57
16-Ha1.95
16-Hb1.76
17-H2.38 (t, 8)
18-Me0.90 (s)
19-Me1.08 (s)
21-Me1.19 (s)
22-H3.33
23-Ha1.32
23-Hb1.65
24-Ha1.75
24-Hb1.43
26-Me1.20 (s)
27-Me1.20 (s)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε)240.6 (4.00) ;

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCRP-HPLC - C6 semi-preparative column eluted with 35% MeOH in water, flow-rate 2 mL/min, Ret 21.0 min; 20E 24.2 min)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 2.5 x 10-7M

REFERENCES

First isolationSARKER, S.D. et al. (1998) Phytochemistry 49, 2305-2310 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 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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