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DIHYDROPOSTSTERONE

Year of first isolation: 1990
Formula:C21H32O5
Molecular weight:364
Occurence in plants:
Silene otites [Caryophyllaceae] » Images of Silene otites Wikipedia: Silene otites [Caryophyllaceae]
Occurence in animals:
 
DIHYDROPOSTSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)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]2C(C)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]2C(C)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]2C(C)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,13R,14S,17S)-2,3,14-trihydroxy-17-[(1S)-1-hydroxyethyl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID138453982
InChiKey
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OIUWMPRXGZDPKO-ZDCYWFNZSA-N
InChIInChI=1S/C21H32O5/c1-11(22)12-5-7-21(26)14-8-16(23)15-9-17(24)18(25)10-19(15,2)13(14)4-6-20(12,21)3/h8,11-13,15,17-18,22,24-26H,4-7,9-10H2,1-3H3/t11?,12-,13+,15+,17-,18+,19-,20-,21-/m1/s1

MASS SPECTRUM

CI-MS (NH3) m/z382 (MH+NH3)+, 365 (MH)+, 347, 345
EI-MS m/z (relative intensity %) 
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 
CD3OD
01-Ha1.42 (dd, 13, 12)
01-Hb 
02-Ha3.84 (m )
03-He3.95 (m, w1/2 = 8)
04-Ha 
04-He 
05-H2.38 (dd, 12, 5)
07-H5.82 (d, 2.5)
09-Ha3.14 (m, w1/2 = 22)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.69 (s )
19-Me0.96 (s )
20-CH-OH~ 3.65 (m )
21-Me1.22 (d, 6.5)

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC1- Retention time 14.7 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:40:3 v/v/v, flow-rate 1 ml.min-1] (20E : 16.8 min); 2-Retention time 26.8 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:25:2 v/v/v, flow-rate 1 ml.min-1] (20E 37.4 min)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 7.4 x 10-4M and 1.2 x 10--4M (two epimers)

REFERENCES

First isolationGIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 Search more
BioactivitiesDINAN, L. et al. (2003) In: Studies in Natural Products Chemisty (ed. Atta-ur-Rahman), Elsevier, Amsterdam, 29, 3-71 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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