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(5α)-DIHYDRORUBROSTERONE

Year of first isolation: 1996
Formula:C19H28O5
Molecular weight:336
Occurence in plants:
Silene otites [Caryophyllaceae] » Images of Silene otites Wikipedia: Silene otites [Caryophyllaceae]
Occurence in animals:
 
(5α)-DIHYDRORUBROSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2O)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(CCC2O)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]2O)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]2O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5S,9R,10R,13R,14R,17S)-2,3,14,17-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one (NB: for 17b-OH)
CAS-RN19892-42-3
PubChem CID22213160
InChiKey
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IHVPTRBJWKUCFE-IBKDVBTPSA-N
InChIInChI=1S/C19H28O5/c1-17-9-15(22)14(21)8-12(17)13(20)7-11-10(17)3-5-18(2)16(23)4-6-19(11,18)24/h7,10,12,14-16,21-24H,3-6,8-9H2,1-2H3/t10-,12+,14+,15-,16?,17+,18+,19+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z354 (MH+NH3)+, 337 (MH)+, 319, 308, 249, 231, 213
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 
CD3OD
01-Ha 
01-He 
02-He3.96 (m, w1/2 = 8)
03-Ha3.57 (m, w1/2 = 22)
04-Ha 
04-He 
05-H2.38 (dd )
07-H5.82 (d, 2.5)
09-Ha2.74 (m, w1/2 = 22)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H4.29 (dd, 8.8, 6.4)
18-Me0.71 (s )
19-Me1.03 (s )

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCNP-HPLC, column Zorbax-SIL (25 cm long, 4.6 mm i.d.), flow-rate 1 ml.min-1, solvent CH2Cl2-iPrOH-H2O (125:50:4), Ret 8.8 min (9.6 min for the 5beta isomer); solvent cyclohexane-iPrOH-H2O (100:40:3), Ret 23.1 min (20.6 min for the 5beta isomer).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 5.6 x 10-6M

REFERENCES

GeneralCOCHRANE, J.S. et al. (1971) J. Chem. Soc., Chem. Commun. 3730-3732 Search more
First isolationBÁTHORI, M. et al. (2000) Biomed. Chromatogr. 14, 464-467 Search more
BioactivitiesRAVI, M. et al. (2001) J. Chem. Inf. Comput. Sci. 41, 1587-1604 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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