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29-NORSENGOSTERONE

Year of first isolation: 1982
Formula:C28H42O9
Molecular weight:522
Occurence in plants:
Ajuga reptans [Lamiaceae (alt. Labiatae)] » Images of Ajuga reptans Wikipedia: Ajuga reptans [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
29-NORSENGOSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC1C(COC1=O)CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5(C4(CC(C(C5)O)O)C)O)C)O)O)O
Isomeric SMILES
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C1[C@]2([C@@](C[C@H]([C@H]1O)O)(C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H](O)C[C@@H]1COC(=O)[C@H]1C)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(3S,4S)-4-[(2R,3R)-2,3-dihydroxy-3-[(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-6-oxo-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]butyl]-3-methyloxolan-2-one
CAS-RN 
PubChem CID14693881
InChiKey
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AJPNSKWVBMZHRH-HDWGAXEUSA-N
InChIInChI=1S/C28H42O9/c1-14-15(13-37-23(14)33)9-21(31)26(4,34)20-6-8-27(35)17-10-22(32)28(36)12-19(30)18(29)11-25(28,3)16(17)5-7-24(20,27)2/h10,14-16,18-21,29-31,34-36H,5-9,11-13H2,1-4H3/t14-,15+,16-,18-,19+,20-,21+,24+,25+,26+,27+,28+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z540 (M+NH4)+, 523 (MH)+, 505, 487, 469, 451, 378, 361, 343, 325, 267, 245, 229, 204, 187, 171, 160, 143
EI-MS m/z (relative intensity %)504 (M-18)+, 361, 343, 325, 187, 169, 143
HR-MS 

CARBON NMR

PROTON NMR

CDCl3
0134.7 (t )
0267.9 (d )
0369.8 (d )
0435.9 (t )
0579.8 (s )
06201.0 (s )
07120.0 (d )
08166.7 (s )
0938.2 (d )
1044.8 (s )
1122.0 (t )$
1231.7 (t )*
1348.2 (s )
1484.0 (s )
1532.1 (t )*
1621.3 (t )$
1750.0 (d )
1817.9 (q )
1917.1 (q )
2076.7 (s )
2121.3 (q )
2276.0 (d )
2334.7 (t )
2440.7 (d )
2543.3 (d )
26179.8 (s )
2714.5 (q )
2872.9 (t )
CDCl3
01-Ha 
01-He 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H6.25 (d, 2)
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.13 (s )
19-Me1.13 (s )
21-Me1.53 (s )
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me?
27-Me1.18 (d, 7)

PHYSICAL PROPERTIES

M.P. 
[α]D20+ 51.0 ° (c 4.7 ; MeOH)
IR (KBr) ν max (cm-1)1755 (lactone), 1670 (cyclohexenone)
UV (EtOH) λ max (log ε)238 (3.954)

CHROMATOGRAPHY

NP-HPLCcolumn Zorbax-SIL (25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1), solvent cyclohexane-iPrOH-H2O (100:40:3), Ret 21.6 min (20E 19.2 min); solvent CH2Cl2-iPrOH-H2O (125:40:3) Ret 7.0 min (20E 19.5 min).
TLC 
GLC 
RP-HPLCcolumn Spherisorb-5ODS2 (25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1), solvent iPrOH-H2O (7:93), 35°C, Ret 11.7 min (20E 19.8 min).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 1.3 x 10-7M

REFERENCES

First isolationCAMPS, F. et al. (1982) Chem. Lett., 1313-1316 Search more
GeneralMORGAN, E.D. et al. (1989) Invertebr. Reprod. Devel. 18, 55-66 Search more
GeneralCAMPS, F. et al. (1990) J. Chromatogr. 514, 199-207 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 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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