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KALADASTERONE

Year of first isolation: 1973
Formula:C27H42O7
Molecular weight:478
Occurence in plants:
Ipomoea calonyction [Convolvulaceae] » Images of Ipomoea calonyction Wikipedia: Ipomoea calonyction [Convolvulaceae]
Occurence in animals:
 
KALADASTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)(C1CCC2(C1(CC=C3C2=CC(=O)C4(C3(CC(C(C4)O)O)C)O)C)O)O)O
Isomeric SMILES
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CC(C)CC[C@H]([C@@](C)([C@H]1CC[C@@]2([C@@]1(CC=C3C2=CC(=O)[C@]4([C@@]3(C[C@@H]([C@@H](C4)O)O)C)O)C)O)O)O » JSMol: View in 3D
IUPAC Name(2S,3R,5S,10R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,5,14-tetrahydroxy-10,13-dimethyl-1,2,3,4,12,15,16,17-octahydrocyclopenta[a]phenanthren-6-one
CAS-RN52591-06-7
PubChem CID21723377
InChiKey
[ ChemIDPlus: search ]
ZKUKSIKBNQQCOB-DPKIEXNISA-N
InChIInChI=1S/C27H42O7/c1-15(2)6-7-21(30)25(5,32)20-9-11-26(33)17-12-22(31)27(34)14-19(29)18(28)13-24(27,4)16(17)8-10-23(20,26)3/h8,12,15,18-21,28-30,32-34H,6-7,9-11,13-14H2,1-5H3/t18-,19+,20-,21+,23+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z478 (M)+, 460, 445, 422, 377, 359 (base peak), 341, 323, 305, 145, 109, 105, 99, 91, 85, 83, 81
HR-MS478.2941

CARBON NMR

PROTON NMR

C5D5N
0138.6
0267.9 *
0369.5 *
0435.2
0579.7
06201.1
07116.8
08156.0
09137.4
1045.4
11132.9
1238.6
1347.4
1483.2
1531.3
1621.5
1749.9
1826.3
1917.9
2076.5
2121.2
2276.8
2330.2
2437.0
2528.2
2622.4 **
2723.3 **
DMSO-d6
01-Ha 
01-Hb 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H5.65 (s )
09-Ha 
11-H6.18 (m, w1/2 = 10)
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.73 (s )
19-Me0.96 (s )
21-Me1.06 (s )
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me0.86 (d, 7)
27-Me0.86 (d, 7)

PHYSICAL PROPERTIES

M.P.242-243 °C
[α]D24+ 79.3° (c ; MeOH)
IR (KBr) ν max (cm-1)3600-3200 (OH), 1652 (cyclohexenone), 1604
UV (EtOH) λ max (log ε)298 (4.03)

CHROMATOGRAPHY

HPTLC 
TLCNP-TLC on silicagel Rf 0.49 (CHCl3-EtOH 4:1); RP-TLC on paraffin coated silica gel Rf 0.28 (MeOH-H2O 50:50); RP-TLC on C18-bonded silica gel Rf 0.26 (MeOH-H2O 65:35)
GLCGLC Ret 4.1 min on 1.5% OV101 (0.9 m x 4.5 mm i.d.) at 285°C after silylation at 140°C for 60 h.
HPLC 

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 3.4 x 10-7M

REFERENCES

First isolationCANONICA, L. et al. (1973) Experientia 29, 1062-1063 Search more
GeneralCANONICA, L. et al. (1975) Phytochemistry 14, 525-527 Search more
GeneralKREPINSKY, J. et al. (1977) Org. Magn. Reson. 10, 255-257 Search more
GeneralCANONICA, L. et al. (1977) Gazz. Chim. Ital. 107, 123-130 Search more
GeneralWILSON, I.D. et al. (1985) J. Chromatogr. 318, 373-377 Search more
GeneralBIELBY, C.R. et al. (1986) J. Chromatogr. 351, 57-64 Search more
BioactivitiesBOURNE, P. et al. (2002) J. Insect Sci. 2:11 (pp. 11) 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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