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RAPISTERONE B

Year of first isolation: 1991
Formula:C27H44O8
Molecular weight:496
Occurence in plants:
Rhaponticum carthamoides [Asteraceae] » Images of Rhaponticum carthamoides Wikipedia: Rhaponticum carthamoides [Asteraceae]
Occurence in animals:
 
RAPISTERONE B

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)C(CCC(C)(C1CCC2(C1(CC(C3C2=CC(=O)C4C3(CC(C(C4)O)O)C)O)C)O)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]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H](O)CC(C(C)C)O)O)O)C)O)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H](O)C[C@H](C(C)C)O)O)O)C)O)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H](O)C[C@@H](C(C)C)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,11R,13R,14S,17S)-17-[(2S)-2,5-dihydroxy-6-methylheptan-2-yl]-2,3,11,14-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID21770573
InChiKey
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JOMGMALSBMJPBU-RHOMHJKWSA-N
InChIInChI=1S/C27H44O7/c1-14(2)17(28)6-8-26(5,33)22-7-9-27(34)16-11-18(29)15-10-19(30)20(31)12-24(15,3)23(16)21(32)13-25(22,27)4/h11,14-15,17,19-23,28,30-34H,6-10,12-13H2,1-5H3/t15-,17?,19+,20-,21+,22-,23+,24-,25+,26-,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)462 (M-H2O)+ (3), 444 (4), 426 (6), 408 (6), 393 (3), 379 (12), 361 (30), 343 (100), 325 (75), 301 (60), 267 (45), 145 (21), 109 (15), 83 (12), 55 (25)
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 
22 
23 
24 
25 
26 
27 
C5D5N
01-Ha 
01-He 
02-Ha4.45 (m )
03-He4.12 (m )
04-Ha 
04-He 
05-H 
07-H6.11 (s )
09-Ha3.61-3.72 (m )
11-H4.45 (m )
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.10 (s )
19-Me1.15 (s )
21-Me1.42 (s )
22-H 
23-H 
24-H3.61-3.72 (m )
25-H 
26-Me0.67 (d )
27-Me0.67 (d )

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3550-3500 (OH), 1655 (cyclohexenone)
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 2.3 x 10-7M

REFERENCES

First isolationBALTAYEV, U.A. et al. (1991) Khim. Prir. Soedin., 806-808 Search more
BioactivitiesDINAN, L. et al. (2005) In: Comprehensive Molecular Insect Science (eds. L. I. Gilbert, C. Iatrou, S. Gill), Elsevier, Oxford, III, 197-242 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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