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SIDASTERONE A

Year of first isolation: 1976
Formula:C28H44O7
Molecular weight:492
Occurence in plants:
Sida cordifolia [Malvaceae] » Images of Sida cordifolia Wikipedia: Sida cordifolia [Malvaceae]
Sida rhombifolia [Malvaceae] » Images of Sida rhombifolia Wikipedia: Sida rhombifolia [Malvaceae]
Sida spinosa [Malvaceae] » Images of Sida spinosa Wikipedia: Sida spinosa [Malvaceae]
Occurence in animals:
 
SIDASTERONE A

STRUCTURE DESCRIPTORS

Canonical SMILES 
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]2[C@](C)([C@H](O)C[C@H](C(=C)CO)C)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-((2R,3R,5R)-2,3-dihydroxy-6-(hydroxymethyl)-5-methylhept-6-en-2-yl)-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
YRAMRUGGFATRDU-UAKLZHGLSA-N
InChIInChI=1S/C28H44O7/c1-15(16(2)14-29)10-24(33)27(5,34)23-7-9-28(35)18-11-20(30)19-12-21(31)22(32)13-25(19,3)17(18)6-8-26(23,28)4/h11,15,17,19,21-24,29,31-35H,2,6-10,12-14H2,1,3-5H3/t15-,17+,19+,21-,22+,23+,24-,25-,26-,27-,28-/m1/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)474 (M-18)+
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 
28 
CD3OD
01-Ha 
01-He 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me 
19-Me 
20-H 
21-Me 
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me 
27-Me 

PHYSICAL PROPERTIES

M.P.238-240 °C
[α]D20+ 67.8 ° (c ; dioxane)
IR (KBr) ν max (cm-1)3500, 3410 (OH), 1662 (cyclohexenone), 1632, 890
UV (EtOH) λ max (log ε)243 (4.08)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationGHOSAL, S. et al. (1976) In: 4th Indo-Soviet Symp. on Chem. and Pharm. of Nat. Prod. (Lucknow), Abstract book, p. 142 Search more
GeneralPRAKASH, A. et al. (1979) J. Sci. Ind. Res. 38, 632-647 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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