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VIPERIDONE

Year of first isolation: 1964
Formula:C27H44O3
Molecular weight:416
Occurence in plants:
Wilcoxia viperina [Cactaceae] » Images of Wilcoxia viperina Wikipedia: Wilcoxia viperina [Cactaceae]
Occurence in animals:
 
VIPERIDONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCCC(C)C1CCC2C1(CCC3(C2=CC(=O)C4C3(CCC(C4)O)C)O)C
Isomeric SMILES
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C1[C@]2([C@H](C[C@H](C1)O)C(=O)C=C1[C@@]2(CC[C@]2(C1CC[C@@H]2[C@H](C)CCCC(C)C)C)O)C  » JSMol: View in 3D
C1[C@]2([C@H](C[C@H](C1)O)C(=O)C=C1[C@@]2(CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CCCC(C)C)C)O)C  » JSMol: View in 3D
C1[C@]2([C@H](C[C@H](C1)O)C(=O)C=C1[C@@]2(CC[C@]2([C@@H]1CC[C@@H]2[C@H](C)CCCC(C)C)C)O)C » JSMol: View in 3D
IUPAC Name(3S,5S,9S,10S,13R,14R,17R)-3,9-dihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID21593998
InChiKey
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HGCLEPLEUUJGID-REBIDWDSSA-N
InChIInChI=1S/C27H44O3/c1-17(2)7-6-8-18(3)20-9-10-21-22-16-24(29)23-15-19(28)11-12-26(23,5)27(22,30)14-13-25(20,21)4/h16-21,23,28,30H,6-15H2,1-5H3/t18-,19+,20-,21+,23-,25-,26+,27-/m1/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
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 
20 
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25 
26 
27 
28 
29 
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 
14-H 
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 
25-H 
26-Me 
27-Me 

PHYSICAL PROPERTIES

M.P.208-210 °C ;
[α]D20-59.1 ° (c ; CHCl3)
IR (KBr) ν max (cm-1)1660 (cyclohexenone)
UV (EtOH) λ max (log ε)2.37 (4.033)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationDJERASSI, C. et al. (1964) Chem. Ber. 97, 3118-3130 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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