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2,3,20,22,26-PENTAHYDROXY-14-METHYL-18-NORCHOLESTA-7,12-DIEN-6-ONE

Year of first isolation: 2007
Formula:C27H42O6
Molecular weight:462
Occurence in plants:
Achyranthes bidentata [Amaranthaceae] » Images of Achyranthes bidentata Wikipedia: Achyranthes bidentata [Amaranthaceae]
Occurence in animals:
 
2,3,20,22,26-PENTAHYDROXY-14-METHYL-18-NORCHOLESTA-7,12-DIEN-6-ONE

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=C2C1(CC[C@@H]2[C@@]([C@H](O)CCC(C)CO)(C)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC=C2[C@]1(CC[C@@H]2[C@@]([C@H](O)CC[C@@H](C)CO)(C)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC=C2[C@]1(CC[C@@H]2[C@@]([C@H](O)CC[C@H](C)CO)(C)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC=C2[C@@]1(CC[C@@H]2[C@@]([C@H](O)CC[C@@H](C)CO)(C)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC=C2[C@@]1(CC[C@@H]2[C@@]([C@H](O)CC[C@H](C)CO)(C)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,17S)-2,3-dihydroxy-10,14-dimethyl-17-((2R,3R)-2,3,7-trihydroxy-6-methylheptan-2-yl)-1,2,3,4,5,9,10,11,14,15,16,17-dodecahydro-6H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
VGYHVIBSTDGROO-YIFLEHEZSA-N
InChIInChI=1S/C27H42O6/c1-15(14-28)5-8-24(32)27(4,33)18-9-10-25(2)16(18)6-7-17-19(25)11-21(29)20-12-22(30)23(31)13-26(17,20)3/h6,11,15,17-18,20,22-24,28,30-33H,5,7-10,12-14H2,1-4H3/t15?,17-,18-,20-,22+,23-,24+,25?,26+,27+/m0/s1

MASS SPECTRUM

ESI-MS m/z 463.2 [M+H]+, 485.2 [M+Na]+

CARBON NMR

PROTON NMR

C5D5N
0137.9
0268.1
0368.4
0432.4
0550.4
06202.6
07123.1
08148.0
0939.6
1040.2
1125.3
12120.4
13174.4
1449.1
1539.4
1621.8
1749.4
1825.3
1923.3
2076.0
2121.0
2276.2
2330.0
2431.7
2536.8
2668.0
C5D5N
01-Ha2.07 (m)
01-He2.07 (m)
02-Ha4.20 (m)
03-He4.45 (m)
04-Ha2.25 (m)
04-He2.25 (m)
05-H2.97 (dd, 3.6, 13.2)
07-H6.21 (s)
09-H2.93 (m)
11-Ha1.81 (m)*
11-He2.10 (m)*
12-H6.05 (m)
15-Ha1.91 (m)
15-Hb1.91 (m)
16-Ha1.92 (m)**
16-Hb2.23 (m)**
17-H3.18 (m)
18-Me1.27 (m)
19-Me0.95 (m)
21-Me1.55 (m)
22-H3.95 (m)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-CH2OH3.83 (m), 3.76 (m)
27-Me1.14 (m)

PHYSICAL PROPERTIES

M.P.222-223 °C ;
[α]D20+ 45 ° (c 0.008 ; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)247 nm () ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationLI, X. et al. (2007) Fitoterapia 78, 607-608 Search more
GeneralWANG, Q.H. et al. (2011) Molecules 16, 5989-5997 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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