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24-EPI-ABUTASTERONE

Year of first isolation: 1997
Formula:C27H44O8
Molecular weight:496
Occurence in plants:
Vitex canescens [Lamiaceae (alt. Labiatae)] » Images of Vitex canescens Wikipedia: Vitex canescens [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
24-EPI-ABUTASTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CC(C(C)(C)O)O)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]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](C[C@H](C(C)(C)O)O)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,5R)-2,3,5,6-tetrahydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID11103069
InChiKey
[ ChemIDPlus: search ]
NXKBQUXBPMOHPK-ZHMUISTKSA-N
InChIInChI=1S/C27H44O8/c1-23(2,33)21(31)12-22(32)26(5,34)20-7-9-27(35)15-10-17(28)16-11-18(29)19(30)13-24(16,3)14(15)6-8-25(20,27)4/h10,14,16,18-22,29-35H,6-9,11-13H2,1-5H3/t14-,16-,18+,19-,20-,21+,22+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %) 
HR-FAB-MS497.3123 [M+H]+, calculated for C27H45O8: 497.3114

CARBON NMR

PROTON NMR

C5D5N
0137.9
0268.1a
0368.0a
0432.3
0551.3
06203.4
07121.6
08166.1
0934.4
1038.6
1121.1
1231.7
1348.1
1484.2
1531.9
1621.3
1750.0
1817.9
1924.4
2076.8
2121.7
2273.7b
2335.2
2475.9b
2572.6
2626.1
2726.0
C5D5N
01-Ha 
01-He 
02-Ha4.18 (m)
03-He4.23 (br, s)
04-Ha 
04-He 
05-H3.01 (dd, 13.1, 3.6)
07-H6.26 (d, 2.7)
09-H3.57 (m)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H3.08 (t, 9.1)
18-Me1.22 (s)
19-Me1.06 (s)
21-Me1.63 (s)
22-H4.51 (dd, 9.6, 2.3) a
23-Ha 
23-Hb 
24-H4.37 (dd, 9.0, 2.7) a
26-Me1.46 (s)
27-Me1.47 (s)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3408, 2962, 1651, 1444, 1383, 1303, 1057, 950, 877
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLCSilica, CHCl3-MeOH 5:1
GLC 
HPLCColumn Spherisorb ODS2 5?m (250x4.6 mm), solvent MeOH-H2O (1:3)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 1.2 x 10-6M

REFERENCES

First isolationSUKSAMRARN, A. et al. (1997) Phytochemistry 45, 1149-1152 Search more
BioactivitiesRAVI, M. et al. (2001) J. Chem. Inf. Comput. Sci. 41, 1587-1604 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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