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AJUGASTERONE C 2-ACETATE

Year of first isolation: 2016
Formula:C29H46O8
Molecular weight:522
Occurence in plants:
Cyanotis arachnoidea [Commelinaceae] » Images of Cyanotis arachnoidea Wikipedia: Cyanotis arachnoidea [Commelinaceae]
Occurence in animals:
 
AJUGASTERONE C 2-ACETATE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
C1[C@]2([C@@H](C[C@H]([C@H]1OC(=O)C)O)C(=O)C=C3[C@@H]2[C@@H](C[C@]4([C@]3(CCC4[C@](C)([C@@H](CCC(C)C)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,11R,13R,14S)-17-((2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl)-3,11,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl acetate
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
OJHBARZZNBDVOD-DUVCGGAPSA-N
InChIInChI=1S/C29H46O8/c1-15(2)7-8-24(34)28(6,35)23-9-10-29(36)18-12-19(31)17-11-20(32)22(37-16(3)30)14-26(17,4)25(18)21(33)13-27(23,29)5/h12,15,17,20-25,32-36H,7-11,13-14H2,1-6H3/t17-,20+,21+,22-,23?,24+,25+,26-,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z
EI-MS m/z (relative intensity %)
HR-MS

CARBON NMR

PROTON NMR

CD3OD
0136.1
0273.4
0365.8
0433.3
0552.6
06206.0
07122.8
08165.7
0943.0
1040.0
1169.6
1243.7
1348.7
1485.0
1531.9
1621.6
1750.4
1819.0
1924.7
2077.9
2121.1
2278.0
2330.6
2437.8
2529.3
2622.9
2723.6
3-OAC21.3, 172.6
CD3OD
01-Ha1.62 (t, 12.5)
01-He2.56 (dd, 12.5, 4.0)
02-Ha5.13 (ddd, 12.5, 4.0, 3.0)
03-He4.18 (q ~3.0)
04-Ha1.68 (ddd, 13.0, 4.0, 3.0)
04-He1.84 (td, 13.0, 3.0
05-H2.39 (dd, 13.0, 4.0)
07-H5.82 (d, 2.5)
09-H3.19 (dd, 9.0, 2.5)
11-H4.09 (ddd, 11.5, 9.0, 6.0)
12-Ha2.15 (dd, 12.0, 6.0)
12-He2.22 (t, ~12.0
15-Ha1.97
15-Hb1.58
16-Ha1.98
16-Hb1.73
17-H2.42 (t, 9.0)
18-Me0.88 (s)
19-Me1.09 (s)
21-Me1.19 (s)
22-H3.32
23-Ha1.57
23-Hb1.23
24-Ha1.47
24-Hb1.23
25-H1.57
26-Me0.92 (d, 6.5))
27-Me0.93 (d, 6.5))
OAc2.05 (s)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D20° (c ; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)() ;

CHROMATOGRAPHY

HPTLC
TLC
GLC
HPLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationHUNYADI, A. et al. (2016) Scientific Reports 6, 37322 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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