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BRAINESTEROSIDE D

Year of first isolation: 2010
Formula:C33H54O10
Molecular weight:610
Occurence in plants:
Brainea insignis [Ferns] » Images of Brainea insignis
Occurence in animals:
 
BRAINESTEROSIDE D

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)OC5C(C(C(C(O5)CO)O)O)O)O)C)C)O)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(C)C)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17R)-2,14-dihydroxy-17-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID101514325
InChiKey
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UVTRNQDEASOAEI-CRTQUAMDSA-N
InChIInChI=1S/C33H50O11/c1-15(2)6-9-23(36)33(5,42)22-8-7-16-24-17(10-11-31(16,22)3)32(4)13-19(35)20(12-18(32)25(37)27(24)39)43-30-29(41)28(40)26(38)21(14-34)44-30/h7,15,19-23,26,28-30,34-38,40-42H,6,8-14H2,1-5H3/t19-,20+,21+,22-,23+,26+,28-,29+,30+,31-,32+,33+/m0/s1

MASS SPECTRUM

ESI-MS (positive) m/z611 [M+H]+, 633 [M+Na]+, 1243 [2M +Na]+
ESI-MS (negative) m/z609 [M-H]-, 645 [M+Cl]-, 1219 [2M-H]-

CARBON NMR

PROTON NMR

DMSO-d6
0137.5
0266.1
0374.2
0429.2
0550.1
06202.4
07120.4
08164.9
0933.1
1037.7
1120.1
1230.3
1346.4
1482.7
1530.6
1625.7
1747.1
1815.3
1923.6
2041.8
2112.8
2271.6
2327.1
2435.9
2527.5
2622.4
2723.0
[sugar] 1'101.1
[sugar] 2'72.8
[sugar] 3'76.5
[sugar] 4'70.1
[sugar] 5'77.0
[sugar] 6'61.0
DMSO-d6
01-Ha1.28 (t, 12.8)
01-He1.62 (m)
02-Ha3.65 (br d, 11.6)
03-He3.94 (br, s)
04-Ha1.49 (m)
04-He1.69 (td, 4.0, 13.2)
05-H2.25 (dd, 4.0, 13.2)
07-H5.64 (d, 2.0)
09-H2.99 (m)
11-Ha1.47 (m)
11-He1.62 (m)
12-Ha1.99 (dt, 8.6, 10.0)
12-He1.58 (m)
15-Ha1.76 (m)
15-Hb1.48 (m)
16-Ha1.74 (m)
16-Hb1.31 (m)
17-H1.83 (td, 8.6, 10.0)
18-Me0.57 (s)
19-Me0.85 (s)
20-H1.55 (m)
21-Me0.81 (d, 6.8)
22-H3.38 (m)
23-Ha1.21 (m)
23-Hb1.06 (m)
24-Ha1.33 (m)
24-Hb1.07 (m)
25-H1.47 (m)
26-Me0.84 (d, 6.8)
27-Me0.86 (d, 6.8)
[sugar] 1'4.22 (d, 7.8)
[sugar] 2'3.03 (t, 8.4)
[sugar] 3'3.15 (t, 8.4)
[sugar] 4'3.01 (t, 8.4)
[sugar] 5'3.10 (m)
[sugar] 6'a3.65 (br, d, 11.6)
[sugar] 6'b3.39 (dd, 5.6, 11.6)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D20+ 32.4 ° (c 0.18; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)243 (3.89) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationWU, P. et al. (2010) Phytochemistry 71, 975-981 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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