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2,22-DIDEOXY-5β-HYDROXYECDYSONE 25-O-β-D-GLUCOPYRANOSYL-(1->2)-β-D-GLUCOPYRANOSIDE

Year of first isolation: 2009
Formula:C39H64O15
Molecular weight:772
Occurence in plants:
Froelichia floridana [Amaranthaceae] » Images of Froelichia floridana Wikipedia: Froelichia floridana [Amaranthaceae]
Occurence in animals:
 
2,22-DIDEOXY-5β-HYDROXYECDYSONE 25-O-β-D-GLUCOPYRANOSYL-(1->2)-β-D-GLUCOPYRANOSIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(CCCC(C)(C)OC1C(C(C(C(O1)CO)O)O)OC2C(C(C(C(O2)CO)O)O)O)C3CCC4(C3(CCC5C4=CC(=O)C6(C5(CCC(C6)O)C)O)C)O
Isomeric SMILES
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C1[C@]2([C@@](C[C@H](C1)O)(C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)CCCC(C)(C)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(3S,5S,9R,10R,13R,14S,17R)-17-[(2R)-6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methylheptan-2-yl]-3,5,14-trihydroxy-10,13-dimethyl-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID102508397
InChiKey
[ ChemIDPlus: search ]
HYPFLSYQWDBEFD-VJWUHOEPSA-N
InChIInChI=1S/C39H64O15/c1-19(21-10-14-38(49)23-15-26(43)39(50)16-20(42)8-12-37(39,5)22(23)9-13-36(21,38)4)7-6-11-35(2,3)54-34-32(30(47)28(45)25(18-41)52-34)53-33-31(48)29(46)27(44)24(17-40)51-33/h15,19-22,24-25,27-34,40-42,44-50H,6-14,16-18H2,1-5H3/t19-,20+,21-,22+,24-,25-,27-,28-,29+,30+,31-,32-,33+,34+,36-,37-,38-,39-/m1/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z
HR-ESI-MS m/z[M+H]+ 773.3975, calculated for C39H64O15H, 773.4324

CARBON NMR

PROTON NMR

CD3OD
0125.5
0229.2
0367.1
0436.7
0581.0
06203.0
07120.4
08167.0
0938.1
1043.4
1122.4
1232.3
1347.9
1486.0
1532.0
1627.9
1752.1
1816.4
1917.2
2037.0
2119.6
2238.0
2321.8
2443.8
2579.8
2626.4
2727.2
[glu 1]  197.3
[glu 1]  282.6
[glu 1]  378.3
[glu 1]  471.7
[glu 1]  578.5
[glu 1]  663.1
[glu 2]  1'105.4
[glu 2]  2'76.4
[glu 2]  3'77.6
[glu 2]  4'71.7
[glu 2]  5'77.8
[glu 2]  6'62.0
CD3OD
01-Ha1.45 (m)
01-He1.83 (m)
02-Ha1.96 (m)
02-He1.77 (m)
03-He4.09 (br, s, w1/2 = 16.2)
04-Ha1.61 (m)
04-He2.03 (m)
05-H-
07-H5.86 (s)
09-H3.38 (m)
11-Ha1.70 (m)
11-He1.55 (m)
12-Ha2.09 (m)
12-He1.76 (m)
15-Ha1.58 (m)
15-Hb1.93 (m)
16-Ha2.01 (m)
16-Hb1.40 (m)
17-H1.94 (t, 9.5)
18-Me0.73 (s)
19-Me0.89 (s)
20-H1.48 (m)
21-Me0.97 (d, 6.5)
22-Ha1.42 (m)
22-Hb1.05 (m)
23-Ha1.45 (m)
23-Hb1.30 (m)
24-Ha1.55 (m)
24-Hb1.44 (m)
26-Me1.27 (s)
27-Me1.29 (s)
[glu 1]  H14.59 (d, 8.1)
[glu 1]  H23.42 (m)
[glu 1]  H33.55 (m)
[glu 1]  H43.63 (m)
[glu 1]  H53.27 (m)
[glu 1]  H63.85 (m), 3.68 (m)
[glu 2]  H1'4.58 (d, 8.1)
[glu 2]  H2'3.24 (m)
[glu 2]  H3'3.39 (m)
[glu 2]  H4'3.28 (m)
[glu 2]  H5'3.26 (m)
[glu 2]  H6'3.83 (m), 3.66 (m)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D21+ 46 ° (c 0.11; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)248 () ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationWANG, P. et al. (2009) Phytochemistry 70, 430-436 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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