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PFAFFIAGLYCOSIDE C

Year of first isolation: 2010
Formula:C33H54O11
Molecular weight:626
Occurence in plants:
Pfaffia glomerata [Amaranthaceae] » Images of Pfaffia glomerata Wikipedia: Pfaffia glomerata [Amaranthaceae]
Occurence in animals:
 
PFAFFIAGLYCOSIDE C

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1CCC2C(C)(CCCC(C)(C)OC5C(C(C(C(O5)CO)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@@](CCCC(C)(C)OC1C(C(C(C(O1)CO)O)O)O)(C)O)O)C)C  » JSMol: View in 3D
(Ecdybase  » JSMol: View in 3D
structure) » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13S,14R,17S)-2,3-dihydroxy-17-[(2S)-2-hydroxy-6-methyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-10,13-dimethyl-1,2,3,4,5,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-one (PubChem structure)
CAS-RN 
PubChem CID101499972
InChiKey
[ ChemIDPlus: search ]
SRRVTIQZLQVYOH-SOWRRTDVSA-N
InChIInChI=1S/C33H54O10/c1-30(2,43-29-28(40)27(39)26(38)24(16-34)42-29)10-6-11-33(5,41)25-8-7-18-17-13-21(35)20-14-22(36)23(37)15-32(20,4)19(17)9-12-31(18,25)3/h13,18-20,22-29,34,36-41H,6-12,14-16H2,1-5H3/t18-,19-,20-,22+,23-,24+,25-,26+,27-,28+,29-,31-,32+,33-/m0/s1

MASS SPECTRUM

HR-FAB-MS m/z 649.3571 [M+Na]+, calculated for C33H54O11Na
EI-MS m/z (relative intensity %)
FAB-MS m/z 649 [M+Na]+

CARBON NMR

PROTON NMR

C5D5N
0137.7
0268.1
0368.0
0432.4
0551.2
06203.7
07121.5
08166.4
0934.2
1038.7
1120.9
1231.8
1347.4
1484.5
1531.5
1621.9
1753.9
1817.9
1924.5
2074.3
2127.0
2245.2
2318.8
2442.8
2577.4
2627.1
2727.2
[Glu] 01'98.7
[Glu] 02'75.4
[Glu] 03'78.7
[Glu] 04'71.8
[Glu] 05'78.2
[Glu] 06'62.9
C5D5N
01-Ha 
01-He 
02-Ha4.15 (m)
03-He4.21 (m)
04-Ha 
04-He 
05-H2.98 (dd, 4.0, 14.0)
07-H6.19 (d, 2.0)
09-H3.56 (m)
11-Ha 
11-He 
12-Ha2.55 (ddd, 4.1, 13.1, 13.1)
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.81 (dd, 8.9, 8.9)
18-Me1.12 (s)
19-Me1.05 (s)
21-Me1.50 (s)
22-Ha 
22-Hb 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.34 (s)
27-Me1.37 (s)
[Glu] H-1´4.96 (d, 8.0)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D23- 16.1 ° (c 0.13; MeOH)
IR (KBr) ν max (cm-1)3430, 2926, 1670, 1074
UV (EtOH) λ max (log ε)() ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationNAKAMURA, S. et al. (2010) Chem. Pharm. Bull. 58, 690-695 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
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