Welcome to online ecdysteroids database ! . .
Access data · History · Contact

PONASTEROSIDE A

Year of first isolation: 1968
Formula:C33H54O11
Molecular weight:626
Occurence in plants:
Pteridium aquilinum var. latiusculum [Dennstaedtiaceae] » Images of Pteridium aquilinum var. latiusculum Wikipedia: Pteridium aquilinum var. latiusculum [Dennstaedtiaceae]
Lygodium japonicum [Lygodiaceae] » Images of Lygodium japonicum Wikipedia: Lygodium japonicum [Lygodiaceae]
Occurence in animals:
 
PONASTEROSIDE A

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)O
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
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@](C)([C@@H](CCC(C)C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,14-dihydroxy-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-RN20117-33-3
PubChem CID12314455
InChiKey
[ ChemIDPlus: search ]
CNAKQRUFJWYXIC-PPOCGGKUSA-N
InChIInChI=1S/C33H54O11/c1-16(2)6-7-25(37)32(5,41)24-9-11-33(42)18-12-20(35)19-13-22(43-29-28(40)27(39)26(38)23(15-34)44-29)21(36)14-30(19,3)17(18)8-10-31(24,33)4/h12,16-17,19,21-29,34,36-42H,6-11,13-15H2,1-5H3/t17-,19-,21-,22+,23+,24-,25+,26+,27-,28+,29+,30+,31+,32+,33+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)626 (M)+
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0138.7
0267.5
0376.8
0430.3
0551.4
06203.1
07121.7
08166.4
0934.3
1039.0
1121.1
1232.0
1348.1
1484.2
1531.8
1621.5
1750.1
1817.9
1924.1
2077.7
2121.6
2276.8
2328.2
2437.2
2530.6
2623.4
2722.4
glu-1104.2
glu-274.7
glu-378.7
glu-471.6
glu-578.5
glu-662.6
C5D5N
01-H1.76 (m), 2.10 (m)
02-H4.10 (brd, 11.4)
03-H4.30 (overlap)
04-H1.73 (m), 2.20 (m)
05-H2.93 (m)
07-H6.23 (d, 1.8)
09-H3.55 (t, 8.4)
11-H1.65 (m), 1.83 (m)
12-H2.02 (m), 2.58 (dt, 4.2, 12.6)
15-H1.92 (m), 2.15 (m)
16-H2.08 (m), 2.44 (m)
17-H2.91 (m)
18-Me1.19 (s)
19-Me0.87 (s)
21-Me1.58 (s)
22-H3.81 (brd, 10.8)
23-H1.47 (m)
24-H1.40 (m), 1.70 (m)
25-H1.54 (m)
26-Me0.81 (d, 6.0)
27-Me0.82 (d, 6.0)
H-1´4.90 (d, 7.8)
H-2´4.03 (m)
H-3´4.20 (m)
H-4´4.18 (m)
H-5´3.93 (m)
H-6´, 6´4.32 (m), 4.53 (brd 10.2)

PHYSICAL PROPERTIES

M.P.278-279.5 °C
[α]D20+ 28.5 ° (pyridine)
IR (KBr) ν max (cm-1)3430 (OH), 1650 (cyclohexenone)
UV (EtOH) λ max (log ε)245

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationTAKEMOTO, T. et al. (1968) Chem. Pharm. Bull. 16, 762 Search more
GeneralHIKINO, H. et al. (1969) Tetrahedron 15, 3389-3394 Search more
IdentificationZHU, L. et al. (2009) J. Nat. Med. 63, 215-219 Search more

see Important notice
© 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
designed by Cybersales a.s.
Powered by Cybersales
PRINTER READY | MEDIUM | WIDE